Vitamin D3

Summary

Vitamin D3 is a form of Vitamin D used in the treatment of specific medical conditions such as refractory rickets, hypoparathyroidism, and familial hypophosphatemia, as well as osteoporosis and chronic kidney disease.

Brand Names

Adrovance, Animi-3 With Vitamin D, Citranatal B-calm Kit, Citranatal Harmony, Fosamax Plus D, Fosavance, Infuvite, Infuvite Pediatric, Mvc-fluoride, Natafort, Pregvit, Vidextra

Generic Name
Cholecalciferol
Commonly known or available as Vitamin D3
DrugBank Accession Number
DB00169
Background

Vitamin D, in general, is a secosteroid generated in the skin when 7-dehydrocholesterol located there interacts with ultraviolet irradiation - like that commonly found in sunlight 9. Both the endogenous form of vitamin D (that results from 7-dehydrocholesterol transformation), vitamin D3 (cholecalciferol), and the plant-derived form, vitamin D2 (ergocalciferol), are considered the main forms of vitamin d and are found in various types of food for daily intake 9. Structurally, ergocalciferol differs from cholecalciferol in that it possesses a double bond between C22 and C23 and has an additional methyl group at C24 9. Finally, ergocalciferol is pharmacologically less potent than cholecalciferol, which makes vitamin D3 the preferred agent for medical use 9.

Appropriate levels of vitamin D must be upheld in the body in order to maintain calcium and phosphorus levels in a healthy physiologic range to sustain a variety of metabolic functions, transcription regulation, and bone metabolism 4,9,10,11,12,13,14. However, studies are also ongoing to determine whether or not cholecalciferol may also play certain roles in cancer, autoimmune disorders, cardiovascular disease, and other medical conditions that may be associated with vitamin D deficiency 9.

Type
Small Molecule
Groups
Approved, Nutraceutical
Structure

Thumb

Image

Weight
Average: 384.6377
Monoisotopic: 384.33921603
Chemical Formula
C27H44O
Synonyms
  • (+)-vitamin D3
  • (3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
  • (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol
  • Activated 7-dehydrocholesterol
  • Calciol
  • CC
  • Cholecalciferol
  • Cholecalciferolum
  • Colecalciferol
  • Colecalciferolum
  • Oleovitamin D3
  • Vitamin D-3
  • Vitamin D3
External IDs
  • NSC-375571
Indication

Cholecalciferol use is indicated for the treatment of specific medical conditions like refractory rickets (or vitamin D resistant rickets), hypoparathyroidism, and familial hypophosphatemia 12,13.

Concurrently, as one of the most commonly utilized forms of vitamin D, cholecalciferol is also very frequently used as a supplement in individuals to maintain sufficient vitamin d levels in the body or to treat vitamin D deficiency, as well as various medical conditions that can be associated directly or indirectly with vitamin d insufficiency like osteoporosis and chronic kidney disease, among others 2,3,15.

Pharmacology

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Associated Conditions
  • Calcium and Vitamin D Deficiencies
  • Deficiency of Vitamin D3
  • Deficiency, Vitamin A
  • Deficiency, Vitamin D
  • Fractures, Bone
  • Hip Fracture
  • Hypoparathyroidism
  • Hypophosphatemia, Familial
  • Menopause
  • Osteomalacia
  • Osteoporosis
  • Postmenopausal Osteoporosis
  • Vertebral Fractures
  • Vitamin D Resistant Rickets
  • Vitamin Deficiency
  • Severe Bone Resorption
  • Spine fracture
Associated Therapies
  • Calcium supplementation
  • Nutritional supplementation
  • Vitamin D Supplementation
  • Vitamin supplementation
Contraindications & Blackbox Warnings

Contraindications

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Pharmacodynamics

The in vivo synthesis of the predominant two biologically active metabolites of vitamin D occurs in two steps. The first hydroxylation of vitamin D3 cholecalciferol (or D2) occurs in the liver to yield 25-hydroxyvitamin D while the second hydroxylation happens in the kidneys to give 1, 25-dihydroxyvitamin D 12,13,14. These vitamin D metabolites subsequently facilitate the active absorption of calcium and phosphorus in the small intestine, serving to increase serum calcium and phosphate levels sufficiently to allow bone mineralization 12,13,14. Conversely, these vitamin D metabolites also assist in mobilizing calcium and phosphate from bone and likely increase the reabsorption of calcium and perhaps also of phosphate via the renal tubules 12,13,14. There exists a period of 10 to 24 hours between the administration of cholecalciferol and the initiation of its action in the body due to the necessity of synthesis of the active vitamin D metabolites in the liver and kidneys 12,13,14. It is parathyroid hormone that is responsible for the regulation of such metabolism at the level of the kidneys 12,13,14.

Mechanism of action

Most individuals naturally generate adequate amounts of vitamin D through ordinary dietary intake of vitamin D (in some foods like eggs, fish, and cheese) and natural photochemical conversion of the vitamin D3 precursor 7-dehydrocholesterol in the skin via exposure to sunlight 9,12,13,14.

Conversely, vitamin D deficiency can often occur from a combination of insufficient exposure to sunlight, inadequate dietary intake of vitamin D, genetic defects with endogenous vitamin D receptor, or even severe liver or kidney disease 1. Such deficiency is known for resulting in conditions like rickets or osteomalacia, all of which reflect inadequate mineralization of bone, enhanced compensatory skeletal demineralization, resultant decreased calcium ion blood concentrations, and increases in the production and secretion of parathyroid hormone 4. Increases in parathyroid hormone stimulate the mobilization of skeletal calcium and the renal excretion of phosphorus 4. This enhanced mobilization of skeletal calcium leads towards porotic bone conditions 4.

