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.6 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 1932.7

Ergocalciferol is considered the first vitamin D analog and it differentiates from cholecalciferol in the presence of a double bond between C22 and C23 and the presence of a methyl group at C24. These modifications reduce the affinity of ergocalciferol to vitamin D binding protein which derives in faster clearance, limits its activation and alters its catabolism.3

The first approved product containing ergocalciferol under the FDA records was developed by US Pharm Holdings and FDA approved in 1941.10

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-forteCapsuleOralEuro Pharm International Canada Inc2017-08-16Not applicableCanada
DrisdolCapsule, liquid filled1.25 mg/1OralValidus Pharmaceuticals LLC2018-04-01Not applicableUs
DrisdolCapsule, liquid filled1.25 mg/1OralValidus Pharmaceuticals1974-01-112018-03-31Us
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-D2CapsuleOralPaladin Labs Inc2008-02-082018-07-04Canada
Radiostol Cap 50000iuCapsuleOralAllen & 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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErgocalciferolCapsule, liquid filled1.25 mg/1OralAphena Pharma Solutions - Tennessee, LLC2015-07-23Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralAv Kare, Inc.2012-06-052016-02-02Us
ErgocalciferolCapsule1.25 mg/1OralGolden State Medical Supply, Inc.2011-11-15Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralBionpharma Inc.2016-06-15Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralReady Meds2010-07-23Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralWinthrop U.S.2009-11-102009-08-27Us
ErgocalciferolCapsule, liquid filled1.25 mg/1OralA-S Medication Solutions2016-06-15Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralUnit Dose Services2010-07-23Not applicableUs
ErgocalciferolCapsule1.25 mg/1OralA-S Medication Solutions2009-08-17Not applicableUs
ErgocalciferolCapsule, liquid filled1.25 mg/1OralSt. Mary's Medical Park Pharmacy2016-06-15Not 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. TabletsTabletOralGeneral 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

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

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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

Ergocalciferol is indicated for the treatment of hypoparathyroidism, refractory rickets, and familial hypophosphatemia.Label

Hypoparathyroidism is the result of inadequate parathyroid hormone production that occurs due to the presence of damage or removal of the parathyroid glands. This condition produces decreased calcium and increased phosphorus levels.11

Rickets is a condition produced due to a deficiency in vitamin D, calcium or phosphorus. However, this condition can also be related to renal diseases. It is characterized to present weak or soft bones.4

Familial hypophosphatemia is characterized by the impaired transport of phosphate and an altered vitamin D metabolism in the kidneys. The presence of this condition can derive in the presence of osteomalacia, bone softening and rickets.12

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.7

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.7

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.7

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.7 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

The vitamin D receptor is a transcription factor and member of the steroid hormone nuclear receptor family. It presents a DNA binding domain (VDRE) that, when activated, recruits coregulatory complexes to regulate the genomic activity.3

Additionally, ergocalciferol presents nongenomic effects such as the stimulation of intestinal calcium transport via transcaltachia.3

TargetActionsOrganism
AVitamin D3 receptor
agonist
Humans
NVoltage-dependent calcium channel
inducer
Humans
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Contraindications

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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.6 However, for absorption to take place, the presence of bile is required.13

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.6

Protein binding

Ergocalciferol is not found significantly distributed circulating in plasma. It is known to be found in its bound form to the vitamin D plasma protein.9 The parent compound of ergocalciferol does not bind directly to plasma proteins, however, 70-90% of its metabolites such as cholecalciferol and calcitriol are found in the bound form.5

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.6 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.7

Additionally, there are reports indicating significant activity of 3-epimerase in the metabolism of ergocalciferol which modifies the hydroxy group in C3 from the alpha position to a beta. The epimers formed seemed to have a reduced affinity for the vitamin D plasma proteins and to the vitamin D receptor.3

