Identification

Name
Ergocalciferol
Accession Number
DB00153  (NUTR00005, APRD00426)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

Ergocalciferol (Vitamin D2) is a derivative of ergosterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from cholecalciferol in having a double bond between C22 and C23 and a methyl group at C24.

Structure
Thumb
Synonyms
  • (3β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
  • (5Z,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol
  • (5Z,7E,22E)-(3S)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
  • Activated ergosterol
  • Ercalciol
  • Ergocalciférol
  • Ergocalciferol
  • Ergocalciferolum
  • Oleovitamin D2
  • Viosterol
  • Vitamin D2
  • Vitamina D2
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
D-forteCapsule50000 unitOralEuro Pharm International Canada Inc2017-08-16Not applicableCanada
D-forteCapsule50000 unitOralSandoz Canada Incorporated1999-12-30Not applicableCanada
DrisdolCapsule, liquid filled1.25 mg/1OralAvera Mc Kennan Hospital2016-02-05Not applicableUs
DrisdolCapsule, liquid filled1.25 mg/1OralSanofi Aventis1974-11-112017-11-18Us
DrisdolCapsule, liquid filled1.25 mg/1OralValidus Pharmaceuticals1974-01-11Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralWinthrop U.S.2009-11-10Not applicableUs
Osto-D2Capsule50000 unitOralPaladin Labs Inc2008-02-08Not applicableCanada
Radiostol Cap 50000iuCapsule50000 unitOralAllen & Hanburys A Glaxo Canada Ltd. Co.1989-12-151996-09-10Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErgocalciferolCapsule, liquid filled1.25 mg/1OralPd Rx Pharmaceuticals, Inc.2016-06-15Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralAidarex Pharmaceuticals LLC2009-08-17Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralReady Meds2010-07-23Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralA S Medication Solutions2009-08-172017-06-20Us
ErgocalciferolCapsule, liquid filled1.25 mg/1OralAv Kare, Inc.2015-07-23Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralBanner Life Sciences Llc.2015-06-01Not applicableUs
ErgocalciferolCapsule1.25 mg/1Oralbryant ranch prepack2009-08-17Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralKaiser Foundations Hospitals2016-04-26Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralRemedy Repack2017-01-25Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralAphena Pharma Solutions Tennessee, Inc.2011-11-15Not applicableUs
International/Other Brands
Calcidol / Deltalin
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Aquasol A & D DropsErgocalciferol (8000 unit) + Vitamin A (40000 unit)Solution / dropsOralRhone Poulenc Rorer1993-12-311996-09-09Canada
Cal/mag 2:1 With DErgocalciferol (100 unit) + Calcium (350 mg) + Magnesium (175 mg)TabletOralWn Pharmaceuticals Ltd.1998-06-262000-02-02Canada
Calcium Mg and Zn Capsules With Vitamin DErgocalciferol (100 unit) + Calcium (333.33 mg) + Magnesium (166.67 mg) + Zinc (6 mg)CapsuleOralRheingold Food International Ltd.1995-12-312007-07-26Canada
Calcium Chelate Plus Vit DErgocalciferol (400 unit) + Calcium (50 mg)TabletOralHall Laboratories, Ltd.1981-12-312003-09-11Canada
Calcium Citrate W Vitamin D TabErgocalciferol (100 unit) + Calcium Citrate (250 mg)TabletOralNutri Dyn Products Ltd.1994-12-311996-09-09Canada
Calcium Magnesium 2:1 Tablets With Vitamin DErgocalciferol (200 unit) + Calcium (300 mg) + Magnesium (150 mg)TabletOralSisu Inc.2004-01-302009-08-04Canada
Calcium Magnesium Avec Vitamine D Et ZincErgocalciferol (135 unit) + Calcium (335 mg) + Magnesium oxide (167 mg) + Zinc gluconate (10 mg)TabletOralLes Aliments Nutri Source Inc.1991-12-311996-09-09Canada
Calcium Magnesium Plus Vitamin D LiquidErgocalciferol (2 unit) + Calcium gluconate (6 mg) + Inositol nicotinate (.6 mg) + Magnesium citrate (3 mg)LiquidOralJamp Pharma Corporation2002-04-222003-02-05Canada
Calcium With Vitamin D2Ergocalciferol (200 unit) + Calcium (250 mg)CapsuleOralSisu Inc.2002-12-182008-07-25Canada
Calcium With Vitamins C and D TabErgocalciferol (200 unit) + Calcium (500 mg) + Vitamin C (10 mg)TabletOralPure Life International Prods Inc.1993-12-312000-07-27Canada
Categories
UNII
VS041H42XC
CAS number
50-14-6
Weight
Average: 396.6484
Monoisotopic: 396.33921603
Chemical Formula
C28H44O
InChI Key
MECHNRXZTMCUDQ-RKHKHRCZSA-N
InChI
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
IUPAC Name
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
SMILES
CC(C)[[email protected]@H](C)\C=C\[[email protected]@H](C)[[email protected]@]1([H])CC[[email protected]@]2([H])\C(CCC[[email protected]]12C)=C\C=C1\C[[email protected]@H](O)CCC1=C

Pharmacology

Indication

For use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin D resistant rickets). This drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).

