Identification

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Name
Cholecalciferol
Accession Number
DB00169  (NUTR00008, APRD00506)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

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].

Structure
Thumb
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
  • Colecalciferol
  • Colecalciferolum
  • Oleovitamin D3
  • Vitamin D-3
  • Vitamin D3
External IDs
NSC-375571
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
AdrovanceTabletOralMerck Sharp & Dohme B.V.2007-01-04Not applicableEu
Cataplex D Tab 400unitTablet400 unitOralStandard Process Inc.Not applicableNot applicableCanada
D-tabs 10000unitTablet10000 unitOralLaboratoire Riva Inc1992-12-31Not applicableCanada
Euro D 10 000Capsule10000 unitOralEuro Pharm International Canada Inc2017-08-16Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jamp-vitamin DCapsule2000 unitOralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-vitamin DTablet10000 unitOralJamp Pharma Corporation2012-05-02Not applicableCanada
Jamp-vitamin DCapsule25000 unitOralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-vitamin DCapsule10000 unitOralJamp Pharma Corporation2015-11-20Not applicableCanada
Jamp-vitamin DCapsule5000 unitOralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-vitamin DCapsule50000 unitOralJamp Pharma Corporation2016-06-23Not applicableCanada
Pharma-D 10000 IuCapsule10000 unitOralPharmascience Inc2011-08-29Not applicableCanada
Pharma-D 5000 IuCapsule5000 unitOralPharmascience IncNot applicableNot applicableCanada
Pharma-D 50000 IuCapsule50000 unitOralPharmascience Inc2011-08-09Not applicableCanada
Riva-DTablet10000 unitOralLaboratoire Riva IncNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
D Vi Sol Infants Drops 400unit/0.6mlSolution / drops400 unitOralMead Johnson Nutritionals1985-12-311998-09-28Canada
Vitamin D 1000iuTablet1000 unitOralWn Pharmaceuticals Ltd.1999-07-082007-08-07Canada
Vitamin D 400 IuTablet400 unitOralWn Pharmaceuticals Ltd.2002-03-132007-08-07Canada
Vitamin D 400 Iu TabletsTablet400 unitOralSwiss Herbal Remedies Ltd.1996-12-112009-08-04Canada
Vitamin D-dry 400 I.U.Tablet400 unitOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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
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
A + D OintmentCholecalciferol (500 unit) + Vitamin A palmitate (2000 unit)OintmentTopicalNational Care Products Ltd.1993-12-312002-10-10Canada
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 Marketing Ltd.1999-02-012006-06-16Canada
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
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
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
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
Actonel Sachet KitCholecalciferol (880 unit) + Calcium (1000 mg) + Risedronate sodium (35 mg)Granule, effervescent; Kit; TabletOralWarner ChilcottNot applicableNot applicableCanada
Adult Infuvite Multiple VitaminsCholecalciferol (200 [iU]/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz Inc2005-05-18Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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
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
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
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
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 saccharate (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)KitPru Gen Pharmaceuticals2012-05-01Not applicableUs
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 saccharate (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)KitPru Gen Pharmaceuticals2012-05-01Not applicableUs
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 Labs2013-01-01Not applicableUs
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
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
Cavan Folate DHACholecalciferol (400 [iU]/1) + Cholecalciferol (400 [iU]/1) + Ascorbic acid (70 mg/1) + Ascorbic acid (70 mg/1) + Beta carotene (2700 [iU]/1) + Beta carotene (2700 [iU]/1) + Calcium Carbonate (100 mg/1) + Calcium Carbonate (100 mg/1) + Cupric oxide (2 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Doconexent (250 mg/1) + Doconexent (250 mg/1) + Ferrous fumarate (65 mg/1) + Ferrous fumarate (65 mg/1) + Folic Acid (1 mg/1) + Folic Acid (1 mg/1) + Magnesium oxide (25 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (18 mg/1) + Nicotinamide (18 mg/1) + Pyridoxine hydrochloride (2.5 mg/1) + Pyridoxine hydrochloride (2.5 mg/1) + Riboflavin (1.8 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Thiamine mononitrate (1.6 mg/1) + Zinc oxide (25 mg/1) + Zinc oxide (25 mg/1)KitSeton Pharmaceuticals2010-06-042012-03-31Us
International/Other Brands
Delta-D / Micro-D / Optimal-D (RV Nutritional, LLC) / Vigantol
Categories
UNII
1C6V77QF41
CAS number
67-97-0
Weight
Average: 384.6377
Monoisotopic: 384.33921603
Chemical Formula
C27H44O
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