An alternative activation metabolic pathway has been reported and this process is characterized by the activity of CYP11A1 and its hydroxylation in the C-20. This 20-hydroxylated vitamin D seems to have similar biological activity than calcitriol.3

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.6 Therefore, ergocalciferol and its metabolites are excreted via the bile with a minor contribution of renal elimination. This major fecal elimination is explained due to the cubilin-megalin receptor system-mediated renal reuptake of vitamin D metabolites bound to vitamin D binding protein.14

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.6

Clearance

There are no formal reports regarding the clearance rate of ergocalciferol. Due to the structural similarity, it is recommended to consult this parameter with cholecalciferol. On the other hand, the proposed renal clearance of calcitriol is of 31 ml/min.8

Toxicity

The reported LD50 for orally administered ergocalciferol in the rat is of 10 mg/kg.MSDS Overdosage with this agent is reported to produce hypervitaminosis characterized by hypercalcemia, renal impairment, calcification of soft tissues, a decline in the rate of linear growth and increase in bone mineralization.15

Once an overdose state is registered, immediate withdrawal of vitamin D is required along with a calcium diet, generous intake of fluids and symptomatic treatment. The administration of loop diuretics is an option to increase renal calcium excretion. On the other hand, dialysis and administration of citrates, sulfates, phosphates, corticosteroids, EDTA and mithramycin are recommended.15

There haven't been long term studies analyzing the carcinogenic and mutagenic potential of ergocalciferol or its effects in fertility.