Structured Indications
Pharmacodynamics

Ergoalcifediol (Vitamin D2) is a fat soluble steroid hormone precursor of vitamin D. The principal biologic 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. Cholecalciferol is synthesized within our bodies naturally, but if UV exposure is inadequate or the metabolism of cholecalciferol is abnormal, then an exogenous source is required. Vitamin D2 is converted to 25-hydroxyvitamin D (25OHD) in the liver, and then to the active form, 1,25-dihydroxyvitamin D (1,25(OH)2D), in the kidney. Once transformed, it binds to the vitamin D receptor, which leads to a variety of regulatory roles. 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. Very few foods naturally contain vitamin D. Sources that contain the vitamin include fatty fish, the liver and fat of aquatic mammals (e.g., seals, polar bears), and eggs from chickens fed vitamin D-fortified feed. As such, many countries have instituted policies to fortify certain foods with vitamin D to compensate for the potentially low exposures of skin to sunlight. Vitamin D deficiency results in inadequate mineralization of bone or compensatory skeletal demineralization and causes decreased ionized calcium concentrations in blood and a resultant increase in the production and secretion of PTH. Increase in PTH stimulates the mobilization of skeletal calcium, inhibits renal excretion of calcium, and stimulates renal excretion of phosphorus. This results in normal fasting serum calcium concentrations and low or near-normal serum phosphorus. The enhanced mobilization of skeletal calcium induced by this secondary hyperparathyroidism leads porotic bone.

Mechanism of action

Activated ergocalciferol increases serum calcium and phosphate concentrations, primarily by increasing intestinal absorption of calcium and phosphate through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein. 25-hydroxyergocalciferol is the intermediary metabolite of ergocalciferol. Although this metabolite exhibits 2–5 times more activity than unactivated ergocalciferol in curing rickets and inducing calcium absorption and mobilization (from bone) in animals, this increased activity is still insufficient to affect these functions at physiologic concentrations. Activated ergocalciferol stimulate resorption of bone and are required for normal mineralization of bone. Physiological doses of ergocalciferol also promotes calcium reabsorption by the kidneys, but the significance of this effect is not known.

TargetActionsOrganism
AVitamin D3 receptor
agonist
Human
Absorption

Readily absorbed from small intestine (proximal or distal), requires presence of bile salts.

Volume of distribution
Not Available
Protein binding

>99.8%

Metabolism

Within the liver, ergocalciferol is hydroxylated to ercalcidiol (25-hydroxyergocalciferol) by the enzyme 25-hydroxylase. Within the kidney, ercalcidiol serves as a substrate for 1-alpha-hydroxylase, yielding ercalcitriol (1,25-dihydroxyergocalciferol), the biologically active form of vitamin D2.

Route of elimination
Not Available
Half life

19 to 48 hours (however, stored in fat deposits in body for prolonged periods).

