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Identification
NameCholecalciferol
Accession NumberDB00169  (APRD00506, NUTR00008)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

Derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. [PubChem]

Structure
Thumb
Synonyms
(+)-vitamin D3
(1S,3Z)-3-[(2e)-2-[(1R,3AR,7as)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol
(3beta,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
delta-D
Oleovitamin D3
Vitamin D3
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cataplex D Tab 400unittablet400 unitoralStandard Process Inc.Not applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Euro D 10000capsule10000 unitoralEuro Pharm International Canada Inc2005-04-06Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Formula 3200 Waf 100unitwafer100 unitoralStandard Process Inc.Not applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Jamp-vitamin Dcapsule50000 unitoralJamp Pharma CorporationNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Jamp-vitamin Dcapsule25000 unitoralJamp Pharma CorporationNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Jamp-vitamin Dcapsule5000 unitoralJamp Pharma CorporationNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Jamp-vitamin Dcapsule2000 unitoralJamp Pharma CorporationNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Jamp-vitamin Dcapsule10000 unitoralJamp Pharma Corporation2015-11-20Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pharma-D 10000 Iucapsule10000 unitoralPharmascience Inc2011-08-29Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pharma-D 5000 Iucapsule5000 unitoralPharmascience IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pharma-D 50000 Iucapsule50000 unitoralPharmascience Inc2011-08-09Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D3-softgel Capsules 10000 Iucapsule10000 unitoralOrimed Pharma Inc2015-10-20Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D3-softgel Capsules 2000 Iucapsule2000 unitoralOrimed Pharma Inc2015-07-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D3-softgel Capsules 25000 Iucapsule25000 unitoralOrimed Pharma Inc2015-07-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D3-softgel Capsules 5000 Iucapsule5000 unitoralOrimed Pharma Inc2015-10-20Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
D Vi Sol Infants Drops 400unit/0.6mldrops400 unitoralMead Johnson Nutritionals1985-12-311998-09-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D 1000iutablet1000 unitoralWn Pharmaceuticals Ltd.1999-07-082007-08-07Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D 400 Iutablet400 unitoralWn Pharmaceuticals Ltd.2002-03-132007-08-07Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D 400 Iu Tabletstablet400 unitoralSwiss Herbal Remedies Ltd.1996-12-112009-08-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin D-dry 400 I.U.tablet400 unitoralGreat Earth Companies, Inc.1998-08-252002-10-02Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
International Brands
NameCompany
Micro-DNot Available
Optimal-DRV Nutritional, LLC
VigantolNot Available
Brand mixtures
NameLabellerIngredients
Acti-A D E LiqActi Form Ltd.
Acti-cal/mag 2:1 + Zinc and D CapletActi Form Ltd.
Acti-halibut CapActi Form Ltd.
Actonel Sachet KitWarner Chilcott Canada Co
Alendronate-cholecalciferolFrosst A Division Of Merck Canada Inc
Animi-3PBM Pharmaceuticals, Inc
Animi-3 With Vitamin DPBM Pharmaceuticals, Inc
ApcalA P J Laboratories Limited
Avon Nutrivance Soft Calcium Chews With Vitamin DAvon Canada Ulc
Bear EssentialsHealth Asure, Inc.
Cal-mag Citrate Zinc & Vitamin D TabletsSwiss Herbal Remedies Ltd.
Cal-mag Complete With Zinc, C and DQuest Vitamins A Div Of Purity Life Health Products
Cal-mag With Zinc & Vitamin DHealth Wise Nutrition Inc.
Cal/mag 1:1 With Zinc and Vitamin D - TabletHealth Wise Nutrition Inc.
Cal/mag 2001 Plus Vitamins C and DDouglas Laboratories
Calci-yum Plus Magnesium + D3Nu Life Nutrition Ltd.
Calcium & Vitamin DQuantofill Inc.
Calcium & Vitamin D TabletsViva Pharmaceutical Inc.
Calcium 250 Mg With Vitamin DGfr Pharma Ltd.
Calcium 250mg With Vitamin DWn Pharmaceuticals Ltd.
Calcium 500 Mg + Vitamin DHolista Health (Canada) Inc.
Calcium 500mg & Vitamin D 200I.U.Swiss Herbal Remedies Ltd.