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1alpha-Hydroxyvitamin D5The risk or severity of adverse effects can be increased when Ergocalciferol is combined with 1alpha-Hydroxyvitamin D5.
1alpha,24S-Dihydroxyvitamin D2The risk or severity of adverse effects can be increased when Ergocalciferol is combined with 1alpha,24S-Dihydroxyvitamin D2.
AcetyldigitoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Ergocalciferol is combined with Acetyldigitoxin.
AcetyldigoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Ergocalciferol is combined with Acetyldigoxin.
AldosteroneThe therapeutic efficacy of Ergocalciferol can be decreased when used in combination with Aldosterone.
AlfacalcidolThe risk or severity of adverse effects can be increased when Ergocalciferol is combined with Alfacalcidol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Ergocalciferol.
Beclomethasone dipropionateThe therapeutic efficacy of Ergocalciferol can be decreased when used in combination with Beclomethasone dipropionate.
BecocalcidiolThe risk or severity of adverse effects can be increased when Ergocalciferol is combined with Becocalcidiol.
BendroflumethiazideThe risk or severity of hypercalcemia can be increased when Bendroflumethiazide is combined with Ergocalciferol.
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  • Severity
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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. Sahay M, Sahay RK: Refractory rickets in the tropics. J Pediatr Endocrinol Metab. 2010 Jun;23(6):597-601. [PubMed:20662333]
  5. Hymoller L, Jensen SK: Plasma transport of ergocalciferol and cholecalciferol and their 25-hydroxylated metabolites in dairy cows. Domest Anim Endocrinol. 2017 Apr;59:44-52. doi: 10.1016/j.domaniend.2016.11.002. Epub 2016 Nov 16. [PubMed:27940098]
  6. Coulston A. and Boushey C. (2008). Nutrition in the Prevention and Treatment of Disease (2nd ed.). Academic Press. [ISBN:978-012-374118-9]
  7. 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]
  8. Rajiv Kumar (1984). Vitamin D: Basic and Clinical Aspects. Martinus Nijhoff Publishing. [ISBN:978-1-4612-9793-2]
  9. Speeckaert M., Speeckaert R., Geel N. and Delanghe J. (2014). Advances in Clinical Chemistry. Elsevier.
  10. FDA approvals [Link]
  11. Endocrine Web [Link]
  12. NORD [Link]
  13. Pediatric Pharmacotherapy [Link]
  14. Pubmed books [Link]
  15. Dailymed [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
FDA label
Download (125 KB)
MSDS
Download (167 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentErgocalciferol1
1Active Not RecruitingTreatmentPeyronie's Disease1
1CompletedDiagnosticHyperparathyroidism1
1CompletedTreatmentInflammatory Reaction / Insulin Resistance1
1, 2SuspendedTreatmentDeficiency, Vitamin D / Orthopedic Disorders / Polytrauma1
2CompletedTreatmentOsteoporosis1
2RecruitingPreventionOsteopenia / Osteoporosis1
2, 3RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
2, 3WithdrawnTreatmentCalcium Nephrolithiasis / Deficiency, Vitamin D1
3CompletedTreatmentChronic Kidney Disease Stage 3 and 41
3Unknown StatusTreatmentBreast Cancer1
4CompletedBasic Science25-Hydroxyvitamin D Concentration / 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 Kidney Disease (CKD) / Deficiency, Vitamin D1
4CompletedTreatmentChronic Kidney Disease (CKD) / Hyperparathyroidism, Secondary1
4CompletedTreatmentDeficiency, Vitamin D1
4CompletedTreatmentDeficiency, Vitamin D / Hypercalcemia / Hypercalciuria / Osteopenia / Osteoporosis / Parathyroid deficiency1
4CompletedTreatmentHip Fracture1
4CompletedTreatmentPruritus1
4Enrolling by InvitationTreatmentVitamin D2 Supplementation in Vitamin D Insufficiency1
4RecruitingTreatmentMyopathic Symptoms1
4RecruitingTreatmentSarcoidosis / Vitamin D Insufficiency1
4TerminatedTreatmentDeficiency, Vitamin D / Renal Failure Chronic Requiring Hemodialysis1
4Unknown StatusTreatmentBone Mineralization Defect1
4Unknown StatusTreatmentDeficiency, Vitamin D / Diabetes Mellitus (DM)1
4Unknown StatusTreatmentDeficiency, Vitamin D / Malnutrition1
4WithdrawnTreatmentAnemias / Chronic Kidney Disease (CKD) / CKD / Ergocalciferol / Hepcidin / Iron-Deficiency / Vitamin D1
Not AvailableActive Not RecruitingTreatmentAsthma / Deficiency, Vitamin D1
Not AvailableCompletedNot AvailableTuberculosis Infection1
Not AvailableCompletedBasic ScienceBlood Pressures / BMI >27 kg/m2 / BMI >30 kg/m2 / Endothelial Function / Renal Function1
Not AvailableCompletedOtherCongestive Heart Failure / Ischaemic Cardiomyopathy1
Not AvailableCompletedPreventionEnd Stage Renal Disease (ESRD)1
Not AvailableCompletedPreventionImpaired Fasting Glucose (IFG) / Impaired Glucose Tolerance / Vitamin D Insufficiency1
Not AvailableCompletedTreatmentBMI >30 kg/m21
Not AvailableCompletedTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Psychosis / Schizoaffective Disorders / Schizophrenic Disorders1
Not AvailableCompletedTreatmentCoronary Artery Disease / Deficiency, Vitamin D / Endothelial Dysfunction / Inflammatory Reaction1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentDeficiency, Vitamin D2
Not AvailableCompletedTreatmentDeficiency, Vitamin D / Healthy Volunteers1
Not AvailableCompletedTreatmentDeficiency, Vitamin D / Osteoporosis1
Not AvailableCompletedTreatmentEnd-Stage Renal Disease (ESRD)1
Not AvailableNot Yet RecruitingPreventionTransient Hypercalciuria1
Not AvailableRecruitingPreventionBone Density1
Not AvailableTerminatedNot AvailableFractures, Bone / Kidney Diseases / Muscle Weakness / Pain1
Not AvailableTerminatedTreatmentChronic Kidney Disease Stages 3-51
Not AvailableTerminatedTreatmentLeg Cramps, Nocturnal / Muscle Cramps1
Not AvailableUnknown StatusTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1
Not AvailableUnknown StatusTreatmentDeficiency, Vitamin D / Rheumatoid Arthritis1
Not AvailableWithdrawnTreatmentBMI >30 kg/m2 / Deficiency, Vitamin D / Insulin Resistance / Insulin Sensitivity1
Not AvailableWithdrawnTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D1