Clearance
Not Available
Toxicity

LD50 = 23.7 mg/kg (Orally in mice); LD50 = 10 mg/kg (Orally in rats ); Nausea, vomiting and diarrhea, weight loss, irritability, weakness, fatigue, lassitude, and headache.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinErgocalciferol may increase the arrhythmogenic activities of Acetyldigitoxin.Approved
AcetyldigoxinErgocalciferol may increase the arrhythmogenic activities of Acetyldigoxin.Experimental
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Ergocalciferol.Approved
AmiodaroneThe metabolism of Ergocalciferol can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Ergocalciferol can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Ergocalciferol can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Ergocalciferol can be decreased when combined with Atomoxetine.Approved
BendroflumethiazideBendroflumethiazide may increase the hypercalcemic activities of Ergocalciferol.Approved
BoceprevirThe metabolism of Ergocalciferol can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Ergocalciferol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Ergocalciferol can be decreased when it is combined with Bosentan.Approved, Investigational
CalcidiolThe risk or severity of adverse effects can be increased when Calcidiol is combined with Ergocalciferol.Approved, Nutraceutical
CalcipotriolThe risk or severity of adverse effects can be increased when Ergocalciferol is combined with Calcipotriol.Approved
Calcium AcetateThe risk or severity of adverse effects can be increased when Calcium Acetate is combined with Ergocalciferol.Approved
Calcium CarbonateThe risk or severity of adverse effects can be increased when Calcium Carbonate is combined with Ergocalciferol.Approved
Calcium ChlorideThe risk or severity of adverse effects can be increased when Calcium Chloride is combined with Ergocalciferol.Approved
Calcium CitrateThe risk or severity of adverse effects can be increased when Calcium Citrate is combined with Ergocalciferol.Approved
Calcium glubionateThe risk or severity of adverse effects can be increased when Calcium glubionate is combined with Ergocalciferol.Approved
Calcium GluceptateThe risk or severity of adverse effects can be increased when Calcium Gluceptate is combined with Ergocalciferol.Approved
Calcium gluconateThe risk or severity of adverse effects can be increased when Calcium gluconate is combined with Ergocalciferol.Approved, Vet Approved
Calcium lactateThe risk or severity of adverse effects can be increased when Calcium lactate is combined with Ergocalciferol.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe risk or severity of adverse effects can be increased when Calcium lactate gluconate is combined with Ergocalciferol.Experimental
Calcium laevulateThe risk or severity of adverse effects can be increased when Calcium laevulate is combined with Ergocalciferol.Experimental
Calcium pangamateThe risk or severity of adverse effects can be increased when Calcium pangamate is combined with Ergocalciferol.Experimental
Calcium PhosphateThe risk or severity of adverse effects can be increased when Calcium Phosphate is combined with Ergocalciferol.Approved
CarbamazepineThe metabolism of Ergocalciferol can be increased when combined with Carbamazepine.Approved, Investigational
CaseinThe risk or severity of adverse effects can be increased when Casein is combined with Ergocalciferol.Approved
CeritinibThe serum concentration of Ergocalciferol can be increased when it is combined with Ceritinib.Approved
ChlorothiazideChlorothiazide may increase the hypercalcemic activities of Ergocalciferol.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypercalcemic activities of Ergocalciferol.Approved
CholestyramineThe serum concentration of Ergocalciferol can be decreased when it is combined with Cholestyramine.Approved
ClarithromycinThe metabolism of Ergocalciferol can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Ergocalciferol can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Ergocalciferol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Ergocalciferol can be decreased when combined with Cobicistat.Approved
ColesevelamThe serum concentration of Ergocalciferol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Ergocalciferol can be decreased when it is combined with Colestipol.Approved
ConivaptanThe serum concentration of Ergocalciferol can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Ergocalciferol can be decreased when combined with Crizotinib.Approved
CyclopenthiazideCyclopenthiazide may increase the hypercalcemic activities of Ergocalciferol.Experimental
CyclosporineThe metabolism of Ergocalciferol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinErgocalciferol may increase the arrhythmogenic activities of Cymarin.Experimental
DabrafenibThe serum concentration of Ergocalciferol can be decreased when it is combined with Dabrafenib.Approved
DanazolDanazol may increase the hypercalcemic activities of Ergocalciferol.Approved
DarunavirThe metabolism of Ergocalciferol can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Ergocalciferol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ergocalciferol can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Ergocalciferol can be decreased when combined with Delavirdine.Approved
DeslanosideErgocalciferol may increase the arrhythmogenic activities of Deslanoside.Approved
DigitoxinErgocalciferol may increase the arrhythmogenic activities of Digitoxin.Approved, Investigational
DigoxinErgocalciferol may increase the arrhythmogenic activities of Digoxin.Approved
Digoxin Immune Fab (Ovine)Ergocalciferol may increase the arrhythmogenic activities of Digoxin Immune Fab (Ovine).Approved
DihydroergotamineThe metabolism of Ergocalciferol can be decreased when combined with Dihydroergotamine.Approved
DihydrotachysterolThe risk or severity of adverse effects can be increased when Ergocalciferol is combined with Dihydrotachysterol.Approved
DiltiazemThe metabolism of Ergocalciferol can be decreased when combined with Diltiazem.Approved
DoxercalciferolThe risk or severity of adverse effects can be increased when Doxercalciferol is combined with Ergocalciferol.Approved
DoxycyclineThe metabolism of Ergocalciferol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Ergocalciferol can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Ergocalciferol can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Ergocalciferol can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Ergocalciferol can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Ergocalciferol can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Ergocalciferol can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Ergocalciferol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Ergocalciferol can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ergocalciferol can be increased when it is combined with Fusidic Acid.Approved
GitoformateErgocalciferol may increase the arrhythmogenic activities of Gitoformate.Experimental
HydrochlorothiazideHydrochlorothiazide may increase the hypercalcemic activities of Ergocalciferol.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypercalcemic activities of Ergocalciferol.Approved, Investigational
ImatinibThe metabolism of Ergocalciferol can be decreased when combined with Imatinib.Approved
IndapamideIndapamide may increase the hypercalcemic activities of Ergocalciferol.Approved
IndinavirThe metabolism of Ergocalciferol can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Ergocalciferol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Ergocalciferol can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Ergocalciferol can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ergocalciferol can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Ergocalciferol can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CErgocalciferol may increase the arrhythmogenic activities of Lanatoside C.Experimental
LopinavirThe metabolism of Ergocalciferol can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Ergocalciferol can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Ergocalciferol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Ergocalciferol can be increased when combined with Lumacaftor.Approved
MethyclothiazideMethyclothiazide may increase the hypercalcemic activities of Ergocalciferol.Approved
MetildigoxinErgocalciferol may increase the arrhythmogenic activities of Metildigoxin.Experimental
MetolazoneMetolazone may increase the hypercalcemic activities of Ergocalciferol.Approved
MifepristoneThe serum concentration of Ergocalciferol can be increased when it is combined with Mifepristone.Approved, Investigational
Mineral oilThe serum concentration of Ergocalciferol can be decreased when it is combined with Mineral oil.Approved, Vet Approved
MitotaneThe serum concentration of Ergocalciferol can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Ergocalciferol can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Ergocalciferol can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Ergocalciferol can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Ergocalciferol can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Ergocalciferol can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Ergocalciferol can be decreased when combined with Olaparib.Approved
OleandrinErgocalciferol may increase the arrhythmogenic activities of Oleandrin.Experimental, Investigational
OrlistatThe serum concentration of Ergocalciferol can be decreased when it is combined with Orlistat.Approved, Investigational
OsimertinibThe serum concentration of Ergocalciferol can be increased when it is combined with Osimertinib.Approved
OuabainErgocalciferol may increase the arrhythmogenic activities of Ouabain.Approved
PalbociclibThe serum concentration of Ergocalciferol can be increased when it is combined with Palbociclib.Approved
ParicalcitolThe risk or severity of adverse effects can be increased when Paricalcitol is combined with Ergocalciferol.Approved, Investigational
PentobarbitalThe metabolism of Ergocalciferol can be increased when combined with Pentobarbital.Approved, Vet Approved
PeruvosideErgocalciferol may increase the arrhythmogenic activities of Peruvoside.Experimental
PhenobarbitalThe metabolism of Ergocalciferol can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Ergocalciferol can be increased when combined with Phenytoin.Approved, Vet Approved
PolythiazidePolythiazide may increase the hypercalcemic activities of Ergocalciferol.Approved
PosaconazoleThe metabolism of Ergocalciferol can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Ergocalciferol can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinErgocalciferol may increase the arrhythmogenic activities of Proscillaridin.Experimental
QuinethazoneQuinethazone may increase the hypercalcemic activities of Ergocalciferol.Approved
RanolazineThe metabolism of Ergocalciferol can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Ergocalciferol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Ergocalciferol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Ergocalciferol can be increased when combined with Rifapentine.Approved
SaquinavirThe metabolism of Ergocalciferol can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Ergocalciferol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Ergocalciferol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ergocalciferol can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Ergocalciferol can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Ergocalciferol can be increased when it is combined with Stiripentol.Approved
SucralfateThe serum concentration of Sucralfate can be increased when it is combined with Ergocalciferol.Approved
SulfisoxazoleThe metabolism of Ergocalciferol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Ergocalciferol can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Ergocalciferol can be decreased when combined with Telithromycin.Approved
TiclopidineThe metabolism of Ergocalciferol can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Ergocalciferol can be decreased when it is combined with Tocilizumab.Approved
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Ergocalciferol.Approved, Vet Approved
VenlafaxineThe metabolism of Ergocalciferol can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Ergocalciferol can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Ergocalciferol can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Ergocalciferol can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