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].

Associated Conditions
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
Additional Data Available
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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].

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].

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.

Affected organisms
  • Humans and other mammals
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Cholecalciferol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Cholecalciferol.
1alpha-Hydroxyvitamin D5The risk or severity of adverse effects can be increased when Cholecalciferol is combined with 1alpha-Hydroxyvitamin D5.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Cholecalciferol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Cholecalciferol.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Cholecalciferol.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Cholecalciferol.
6-Deoxyerythronolide BThe metabolism of Cholecalciferol can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Cholecalciferol.
7-ethyl-10-hydroxycamptothecinThe metabolism of Cholecalciferol can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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. [PubMed:15531486]
  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. [PubMed:28346348]
  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. [PubMed:19803923]
  4. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [PubMed:15585789]
  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. [PubMed:22936122]
  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. [PubMed:24885631]
  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. [PubMed:24915331]
  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]
External Links
Human Metabolome Database
HMDB0000876
KEGG Drug
D00188
KEGG Compound
C05443
PubChem Compound
5280795
PubChem Substance
46506365
ChemSpider
4444353
BindingDB
50030475
ChEBI
28940
ChEMBL
CHEMBL1042
Therapeutic Targets Database
DAP001273
PharmGKB
PA164748138
HET
VD3
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cholecalciferol
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
AHFS Codes
  • 88:16.00 — Vitamin D
MSDS
Download (123 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedPreventionGingival Inflammation1
0CompletedPreventionLong Segment Barrett's Esophagus / Short Segment Barrett's Esophagus1
0CompletedTreatmentChronic Kidney Disease (CKD)1
0RecruitingBasic ScienceStage I-III Colon Cancer / Stage IV Colon Cancer With Resectable Liver Metastases / Stage, Colon Cancer1
0RecruitingPreventionDeficiency, Vitamin D1
0Unknown StatusPreventionDeficiency, Vitamin D / Periodontal Diseases1
1Active Not RecruitingTreatmentHealthy Volunteers1
1Active Not RecruitingTreatmentSarcopenia1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I / Mycobacterium avium complex infection1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedDiagnosticHealthy Volunteers1
1CompletedHealth Services ResearchDeficiency, Vitamin D1
1CompletedOtherOsteoporosis2
1CompletedPreventionCancer, Breast1
1CompletedPreventionHealthy, no Evidence of Disease / Skin Cancers1
1CompletedPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedSupportive CareStable COPD Patients1
1CompletedTreatmentAcute and Chronic Inflammation / Autoimmune Diseases / Disorder of Pleura and Pleural Cavity / Disorder of Synovium / Felty's Syndrome / Rheumatoid Arthritis / Rheumatoid Nodules / Sjögren's Syndrome1
1CompletedTreatmentAdult Women / Estrogen Receptor Positive / Metastatic Breast Cancer (MBC)1
1CompletedTreatmentCalcium Deficiency / Deficiency, Vitamin D1
1CompletedTreatmentDeficiency, Vitamin D1