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
CapsuleOral1.25 mg/1
Capsule, liquid filledOral1.25 mg/1
LiquidOral0.2 mg/1mL
LiquidOral8000 [iU]/1mL
LiquidOral
Tablet, effervescentOral
Injection, powder, lyophilized, for solutionIntravenous
KitIntravenous
CapsuleOral
LiquidIntravenous
SyrupOral
CapsuleOral
TabletOral
Tablet, extended releaseOral
CapsuleOral1.25 1/1
TabletOral
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]
Kind
Protein group
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Voltage-gated calcium channel activity
Specific Function
This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only...

Components:
NameUniProt ID
Voltage-dependent calcium channel gamma-1 subunitQ06432
Voltage-dependent calcium channel gamma-2 subunitQ9Y698
Voltage-dependent calcium channel gamma-3 subunitO60359
Voltage-dependent calcium channel gamma-4 subunitQ9UBN1
Voltage-dependent calcium channel gamma-5 subunitQ9UF02
Voltage-dependent calcium channel gamma-6 subunitQ9BXT2
Voltage-dependent calcium channel gamma-7 subunitP62955
Voltage-dependent calcium channel gamma-8 subunitQ8WXS5
Voltage-dependent calcium channel subunit alpha-2/delta-1P54289
Voltage-dependent calcium channel subunit alpha-2/delta-2Q9NY47
Voltage-dependent calcium channel subunit alpha-2/delta-3Q8IZS8
Voltage-dependent calcium channel subunit alpha-2/delta-4Q7Z3S7
Voltage-dependent L-type calcium channel subunit alpha-1CQ13936
Voltage-dependent L-type calcium channel subunit alpha-1DQ01668
Voltage-dependent L-type calcium channel subunit alpha-1FO60840
Voltage-dependent L-type calcium channel subunit alpha-1SQ13698
Voltage-dependent L-type calcium channel subunit beta-1Q02641
Voltage-dependent L-type calcium channel subunit beta-2Q08289
Voltage-dependent L-type calcium channel subunit beta-3P54284
Voltage-dependent L-type calcium channel subunit beta-4O00305
Voltage-dependent N-type calcium channel subunit alpha-1BQ00975
Voltage-dependent P/Q-type calcium channel subunit alpha-1AO00555
Voltage-dependent R-type calcium channel subunit alpha-1EQ15878
Voltage-dependent T-type calcium channel subunit alpha-1GO43497
Voltage-dependent T-type calcium channel subunit alpha-1HO95180
Voltage-dependent T-type calcium channel subunit alpha-1IQ9P0X4
References
  1. Oxford Academic [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
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
No
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
No
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]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Catalyzes the reversible epimerization of D-ribulose 5-phosphate to D-xylulose 5-phosphate.
Specific Function
Identical protein binding
Gene Name
RPE
Uniprot ID
Q96AT9
Uniprot Name
Ribulose-phosphate 3-epimerase
Molecular Weight
24927.555 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 Da
References
  1. 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]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Vitamin transporter activity
Specific Function
Involved in vitamin D transport and storage, scavenging of extracellular G-actin, enhancement of the chemotactic activity of C5 alpha for neutrophils in inflammation and macrophage activation.
Gene Name
GC
Uniprot ID
P02774
Uniprot Name
Vitamin D-binding protein
Molecular Weight
52963.025 Da
References
  1. Speeckaert M., Speeckaert R., Geel N. and Delanghe J. (2014). Advances in Clinical Chemistry. Elsevier.

Drug created on June 13, 2005 07:24 / Updated on December 15, 2019 16:01