Synthesis Reference

Charles W. Bishop, Glenville Jones, Ronald L. Horst, Nicholas J. Koszewski, Joyce C. Knutson, Raju Penmasta, Robert M. Moriarty, Stephen Strugnell, Timothy A. Reinhardt, Liang Guo, Sanjay K. Singhal, Lei Zhao, "Methods for preparation and use of 1A,24(S)-dihydroxy vitamin D2." U.S. Patent US5789397, issued March, 1992.

US5789397
General References
  1. 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]
External Links
Human Metabolome Database
HMDB00900
KEGG Drug
D00187
KEGG Compound
C05441
PubChem Compound
5280793
PubChem Substance
46505053
ChemSpider
4444351
ChEBI
28934
ChEMBL
CHEMBL1536
Therapeutic Targets Database
DAP000291
PharmGKB
PA449484
HET
D2V
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ergocalciferol
ATC Codes
A11CC01 — Ergocalciferol
AHFS Codes
  • 88:16.00 — Vitamin D
PDB Entries
3czh
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingPreventionDeficiency, Vitamin D1
0CompletedSupportive CareNeoplasms, Breast1
0CompletedTreatmentChronic Kidney Disease (CKD)1
1Active Not RecruitingDiagnosticHyperparathyroidism1
1Active Not RecruitingTreatmentAdult Women / Estrogen Receptor Positive / Metastatic Breast Cancer (MBC)1
1Active Not RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
1Active Not RecruitingTreatmentPeyronie's Disease1
1CompletedBasic ScienceInsulin Sensitivity1
1CompletedDiagnosticBone destruction1
1CompletedHealth Services ResearchDeficiency, Vitamin D1
1CompletedPreventionGastrointestinal Cancers / High Blood Pressure (Hypertension) / Prostate Cancer1
1CompletedPreventionPhysiological Effects of Vitamin D1
1CompletedTreatmentAsthma Bronchial / Deficiency, Vitamin D1
1CompletedTreatmentInflammatory Reaction / Insulin Resistance1
1CompletedTreatmentSarcopenia / Strength, Muscle1
1CompletedTreatmentSolid Cancers1
1CompletedTreatmentType 2 Diabetes Mellitus1
1RecruitingTreatmentDeficiency, Vitamin D1
1RecruitingTreatmentSarcopenia1
1SuspendedNot AvailableHepatocellular,Carcinoma / Liver Cirrhosis1
1, 2CompletedPreventionBiomarker Change Linked to Breast Cancer1
1, 2CompletedPreventionCancer, Breast1
1, 2CompletedTreatmentColorectal Cancers1
1, 2CompletedTreatmentSickle Cell Disorders1
1, 2Not Yet RecruitingTreatmentDeficiency, Vitamin D / Orthopedic Disorders / Polytrauma1
1, 2TerminatedTreatmentBone Diseases / Cancer, Breast1
1, 2WithdrawnTreatmentUlcerative Colitis (UC)1
2Active Not RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
2CompletedNot AvailableDeficiency, Vitamin D / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionRespiratory Tract Infections (RTI) / Vitamin D1
2CompletedTreatmentAllergic Rhinoconjunctivitis1
2CompletedTreatmentCancer, Breast2
2CompletedTreatmentChronic Heart Failure (CHF)1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentDeficiency, Vitamin D1
2CompletedTreatmentDiabetes, Diabetes Mellitus Type 11
2CompletedTreatmentEarly Stage Breast Cancer1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentPulmonary Tuberculosis (TB)1
2CompletedTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentBone destruction1
2Not Yet RecruitingPreventionDeficiency, Vitamin D / High Blood Pressure (Hypertension)1
2Not Yet RecruitingTreatmentDeficiency, Vitamin D / Neurocognitive Dysfunction1
2RecruitingPreventionNeurofibromatosis Type 1 (NF1)1
2RecruitingPreventionBone destruction / Osteopenia1
2RecruitingTreatmentBone Metabolism / Primary Hyperparathyroidism1
2RecruitingTreatmentCancer, Breast1
2RecruitingTreatmentCervical Cancers / Endometrial Cancers / Uterine Cancers1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentPolycystic Ovarian Syndrome1
2RecruitingTreatmentBone destruction / Rheumatoid Arthritis1
2RecruitingTreatmentBone destruction1
2TerminatedPreventionD Vitamin Deficiency Patients1
2Unknown StatusPreventionCancer, Breast1
2Unknown StatusPreventionSickle Cell Disorders1
2Unknown StatusTreatmentAdvanced Intrahepatic Cholangiocarcinoma1
2Unknown StatusTreatmentDeficiency, Vitamin D / Hepatitis C Infection1
2Unknown StatusTreatmentHypovitaminosis D / Type 2 Diabetes Mellitus1
2Unknown StatusTreatmentInsulin Resistance1
2Unknown StatusTreatmentOptic Neuritis1
2Unknown StatusTreatmentPeritoneal dialysis therapy1
2WithdrawnTreatmentAsthma Bronchial1
2, 3CompletedPreventionImpaired Glucose Tolerance (IGT)1
2, 3CompletedTreatmentDeficiency, Vitamin D / Hypercalcemia / Primary Hyperparathyroidism1
2, 3Not Yet RecruitingTreatmentAllergic Bronchopulmonary Aspergilloses1