1CompletedTreatmentDeficiency, Vitamin D / Disseminated Sclerosis1
1CompletedTreatmentMalignancies / Metastases1
1CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
1CompletedTreatmentType 2 Diabetes Mellitus1
1RecruitingTreatmentPneumonia1
1TerminatedBasic ScienceCrohn's Disease (CD) / Deficiency, Vitamin D1
1, 2CompletedPreventionBiomarker Change Linked to Breast Cancer1
1, 2CompletedPreventionCancer, Breast1
1, 2CompletedPreventionDeficiency, Vitamin D / Prophylaxis of preeclampsia1
1, 2CompletedPreventionPrimary Immune Deficiency Disorders (PIDD)1
1, 2CompletedTreatmentDeficiency, Vitamin D / Spinal Cord Injuries (SCI)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentSickle Cell Disorders1
1, 2RecruitingTreatmentDeficiency, Vitamin D1
1, 2RecruitingTreatmentDiabetes Mellitus (DM) / Diabetes, Autoimmune / Diabetes, Diabetes Mellitus Type 1 / Hypoglycemia1
1, 2RecruitingTreatmentGestational Diabetes Mellitus (GDM)1
1, 2SuspendedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
1, 2Unknown StatusTreatmentGlioblastoma Multiforme (GBM)1
1, 2WithdrawnTreatmentCancer, Breast / Ductal Carcinoma In-situ / Invasive Breast Carcinoma1
1, 2WithdrawnTreatmentDeficiency, Vitamin D1
1, 2WithdrawnTreatmentUlcerative Colitis (UC)1
2Active Not RecruitingPreventionBone Loss / Calcifications, Vascular / End Stage Renal Disease (ESRD) / Fracture Bone / Transplantation, Kidney1
2Active Not RecruitingPreventionDiabetes, Diabetes Mellitus Type 1 / Prediabetic State1
2Active Not RecruitingTreatmentAcute Chest Syndrome / Asthma Bronchial / Deficiency, Vitamin D / Respiratory Tract Infections (RTI) / Sickle Cell Disorders1
2Active Not RecruitingTreatmentAsthma Bronchial1
2Active Not RecruitingTreatmentBone Diseases / Diabetic Nephropathies / Sub-optimal Vitamin D Status1
2Active Not RecruitingTreatmentBone Metabolism Biomarkers / Bone Mineral Density / Physical Fitness1
2Active Not RecruitingTreatmentProstate Cancer1
2Active Not RecruitingTreatmentTuberculosis Infection1
2CompletedBasic ScienceDeficiency, Vitamin D1
2CompletedBasic ScienceInsulin Sensitivity / Intraocular Pressure1
2CompletedBasic ScienceProstate Cancer1
2CompletedBasic ScienceType 2 Diabetes Mellitus / Vitamin D Insufficiency1
2CompletedDiagnosticHypersensitivity1
2CompletedPreventionAtherosclerosis / Systemic Lupus Erythematosus (SLE)1
2CompletedPreventionAutistic Disorder1
2CompletedPreventionCancer of the Ovary1
2CompletedPreventionCancer, Breast1
2CompletedPreventionColorectal Cancers1
2CompletedPreventionDeficiency, Vitamin D / High Blood Pressure (Hypertension)1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedSupportive CareAsthma-chronic obstructive pulmonary disease overlap syndrome1
2CompletedSupportive CareArthralgia/joint pain / Muscle pains1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAdenocarcinoma, Prostate / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer1
2CompletedTreatmentAllergic Rhinoconjunctivitis1
2CompletedTreatmentAtopic Dermatitis (AD) / Psoriasis1
2CompletedTreatmentAutism, Early Infantile1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentBronchiolitis1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentCholecalciferol Toxicity / Methicillin Resistant Staphylococcus Aureus (MRSA) / Resistant Staphylococcus Aureus: [Methicillin] or [Multiple] / Staphylococcus Aureus Infections / Vitamin D3 Deficiency1
2CompletedTreatmentChronic Heart Failure (CHF)1
2CompletedTreatmentChronic Kidney Disease (CKD)1
2CompletedTreatmentCongestive Heart Failure (CHF) / Deficiency, Vitamin D / Heart Failure / Prophylaxis of cardiomyopathy1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentDeficiency, Vitamin D / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / Lipid Metabolism Disorders / Obesity, Abdominal1
