Vitamin D3

Identification

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
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

Pharmacology

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
Associated Therapies
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.

TargetActionsOrganism
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
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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
PathwayCategory
Lovastatin Action PathwayDrug action
Cerivastatin Action PathwayDrug action
HypercholesterolemiaDisease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)Disease
Smith-Lemli-Opitz Syndrome (SLOS)Disease
Mevalonic AciduriaDisease
Simvastatin Action PathwayDrug action
Pravastatin Action PathwayDrug action
Rosuvastatin Action PathwayDrug action
Zoledronate Action PathwayDrug action
Pamidronate Action PathwayDrug action
Fluvastatin Action PathwayDrug action
Lysosomal Acid Lipase Deficiency (Wolman Disease)Disease
Cholesteryl Ester Storage DiseaseDisease
Steroid BiosynthesisMetabolic
Ibandronate Action PathwayDrug action
Alendronate Action PathwayDrug action
Risedronate Action PathwayDrug action
Atorvastatin Action PathwayDrug action
DesmosterolosisDisease
CHILD SyndromeDisease
Hyper-IgD SyndromeDisease
Wolman DiseaseDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

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.
DrugInteraction
AbametapirThe serum concentration of Cholecalciferol can be increased when it is combined with Abametapir.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Cholecalciferol.
AcetaminophenThe metabolism of Cholecalciferol can be decreased when combined with Acetaminophen.
AcetyldigitoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Cholecalciferol is combined with Acetyldigitoxin.
AlfacalcidolThe risk or severity of adverse effects can be increased when Cholecalciferol is combined with Alfacalcidol.
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Cholecalciferol.
AlogliptinThe metabolism of Alogliptin can be decreased when combined with Cholecalciferol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Cholecalciferol.
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Cholecalciferol.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Cholecalciferol.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Images
International/Other Brands
Delta-D / Micro-D / Optimal-D (RV Nutritional, LLC) / Vigantol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
D-tabs 10000unitTabletOralLaboratoire Riva Inc1992-12-31Not applicableCanada flag
Luxa-DCapsuleOralOrimed Pharma Corporation2015-07-31Not applicableCanada flag
Luxa-DCapsuleOralOrimed Pharma Corporation2015-10-20Not applicableCanada flag
Luxa-DCapsuleOralOrimed Pharma Corporation2015-10-20Not applicableCanada flag
Luxa-DCapsuleOralOrimed Pharma Corporation2015-07-31Not applicableCanada flag
VidextraTabletOralOrimed Pharma Corporation2014-03-20Not applicableCanada flag
Vitamin DCapsule2000 unitOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Vitamin D3CapsuleOralOxlee Pharmaceuticals IncNot applicableNot applicableCanada flag
Vitamin D3CapsuleOralOxlee Pharmaceuticals IncNot applicableNot applicableCanada flag
Vitamin D3 Oral SolutionSolutionOralGalephar Pharmaceutical Research IncNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-vitamin DCapsuleOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-vitamin DTabletOralAngita Pharma Inc.2020-12-21Not applicableCanada flag
Euro D 10 000CapsuleOralEuro Pharm International Canada Inc2017-08-16Not applicableCanada flag
Euro-D 10000 IuCapsuleOralEuro Pharm International Canada Inc2011-08-29Not applicableCanada flag
Euro-D 5000 IuCapsuleOralEuro Pharm International Canada IncNot applicableNot applicableCanada flag
Euro-D 50000 IuCapsuleOralEuro Pharm International Canada Inc2011-08-09Not applicableCanada flag
Jamp-vitamin DCapsuleOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Jamp-vitamin DCapsuleOralJamp Pharma Corporation2015-11-20Not applicableCanada flag
Jamp-vitamin DCapsuleOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Jamp-vitamin DCapsuleOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BLACKMORES VITAMIN D3 1000IU CAPSULESCapsuleOralBLACKMORES (MALAYSIA) SDN. BHD.2020-09-08Not applicableMalaysia flag
D Vi Sol Infants Drops 400unit/0.6mlSolution / dropsOralMead Johnson Nutritionals1985-12-311998-09-28Canada flag
Vitamin D 1000iuTabletOralWn Pharmaceuticals Ltd.1999-07-082007-08-07Canada flag
Vitamin D 400 IuTabletOralWn Pharmaceuticals Ltd.2002-03-132007-08-07Canada flag
Vitamin D 400 Iu TabletsTabletOralSwiss Herbal Remedies Ltd.1996-12-112009-08-04Canada flag
Vitamin D-dry 400 I.U.TabletOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada flag
เฮลโหล-ดีTablet, film coated10 mgOralบริษัท ยูเมด้า จำกัด2017-12-20Not applicableThailand flag