2, 3Not Yet RecruitingTreatmentRestless Legs Syndrome (RLS)1
2, 3RecruitingTreatmentAllergies1
2, 3RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
2, 3Unknown StatusTreatmentCrohns Disease1
2, 3WithdrawnTreatmentCalcium Nephrolithiasis / Deficiency, Vitamin D1
3Active Not RecruitingPreventionCancers / Cardiovascular Disease (CVD) / Fracture Bone1
3Active Not RecruitingPreventionHeart Failure, Unspecified1
3Active Not RecruitingPreventionVitamin D Status During Pregnancy1
3CompletedHealth Services ResearchDeficiency, Vitamin D1
3CompletedHealth Services ResearchDiabetes, Diabetes Mellitus Type 11
3CompletedPreventionBone destruction / Bone Diseases / Cardiovascular Disease (CVD) / Colonic Neoplasms / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia / Neoplasms, Breast / One to five years postmenopausal1
3CompletedPreventionMigraine According to International Headache Society (IHS) Criteria (ICHD-II)1
3CompletedPreventionBone destruction1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentChronic Kidney Disease Stage 3 and 41
3CompletedTreatmentChronic Renal Insufficiency / Proteinuria1
3CompletedTreatmentDeficiency, Vitamin D1
3CompletedTreatmentDeficiency, Vitamin D / Heart Failure, Unspecified1
3CompletedTreatmentKnee Osteoarthritis (Knee OA)1
3CompletedTreatmentMalignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
3CompletedTreatmentSmear Positive Pulmonary Tuberculosis1
3CompletedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentBone destruction1
3Not Yet RecruitingPreventionHypovitaminosis D1
3Not Yet RecruitingTreatmentSchizophrenic Disorders1
3RecruitingPreventionDisseminated Sclerosis1
3RecruitingTreatmentChronic Rhinosinusitis With Nasal Polyps1
3RecruitingTreatmentCutaneous Malignant Melanoma1
3RecruitingTreatmentFracture of Neck of Femur1
3RecruitingTreatmentMyocardial Infarction (MI)1
3TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3TerminatedTreatmentCoronary Artery Disease / Deficiency, Vitamin D / Hyperglycemia, Postprandial1
3Unknown StatusPreventionDeficiency, Vitamin D / Pneumonia1
3Unknown StatusPreventionFalls / Fracture Bone1
3Unknown StatusTreatmentDisseminated Sclerosis1
3Unknown StatusTreatmentNon.Alcoholic Fatty Liver Disease1
3Unknown StatusTreatmentTuberculosis1
3WithdrawnTreatmentMinor burns1
4Active Not RecruitingPreventionAllergies / Wheezing1
4CompletedNot AvailableCrohn's Disease (CD) / Low Bone Mineral Density1
4CompletedBasic ScienceDeficiency, Vitamin D1
4CompletedPreventionAllograft Rejection / Obliterative Bronchiolitis / Transplantation, Lung1
4CompletedPreventionBMI >27 kg/m2 / BMI >30 kg/m2 / Insulin Resistance1
4CompletedPreventionBone destruction / Bone Loss / Epilepsies / Fracture Bone1
4CompletedPreventionCrohn's Disease (CD)1
4CompletedPreventionDeficiency, Vitamin D2
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentBMI >30 kg/m21
4CompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D1
4CompletedTreatmentCalcium Nephrolithiasis / Deficiency, Vitamin D / Disorder of Vitamin D / Idiopathic Hypercalciuria / Urolithiasis1
4CompletedTreatmentChronic Heart Failure (CHF) / Deficiency, Vitamin D1
4CompletedTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1
4CompletedTreatmentChronic Kidney Disease (CKD) / Hyperparathyroidism, Secondary2
4CompletedTreatmentCongestive Heart Failure (CHF)1
4CompletedTreatmentDeficiency, Vitamin D1
4CompletedTreatmentDeficiency, Vitamin D / Heart Failure, Unspecified1
4CompletedTreatmentBone destruction / Deficiency, Vitamin D / Hypercalcemia / Hypercalciuria / Osteopenia / Parathyroid deficiency1
4CompletedTreatmentHip Fractures1
4CompletedTreatmentHyperparathyroidism, Secondary1
4CompletedTreatmentNutritional Rickets1
4CompletedTreatmentPost Menopausal Osteoporosis1
4CompletedTreatmentPostmenopausal Osteoporosis (PMO)2
4CompletedTreatmentPruritis1
4CompletedTreatmentBone destruction2
4Enrolling by InvitationTreatmentGestational Diabetes Mellitus (GDM)1
4Enrolling by InvitationTreatmentVitamin D2 Supplementation in Vitamin D Insufficiency1
4Not Yet RecruitingTreatmentAnemias / Chronic Kidney Disease (CKD) / CKD / Ergocalciferol / Hepcidin / Iron-Deficiency / Vitamin D1
4Not Yet RecruitingTreatmentDeficiency, Vitamin D / Hip Fractures1
4RecruitingBasic Science25-Hydroxyvitamin D Concentration / Deficiency, Vitamin D1
4RecruitingPreventionEclampsia / Gestational Hypertension / HELLP Syndrome / Superimposed Preeclampsia / Toxemia1