2CompletedTreatmentDeficiency, Vitamin D / High Blood Pressure (Hypertension)1
2CompletedTreatmentDeficiency, Vitamin D / Homocystinaemia1
2CompletedTreatmentDeficiency, Vitamin D / Human Immunodeficiency Virus (HIV) / Hyperparathyroidism / Hypovitaminosis D1
2CompletedTreatmentDepression / Diabetes Mellitus (DM) / Quality of Life1
2CompletedTreatmentDiabetes Mellitus (DM) / Executive Dysfunction1
2CompletedTreatmentEnd-Stage Renal Disease (ESRD)1
2CompletedTreatmentFalls, Accidental / Parkinson's Disease (PD)1
2CompletedTreatmentGaucher's Disease / Osteopenia1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHypovitaminosis D1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedTreatmentInsulin Resistance1
2CompletedTreatmentLupus / Systemic Lupus Erythematosus (SLE)1
2CompletedTreatmentNon-Alcoholic Steatohepatitis (NASH)1
2CompletedTreatmentOsteoporosis / Postmenopausal Osteoporosis (PMO)1
2CompletedTreatmentPolycystic Ovarian Syndrome / Reproductive Endocrinology1
2CompletedTreatmentProstate Cancer2
2CompletedTreatmentPulmonary Tuberculosis (TB)1
2CompletedTreatmentType 2 Diabetes Mellitus1
2Enrolling by InvitationBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
2RecruitingOtherFracture Bone1
2RecruitingPreventionChronic Pain Due to Trauma1
2RecruitingPreventionDeficiency, Vitamin D / Peritoneal Dialysis-associated Peritonitis1
2RecruitingPreventionNeurofibromatosis Type 1 (NF1)1
2RecruitingPreventionOsteopenia / Osteoporosis1
2RecruitingTreatmentAtopic Dermatitis (AD)1
2RecruitingTreatmentDeficiency, Vitamin D1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kidney Diseases1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentNeoplasms, Hematologic1
2RecruitingTreatmentOptic Neuritis1
2TerminatedBasic ScienceCancer, Breast1
2TerminatedOtherDisseminated Sclerosis1
2TerminatedSupportive CareNeurologic toxicity1
2TerminatedTreatmentSystemic Lupus Erythematosus (SLE)1
2Unknown StatusPreventionSickle Cell Disorders1
2Unknown StatusTreatmentAnemia of Chronic Kidney Disease1
2Unknown StatusTreatmentBMI >30 kg/m2 / Bypass, Gastric / Gastric Resection1
2Unknown StatusTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Insulin Resistance1
2Unknown StatusTreatmentDeficiency, Vitamin D1
2Unknown StatusTreatmentDeficiency, Vitamin D / Human Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentHypovitaminosis D / Type 2 Diabetes Mellitus1
2WithdrawnBasic ScienceBMI >30 kg/m21
2WithdrawnTreatmentDeficiency, Vitamin D / Rheumatoid Arthritis1
2WithdrawnTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2, 3CompletedPreventionAdenoma benign / Colorectal Cancers / Polyps1
2, 3CompletedPreventionImpaired Glucose Tolerance (IGT)1
2, 3CompletedTreatmentCalcifications, Vascular / Deficiency, Vitamin D / Hemodialysis Complication1
2, 3CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / The Mortality Rate1
2, 3CompletedTreatmentCraniocerebral Trauma / Critical Illness / Deficiency, Vitamin D / Intracranial Aneurysms / Intracranial Hemorrhages / Meningitis / Neoplasms, Brain / Seizures / Spinal Cord Injuries (SCI) / Strokes1
2, 3CompletedTreatmentDeficiency, Vitamin D / Hypercalcemia / Primary Hyperparathyroidism1
2, 3CompletedTreatmentDisseminated Sclerosis1
2, 3CompletedTreatmentMale Infertility1
2, 3CompletedTreatmentType 2 Diabetes Mellitus1
2, 3Not Yet RecruitingPreventionCritical Illness / Deficiency, Vitamin D1
2, 3RecruitingTreatmentAllergies1
2, 3TerminatedTreatmentCancer, Breast / Musculoskeletal Disorders1
2, 3Unknown StatusTreatmentDeficiency, Vitamin D / Heart Failure1
3Active Not RecruitingPreventionCardiovascular Disease (CVD) / Fracture Bone / Malignancies1
