Identification

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

Ergocalciferol is an inactivated vitamin D analog.[1] It is a form of vitamin synthesized by some plants in the presence of UVB light.[4] The production of ergocalciferol was impulsed by the identification of dietary deficiency, more specifically vitamin D, as the main causative agent for rickets. Impulsed by this research, ergocalciferol was isolated for the first time from yeast in 1931 and its structure was elucidated in 1932.[5]

The first approved product containing ergocalciferol under the FDA records was developed by US Pharm Holdings and FDA approved in 1941.[6]

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/1OralValidus Pharmaceuticals1974-01-112018-03-31Us
DrisdolCapsule, liquid filled1.25 mg/1OralValidus Pharmaceuticals LLC2018-04-01Not applicableUs
DrisdolCapsule, liquid filled1.25 mg/1OralAvera McKennan Hospital2016-02-052018-07-05Us
DrisdolCapsule, liquid filled1.25 mg/1OralSanofi Aventis1974-11-112017-02-28Us
DrisdolCapsule1.25 mg/1OralSanofi Aventis1974-11-112014-04-30Us
Osto-D2Capsule50000 unitOralPaladin Labs Inc2008-02-08Not applicableCanada
Radiostol Cap 50000iuCapsule50000 unitOralAllen & Hanburys A Glaxo Canada Ltd. Co.1989-12-151996-09-10Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErgocalciferolCapsule, liquid filled1.25 mg/1Oralbryant ranch prepack2016-06-15Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralTeva2002-06-012017-04-30Us50111 0990 01 nlmimage10 ef3677d3
ErgocalciferolCapsule1.25 mg/1OralWinthrop U.S.2009-11-102009-08-27Us
ErgocalciferolCapsule1.25 mg/1OralGolden State Medical Supply, Inc.2011-11-15Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralAphena Pharma Solutions - Tennessee, LLC2009-05-20Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralAmerican Health Packaging2011-01-282019-10-31Us
ErgocalciferolCapsule, liquid filled1.25 mg/1OralRising Pharamceuticals, Inc2010-07-23Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralAlembic Pharmaceuticals Inc.2018-04-30Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralSt. Mary's Medical Park Pharmacy2016-06-15Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralPhysicians Total Care, Inc.2007-07-12Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vitamin D 400 I.U. TabletsTablet400 unitOralGeneral Nutrition Canada Inc.1997-04-182001-09-12Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

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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 and Magnesium Citrate With Vitamin DErgocalciferol (100 unit) + Calcium (275 mg) + Magnesium (137.5 mg)TabletOralSisu Inc.1997-10-282005-07-13Canada
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 (.6 mg) + Magnesium citrate (3 mg)LiquidOralJamp Pharma Corporation2002-04-222003-02-05Canada
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 With Vitamin D2Ergocalciferol (200 unit) + Calcium (250 mg)CapsuleOralSisu Inc.2002-12-182008-07-25Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Se-NatalErgocalciferol (400 [iU]/1) + Calcium Carbonate (250 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Docusate sodium (50 mg/1) + Ferrous fumarate (90 mg/1) + Folic Acid (1 mg/1) + Niacin (20 mg/1) + Niacinamide ascorbate (120 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin A acetate (4000 [iU]/1) + Zinc oxide (25 ug/1)TabletOralSeton Pharmaceuticals2009-04-162011-07-31Us
International/Other Brands
Deltalin (Lilly)
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)[C@@H](C)\C=C\[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

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).

Associated Conditions
Associated Therapies
Pharmacodynamics

After the activation of the vitamin D receptor, some of the biological changes produced by ergocalciferol include mobilization and accretion of calcium and phosphorus in the bone, absorption of calcium and phosphorus in the intestine, and reabsorption of calcium and phosphorus in the kidney.[5]

Some other effects known to be produced due to the presence of vitamin D are osteoblast formation, fetus development, induction of pancreatic function, induction of neural function, improvement of immune function, cellular growth and cellular differentiation.[5]

When compared to its vitamin D counterpart cholecalciferol, ergocalciferol has been shown to present a reduced induction of calcidiol and hence, it is less potent.[2]

Ergocalciferol supplementation in patients with end-stage renal disease has been shown to generate a significant benefit in lab parameters of bone and mineral metabolism as well as improvement in glycemic control, serum albumin levels and reduced levels of inflammatory markers.[1]