4RecruitingPreventionFood Allergy1
4RecruitingTreatmentAdynamic Bone Disease / Deficiency, Vitamin D / Hyperparathyroidism, Secondary / Renal Disease Bone / Renal Disease, End Stage / Restless Leg Disorder1
4RecruitingTreatmentInfertilities1
4RecruitingTreatmentMyopathic Symptoms1
4RecruitingTreatmentPostoperative pain1
4TerminatedTreatmentChronic Hepatitis C Infection / Flaviviridae Infections / Hepatitis C, Chronic / RNA Virus Infections1
4TerminatedTreatmentCrohn's Disease (CD) / Deficiency, Vitamin D1
4TerminatedTreatmentDeficiency, Vitamin D / Renal Failure Chronic Requiring Hemodialysis1
4Unknown StatusBasic ScienceAcute Coronary Syndromes (ACS) / Cytokines1
4Unknown StatusPreventionBMI >30 kg/m2 / Insulin Resistance / Vitamin D25 Insufficiency1
4Unknown StatusPreventionCoronary Artery Calcifications / Kidney Diseases1
4Unknown StatusTreatmentAcute Lower Respiratory Tract Infection / Bronchiolitis / Pneumonia1
4Unknown StatusTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Hyperparathyroidism, Secondary1
4Unknown StatusTreatmentBone Mineralization Defect1
4Unknown StatusTreatmentChronic Pain Syndrome / Deficiency, Vitamin D / Inflammatory Responses1
4Unknown StatusTreatmentDeficiency, Vitamin D / Diabetes Mellitus (DM)1
4Unknown StatusTreatmentDeficiency, Vitamin D / Malnutrition1
4Unknown StatusTreatmentDisseminated Sclerosis1
4Unknown StatusTreatmentMetabolic Syndromes1
4Unknown StatusTreatmentPersistent Asthma1
Not AvailableActive Not RecruitingTreatmentDeficiency, Vitamin D1
Not AvailableCompletedNot AvailableAsthma Bronchial / Deficiency, Vitamin D1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD)1
Not AvailableCompletedNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableCompletedNot AvailableHMG COA Reductase Inhibitor Adverse Reaction1
Not AvailableCompletedNot AvailableTuberculosis1
Not AvailableCompletedNot AvailableWilliams Syndrome1
Not AvailableCompletedBasic ScienceBlood Pressures / BMI >27 kg/m2 / BMI >30 kg/m2 / Endothelial Function / Renal Function1
Not AvailableCompletedOtherType 2 Diabetes Mellitus1
Not AvailableCompletedPreventionBMI >30 kg/m2 / Diabetes Mellitus, Non-Insulin-Dependent1
Not AvailableCompletedPreventionDeficiency, Vitamin D1
Not AvailableCompletedPreventionDiabetes Mellitus, Non-Insulin-Dependent1
Not AvailableCompletedPreventionEnd Stage Renal Disease (ESRD)1
Not AvailableCompletedPreventionMalignant Melanoma of Skin1
Not AvailableCompletedPreventionPre-Diabetic1
Not AvailableCompletedPreventionRisperidone-induced Hyperprolactinemia1
Not AvailableCompletedPreventionSarcopenia1
Not AvailableCompletedSupportive CareDiabetic Neuropathies1
Not AvailableCompletedSupportive CareTuberculosis, Pulmonary1
Not AvailableCompletedTreatmentAtopic Dermatitis (AD)1
Not AvailableCompletedTreatmentBMI >30 kg/m21
Not AvailableCompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Psychosis / Schizoaffective Disorders / Schizophrenic Disorders1
Not AvailableCompletedTreatmentBack Pain / Hypovitaminosis D1
Not AvailableCompletedTreatmentCoronary Artery Disease / Deficiency, Vitamin D / Endothelial Dysfunction / Inflammatory Reaction1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentDeficiency of Vitamin D3 / Gingival and Periodontal Disease / Pregnancy1
Not AvailableCompletedTreatmentDeficiency, Vitamin D5
Not AvailableCompletedTreatmentDeficiency, Vitamin D / End-Stage Renal Disease (ESRD)1
Not AvailableCompletedTreatmentDeficiency, Vitamin D / Healthy Volunteers1
Not AvailableCompletedTreatmentBone destruction / Deficiency, Vitamin D1
Not AvailableCompletedTreatmentDiabetes Mellitus (DM)1
Not AvailableCompletedTreatmentHIV Seropositive1
Not AvailableCompletedTreatmentHeart Failure, Unspecified1
Not AvailableCompletedTreatmentPsoriasis Vulgaris1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentTransplant Bone Disease1
Not AvailableEnrolling by InvitationTreatmentDeficiency, Vitamin D / Psoriasis1
Not AvailableNot Yet RecruitingPreventionTransient Hypercalciuria1
Not AvailableRecruitingPreventionBone Density1
Not AvailableRecruitingSupportive CareHyperparathyroidism, Secondary1
Not AvailableRecruitingTreatmentBMI >30 kg/m21
Not AvailableRecruitingTreatmentCardiovascular Disease (CVD) / Deficiency, Vitamin D / High Blood Pressure (Hypertension) / Insulin Resistance / Type 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingTreatmentDeficiency, Vitamin D2