3Active Not RecruitingTreatmentLocally Advanced Breast Cancer and Large Operable Breast Cancer1
3Active Not RecruitingTreatmentOsteopenia1
3CompletedHealth Services ResearchDeficiency, Vitamin D1
3CompletedPreventionAcute Tracheobronchitis / Bronchiolitis Acute / Upper Respiratory Tract Infections1
3CompletedPreventionDeficiency, Vitamin D2
3CompletedPreventionDeficiency, Vitamin D / Pregnancy1
3CompletedPreventionImprove Healthy Ageing in Seniors; Prevent Disease at Older Age1
3CompletedPreventionOsteoporosis1
3CompletedTreatmentAcute Respiratory Distress Syndrome (ARDS) / Critical Illness / Deficiency, Vitamin D1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentAnemias1
3CompletedTreatmentArterial Dysfunction / Chronic Kidney Disease (CKD)1
3CompletedTreatmentAsthma Bronchial2
3CompletedTreatmentBypass, Gastric / Parathyroid Hormone1
3CompletedTreatmentCKd Patients With Stage 3 and 41
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentChronic Kidney Disease Stage 3 and 41
3CompletedTreatmentCritical Illness / Deficiency, Vitamin D1
3CompletedTreatmentDeficiency, Vitamin D4
3CompletedTreatmentDeficiency, Vitamin D / Heart Failure1
3CompletedTreatmentDeficiency, Vitamin D / Renal Insufficiency,Chronic1
3CompletedTreatmentDiabetes Mellitus (DM) / Insulin Resistance / Low-intensity Chronic Inflammation1
3CompletedTreatmentHepatitis C Viral Infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pulmonary Tuberculosis (TB)1
3CompletedTreatmentHypovitaminosis D2
3CompletedTreatmentHypovitaminosis D / Polycystic Ovaries Syndrome1
3CompletedTreatmentInfection NOS1
3CompletedTreatmentOsteoporosis2
3CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
3CompletedTreatmentPulmonary Tuberculosis (TB)1
3Not Yet RecruitingPreventionEnd Organ Damage / Multiple Organ Failure / Sepsis / Severe Sepsis1
3Not Yet RecruitingTreatmentCritical Illness / Deficiency, Vitamin D / Sarcopenia1
3Not Yet RecruitingTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
3Not Yet RecruitingTreatmentDeficiency, Vitamin D2
3Not Yet RecruitingTreatmentDrug Resistant Epilepsy1
3Not Yet RecruitingTreatmentSchizophrenic Disorders1
3Not Yet RecruitingTreatmentVitamin D31
3RecruitingPreventionDisseminated Sclerosis1
3RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3RecruitingTreatmentCritical Illness / Deficiency, Vitamin D1
3RecruitingTreatmentCrohn's Disease (CD)1
3RecruitingTreatmentCutaneous Malignant Melanoma1
3RecruitingTreatmentDyslipidemias1
3RecruitingTreatmentHypogonadism / Pre-frail Seniors1
3RecruitingTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
3RecruitingTreatmentUrticarias1
3TerminatedPreventionPolymorphic Light Eruption (PLE)1
3TerminatedPreventionType 2 Diabetes Mellitus1
3TerminatedTreatmentDeficiency, Vitamin D / Diabetes Mellitus (DM)1
3TerminatedTreatmentMelanoma1
3Unknown StatusNot AvailableAnemias / Low Birth Weight / Neonatal Mortality1
3Unknown StatusPreventionFalls, Accidental / Fracture Bone / Hip Fractures1
3Unknown StatusTreatmentAlzheimer's Disease (AD) / Down Syndrome (DS)1
3Unknown StatusTreatmentChronic Lymphocytic Leukaemia (CLL)1
3Unknown StatusTreatmentDeficiency, Vitamin D / Renal Osteodystrophy / Transplantation, Kidney1
3Unknown StatusTreatmentTuberculosis Infection1
3Unknown StatusTreatment[X]Statin Causing Adverse Effect in Therapeutic Use1
3WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingPreventionHypocalcemia1
4Active Not RecruitingTreatmentAsthma Bronchial1
4Active Not RecruitingTreatmentCalcifications, Vascular / Deficiency, Vitamin D / End Stage Renal Failure on Dialysis / Impaired Renal Function1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedBasic Science25-Hydroxyvitamin D Concentration / Deficiency, Vitamin D1