Ordinarily, while vitamin D3 is made naturally via photochemical processes in the skin, both itself and vitamin D2 can be found in various food and pharmaceutical sources as dietary supplements. The principal biological function of vitamin D is the maintenance of normal levels of serum calcium and phosphorus in the bloodstream by enhancing the efficacy of the small intestine to absorb these minerals from the diet 4. At the liver, vitamin D3 or D2 is hydroxylated to 25-hydroxyvitamin D and then finally to the primary active metabolite 1,25-dihydroxyvitamin D in the kidney via further hydroxylation 4,1. This final metabolite binds to endogenous vitamin d receptors, which results in a variety of regulatory roles - including maintaining calcium balance, the regulation of parathyroid hormone, the promotion of the renal reabsorption of calcium, increased intestinal absorption of calcium and phosphorus, and increased calcium and phosphorus mobilization of calcium and phosphorus from bone to plasma to maintain balanced levels of each in bone and the plasma 4,1.

In particular, calcitriol interacts with vitamin D receptors in the small intestine to enhance the efficiency of intestinal calcium and phosphorous absorption from about 10-15% to 30-40% and 60% increased to 80%, respectively 9. Furthermore, calcitriol binds with vitamin D receptors in osteoblasts to stimulate a receptor activator of nuclear factor kB ligand (or RANKL) which subsequently interacts with receptor activator of nuclear factor kB (NFkB) on immature preosteoclasts, causing them to become mature bone-resorbing osteoclasts 9. Such mature osteoclasts ultimately function in removing calcium and phosphorus from bone to maintain blood calcium and phosphorus levels 9. Moreover, calcitriol also stimulates calcium reabsorption from the glomerular filtrate in the kidneys 9.

Additionally, it is believed that when calcitriol binds with nuclear vitamin D receptors, that this bound complex itself binds to retinoic acid X receptor (RXR) to generate a heterodimeric complex that consequently binds to specific nucleotide sequences in the DNA called vitamin D response elements 9. When bound, various transcription factors attach to this complex, resulting in either up or down-regulation of the associated gene's activity. It is thought that there may be as much as 200 to 2000 genes that possess vitamin D response elements or that are influenced indirectly to control a multitude of genes across the genome 9. It is in this way that cholecalciferol is believed to function in regulating gene transcription associated with cancer risk, autoimmune disorders, and cardiovascular disease linked to vitamin D deficiency 9. In fact, there has been some research to suggest calcitriol may also be able to prevent malignancies by inducing cellular maturation and inducing apoptosis and inhibiting angiogenesis, exhibit anti-inflammatory effects by inhibiting foam cell formation and promoting angiogenesis in endothelial colony-forming cells in vitro, inhibit immune reactions by enhancing the transcription of endogenous antibiotics like cathelicidin and regulate the activity and differentiation of CD4+ T cells, amongst a variety of other proposed actions 9.

Target Actions Organism
AVitamin D3 receptor

agonist

 Humans
Absorption

Cholecalciferol is readily absorbed from the small intestine if fat absorption is normal 12,13,14. Moreover, bile is necessary for absorption as well 12,13,14.

In particular, recent studies have determined aspects about the absorption of vitamin D, like the fact that a) the 25-hydroxyvitamin D metabolite of cholecalciferol is absorbed to a greater extent than the nonhydroxy form of cholecalciferol, b) the quantity of fat with which cholecalciferol is ingested does not appear to largely affect its bioavailability, and c) age does not apparently effect vitamin D cholecalciferol 7.

Volume of distribution

Studies have determined that the mean central volume of distribution of administered cholecalciferol supplementation in a group of 49 kidney transplant patients was approximately 237 L 5.

Protein binding

The protein binding documented for cholecalciferol is 50 to 80% 8. Specifically, in the plasma, vitamin D3 (from either diet or the skin) is bound to vitamin D-binding protein (DBP) produced in the liver, for transport to the liver. Ultimately, the form of vitamin D3 reaching the liver is 25-hydroxylated, and such 25-hydroxycholecalciferol is bound to DBP (α2-globulin) whilst circulating in the plasma 14.

Metabolism

Within the liver, cholecalciferol is hydroxylated to calcifediol (25-hydroxycholecalciferol) by the enzyme vitamin D-25-hydroxylase 12,13,14. At the kidney, calcifediol subsequently serves as a substrate for 1-alpha-hydroxylase, yielding calcitriol (1,25-dihydroxycholecalciferol), the biologically active form of vitamin D3 12,13,14.

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Route of elimination

It has been observed that administered cholecalciferol and its metabolites are excreted primarily in the bile and feces 8.

Half-life

At this time, there have been resources that document the half-life of cholecalciferol as being about 50 days 8 while other sources have noted that the half-life of calcitriol (1,25-dihydroxyvitamin D3) is approximately 15 hours while that of calcidiol (25-hydroxyvitamin D3) is about 15 days 10.

Moreover, it appears that the half-lives of any particular administration of vitamin d can vary due to variations in vitamin d binding protein concentrations and genotype in particular individuals 6.

Clearance

Studies have determined that the mean clearance value of administered cholecalciferol supplementation in a group of 49 kidney transplant patients was approximately 2.5 L/day 5.

Adverse Effects

Adverseeffects

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Toxicity

Chronic or acute administration of excessive doses of cholecalciferol may lead to hypervitaminosis D, manifested by hypercalcemia and its sequelae 12,13,14. Early symptoms of hypercalcemia may include weakness, fatigue, somnolence, headache, anorexia, dry mouth, metallic taste, nausea, vomiting, vertigo, tinnitus, ataxia, and hypotonia 12,13,14. Later and possibly more serious manifestation include nephrocalcinosis, renal dysfunction, osteoporosis in adults, impaired growth in children, anemia, metastatic calcification, pancreatitis, generalized vascular calcification, and seizures 12,13,14.

Safety of doses in excess of 400 IU (10mcg) of vitamin D3 daily during pregnancy has not been established 12,13,14. Maternal hypercalcemia, possibly caused by excessive vitamin D intake during pregnancy, has been associated with hypercalcemia in neonates, which may lead to supravalvular aortic stenosis syndrome, the features of which may include retinopathy, mental or growth retardation, strabismus, and other effects 12,13,14. Hypercalcemia during pregnancy may also lead to suppression of parathyroid hormone release in the neonate, resulting in hypocalcemia, tetany, and seizures 12,13,14.