Not AvailableRecruitingTreatmentDeficiency, Vitamin D / Glucose tolerance impaired / Insulin Resistance / Oxidative Stress1
Not AvailableRecruitingTreatmentLiver Diseases1
Not AvailableRecruitingTreatmentNeoplasms, Brain1
Not AvailableTerminatedNot AvailableFractures, Bone / Kidney Diseases / Muscle Weakness / Pain1
Not AvailableTerminatedTreatmentAtopic Dermatitis (AD) / Deficiency, Vitamin D1
Not AvailableTerminatedTreatmentMuscle Cramps1
Not AvailableUnknown StatusNot AvailableChronic Hepatitis C Virus (HCV) Infection1
Not AvailableUnknown StatusTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1
Not AvailableUnknown StatusTreatmentChronic Musculoskeletal Pain / Vitamin D Supplementation1
Not AvailableUnknown StatusTreatmentChronic Rhinosinusitis1
Not AvailableUnknown StatusTreatmentDeficiency, Vitamin D1
Not AvailableUnknown StatusTreatmentDeficiency, Vitamin D / Rheumatoid Arthritis1
Not AvailableUnknown StatusTreatmentGlucose tolerance impaired / Insulin Resistance1
Not AvailableUnknown StatusTreatmentImpaired Renal Function1
Not AvailableUnknown StatusTreatmentProstatic Neoplasms1
Not AvailableWithdrawnPreventionHypocalcemia1
Not AvailableWithdrawnTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1
Not AvailableWithdrawnTreatmentHMG COA Reductase Inhibitor Adverse Reaction1
Not AvailableWithdrawnTreatmentHigh Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
  • Eli lilly and co
  • Sanofi aventis us llc
  • Orit laboratories llc
  • Sigmapharm laboratories llc
  • Strides arcolab ltd
  • Sun pharmaceutical industries inc
  • Banner pharmacaps inc
  • Chase chemical co lp
  • Everylife
  • Impax laboratories inc
  • Lannett co inc
  • Vitarine pharmaceuticals inc
  • West ward pharmaceutical corp
Packagers
Dosage forms
FormRouteStrength
Solution / dropsOral
CapsuleOral
TabletOral
CapsuleOral1.25 mg/1
Capsule, liquid filledOral1.25 mg/1
Tablet, effervescentOral
Injection, powder, lyophilized, for solutionIntravenous
Injection, solution, concentrateIntravenous
SyrupOral
CapsuleOral50000 unit
CapsuleOral1.25 1/1
LiquidOral
Prices
Unit descriptionCostUnit
Ergocalciferol powder234.4USD g
Doral 15 mg tablet3.41USD tablet
Doral 7.5 mg tablet3.37USD tablet
Drisdol 50000 unit capsule2.34USD capsule
Drisdol 8288 unit/ml Liquid0.48USD ml
Vitamin d 400 unit softgel0.04USD softgel capsule
Longs vitamin d 400 unit tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)116.5 °CPhysProp
water solubility50 mg/LTOMLIN,C (1994)
logP7.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000433 mg/mLALOGPS
logP7.59ALOGPS
logP7.05ChemAxon
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 Count5ChemAxon
Refractivity128.89 m3·mol-1ChemAxon
Polarizability50.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9428
Caco-2 permeable+0.8323
P-glycoprotein substrateSubstrate0.6628
P-glycoprotein inhibitor IInhibitor0.7614
P-glycoprotein inhibitor IINon-inhibitor0.8391
Renal organic cation transporterNon-inhibitor0.796
CYP450 2C9 substrateNon-substrate0.8432
CYP450 2D6 substrateNon-substrate0.9003
CYP450 3A4 substrateSubstrate0.7362
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8924
CYP450 2D6 inhibitorNon-inhibitor0.9519
CYP450 2C19 inhibitorNon-inhibitor0.8784
CYP450 3A4 inhibitorNon-inhibitor0.8142
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8163
Ames testNon AMES toxic0.9401
CarcinogenicityNon-carcinogens0.9169
BiodegradationNot ready biodegradable0.9742
Rat acute toxicity3.6931 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8502
hERG inhibition (predictor II)Non-inhibitor0.7513
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.78 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-003u-3911000000-dba9e396497310b31715
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-003u-3911000000-dba9e396497310b31715
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0002-0129000000-77bd32807ec8ea97183b
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0601-5902000000-ae4a4363ac10f9f0feb7
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-05mo-9800000000-1ea9f4fa17117a9e6515
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01ot-9801000000-17d2120d47f9c718ea95
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ot-9801000000-c10341d61ee2d6369219
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
hydroxy seco-steroid, seco-ergostane, vitamin D (CHEBI:28934) / Vitamin D2 and derivatives, Fat-soluble vitamins (C05441) / Vitamin D2 and derivatives (LMST03010000)