Mechanism of action

For its activity, ergocalciferol is required to be transformed to its major active circulating hydroxylated metabolite and transported to the target organs in order to bind to its target, the vitamin D receptor.[5]

The activation of the vitamin D receptor is part of the vitamin D endocrine system and it is described by the production of a change in the transcription rates of the vitamin D receptor target genes.[5] The target genes in the DNA affected by the presence of ergocalciferol are called vitamin D response elements which are dependent on co-modulators.[3]

TargetActionsOrganism
AVitamin D3 receptor
agonist
Humans
Additional Data Available
Adverse Effects

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Absorption

Ergocalciferol is absorbed in the intestine and carried to the liver in chylomicrons. Its intestinal absorption does not present limitations unless the presence of conditions related to fat malabsorption.[4]

Volume of distribution

The amount of circulating ergocalciferol is very limited as this compound is rapidly stored in fat tissue such as adipose tissue, liver and muscle. This is very obvious in reports that indicate that circulating ergocalciferol is significantly reduced in obese patients.[4]

Protein binding

>99.8%

Metabolism

Ergocalciferol is inactive and hence, the first step in the body is ruled by the conversion of this parent compound to 25-hydroxyvitamin D by the action of CYP2R1 followed by the generation of the major circulating metabolite, 1,25-dihydroxyvitamin D or calcitrol.[4] The generation of this major metabolite is ruled by the activity of CYP27B1 which is a key 1-hydroxylase and CYP24A1 which is responsible for the 25-hydroxylation.[3]

As part of the minor metabolism, ergocalciferol is transformed into 25-hydroxyvitamin D in the liver by the activity of D-25-hydroxylase and CYP2R1. As well, the formation of 24(R),25dihydroxyvitamin D is performed mainly in the kidneys by the action of 25-(OH)D-1-hydroxylase and 25-(OH)D-24-hydroxylase.[5]

Route of elimination

The active form of ergocalciferol, calcitrol, cannot be maintained for long periods in storage tissue mainly in periods of dietary or UVB deprivation.[4]

Half life

Ergocalciferol can be found circulation for 1-2 days. This quick turnover is presented due to hepatic conversion and uptake by fat and muscle cells where it is transformed to the active form.[4]

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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ergocalciferol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Ergocalciferol.
1alpha-Hydroxyvitamin D5The risk or severity of adverse effects can be increased when Ergocalciferol is combined with 1alpha-Hydroxyvitamin D5.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Ergocalciferol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Ergocalciferol.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Ergocalciferol.
6-Deoxyerythronolide BThe metabolism of Ergocalciferol can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Ergocalciferol.
7-ethyl-10-hydroxycamptothecinThe metabolism of Ergocalciferol can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Ergocalciferol.
Additional Data Available
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    Extended Description

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  • Severity
    Severity

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    Evidence Level

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  • Action
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Food Interactions
Not Available