Vitamin D is deficient in maternal milk; therefore, breastfed infants may require supplementation. Use of excessive amounts of Vitamin D in nursing mothers may result in hypercalcemia in infants. Doses of Vitamin D3 in excess of 10 µg daily should not be administered daily to nursing women.

Pathways
Pathway Category
Lovastatin Action Pathway Drug action
Cerivastatin Action Pathway Drug action
Hypercholesterolemia Disease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) Disease
Smith-Lemli-Opitz Syndrome (SLOS) Disease
Mevalonic Aciduria Disease
Simvastatin Action Pathway Drug action
Pravastatin Action Pathway Drug action
Rosuvastatin Action Pathway Drug action
Zoledronate Action Pathway Drug action
Pamidronate Action Pathway Drug action
Fluvastatin Action Pathway Drug action
Lysosomal Acid Lipase Deficiency (Wolman Disease) Disease
Cholesteryl Ester Storage Disease Disease
Steroid Biosynthesis Metabolic
Ibandronate Action Pathway Drug action
Alendronate Action Pathway Drug action
Risedronate Action Pathway Drug action
Atorvastatin Action Pathway Drug action
Desmosterolosis Disease
CHILD Syndrome Disease
Hyper-IgD Syndrome Disease
Wolman Disease Disease
Pharmacogenomic Effects/ADRs
Not Available
Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

  • Approved
  • Vet approved
  • Nutraceutical
  • Illicit
  • Withdrawn
  • Investigational
  • Experimental
  • All Drugs
Drug Interaction

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Abametapir The serum concentration of Cholecalciferol can be increased when it is combined with Abametapir.
Abiraterone The metabolism of Cholecalciferol can be decreased when combined with Abiraterone.
Acebutolol The metabolism of Acebutolol can be decreased when combined with Cholecalciferol.
Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Cholecalciferol.
Acetyldigitoxin The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Cholecalciferol is combined with Acetyldigitoxin.
Alfacalcidol The risk or severity of adverse effects can be increased when Cholecalciferol is combined with Alfacalcidol.
Almotriptan The metabolism of Almotriptan can be decreased when combined with Cholecalciferol.
Alogliptin The metabolism of Alogliptin can be decreased when combined with Cholecalciferol.
Aluminum hydroxide The serum concentration of Aluminum hydroxide can be increased when it is combined with Cholecalciferol.
Aminophenazone The metabolism of Aminophenazone can be decreased when combined with Cholecalciferol.
Food Interactions
No interactions found.