เฮลโหล-ดี 2000 ไอยูTablet, coatedOralบริษัท ยูเมด้า จำกัด2017-08-05Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
24 Multivitamins + MineralsCholecalciferol (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)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1997-04-302002-07-31Canada flag
50 Plus Multiple Vitamins & MineralsCholecalciferol (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)TabletOralGfr Pharma Ltd.2002-10-202004-06-15Canada flag
A + D OintmentCholecalciferol (500 unit) + Vitamin A palmitate (2000 unit)OintmentTopicalNational Care Products Ltd.1993-12-312002-10-10Canada flag
A.R.T.H. Away FormulaCholecalciferol (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)CapsuleOralAbundance Naturally Ltd1999-02-012006-06-16Canada flag
Aces TabCholecalciferol (200 unit) + Calcium ascorbate (350 mg) + Chromium (25 mcg) + Selenium (100 mcg) + Vitamin A (5000 unit) + Vitamin E (200 unit) + Zinc (25 mg)TabletOralNu Life Nutrition Ltd.1987-12-312005-03-15Canada flag
Acti-cal/mag 2:1 + Zinc and D CapletCholecalciferol (100 unit) + Calcium (350.0 mg) + Magnesium (175.0 mg) + Zinc (6.0 mg)TabletOralActi Form Ltd.1991-12-312005-03-21Canada flag
Actical Plus Calcium-magnesium-vitamin D3-silicon ChewableCholecalciferol (100 unit) + Calcium (200 mg) + Magnesium (100 mg) + Silicon (2 mg)TabletOralUsana Health Sciences, Inc.1999-09-302004-07-27Canada flag
Active Calcium Plus Magnesium, Vitamin D and SiliconCholecalciferol (100 unit) + Calcium (200 mg) + Magnesium (100 mg) + Silicon (2.25 mg)TabletOralUsana Health Sciences, Inc.2002-07-082007-07-18Canada flag
Actonel Sachet KitCholecalciferol (880 unit) + Calcium (1000 mg) + Risedronate sodium (35 mg)Granule, effervescent; Kit; TabletOralWarner ChilcottNot applicableNot applicableCanada flag
Adeks TabletsCholecalciferol (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 (7.5 mg)TabletOralAxcan Pharma1998-01-202011-04-20Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Active FECholecalciferol (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)TabletOralGm Pharmaceuticals2013-11-11Not applicableUS flag
Active OBCholecalciferol (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 filledOralGm Pharmaceuticals2013-10-282017-03-31US flag
Animi-3Cholecalciferol (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)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUS flag
Animi-3 with Vitamin DCholecalciferol (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)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUS flag
Bal-Care DHACholecalciferol (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)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUS flag
Bal-Care DHA EssentialCholecalciferol (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)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUS flag
C-Nate DHACholecalciferol (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 coatedOralCenturion Labs, LLC2013-01-01Not applicableUS flag
CALCIMED D3 20 EFF. TABLETCholecalciferol (400 IU) + Calcium (1500 mg)Tablet, effervescentOralGENESİS İLAÇ VE SAĞLIK ÜRÜNLERİ A.Ş.2020-08-14Not applicableTurkey flag
Calcium Folic Acid Plus D ChewableCholecalciferol (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)WaferOralAcella Pharmaceuticals, LLC2009-03-20Not applicableUS flag
Cavan AlphaCholecalciferol (800 [iU]/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (230 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (220 ug/1) + Iron (27 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (300 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralSeton Pharmaceuticals2010-07-012013-09-30US flag

Categories

ATC Codes
M05BB09 — Ibandronic acid and colecalciferolM05BX53 — Strontium ranelate and colecalciferolM05BB07 — Risedronic acid and colecalciferolM05BB08 — Zoledronic acid, calcium and colecalciferol, sequentialA11CC55 — Colecalciferol, combinationsM05BB05 — Alendronic acid, calcium and colecalciferol, sequentialA11CC05 — ColecalciferolM05BB03 — Alendronic acid and colecalciferolM05BB04 — Risedronic acid, calcium and colecalciferol, sequential
Drug Categories
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

Chemical Identifiers

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

References

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
AHFS Codes
  • 88:16.00 — Vitamin D
MSDS
Download (123 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAtopic Dermatitis (AD)1
4CompletedBasic Science25-Hydroxyvitamin D Concentration / Deficiency, Vitamin D1
4CompletedBasic ScienceDeficiency, Vitamin D2
4CompletedBasic SciencePremature Births1
4CompletedHealth Services ResearchCritically-ill Patients1
4CompletedOtherChronic Kidney Disease (CKD) / Nephrotic Syndrome / Transplantation, Renal1
4CompletedPreventionAllergies / Wheezing1
4CompletedPreventionBenign Paroxysmal Positional Vertigo (BPPV)1
4CompletedPreventionDeficiency, Vitamin D1
4CompletedPreventionDeficiency, Vitamin D / Pre-Diabetic1