Calcium 500mg With Vitamin DWn Pharmaceuticals Ltd.
Calcium 600 + DLaboratoire Riva Inc
Calcium 600mg + Vit D3 125unit TabPharmetics (2011) Inc
Calcium and Magnesium Citrate and Vitamin D 250mg/125mg/200iuWn Pharmaceuticals Ltd.
Calcium and Magnesium With Vitamin DVita Health Products Inc
Calcium Citrate and Vitamin D 200mg/160iuWn Pharmaceuticals Ltd.
Calcium Citrate With Vitamin DWn Pharmaceuticals Ltd.
Calcium Et Magnesium Plus Vitamin DLaboratoire Lalco Inc.
Calcium Folic Acid Plus D ChewableAcella Pharmaceuticals, LLC
Calcium Magnesium W Vit D3Avacare, Division Of Jeunique International Inc.
Calcium With Vitamin D 200 Mg/160 IuWn Pharmaceuticals Ltd.
Calcium, Magnesium Et Vitamine DGamme Nature
Calcium, Magnesium With Vitamin D and ZincPharmetics (2011) Inc
Calcium-iron-magnesium With A,d,c TabBioforce Canada Inc.
Calcium-magnesium With K & Zn and Vitamin D3Holista Health (Canada) Inc.
Calcium/magnesium/vitamin D - CapsuleHolista Health (Canada) Inc.
Calma-DWn Pharmaceuticals Ltd.
Caltrate 600 Plus D - TabletWhitehall Robins Inc.
Catalyn TabStandard Process Inc.
Centrum Junior (chewable)Whitehall Robins Inc.
Centrum Junior Regular (chewable Tablets)Whitehall Robins Inc.
Chela Calmag-100 Plus Zinc D3Nu Life Nutrition Ltd.
Chela Calmag-300 Plus Zinc D3Nu Life Nutrition Ltd.
Chewable Children's Complete Multivitamins With Essential MineralsWn Pharmaceuticals Ltd.
Chewable MultivitaminsWn Pharmaceuticals Ltd.
Chewable Multivitamins Plus IronWn Pharmaceuticals Ltd.
Chewable Multivitamins With Extra CWn Pharmaceuticals Ltd.
Children Choice Multivit Chewable TabSwiss Herbal Remedies Ltd.
Children Vitamin DropsWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.
Children's Chewable Multi-vitaminWn Pharmaceuticals Ltd.
Children's Chewable Multi-vitamin Complete With MineralsWn Pharmaceuticals Ltd.
Children's Chewable Multiple VitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Children's Chewable Multivitamins With MineralsWn Pharmaceuticals Ltd.
Children's Vitamins ChewableVita Health Products Inc
CiferexAdler Stern Pharmaceuticals, Llc
Citranatal Harmony 3.0Mission Pharmacal Company
Cod Liver Oil Oleovitamin A & D Caps 20minNutricorp International
Cod Liver Oil USPNu Life Nutrition Ltd.
Coral Calcium Plus Vitamin D 210mg/100iuWn Pharmaceuticals Ltd.
Dry Super Vitamin A Plus D - CapGeneral Nutrition Canada Inc.
DuracholSterling Knight Pharmaceuticals,Llc
Efferlife Calcium 500mg + Vitamin D3 440 Iu + Vitamin C 125mgNaturale Science Inc.
FlorivaBon Geo Pharmaceuticals, Inc.
Folcaps Care OneMidlothian Laboratories
Folcaps Omega-3Midlothian Laboratories
For Kids Only Chewable MultivitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Fosamax Plus DMerck Sharp & Dohme Corp.
FosavanceMerck Canada Inc
Gnc Calcium With Magnesium and Vitamin DGeneral Nutrition Canada Inc.
Hemenatal ObWh Nutritionals, Llc
Hormodausse Plus Calc Et D TabLaboratoires Charton Laboratories
Hvp Chelated Cal/mag With Zinc and Vitamins C and DDarwen Holdings Ltd.
IpricalPep Products Inc.
Isotonix Calcium Plus FormulaMarket America, Inc.
Junior Multi Vitamins - RegularVita Health Products Inc
Kid's Choice Children's Chewable Vitamins - TabVita Health Products Inc
Kids Stuff TabletsVita Health Products Inc
Kids Stuff With Iron TabletsVita Health Products Inc
Kimchi Vitamin Chewable MultivitaminTobico
Liqui Cal-DTwin Laboratories Inc.
Liquid Cal/mag Plus DGahler Enterprises Ltd.
Liquid Calcium and Magnesium With Vit.dRheingold Food International Ltd.
MagnacalHolista Health (Canada) Inc.
Menocal TabLes Aliments Nutri Source Inc.
Mid-life Magnacal 2Holista Health (Canada) Inc.
Multi #2W 7 Clay Inc.
Multi Vitamin & MineralsWn Pharmaceuticals Ltd.
Multi Vitamin and FluorideLibertas Pharma, Inc.
Multi Vitamin Drops With FluorideSeton Pharmaceuticals
Multi Vitamin Drops With Fluoride and IronSeton Pharmaceuticals
Multi Vitamin Drops With Fluoride With IronStratus Pharmaceuticals
Multi Vitamin Plus IronWn Pharmaceuticals Ltd.
Multi Vitamin, Iron and FluorideLibertas Pharma, Inc.
Multi-vitamin FluorideStratus Pharmaceuticals
Multi-vitamin Fluoride and Iron DropsBoca Pharmacal, LLC
Multi-vitamin Fluoride DropsH.J. Harkins Company, Inc.
Multi-vitaminsWn Pharmaceuticals Ltd.
Multiple VitaminsGfr Pharma Ltd.
MultivitaminLaboratoires Confab Inc