Products2

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Product Images
International/Other Brands
Delta-D / Micro-D / Optimal-D (RV Nutritional, LLC) / Vigantol
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
D-tabs 10000unit Tablet 10000 unit Oral Laboratoire Riva Inc 1992-12-31 Not applicable Canada flag
Luxa-D Capsule 2000 unit Oral Orimed Pharma Corporation 2015-07-31 Not applicable Canada flag
Luxa-D Capsule 5000 unit Oral Orimed Pharma Corporation 2015-10-20 Not applicable Canada flag
Luxa-D Capsule 50000 unit Oral Orimed Pharma Corporation 2015-10-20 Not applicable Canada flag
Luxa-D Capsule 25000 unit Oral Orimed Pharma Corporation 2015-07-31 Not applicable Canada flag
Vidextra Tablet 10000 unit Oral Orimed Pharma Corporation 2014-03-20 Not applicable Canada flag
Vitamin D Capsule 2000 unit Oral Jamp Pharma Corporation Not applicable Not applicable Canada flag
Vitamin D3 Capsule 40000 unit Oral Oxlee Pharmaceuticals Inc Not applicable Not applicable Canada flag
Vitamin D3 Capsule 20000 unit Oral Oxlee Pharmaceuticals Inc Not applicable Not applicable Canada flag
Vitamin D3 Oral Solution Solution 25000 unit / amp Oral Galephar Pharmaceutical Research Inc Not applicable Not applicable Canada flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Ag-vitamin D Tablet 10000 unit Oral Angita Pharma Inc. 2020-12-21 Not applicable Canada flag
Ag-vitamin D Capsule 10000 unit Oral Angita Pharma Inc. Not applicable Not applicable Canada flag
Euro D 10 000 Capsule 10000 unit Oral Euro Pharm International Canada Inc 2017-08-16 Not applicable Canada flag
Euro-D 10000 Iu Capsule 10000 unit Oral Euro Pharm International Canada Inc 2011-08-29 Not applicable Canada flag
Euro-D 5000 Iu Capsule 5000 unit Oral Euro Pharm International Canada Inc Not applicable Not applicable Canada flag
Euro-D 50000 Iu Capsule 50000 unit Oral Euro Pharm International Canada Inc 2011-08-09 Not applicable Canada flag
Jamp-vitamin D Capsule 5000 unit Oral Jamp Pharma Corporation Not applicable Not applicable Canada flag
Jamp-vitamin D Capsule 2000 unit Oral Jamp Pharma Corporation Not applicable Not applicable Canada flag
Jamp-vitamin D Capsule 10000 unit Oral Jamp Pharma Corporation 2015-11-20 Not applicable Canada flag
Jamp-vitamin D Capsule 25000 unit Oral Jamp Pharma Corporation Not applicable Not applicable Canada flag
Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
BLACKMORES VITAMIN D3 1000IU CAPSULES Capsule Oral BLACKMORES (MALAYSIA) SDN. BHD. 2020-09-08 Not applicable Malaysia flag
D Caps 400 Units Capsule 400 unit Oral Twin Laboratories Inc. 1995-12-31 1999-11-10 Canada flag
D Vi Sol Infants Drops 400unit/0.6ml Solution / drops 400 unit / .6 mL Oral Mead Johnson Nutritionals 1985-12-31 1998-09-28 Canada flag
Vitamin D 1000iu Tablet 1000 unit Oral Wn Pharmaceuticals Ltd. 1999-07-08 2007-08-07 Canada flag
Vitamin D 400 Iu Tablet 400 unit Oral Wn Pharmaceuticals Ltd. 2002-03-13 2007-08-07 Canada flag
Vitamin D 400 Iu Tablets Tablet 400 unit Oral Swiss Herbal Remedies Ltd. 1996-12-11 2009-08-04 Canada flag
Vitamin D-dry 400 I.U. Tablet 400 unit / tab Oral Great Earth Companies, Inc. 1998-08-25 2002-10-02 Canada flag
เฮลโหล-ดี Tablet, film coated 10 mg Oral บริษัท ยูเมด้า จำกัด 2017-12-20 Not applicable Thailand flag
เฮลโหล-ดี 2000 ไอยู Tablet, coated 2000 iu Oral บริษัท ยูเมด้า จำกัด 2017-08-05 Not applicable Thailand flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
24 Multivitamins + Minerals Cholecalciferol (400 unit) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Biotin (25 mcg) + Calcium (130 mg) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Cyanocobalamin (25 mcg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin A palmitate (5000 unit) + Vitamin E (50 unit) + Zinc (10 mg) Tablet Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1997-04-30 2002-07-31 Canada flag
50 Plus Multiple Vitamins & Minerals Cholecalciferol (400 unit) + Ascorbic acid (90 mg) + Biotin (45 mcg) + Calcium (200 mg) + Chromium (10 mcg) + Copper (2 mg) + Cyanocobalamin (25 mcg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3.2 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Vitamin A palmitate (6000 unit) + Zinc (15 mg) Tablet Oral Gfr Pharma Ltd. 2002-10-20 2004-06-15 Canada flag
A + D Ointment Cholecalciferol (500 unit / g) + Vitamin A palmitate (2000 unit / g) Ointment Topical National Care Products Ltd. 1993-12-31 2002-10-10 Canada flag
A.R.T.H. Away Formula Cholecalciferol (45 unit) + Calcium (24 mg) + Copper (0.232 mg) + Folic acid (0.025 mg) + Manganese (0.58 mg) + Pyridoxine hydrochloride (0.5 mg) + Selenium (1.54 mcg) + Zinc (0.63 mg) Capsule Oral Abundance Naturally Ltd 1999-02-01 2006-06-16 Canada flag
Aces Tab Cholecalciferol (200 unit) + Calcium ascorbate (350 mg) + Chromium (25 mcg) + Selenium (100 mcg) + Vitamin A (5000 unit) + Vitamin E (200 unit) + Zinc (25 mg) Tablet Oral Nu Life Nutrition Ltd. 1987-12-31 2005-03-15 Canada flag
Acti-cal/mag 2:1 + Zinc and D Caplet Cholecalciferol (100 unit) + Calcium (350.0 mg) + Magnesium (175.0 mg) + Zinc (6.0 mg) Tablet Oral Acti Form Ltd. 1991-12-31 2005-03-21 Canada flag
Actical Plus Calcium-magnesium-vitamin D3-silicon Chewable Cholecalciferol (100 unit) + Calcium (200 mg) + Magnesium (100 mg) + Silicon (2 mg) Tablet Oral Usana Health Sciences, Inc. 1999-09-30 2004-07-27 Canada flag
Active Calcium Plus Magnesium, Vitamin D and Silicon Cholecalciferol (100 unit) + Calcium (200 mg) + Magnesium (100 mg) + Silicon (2.25 mg) Tablet Oral Usana Health Sciences, Inc. 2002-07-08 2007-07-18 Canada flag
Actonel Sachet Kit Cholecalciferol (880 unit) + Calcium carbonate (1000 mg) + Risedronate sodium (35 mg) Granule, effervescent; Kit; Tablet Oral Warner Chilcott Not applicable Not applicable Canada flag
Adeks Tablets Cholecalciferol (400 unit) + Ascorbic acid (60 mg) + Beta carotene (3 mg) + Biotin (50 mcg) + Cyanocobalamin (12 mcg) + Folic acid (0.2 mg) + Niacin (10 mg) + Calcium pantothenate (10 mg) + Phylloquinone (0.15 mg) + Pyridoxine (1.5 mg) + Riboflavin (1.3 mg) + Thiamine (1.2 mg) + Vitamin A palmitate (4000 unit) + Vitamin E (150 unit) + Zinc gluconate (7.5 mg) Tablet Oral Axcan Pharma 1998-01-20 2011-04-20 Canada flag
Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Abavite Cholecalciferol (0.025 mg/1) + Ascorbic acid (60 mg/1) + DL-alpha tocopheryl acetate (13.5 mg/1) + Ferrous sulfate (30 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Mecobalamin (0.5 mg/1) + Niacin (15 mg/1) + Calcium pantothenate (5 mg/1) + Potassium Iodide (0.25 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Vitamin A palmitate (0.33 mg/1) + Zinc oxide (15 mg/1) Tablet Oral ABACOS HEALTH 2021-03-31 Not applicable US flag
Active FE Cholecalciferol (400 [iU]/1) + Ascorbic acid (160 mg/1) + Beta carotene (2100 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (30 ug/1) + DL-alpha tocopheryl acetate (40 [iU]/1) + Folic acid (1250 ug/1) + Iron (75 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine hydrochloride (4 mg/1) + Zinc oxide (20 mg/1) Tablet Oral Gm Pharmaceuticals 2013-11-11 Not applicable US flag
Active OB Cholecalciferol (400 [iU]/1) + Ascorbic acid (100 mg/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (30 ug/1) + D-alpha-Tocopherol acetate (30 [iU]/1) + Doconexent (320 mg/1) + Folic acid (1 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc oxide (30 mg/1) Capsule, liquid filled Oral Gm Pharmaceuticals 2013-10-28 2017-03-31 US flag
Animi-3 Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1) Capsule Oral Pbm Pharmaceuticals Inc. 2011-06-01 Not applicable US flag
Animi-3 with Vitamin D Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1) Capsule Oral Pbm Pharmaceuticals Inc. 2011-06-01 Not applicable US flag
Bal-Care DHA Cholecalciferol (840 [iU]/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (.012 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (430 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1) Kit Oral Pru Gen Pharmaceuticals 2012-05-01 Not applicable US flag
Bal-Care DHA Essential Cholecalciferol (840 [iU]/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (.012 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (374 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1) Kit Oral Pru Gen Pharmaceuticals 2012-05-01 Not applicable US flag
C-Nate DHA Cholecalciferol (400 [iU]/1) + Ascorbic acid (100 mg/1) + Cupric sulfate pentahydrate (1 mg/1) + Cyanocobalamin (15 ug/1) + Ferrous fumarate (28 mg/1) + Folic acid (1 mg/1) + Magnesium (30 mg/1) + Omega-3 fatty acids (200 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc oxide (20 mg/1) Capsule, gelatin coated Oral Centurion Labs, LLC 2013-01-01 Not applicable US flag
CALCIMED D3 20 EFF. TABLET Cholecalciferol (400 IU) + Calcium (1500 mg) Tablet, effervescent Oral GENESİS İLAÇ VE SAĞLIK ÜRÜNLERİ A.Ş. 2020-08-14 Not applicable Turkey flag
Calcium Folic Acid Plus D Chewable Cholecalciferol (300 [iU]/1) + Boron (250 ug/1) + Calcium carbonate (1342 mg/1) + Cyanocobalamin (125 ug/1) + Folic acid (1 mg/1) + Magnesium (50 mg/1) + Pyridoxine (10 mg/1) Wafer Oral Acella Pharmaceuticals, LLC 2009-03-20 2022-08-02 US flag
ATC Codes
M05BB09 — Ibandronic acid and colecalciferol
  • M05BB — Bisphosphonates, combinations
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
M05BX53 — Strontium ranelate and colecalciferol
  • M05BX — Other drugs affecting bone structure and mineralization
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
M05BB07 — Risedronic acid and colecalciferol
  • M05BB — Bisphosphonates, combinations
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
M05BB08 — Zoledronic acid, calcium and colecalciferol, sequential
  • M05BB — Bisphosphonates, combinations
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
A11CC55 — Colecalciferol, combinations
  • A11CC — Vitamin D and analogues
  • A11C — VITAMIN A AND D, INCL. COMBINATIONS OF THE TWO
  • A11 — VITAMINS
  • A — ALIMENTARY TRACT AND METABOLISM
M05BB05 — Alendronic acid, calcium and colecalciferol, sequential
  • M05BB — Bisphosphonates, combinations
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
A11CC05 — Colecalciferol
  • A11CC — Vitamin D and analogues
  • A11C — VITAMIN A AND D, INCL. COMBINATIONS OF THE TWO
  • A11 — VITAMINS
  • A — ALIMENTARY TRACT AND METABOLISM
M05BB03 — Alendronic acid and colecalciferol
  • M05BB — Bisphosphonates, combinations
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
M05BB04 — Risedronic acid, calcium and colecalciferol, sequential
  • M05BB — Bisphosphonates, combinations
  • M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
  • M05 — DRUGS FOR TREATMENT OF BONE DISEASES
  • M — MUSCULO-SKELETAL SYSTEM
Drug Categories
  • Alimentary Tract and Metabolism
  • Bone Density Conservation Agents
  • Calcium-Regulating Hormones and Agents
  • Cholecalciferol, antagonists & inhibitors
  • Cholestanes
  • Cholestenes
  • Cytochrome P-450 CYP2C8 Inhibitors
  • Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Cytochrome P-450 CYP2D6 Inhibitors (moderate)
  • Cytochrome P-450 CYP3A Substrates
  • Cytochrome P-450 CYP3A4 Substrates
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Substrates
  • Diet, Food, and Nutrition
  • Drugs Affecting Bone Structure and Mineralization
  • Drugs for Treatment of Bone Diseases
  • Food
  • Fused-Ring Compounds
  • Growth Substances
  • Lipids
  • Membrane Lipids
  • Micronutrients
  • Musculo-Skeletal System
  • Physiological Phenomena
  • Secosteroids
  • Steroids
  • Sterols
  • Vitamin D and Analogues
  • Vitamins
  • Vitamins (Fat Soluble)
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Vitamin D and derivatives
Direct Parent
Vitamin D and derivatives
Alternative Parents
Triterpenoids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Triterpenoid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
secondary alcohol, steroid hormone, seco-cholestane, hydroxy seco-steroid, D3 vitamins (CHEBI:28940) / Vitamin D3 and derivatives, Fat-soluble vitamins (C05443) / Vitamin D3 and derivatives (LMST03020000)
Affected organisms
  • Humans and other mammals
UNII
1C6V77QF41
CAS number
67-97-0
InChI Key
QYSXJUFSXHHAJI-YRZJJWOYSA-N
InChI

InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

IUPAC Name

(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

SMILES

CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C

Synthesis Reference

Jean Jolly, Primo Rizzi, Jean Taillardat, "1.alpha.,25.alpha.-Dihydroxy-cholecalciferol and methods for the production thereof." U.S. Patent US4435325, issued May, 1977.

US4435325
General References
  1. Armas LA, Hollis BW, Heaney RP: Vitamin D2 is much less effective than vitamin D3 in humans. J Clin Endocrinol Metab. 2004 Nov;89(11):5387-91. [Article]
  2. Jean G, Souberbielle JC, Chazot C: Vitamin D in Chronic Kidney Disease and Dialysis Patients. Nutrients. 2017 Mar 25;9(4). pii: nu9040328. doi: 10.3390/nu9040328. [Article]
  3. Heaney RP: Alendronate plus cholecalciferol for the treatment of osteoporosis. Womens Health (Lond). 2006 Jan;2(1):23-7. doi: 10.2217/17455057.2.1.23. [Article]
  4. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [Article]
  5. Benaboud S, Urien S, Thervet E, Prie D, Legendre C, Souberbielle JC, Hirt D, Friedlander G, Treluyer JM, Courbebaisse M: Determination of optimal cholecalciferol treatment in renal transplant recipients using a population pharmacokinetic approach. Eur J Clin Pharmacol. 2013 Mar;69(3):499-506. doi: 10.1007/s00228-012-1378-3. Epub 2012 Aug 31. [Article]
  6. Jones KS, Assar S, Harnpanich D, Bouillon R, Lambrechts D, Prentice A, Schoenmakers I: 25(OH)D2 half-life is shorter than 25(OH)D3 half-life and is influenced by DBP concentration and genotype. J Clin Endocrinol Metab. 2014 Sep;99(9):3373-81. doi: 10.1210/jc.2014-1714. Epub 2014 Jun 2. [Article]
  7. Borel P, Caillaud D, Cano NJ: Vitamin D bioavailability: state of the art. Crit Rev Food Sci Nutr. 2015;55(9):1193-205. doi: 10.1080/10408398.2012.688897. [Article]
  8. Caroline Ashley, Aileen Dunleavy (2018). The Renal Drug Handbook: The Ultimate Prescribing Guide for Renal Practitioners, 5th Edition (5th ed.). CRC Press. [ISBN:0429863632]
  9. Cholecalciferol (Vitamin D3) – Pharmacological Properties, Therapeutic Utility and Potential New Fields of Clinical Application by Yulian Voynikov, Georgi Momekov, Plamen Peikov [Link]
  10. Vitamin D Supplementation: An Update [Link]
  11. NIH Vitamin D Fact Sheet for Health Professionals [Link]
  12. Cholecalciferol Canadian Prescribing Information [File]
  13. Decalcitrol (coated cholecalciferol tablet) US FDA Monograph [File]
  14. CLH Report for Cholecalciferol [File]
  15. Alendronate sodium and cholecalciferol Canadian Product Monograph [File]
Human Metabolome Database
HMDB0000876
KEGG Drug
D00188
KEGG Compound
C05443
PubChem Compound
5280795
PubChem Substance
46506365
ChemSpider
4444353
BindingDB
50030475
RxNav
1244014
ChEBI
28940
ChEMBL
CHEMBL1042
ZINC
ZINC000004474460
Therapeutic Targets Database
DAP001273
PharmGKB
PA164748138
PDBe Ligand
VD3
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cholecalciferol
MSDS
Clinical Trials
Phase Status Purpose Conditions Count
4 Active Not Recruiting Treatment Atopic Dermatitis 1
4 Active Not Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) 1
4 Completed Basic Science 25-Hydroxyvitamin D Concentration / Deficiency, Vitamin D 1
4 Completed Basic Science Deficiency, Vitamin D 2
4 Completed Basic Science Premature Births 1
4 Completed Health Services Research Critically Ill Patients 1
4 Completed Other Chronic Kidney Disease (CKD) / Kidney Transplantation / Nephrotic Syndrome 1
4 Completed Prevention Benign Paroxysmal Positional Vertigo (BPPV) 1
4 Completed Prevention Deficiency, Vitamin D 1
4 Completed Prevention Deficiency, Vitamin D / Impaired Glucose Tolerance 1
Manufacturers