Pharmacoeconomics

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
FormRouteStrength
OintmentTopical
Granule, effervescent; kit; tabletOral
Injection, solutionIntramuscular; Oral
Tablet, chewableOral1000 [iU]/1
CapsuleOral
CreamTopical
Injection, solutionParenteral
Bar, chewableOral
Powder, for solutionOral
Tablet, effervescentOral2500 mg
GranuleOral
Powder, for suspensionOral
Tablet, coatedOral1500 mg
SyrupOral
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral
Injection, solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous
CapsuleOral
Solution / dropsOral
Tablet, coatedOral50000 [iU]/1
CapsuleOral10000 [iU]/1
CapsuleOral25000 [iU]/1
CapsuleOral50000 [iU]/1
Capsule, liquid filledOral
SolutionIntramuscular
Injection, solutionIntramuscular
Tablet, film coatedOral
Tablet, effervescentOral
Powder, for solutionIntravenous
SolutionOral
Tablet, chewableBuccal
WaferOral
PowderOral
GelOral
Capsule, delayed releaseOral
Tablet, coatedOral
SuspensionOral
TabletOral
Granule, effervescentOral
SolutionIntramuscular; Oral
SolutionIntravenous
SolutionOral
TabletOral
CapsuleOral50 mg
Tablet, coatedOral
Tablet, orally disintegratingOral
CapsuleOral7 mg
Powder
InjectionIntravenous
Injection, solutionIntravenous
Suspension / dropsOral
Solution / dropsOral
Capsule, liquid filledOral
Tablet, film coatedOral
Capsule, gelatin coatedOral
PillOral
Tablet, chewableOral
WaferOral
Syrup
CapsuleOral20000 i.u.
Powder, for solutionIntramuscular; Intravenous
LiquidOral
Tablet
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous
CapsuleOral125 mg/1
Tablet, chewableOral
StripOral
CapsuleOral2000 unit
CapsuleOral7000 iu
KitOral
Solution / dropsOral25 ug/0.04mL
Solution / dropsOral10 ug/0.04mL
Solution / dropsOral15 ug/0.04mL
Tablet, film coatedOral10 mg
Capsule
Tablet, film coatedOral1000 iu
Tablet, film coated
Prices
Unit descriptionCostUnit
Cholecalciferol crystals104.3USD g
Vitamin d3 2400 unit/ml liquid0.8USD ml
Vitamin d3 2000 unit spray0.44USD ml
Vitamin d3 3000 unit tablet0.11USD tablet
Vitamin d-3 2000 unit tablet0.07USD tablet
CVS Pharmacy vitamin d 1000 unit tablet0.04USD tablet
Delta d3 400 unit tablet0.04USD each
Vitamin d 1000 unit tablet0.03USD tablet
Pv vitamin d 2000 unit tablet0.02USD tablet
Pv vitamin d 5000 unit tablet0.02USD tablet
Vitamin d 400 unit tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5994329Yes1999-11-302019-01-17US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)84.5 °CPhysProp
water solubilityInsolubleNot Available
logP7.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00038 mg/mLALOGPS
logP7.98ALOGPS
logP7.13ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.22 m3·mol-1ChemAxon
Polarizability49.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.959
Caco-2 permeable+0.8342
P-glycoprotein substrateSubstrate0.6706
P-glycoprotein inhibitor IInhibitor0.7603
P-glycoprotein inhibitor IINon-inhibitor0.5346
Renal organic cation transporterNon-inhibitor0.7818
CYP450 2C9 substrateNon-substrate0.8384
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7302
CYP450 1A2 substrateNon-inhibitor0.9256
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9551
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.7881
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7093
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.921
BiodegradationNot ready biodegradable0.9878
Rat acute toxicity3.9310 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.773
hERG inhibition (predictor II)Non-inhibitor0.7589
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.1 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da
References
  1. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. Fujishima T, Tsuji G, Tanaka C, Harayama H: Novel vitamin D receptor ligands having a carboxyl group as an anchor to arginine 274 in the ligand-binding domain. J Steroid Biochem Mol Biol. 2010 Jul;121(1-2):60-2. doi: 10.1016/j.jsbmb.2010.04.020. Epub 2010 May 6. [Article]

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
Curator comments
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 on June 13, 2005 13:24 / Updated on May 11, 2021 01:04