References

Synthesis Reference
US5789397
General References
  1. Porter A, Gilmartin C, Srisakul U, Arruda J, Akkina S: Prevalence of 25-OH vitamin D deficiency in a population of hemodialysis patients and efficacy of an oral ergocalciferol supplementation regimen. Am J Nephrol. 2013;37(6):568-74. doi: 10.1159/000351185. Epub 2013 May 30. [PubMed:23735861]
  2. Lee JY, So TY, Thackray J: A review on vitamin d deficiency treatment in pediatric patients. J Pediatr Pharmacol Ther. 2013 Oct;18(4):277-91. doi: 10.5863/1551-6776-18.4.277. [PubMed:24719588]
  3. Gallagher JC, Bikle DD: Vitamin D: Mechanisms of Action and Clinical Applications. Endocrinol Metab Clin North Am. 2017 Dec;46(4):xvii-xviii. doi: 10.1016/j.ecl.2017.09.001. Epub 2017 Sep 28. [PubMed:29080648]
  4. Coulston A. and Boushey C. (2008). Nutrition in the Prevention and Treatment of Disease (2nd ed.). Academic Press. [ISBN:978-012-374118-9]
  5. Eitenmiller R., Ye L. and Landen W. (2008). Vitamin analysis for the health and food sciences (2nd ed.). Taylor and Francis. [ISBN:978-0-8493-9771-4]
  6. FDA approvals [Link]
External Links
Human Metabolome Database
HMDB0000900
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 RecruitingTreatmentSeasonal Mood Disorder1
0CompletedSupportive CareNeoplasms, Breast1
0CompletedTreatmentChronic Kidney Disease (CKD)1
0Not Yet RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
0RecruitingPreventionDeficiency, Vitamin D1
0RecruitingPreventionVitamin D Intake in First Trimester and Incidence of Gestational Diabetes Recurrence1
0RecruitingTreatmentDeficiency, Vitamin D / Fat malabsorption1
0RecruitingTreatmentErgocalciferol1
1Active Not RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
1Active Not RecruitingTreatmentPeyronie's Disease1
1Active Not RecruitingTreatmentSarcopenia1
1CompletedBasic ScienceInsulin Sensitivity1
1CompletedDiagnosticHyperparathyroidism1
1CompletedDiagnosticOsteoporosis1
1CompletedHealth Services ResearchDeficiency, Vitamin D1
1CompletedPreventionGastrointestinal Cancers / High Blood Pressure (Hypertension) / Prostate Cancer1
1CompletedPreventionPhysiological Effects of Vitamin D1
1CompletedTreatmentAdult Women / Estrogen Receptor Positive / Metastatic Breast Cancer (MBC)1
1CompletedTreatmentAsthma Bronchial / Deficiency, Vitamin D1
1CompletedTreatmentImmune Defect / Infants, Premature1
1CompletedTreatmentInflammatory Reaction / Insulin Resistance1
1CompletedTreatmentSarcopenia / Strength, Muscle1
1CompletedTreatmentSolid Cancers1
1CompletedTreatmentType 2 Diabetes Mellitus1
1Not Yet RecruitingTreatmentCancer of the Pancreas / Malignant Neoplasm of Pancreas1
1RecruitingTreatmentDeficiency, Vitamin D1
1WithdrawnOtherHepatocellular,Carcinoma / Liver Cirrhosis1
1, 2CompletedPreventionBiomarker Change Linked to Breast Cancer1
1, 2CompletedPreventionCancer, Breast1
1, 2CompletedTreatmentColorectal Cancers1
1, 2CompletedTreatmentSickle Cell Disorders1
1, 2RecruitingTreatmentDiabetes Mellitus (DM) / Diabetes, Autoimmune / Diabetes, Diabetes Mellitus Type 1 / Hypoglycemia1
1, 2SuspendedTreatmentDeficiency, 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
2CompletedPreventionDeficiency, Vitamin D / High Blood Pressure (Hypertension)1
2CompletedPreventionRespiratory Tract Infections (RTI) / Vitamin D1
2CompletedTreatmentAllergic Rhinoconjunctivitis1
2CompletedTreatmentBronchiolitis1
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
2CompletedTreatmentInsulin Resistance1
2CompletedTreatmentOsteoporosis1
2CompletedTreatmentPolycystic Ovarian Syndrome1
2CompletedTreatmentPulmonary Tuberculosis (TB)1
2CompletedTreatmentType 2 Diabetes Mellitus1
2Not Yet RecruitingTreatmentDeficiency, Vitamin D / Neurocognitive Dysfunction1
2RecruitingPreventionNeurofibromatosis Type 1 (NF1)1
2RecruitingPreventionOsteopenia / Osteoporosis1
2RecruitingTreatmentBone Metabolism / Primary Hyperparathyroidism1
2RecruitingTreatmentCancer, Breast1
2RecruitingTreatmentCervical Cancers / Endometrial Cancers / Uterine Malignancies1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentOsteoporosis1
2RecruitingTreatmentOsteoporosis / Rheumatoid Arthritis1
2TerminatedBasic ScienceCancer, Breast1
2TerminatedPreventionD Vitamin Deficiency Patients1
2Unknown StatusPreventionSickle Cell Disorders1
2Unknown StatusTreatmentAdvanced Intrahepatic Cholangiocarcinoma1
2Unknown StatusTreatmentDeficiency, Vitamin D / Hepatitis C Infection1