Not Available

Packagers
  • Chain Drug
  • CVS Pharmacy
  • Freeda Vitamins
  • Major Pharmaceuticals
  • Mason Distributors
  • Merck & Co.
  • MSD Frosst Iberica SA
  • Pharmavite
  • Physicians Total Care Inc.
  • Professional Co.
  • Spectrum Pharmaceuticals
Dosage Forms
Form Route Strength
Ointment Topical
Granule, effervescent; kit; tablet Oral
Injection, solution Intramuscular; Oral
Tablet, chewable Oral 1000 [iU]/1
Capsule Oral
Solution Oral 50000 U.I./5ML
Solution / drops Oral 10000 UI/1ML
Cream Topical
Injection, solution Parenteral
Bar, chewable Oral
Powder, for solution Oral
Solution Oral 25000 UI
Solution Oral 50000 UI
Solution / drops Oral 10000 UI/ML
Tablet, coated Oral 0.4 mg
Tablet, effervescent Oral 2500 mg
Granule Oral
Tablet, effervescent Oral
Powder, for suspension Oral
Tablet, coated Oral 1500 mg
Injection, powder, for solution Intramuscular; Intravenous
Injection, powder, for solution Parenteral
Injection, powder, for solution Intravenous 125 mg
Injection, solution Intramuscular; Intravenous
Injection, powder, for solution Intravenous
Capsule Oral
Solution / drops Oral
Capsule Oral 10000 UI
Capsule Oral 100000 UI
Capsule Oral 25000 UI
Capsule Oral 50000 UI
Solution Oral 25000 UI/2.5ML
Solution / drops Oral 10000 U.I./ML
Solution Oral 25000 IU/2.5ml
Solution Oral 50000 UI/2.5ML
Capsule Oral 400 unit
Solution / drops Oral 400 unit / .6 mL
Capsule Oral 1.25 mg/1
Solution Oral 25000 IU
Tablet Oral 10000 unit
Solution Oral 400 [iU]/1mL
Capsule, liquid filled Oral 100000 IU
Tablet, coated Oral 50000 [iU]/1
Capsule Oral 10000 [iU]/1
Capsule Oral 25000 [iU]/1
Capsule Oral 50000 [iU]/1
Capsule, liquid filled Oral 2000 IU
Tablet Oral 1000 IE
Tablet Oral 400 IE
Tablet Oral 500 IE
Tablet Oral 400 IU/1
Solution Intramuscular
Syrup Oral
Capsule Oral 2000 U.I.
Capsule Oral 6000 U.I.
Injection, solution Intramuscular 100000 UI/ML
Injection, solution Intramuscular 300000 UI/ML
Solution Oral 100000 U.I.
Solution Oral 25000 U.I./2.5ML
Solution Oral 50000 U.I./2.5ML
Solution / drops Oral 10000 UI
Tablet, film coated Oral
Powder, for solution Intravenous
Capsule Oral 10000 unit
Capsule Oral 5000 unit
Capsule Oral 50000 unit
Capsule, liquid filled Oral 1 mg
Capsule, liquid filled Oral 5000 IU
Wafer Oral 100 unit / waf
Tablet Oral 70 mg
Powder Oral
Gel Oral
Capsule, delayed release Oral
Tablet, chewable Oral
Tablet, coated Oral
Capsule Oral 2000 unit
Capsule Oral 25000 unit
Suspension Oral
Tablet Oral
Granule, effervescent Oral
Solution Oral 50000 U.I.
Solution Intramuscular; Oral
Solution Intravenous
Solution Oral
Tablet Oral
Capsule Oral 50 mg
Tablet, coated Oral 1000 iu
Tablet, orally disintegrating Oral
Capsule Oral 1000 U.I.
Capsule Oral 10000 U.I.
Capsule Oral 20000 U.I.
Capsule Oral 50000 U.I.
Capsule, liquid filled Oral 7000 IU
Solution Oral 5600 IU
Solution Oral 0.00014 g
Solution Oral 100000 IU
Tablet, coated Oral 7000 IU
Capsule Oral 7 mg
Powder
Injection Intravenous
Injection, solution Intravenous
Suspension / drops Oral
Solution / drops Oral
Capsule, liquid filled Oral
Tablet, film coated Oral
Capsule, gelatin coated Oral
Pill Oral
Tablet, chewable Buccal
Tablet, chewable Buccal 1500 mg
Tablet, chewable Oral
Wafer Oral
Syrup
Capsule Oral 20000 i.u.
Powder, for solution Intramuscular; Intravenous
Solution Oral
Liquid Oral
Tablet
Injection, powder, lyophilized, for solution Intramuscular; Intravenous
Capsule Oral 125 mg/1
Tablet, chewable Oral 1000 IU
Strip Oral
Tablet Oral 1000 unit
Tablet Oral 1000 IU
Tablet Oral 400 unit
Capsule Oral 7000 iu
Tablet Oral 400 unit / tab
Tablet Oral 500 IU
Capsule Oral 20000 unit
Capsule Oral 40000 unit
Capsule, liquid filled Oral 50 ug/1
Solution Oral 25000 unit / amp
Capsule Oral 100000 unit
Solution Oral 2000 IU
Capsule, liquid filled Oral 1000 IU
Kit Oral
Capsule Oral 25000 U.I.
Tablet, coated Oral
Injection, solution Intramuscular 100000 U.I./ML
Injection, solution Intramuscular 300000 U.I./ML
Solution / drops Oral 25 ug/0.04mL
Solution / drops Oral 10 ug/0.04mL
Solution / drops Oral 15 ug/0.04mL
Tablet, film coated Oral 10 mg
Tablet, coated Oral 2000 iu
Tablet, film coated Oral 1000 iu
Tablet, film coated
Prices
Unit description Cost Unit
Cholecalciferol crystals 104.3USD g
Vitamin d3 2400 unit/ml liquid 0.8USD ml
Vitamin d3 2000 unit spray 0.44USD ml
Vitamin d3 3000 unit tablet 0.11USD tablet
Vitamin d-3 2000 unit tablet 0.07USD tablet
CVS Pharmacy vitamin d 1000 unit tablet 0.04USD tablet
Delta d3 400 unit tablet 0.04USD each
Vitamin d 1000 unit tablet 0.03USD tablet
Pv vitamin d 2000 unit tablet 0.02USD tablet
Pv vitamin d 5000 unit tablet 0.02USD tablet
Vitamin d 400 unit tablet 0.02USD tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region
US5994329 Yes 1999-11-30 2019-01-17 US flag
State
Solid
Experimental Properties
Property Value Source
melting point (°C) 84.5 °C PhysProp
water solubility Insoluble Not Available
logP 7.5 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.00038 mg/mL ALOGPS
logP 7.98 ALOGPS
logP 7.13 ChemAxon
logS -6 ALOGPS
pKa (Strongest Acidic) 18.38 ChemAxon
pKa (Strongest Basic) -1.3 ChemAxon
Physiological Charge 0 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 Å2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 123.22 m3·mol-1 ChemAxon
Polarizability 49.6 Å3 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five No ChemAxon
Ghose Filter No ChemAxon
Veber's Rule Yes ChemAxon
MDDR-like Rule Yes ChemAxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.959
Caco-2 permeable + 0.8342
P-glycoprotein substrate Substrate 0.6706
P-glycoprotein inhibitor I Inhibitor 0.7603
P-glycoprotein inhibitor II Non-inhibitor 0.5346
Renal organic cation transporter Non-inhibitor 0.7818
CYP450 2C9 substrate Non-substrate 0.8384
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.7302
CYP450 1A2 substrate Non-inhibitor 0.9256
CYP450 2C9 inhibitor Non-inhibitor 0.9071
CYP450 2D6 inhibitor Non-inhibitor 0.9551
CYP450 2C19 inhibitor Non-inhibitor 0.9026
CYP450 3A4 inhibitor Non-inhibitor 0.7881
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7093
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.921
Biodegradation Not ready biodegradable 0.9878
Rat acute toxicity 3.9310 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.773
hERG inhibition (predictor II) Non-inhibitor 0.7589