4CompletedBasic ScienceDeficiency, Vitamin D2
4CompletedBasic SciencePremature Births1
4CompletedPreventionAllergies / Wheezing1
4CompletedPreventionBenign Paroxysmal Positional Vertigo (BPPV)1
4CompletedPreventionDeficiency, Vitamin D1
4CompletedPreventionDiabetes, Diabetes Mellitus Type 12
4CompletedPreventionHealthy Humans1
4CompletedPreventionImmune Tolerance1
4CompletedPreventionRecurrent Respiratory Tract Infections1
4CompletedTreatmentAnovulatory cycle / Polycystic Ovaries Syndrome1
4CompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D2
4CompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Hyperparathyroidism, Secondary1
4CompletedTreatmentBariatric Surgery Candidate1
4CompletedTreatmentCardiorenal Syndrome / Chronic Allograft Nephropathy (CAN)1
4CompletedTreatmentDeficiency, Vitamin D2
4CompletedTreatmentDeficiency, Vitamin D / Glucose tolerance impaired / Type 2 Diabetes Mellitus1
4CompletedTreatmentDeficiency, Vitamin D / Hemodialysis Patient1
4CompletedTreatmentDeficiency, Vitamin D / Polycystic Ovaries Syndrome2
4CompletedTreatmentDiabetes Mellitus (DM)1
4CompletedTreatmentEnd Stage Kidney Disease1
4CompletedTreatmentEpilepsies1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentOsteopenia / Osteoporosis1
4CompletedTreatmentPancreatitis, Chronic1
4CompletedTreatmentPneumonia1
4CompletedTreatmentPostmenopausal Osteoporosis (PMO)1
4CompletedTreatmentPregnancy1
4CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
4Not Yet RecruitingPreventionHepatocellular,Carcinoma / Viral Hepatitis B1
4Not Yet RecruitingTreatmentVitamin D Substitution1
4RecruitingPreventionEclampsia / Gestational Hypertension / HELLP Syndrome / Superimposed Preeclampsia / Toxemia1
4RecruitingPreventionFood Allergy1
4RecruitingTreatmentBone Diseases, Metabolic / Renal Insufficiency,Chronic / Vascular Stiffness1
4RecruitingTreatmentBronchiectasis1
4RecruitingTreatmentCKD Stage 3 / Deficiency, Vitamin D / Secondary Hyperparathyroidism Due to Renal Causes / Stage 4 Chronic Kidney Disease1
4RecruitingTreatmentCerebral Vascular Accident (CVA) / Heart Failure Hospitalization / Myocardial Infarction / The Mortality Rate1
4RecruitingTreatmentDeficiency, Vitamin D1
4RecruitingTreatmentDeficiency, Vitamin D / Depression / Insulin Resistance / Polycystic Ovarian Syndrome1
4RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
4TerminatedTreatmentCrohn's Disease (CD) / Deficiency, Vitamin D1
4TerminatedTreatmentHeart Failure1
4TerminatedTreatmentPeripheral Arterial Disease (PAD)1
4Unknown StatusDiagnosticThalassemia Major (TM)1
4Unknown StatusTreatmentAcute Lower Respiratory Tract Infection / Bronchiolitis / Pneumonia1
4Unknown StatusTreatmentBMI >30 kg/m2 / Insulin Resistance1
4Unknown StatusTreatmentDisseminated Sclerosis1
4Unknown StatusTreatmentMetabolic Syndromes1
4Unknown StatusTreatmentOsteoporosis1
4Unknown StatusTreatmentPersistent Asthma1
4WithdrawnTreatmentCrohn's Disease (CD)1
4WithdrawnTreatmentNephritis / Proteinuria / Systemic Lupus Erythematosus (SLE)1
Not AvailableActive Not RecruitingTreatmentAsthma Bronchial / Deficiency, Vitamin D1
Not AvailableCompletedNot AvailableDeficiency, Vitamin D1
Not AvailableCompletedNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableCompletedNot AvailableHMG COA Reductase Inhibitor Adverse Reaction1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableOsteoporosis1
Not AvailableCompletedPreventionBlood Platelet Disorders / Deficiency, Vitamin D1
Not AvailableCompletedPreventionCancer, Breast1
Not AvailableCompletedPreventionDeficiency, Vitamin D1
Not AvailableCompletedPreventionHypovitaminosis D1
Not AvailableCompletedPreventionMalignant Melanoma of Skin1
Not AvailableCompletedPreventionNeural Tube Defects (NTDs)1