Multivitamines Plus C Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Plus Fer Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamins for ChildrenQuest Vitamins A Div Of Purity Life Health Products
MvcSancilio & Company Inc
Nata KompleteWh Nutritionals, Llc
Natural Source Vitamin A and D CapFoodscience Laboratories, Division Of Foodscience Corporation
Neo Cal D3Neolab Inc
Neo-vites & Minerals TabNeolab Inc
Nexa PlusUpsher Smith Laboratories, Inc.
Nexa Select Rx Prenatal Vitamin With Plant-based DHAUpsher Smith Laboratories, Inc.
Nutri-chem Calcium Magnesium With D and ZincNutri Chem Pharmacy Ltd
O Calcium 500mg Plus D TabVita Health Products Inc
O-cal Prenatal VitaminPharmics, Inc.
O-calcium 250mg Plus DVita Health Products Inc
Opti-cal Chewable +d CapletNu Life Nutrition Ltd.
Osteo FormulaNutramed Laboratories Inc.
Osteo-lifeViva Pharmaceutical Inc.
Osteo-plusRolmex International Inc.
Oyster Shell Calcium With Vitamin DCardinal Health
Port A Mins Super Cal-mag 300/150 With Vitamin D3Great Earth Companies, Inc.
Port A Mins Super Cal-mag-zincGreat Earth Companies, Inc.
Port A Mins Super Calcium 375 With Vitamin D3Great Earth Companies, Inc.
Port A Mins Super Calcium 750 With Vitamin D3Great Earth Companies, Inc.
Prefera Ob Plus DHAAlaven Pharmaceutical LLC
PreferaobMEDA Pharmaceuticals
Preferaob Plus DHAAlaven Pharmaceutical LLC
Prenatal Vitamins Plusbryant ranch prepack
Prenate StarAvion Pharmaceuticals, Llc
Prevital TabBio Vita
Pure Calcium CalciumSaimdang Cosmetics Co., Ltd
Redoxon-calBayer Inc Consumer Care
Sandoz Alendronate/cholecalciferolSandoz Canada Incorporated
Strovite One CapletsEverett Laboratories, Inc.
Supplement De Vitamines Et MinerauxLand Art Inc.
Swical-1 TabLes Aliments Nutri Source Inc.
Swical-2 TabLes Aliments Nutri Source Inc.
T-PA CapSeroyal International Inc.
T.A. Vit A & D OintmentJamieson Laboratories Ltd
Teva-alendronate/cholecalciferolTeva Canada Limited
TozalFocus Laboratories, Inc.
Tri-VI-sol DropsMead Johnson Nutritionals
Tri-vit With Fluoride and Iron DropsQualitest Pharmaceuticals
Tri-vit With Fluoride DropsQualitest Pharmaceuticals
Triple Vitamin Drops With FluorideStratus Pharmaceuticals
Triple-vitamin Drops With FluorideSeton Pharmaceuticals
Usana Active CalciumUsana Health Sciences, Inc.
V-natalVirtus Pharmaceuticals
Virt-bal DHA PlusVirtus Pharmaceuticals
Virt-PNVirtus Pharmaceuticals
Virt-PN PlusVirtus Pharmaceuticals LLC
Vitafol NanoEverett Laboratories, Inc.
Vitamin D3dietary Supplemen Dietary SupplementNnodum Pharmaceuticals
Vitamines A - D CalciumLaboratoire Lalco Inc.
Vitamins A Plus D CapsulesRoyal Bodycare Canada Inc.
Vitamins A, C, D and FluorideLibertas Pharma, Inc.
Vp-heme ObVirtus Pharmaceuticals LLC
Vp-heme OneVirtus Pharmaceuticals LLC
ZavaraMisemer Pharmaceuticals, Inc.
SaltsNot Available
Categories
CAS number67-97-0
WeightAverage: 384.6377
Monoisotopic: 384.33921603
Chemical FormulaC27H44O
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Steroid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of vitamin D deficiency or insufficiency, refractory rickets (vitamin D resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. Also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis.
PharmacodynamicsCholecalciferol (vitamin D3) is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of Vitamin A. The classical manifestations of vitamin D deficiency is rickets, which is seen in children and results in bony deformaties including bowed long bones. Deficiency in adults leads to the disease osteomalacia. Both rickets and osteomalacia reflect impaired mineralization of newly synthesized bone matrix, and usually result from a combination of inadequate exposure to sunlight and decreased dietary intake of vitamin D. Common causes of vitamin D deficiency include genetic defects in the vitamin D receptor, severe liver or kidney disease, and insufficient exposure to sunlight. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma.
Mechanism of actionThe first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. The active form of vitamin D3 (calcitriol) binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
AbsorptionReadily absorbed
Volume of distributionNot Available
Protein binding50% to 80%
Metabolism