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)
Download (11.1 KB)
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Has a D-25-hydroxylase activity on both forms of vitamin D, vitamin D(2) and D(3).
Gene Name
CYP2R1
Uniprot ID
Q6VVX0
Uniprot Name
Vitamin D 25-hydroxylase
Molecular Weight
57358.82 Da
References
  1. Flanagan JN, Young MV, Persons KS, Wang L, Mathieu JS, Whitlatch LW, Holick MF, Chen TC: Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D. Anticancer Res. 2006 Jul-Aug;26(4A):2567-72. [Article]
  2. Segura-Aguilar J: Peroxidase activity of liver microsomal vitamin D 25-hydroxylase and cytochrome P450 1A2 catalyzes 25-hydroxylation of vitamin D3 and oxidation of dopamine to aminochrome. Biochem Mol Med. 1996 Jun;58(1):122-9. [Article]
  3. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99. doi: 10.1016/j.bbapap.2010.06.022. Epub 2010 Jul 7. [Article]
  4. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase a...
Gene Name
CYP27A1
Uniprot ID
Q02318
Uniprot Name
Sterol 26-hydroxylase, mitochondrial
Molecular Weight
60234.28 Da
References
  1. Lehmann B, Tiebel O, Meurer M: Expression of vitamin D3 25-hydroxylase (CYP27) mRNA after induction by vitamin D3 or UVB radiation in keratinocytes of human skin equivalents--a preliminary study. Arch Dermatol Res. 1999 Sep;291(9):507-10. [Article]
  2. Sawada N, Sakaki T, Yoneda S, Kusudo T, Shinkyo R, Ohta M, Inouye K: Conversion of vitamin D3 to 1alpha,25-dihydroxyvitamin D3 by Streptomyces griseolus cytochrome P450SU-1. Biochem Biophys Res Commun. 2004 Jul 16;320(1):156-64. [Article]
  3. Uchida E, Kagawa N, Sakaki T, Urushino N, Sawada N, Kamakura M, Ohta M, Kato S, Inouye K: Purification and characterization of mouse CYP27B1 overproduced by an Escherichia coli system coexpressing molecular chaperonins GroEL/ES. Biochem Biophys Res Commun. 2004 Oct 15;323(2):505-11. [Article]
  4. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [Article]
  5. Tokar EJ, Webber MM: Cholecalciferol (vitamin D3) inhibits growth and invasion by up-regulating nuclear receptors and 25-hydroxylase (CYP27A1) in human prostate cancer cells. Clin Exp Metastasis. 2005;22(3):275-84. [Article]
  6. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99. doi: 10.1016/j.bbapap.2010.06.022. Epub 2010 Jul 7. [Article]
  7. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Steroid hydroxylase activity
Specific Function
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
Molecular Weight
57610.165 Da
References
  1. Aiba I, Yamasaki T, Shinki T, Izumi S, Yamamoto K, Yamada S, Terato H, Ide H, Ohyama Y: Characterization of rat and human CYP2J enzymes as Vitamin D 25-hydroxylases. Steroids. 2006 Oct;71(10):849-56. Epub 2006 Jul 13. [Article]
  2. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99. doi: 10.1016/j.bbapap.2010.06.022. Epub 2010 Jul 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99. doi: 10.1016/j.bbapap.2010.06.022. Epub 2010 Jul 7. [Article]
  2. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 Da
References
  1. Tuckey RC, Janjetovic Z, Li W, Nguyen MN, Zmijewski MA, Zjawiony J, Slominski A: Metabolism of 1alpha-hydroxyvitamin D3 by cytochrome P450scc to biologically active 1alpha,20-dihydroxyvitamin D3. J Steroid Biochem Mol Biol. 2008 Dec;112(4-5):213-9. doi: 10.1016/j.jsbmb.2008.10.005. Epub 2008 Oct 21. [Article]
  2. Tuckey RC, Nguyen MN, Slominski A: Kinetics of vitamin D3 metabolism by cytochrome P450scc (CYP11A1) in phospholipid vesicles and cyclodextrin. Int J Biochem Cell Biol. 2008;40(11):2619-26. doi: 10.1016/j.biocel.2008.05.006. Epub 2008 May 20. [Article]
  3. Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. Epub 2003 Dec 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Inhibitor

General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Yamazaki H, Shimada T: Effects of arachidonic acid, prostaglandins, retinol, retinoic acid and cholecalciferol on xenobiotic oxidations catalysed by human cytochrome P450 enzymes. Xenobiotica. 1999 Mar;29(3):231-41. doi: 10.1080/004982599238632 . [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Inhibitor

This enzyme action is supported by the results of 1 in vitro study. The clinical correlation is unknown.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Yamazaki H, Shimada T: Effects of arachidonic acid, prostaglandins, retinol, retinoic acid and cholecalciferol on xenobiotic oxidations catalysed by human cytochrome P450 enzymes. Xenobiotica. 1999 Mar;29(3):231-41. doi: 10.1080/004982599238632 . [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action

No

General Function
Vitamin transporter activity
Specific Function
Involved in vitamin D transport and storage, scavenging of extracellular G-actin, enhancement of the chemotactic activity of C5 alpha for neutrophils in inflammation and macrophage activation.
Gene Name
GC
Uniprot ID
P02774
Uniprot Name
Vitamin D-binding protein
Molecular Weight
52963.025 Da
References
  1. Nykjaer A, Dragun D, Walther D, Vorum H, Jacobsen C, Herz J, Melsen F, Christensen EI, Willnow TE: An endocytic pathway essential for renal uptake and activation of the steroid 25-(OH) vitamin D3. Cell. 1999 Feb 19;96(4):507-15. [Article]
  2. Verboven C, Rabijns A, De Maeyer M, Van Baelen H, Bouillon R, De Ranter C: A structural basis for the unique binding features of the human vitamin D-binding protein. Nat Struct Biol. 2002 Feb;9(2):131-6. [Article]
  3. Houghton LA, Vieth R: The case against ergocalciferol (vitamin D2) as a vitamin supplement. Am J Clin Nutr. 2006 Oct;84(4):694-7. [Article]
  4. Yamamoto N, Naraparaju VR: Vitamin D3-binding protein as a precursor for macrophage activating factor in the inflammation-primed macrophage activation cascade in rats. Cell Immunol. 1996 Jun 15;170(2):161-7. [Article]
  5. Yamamoto N, Naraparaju VR: Role of vitamin D3-binding protein in activation of mouse macrophages. J Immunol. 1996 Aug 15;157(4):1744-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 04, 2021 10:27