Targets

Kind
Protein
Organism
Human
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. Carvallo L, Henriquez B, Olate J, van Wijnen AJ, Lian JB, Stein GS, Onate S, Stein JL, Montecino M: The 1alpha,25-dihydroxy Vitamin D3 receptor preferentially recruits the coactivator SRC-1 during up-regulation of the osteocalcin gene. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):420-4. Epub 2007 Jan 10. [PubMed:17218095]
  2. Liu W, Tretiakova M, Kong J, Turkyilmaz M, Li YC, Krausz T: Expression of vitamin D3 receptor in kidney tumors. Hum Pathol. 2006 Oct;37(10):1268-78. Epub 2006 Jul 27. [PubMed:16949927]
  3. Ewing AK, Attner M, Chakravarti D: Novel regulatory role for human Acf1 in transcriptional repression of vitamin D3 receptor-regulated genes. Mol Endocrinol. 2007 Aug;21(8):1791-806. Epub 2007 May 22. [PubMed:17519354]
  4. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913]
  5. Straube S, Derry S, Moore RA, McQuay HJ: Vitamin D for the treatment of chronic painful conditions in adults. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD007771. doi: 10.1002/14651858.CD007771.pub2. [PubMed:20091647]
  6. Jurutka PW, Bartik L, Whitfield GK, Mathern DR, Barthel TK, Gurevich M, Hsieh JC, Kaczmarska M, Haussler CA, Haussler MR: Vitamin D receptor: key roles in bone mineral pathophysiology, molecular mechanism of action, and novel nutritional ligands. J Bone Miner Res. 2007 Dec;22 Suppl 2:V2-10. doi: 10.1359/jbmr.07s216. [PubMed:18290715]
  7. Mikhak B, Hunter DJ, Spiegelman D, Platz EA, Hollis BW, Giovannucci E: Vitamin D receptor (VDR) gene polymorphisms and haplotypes, interactions with plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D, and prostate cancer risk. Prostate. 2007 Jun 15;67(9):911-23. [PubMed:17440943]
  8. Marks HD, Fleet JC, Peleg S: Transgenic expression of the human Vitamin D receptor (hVDR) in the duodenum of VDR-null mice attenuates the age-dependent decline in calcium absorption. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):513-6. Epub 2007 Jan 5. [PubMed:17207992]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can...
Gene Name
CYP24A1
Uniprot ID
Q07973
Uniprot Name
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
Molecular Weight
58874.695 Da
References
  1. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540]
  2. 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]
  3. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. [PubMed:15764712]
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472]
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. [PubMed:11686044]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Iron ion binding
Specific Function
Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name
CYP27B1
Uniprot ID
O15528
Uniprot Name
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial
Molecular Weight
56503.475 Da
References
  1. Turunen MM, Dunlop TW, Carlberg C, Vaisanen S: Selective use of multiple vitamin D response elements underlies the 1 alpha,25-dihydroxyvitamin D3-mediated negative regulation of the human CYP27B1 gene. Nucleic Acids Res. 2007;35(8):2734-47. Epub 2007 Apr 10. [PubMed:17426122]
  2. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913]
  3. 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]
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472]
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. [PubMed:11686044]
Kind
Protein
Organism
Human
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. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. doi: 10.1016/j.ecl.2010.02.008. [PubMed:20511052]
  2. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540]
  3. 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]
  4. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. [PubMed:15764712]
  5. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472]
Kind
Protein
Organism
Human
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. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. doi: 10.1016/j.ecl.2010.02.008. [PubMed:20511052]
Kind
Protein
Organism
Human
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. Ramos-Lopez E, Bruck P, Jansen T, Pfeilschifter JM, Radeke HH, Badenhoop K: CYP2R1-, CYP27B1- and CYP24-mRNA expression in German type 1 diabetes patients. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):807-10. Epub 2007 Jan 16. [PubMed:17223345]
  2. Ramos-Lopez E, Bruck P, Jansen T, Herwig J, Badenhoop K: CYP2R1 (vitamin D 25-hydroxylase) gene is associated with susceptibility to type 1 diabetes and vitamin D levels in Germans. Diabetes Metab Res Rev. 2007 Nov;23(8):631-6. [PubMed:17607662]
  3. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18