Within the liver, cholecalciferal is hydroxylated to calcidiol (25-hydroxycholecalciferol) by the enzyme 25-hydroxylase. Within the kidney, calcidiol serves as a substrate for 1-alpha-hydroxylase, yielding calcitriol (1,25-dihydroxycholecalciferol), the biologically active form of vitamin D3.

SubstrateEnzymesProduct
Cholecalciferol
Not Available
(23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide)Details
Route of eliminationNot Available
Half lifeSeveral weeks
ClearanceNot Available
ToxicityHypercalcemia - Early symptoms of hypercalcemia, include nausea and vomiting, weakness, headache, somnolence, dry mouth, constipation, metallic taste, muscle pain and bone pain. Late symptoms and signs of hypercalcemia, include polyuria, polydipsia, anorexia, weight loss, nocturia, conjunctivitis, pancreatitis, photophobia, rhinorrhea, pruritis, hyperthermia, decreased libido, elevated BUN, albuminuria, hypercholesterolemia, elevated ALT (SGPT) and AST (SGOT), ectopic calcification, nephrocalcinosis, hypertension and cardiac arrhythmias.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Granules (effervescents); kit; tabletoral
Piece (chewable)oral
Waferoral
Capsule, gelatin coatedoral
Dropsoral400 unit
Capsuleoral10000 unit
Liquidoral
Waferoral100 unit
Tabletoral
Powderoral
Solution/ dropsoral
Tablet, chewableoral
Capsuleoral
Tablet, film coatedoral
Capsuleoral5000 unit
Capsuleoral50000 unit
Tablet, coatedoral
Tablet (effervescent)oral
Ointmenttopical
Solutionoral
Kit
Tabletoral1000 unit
Tabletoral400 unit
Capsuleoral2000 unit
Capsuleoral25000 unit
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point84.5 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.1 KB)
SpectraNot 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
External Links
ATC CodesA11CC05
AHFS Codes
  • 88:16.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (123 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolCholecalciferol may decrease the anticoagulant activities of Acenocoumarol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Cholecalciferol.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Cholecalciferol.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Cholecalciferol.
ColesevelamThe serum concentration of Cholecalciferol can be decreased when it is combined with Colesevelam.
DanazolDanazol may increase the hypercalcemic activities of Cholecalciferol.
DigoxinCholecalciferol may increase the arrhythmogenic activities of Digoxin.
DihydrotachysterolThe risk or severity of adverse effects can be increased when Dihydrotachysterol is combined with Cholecalciferol.
Mineral oilThe serum concentration of Cholecalciferol can be decreased when it is combined with Mineral oil.
OrlistatThe serum concentration of Cholecalciferol can be decreased when it is combined with Orlistat.
SucralfateThe serum concentration of Sucralfate can be increased when it is combined with Cholecalciferol.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Cholecalciferol.
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Cholecalciferol.
WarfarinCholecalciferol may decrease the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

1. Vitamin D3 receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Vitamin D3 receptor P11473 Details

References:

  1. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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. Epub 2010 May 6. Pubmed

Enzymes

1. Vitamin D 25-hydroxylase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Vitamin D 25-hydroxylase Q6VVX0 Details

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
  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
  3. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed
  4. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. Pubmed

2. Sterol 26-hydroxylase, mitochondrial

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Sterol 26-hydroxylase, mitochondrial Q02318 Details

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
  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
  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
  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
  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
  6. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed
  7. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. Pubmed

3. Cytochrome P450 2J2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2J2 P51589 Details

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
  2. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed

4. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed
  2. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. Pubmed

5. Cholesterol side-chain cleavage enzyme, mitochondrial

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 Details

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. Epub 2008 Oct 21. Pubmed
  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. Epub 2008 May 20. Pubmed
  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

6. Cytochrome P450 1A1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2B6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

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. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 2C19

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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. Epub 2009 Nov 24. Pubmed
  2. Lexicomp.

9. Cytochrome P450 2C8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 2C9

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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. Epub 2009 Nov 24. Pubmed
  2. Lexicomp.

11. Cytochrome P450 2D6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

Carriers

1. Vitamin D-binding protein

Kind: Protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Vitamin D-binding protein P02774 Details

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
  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
  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
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08