Not AvailableCompletedPreventionOsteoporosis1
Not AvailableCompletedPreventionSarcopenia1
Not AvailableCompletedSupportive CareBurn Injuries / Vitamin D1
Not AvailableCompletedSupportive CareDiabetic Neuropathies1
Not AvailableCompletedSupportive CarePrimary Hyperparathyroidism1
Not AvailableCompletedSupportive CarePulmonary Tuberculosis (TB)1
Not AvailableCompletedTreatmentAngioedema / Hives / Swelling / Urticarias1
Not AvailableCompletedTreatmentAsthma Bronchial / Deficiency, Vitamin D / Disease Exacerbation1
Not AvailableCompletedTreatmentAtherosclerosis / Leukocyte Activation Disorder / Oxidative Stress1
Not AvailableCompletedTreatmentBipolar Disorder (BD) / Depression, Bipolar1
Not AvailableCompletedTreatmentCardiovascular Disease (CVD) / Deficiency, Vitamin D / High Blood Pressure (Hypertension) / Insulin Resistance / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D / Insulin Resistance1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / End-Stage Renal Disease (ESRD)1
Not AvailableCompletedTreatmentClozapine Resistant Schizophrenia1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentCystic Fibrosis (CF) / Osteoporosis1
Not AvailableCompletedTreatmentDeficiency of Vitamin D3 / Gingival and Periodontal Disease / Pregnancy1
Not AvailableCompletedTreatmentDeficiency, Vitamin D4
Not AvailableCompletedTreatmentDeficiency, Vitamin D / End-Stage Renal Disease (ESRD)1
Not AvailableCompletedTreatmentDeficiency, Vitamin D / High Blood Pressure (Hypertension) / Pre-Hypertension1
Not AvailableCompletedTreatmentDeficiency, Vitamin D / Renal Failure Chronic Requiring Hemodialysis1
Not AvailableCompletedTreatmentEnd-Stage Renal Disease (ESRD)2
Not AvailableCompletedTreatmentEndometriosis1
Not AvailableCompletedTreatmentHeart Failure1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHyperparathyroidism, Secondary / Renal Insufficiency,Chronic1
Not AvailableCompletedTreatmentHypovitaminosis D1
Not AvailableCompletedTreatmentIntestinal Malabsorption / Pancreatitis, Chronic1
Not AvailableCompletedTreatmentNeoplasms, Brain2
Not AvailableCompletedTreatmentPolycystic Ovaries Syndrome1
Not AvailableCompletedTreatmentRenal Osteodystrophy / Secondary Hyperparathyroidism in Chronic Kidney Disease Stage 3 and 41
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableNot Yet RecruitingPreventionTransient Hypercalciuria1
Not AvailableNot Yet RecruitingTreatmentSchizophrenic Disorders1
Not AvailableRecruitingNot AvailableCognitive Decline1
Not AvailableRecruitingSupportive CareHematopoietic Stem Cell Transplant (HSCT)1
Not AvailableRecruitingTreatmentBMI >30 kg/m21
Not AvailableRecruitingTreatmentCancer of the Ovary1
Not AvailableRecruitingTreatmentDeficiency, Vitamin D / Glucose tolerance impaired / Insulin Resistance / Oxidative Stress1
Not AvailableRecruitingTreatmentPeripheral Arterial Disease (PAD)1
Not AvailableRecruitingTreatmentProphylaxis of Contrast-induced nephropathy1
Not AvailableTerminatedNot AvailableUrolithiasis1
Not AvailableTerminatedTreatmentCancer, Breast1
Not AvailableTerminatedTreatmentDeficiency, Vitamin D1
Not AvailableTerminatedTreatmentHMG-CoA Reductase Inhibitors-related Myalgias1
Not AvailableUnknown StatusTreatmentChronic Musculoskeletal Pain / Vitamin D Supplementation1
Not AvailableUnknown StatusTreatmentDeficiency, Vitamin D / Hepatocellular,Carcinoma1
Not AvailableUnknown StatusTreatmentDyslipidemia (Fredrickson Type Ⅱa)1
Not AvailableWithdrawnTreatmentChronic Rhinosinusitis1
Not AvailableWithdrawnTreatmentHMG COA Reductase Inhibitor Adverse Reaction1
Not AvailableWithdrawnTreatmentInflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
Not AvailableWithdrawnTreatmentTuberculosis Infection1