2Unknown StatusTreatmentHypovitaminosis D / Type 2 Diabetes Mellitus1
2Unknown StatusTreatmentOptic Neuritis1
2Unknown StatusTreatmentPeritoneal dialysis therapy1
2WithdrawnTreatmentAsthma Bronchial1
2, 3CompletedPreventionImpaired Glucose Tolerance (IGT)1
2, 3CompletedTreatmentAllergic Bronchopulmonary Aspergilloses1
2, 3CompletedTreatmentDeficiency, Vitamin D / Hypercalcemia / Primary Hyperparathyroidism1
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 RecruitingPreventionCardiovascular Disease (CVD) / Fracture Bone / Malignancies1
3Active Not RecruitingPreventionHeart Failure1
3Active Not RecruitingTreatmentFracture of Neck of Femur1
3CompletedHealth Services ResearchDeficiency, Vitamin D1
3CompletedHealth Services ResearchDiabetes, Diabetes Mellitus Type 11
3CompletedPreventionBone Diseases / Cardiovascular Disease (CVD) / Colonic Neoplasms / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia / Neoplasms, Breast / One to five years postmenopausal / Osteoporosis1
3CompletedPreventionHypovitaminosis D1
3CompletedPreventionMigraine According to International Headache Society (IHS) Criteria (ICHD-II)1
3CompletedPreventionOsteoporosis1
3CompletedPreventionRisperidone-induced Hyperprolactinemia1
3CompletedPreventionVitamin D Status During Pregnancy / Vitamin D3 Deficiency1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentChronic Kidney Disease Stage 3 and 41
3CompletedTreatmentDeficiency, Vitamin D1
3CompletedTreatmentDeficiency, Vitamin D / Heart Failure1
3CompletedTreatmentKnee Osteoarthritis (Knee OA)1
3CompletedTreatmentMalignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
3CompletedTreatmentOsteoporosis1
3CompletedTreatmentProteinuria / Renal Insufficiency,Chronic1
3CompletedTreatmentSmear Positive Pulmonary Tuberculosis1
3CompletedTreatmentType 2 Diabetes Mellitus1
3Not Yet RecruitingTreatmentDeficiency, Vitamin D1
3Not Yet RecruitingTreatmentSchizophrenic Disorders1
3RecruitingPreventionDisseminated Sclerosis1
3RecruitingTreatmentChronic Rhinosinusitis With Nasal Polyps1
3RecruitingTreatmentCutaneous Malignant Melanoma1
3RecruitingTreatmentMyocardial Infarction1
3RecruitingTreatmentOvulation induction therapy1
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 StatusTreatmentTuberculosis Infection1
3WithdrawnTreatmentMinor burns1
4CompletedNot AvailableCrohn's Disease (CD) / Low Bone Mineral Density1
4CompletedBasic Science25-Hydroxyvitamin D Concentration / Deficiency, Vitamin D1
4CompletedBasic ScienceDeficiency, Vitamin D1
4CompletedPreventionAllergies / Wheezing1
4CompletedPreventionAllograft Rejection / Obliterative Bronchiolitis / Transplantation, Lung1
4CompletedPreventionBMI >27 kg/m2 / BMI >30 kg/m2 / Insulin Resistance1
4CompletedPreventionBone Loss / Epilepsies / Fracture Bone / Osteoporosis1
4CompletedPreventionCrohn's Disease (CD)1
4CompletedPreventionDeficiency, Vitamin D2
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentBMI >30 kg/m21
4CompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D1
4CompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Hyperparathyroidism, Secondary1
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 Failure1
4CompletedTreatmentDeficiency, Vitamin D / Hypercalcemia / Hypercalciuria / Osteopenia / Osteoporosis / Parathyroid deficiency1
4CompletedTreatmentDeficiency, Vitamin D / Relapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedTreatmentHip Fractures1
4CompletedTreatmentHyperparathyroidism, Secondary1
4CompletedTreatmentNutritional Rickets1
4CompletedTreatmentOsteoporosis2
4CompletedTreatmentPostmenopausal Osteoporosis (PMO)3
4CompletedTreatmentPruritis1
4Enrolling by InvitationTreatmentGestational Diabetes Mellitus (GDM)1
4Enrolling by InvitationTreatmentVitamin D2 Supplementation in Vitamin D Insufficiency1
4Not Yet RecruitingTreatmentAcne Vulgaris1
4Not Yet RecruitingTreatmentChronic Renal Failure (CRF) / Renal Insufficiency,Chronic1
4Not Yet RecruitingTreatmentPsoriasis1
4Not Yet RecruitingTreatmentSarcoidosis / Vitamin D Insufficiency1
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 Legs Syndrome (RLS)1
4RecruitingTreatmentDeficiency, Vitamin D / Depression / Insulin Resistance / Polycystic Ovarian Syndrome1
4RecruitingTreatmentDeficiency, Vitamin D / Hip Fractures1
4RecruitingTreatmentInfertilities1
4RecruitingTreatmentMyopathic Symptoms1
4RecruitingTreatmentPolycystic Ovarian Syndrome1
4RecruitingTreatmentPolycystic Ovaries Syndrome1
4RecruitingTreatmentPostoperative pain1
4TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection / Flaviviridae Infections / Hepatitis C Viral Infection / 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 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
4WithdrawnTreatmentAnemias / Chronic Kidney Disease (CKD) / CKD / Ergocalciferol / Hepcidin / Iron-Deficiency / 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 AvailableTuberculosis Infection1
Not AvailableCompletedNot AvailableWilliams Syndrome1
Not AvailableCompletedBasic ScienceBlood Pressures / BMI >27 kg/m2 / BMI >30 kg/m2 / Endothelial Function / Renal Function1
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 AvailableCompletedPreventionSarcopenia1
Not AvailableCompletedSupportive CareDiabetic Neuropathies1
Not AvailableCompletedSupportive CarePulmonary Tuberculosis (TB)1
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 AvailableCompletedTreatmentCardiovascular Disease (CVD) / Deficiency, Vitamin D / High Blood Pressure (Hypertension) / Insulin Resistance / Type 2 Diabetes Mellitus1
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 AvailableCompletedTreatmentDeficiency, Vitamin D / Osteoporosis1
Not AvailableCompletedTreatmentDiabetes Mellitus (DM)1
Not AvailableCompletedTreatmentHIV Seropositive1
Not AvailableCompletedTreatmentHeart Failure1
Not AvailableCompletedTreatmentNeoplasms, Brain2
Not AvailableCompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentTransplant Bone Disease1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableNot Yet RecruitingPreventionBurn Surgery1
Not AvailableNot Yet RecruitingPreventionTransient Hypercalciuria1
Not AvailableNot Yet RecruitingTreatmentDevelopment, Child1
Not AvailableRecruitingPreventionBone Density1
Not AvailableRecruitingSupportive CareHematopoietic Stem Cell Transplant (HSCT)1
Not AvailableRecruitingSupportive CareHyperparathyroidism, Secondary1
Not AvailableRecruitingTreatmentBMI >30 kg/m21
Not AvailableRecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingTreatmentDeficiency, Vitamin D1
Not AvailableRecruitingTreatmentDeficiency, Vitamin D / Psoriasis1
Not AvailableRecruitingTreatmentLiver Diseases1
Not AvailableTerminatedNot AvailableFractures, Bone / Kidney Diseases / Muscle Weakness / Pain NOS1
Not AvailableTerminatedTreatmentAtopic Dermatitis (AD) / Deficiency, Vitamin D1
Not AvailableTerminatedTreatmentDeficiency, 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 StatusTreatmentDeficiency, Vitamin D1
Not AvailableUnknown StatusTreatmentDeficiency, Vitamin D / Rheumatoid Arthritis1
Not AvailableUnknown StatusTreatmentGlucose tolerance impaired / Insulin Resistance1
Not AvailableUnknown StatusTreatmentProstatic Neoplasms1
Not AvailableWithdrawnPreventionHypocalcemia1
Not AvailableWithdrawnTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1
Not AvailableWithdrawnTreatmentChronic Rhinosinusitis1
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
  • Banner Pharmacaps Inc.
  • Bayer Healthcare
  • Breckenridge Pharmaceuticals
  • Caraco Pharmaceutical Labs
  • Gallipot
  • Longs Drug Store
  • Major Pharmaceuticals
  • Optimum Pharmacueticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Rising Pharmaceuticals
  • Sanofi-Aventis Inc.
  • Superior Pharmeceuticals
  • Walgreen Co.
  • Winthrop Us
Dosage forms
FormRouteStrength
Solution / dropsOral
CapsuleOral
TabletOral
CapsuleOral1.25 mg/1
Capsule, liquid filledOral1.25 mg/1
Tablet, effervescentOral
Injection, powder, lyophilized, for solutionIntravenous
Kit
LiquidIntravenous
SyrupOral
CapsuleOral50000 unit
CapsuleOral1.25 1/1
TabletOral400 unit
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)115-117°CSaxena P. 2007. Chemistry of alkaloids
boiling point (°C)Decomposes'MSDS'
water solubilityInsoluble'MSDS'
logP8.89'MSDS'
pKa6.35Hart J. and Norman M. 1992. The Analyst.
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
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. 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
Humans
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
Humans
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
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. 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
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. 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
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. 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 April 24, 2019 17:05