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
TabletOral
CreamTopical
Tablet, chewableOral
Granule, effervescentOral
CapsuleOral
Solution / dropsOral400 unit
TabletOral10000 unit
PowderOral
WaferOral100 unit
Tablet, coatedOral
Solution / dropsOral
CapsuleOral2000 unit
CapsuleOral25000 unit
LiquidOral
SolutionOral
Tablet, orally disintegratingOral
Injection, solutionIntravenous
CapsuleOral10000 unit
CapsuleOral5000 unit
CapsuleOral50000 unit
Tablet, film coatedOral
Capsule, gelatin coatedOral
PillOral
KitOral
WaferOral
Tablet, effervescentOral
Capsule, liquid filledOral
TabletOral
TabletOral1000 unit
TabletOral400 unit
CapsuleOral100000 unit
Kit
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)
US5994329Yes1999-11-302019-01-17Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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

Taxonomy

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
Triterpenoid / Cyclic alcohol / Secondary alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aliphatic homopolycyclic compound
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)

Targets

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. [PubMed:15503649]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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. [PubMed:20435140]

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. [PubMed:16886665]
  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. [PubMed:8809353]
  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. [PubMed:20619365]
  4. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. [PubMed:15353333]
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. [PubMed:10541881]
  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. [PubMed:15207715]
  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. [PubMed:15369780]
  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. [PubMed:15574355]
  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. [PubMed:16158255]
  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. [PubMed:20619365]
  7. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. [PubMed:15353333]
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. [PubMed:16842832]
  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. [PubMed:20619365]
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. [PubMed:20619365]
  2. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. [PubMed:15353333]
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. [PubMed:19000766]
  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. [PubMed:18573681]
  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. [PubMed:14657394]
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

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. [PubMed:10052453]
  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. [PubMed:11799400]
  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. [PubMed:17023693]
  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. [PubMed:8660814]
  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. [PubMed:8759764]

Drug created on June 13, 2005 07:24 / Updated on April 24, 2019 15:17