Calcipotriol

Identification

Summary

Calcipotriol is a topical synthetic vitamin D2 derivative used in the treatment of plaque psoriasis.

Brand Names
Calcitrene, Dovobet, Dovonex, Enstilar, Sorilux, Taclonex, Wynzora
Generic Name
Calcipotriol
DrugBank Accession Number
DB02300
Background

Calcipotriol (INN) or calcipotriene (USAN) is a sythetic derivative of calcitriol or Vitamin D.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 412.6047
Monoisotopic: 412.297745146
Chemical Formula
C27H40O3
Synonyms
  • Calcipotriene
  • Calcipotriol
External IDs
  • MC 903
  • MC-903

Pharmacology

Indication

For the treatment of moderate plaque psoriasis in adults.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Calcipotriene is a synthetic analog of vitamin D. In humans, the natural supply of vitamin D depends mainly on exposure to the ultraviolet rays of the sun for conversion of 7-dehydrocholesterol to vitamin D3 (cholecalciferol) in the skin.

Mechanism of action

The precise mechanism of calcipotriol in remitting psoriasis is not well-understood, however, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor while being less than 1% the activity in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis and are believed to undergo modulation of gene expression with binding of calcipotriol to the VDR. This modulation is thought to affect gene products related to cell differentiation and proliferation.

TargetActionsOrganism
UVitamin D3 receptor
antagonist
Humans
Absorption

Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound.

Route of elimination

The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Topically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.

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
Calcium acetateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium acetate.
Calcium carbonateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium carbonate.
Calcium chlorideThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium chloride.
Calcium citrateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium citrate.
Calcium glubionate anhydrousThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium glubionate anhydrous.
Calcium glucoheptonateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium glucoheptonate.
Calcium gluconateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium gluconate.
Calcium lactateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium lactate.
Calcium levulinateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium levulinate.
Calcium PhosphateThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Calcium Phosphate.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Calcipotriol hydrateS7499TYY6G147657-22-5XBKHACNRWFKJNC-MANNPBRJSA-N
International/Other Brands
Daivonex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CalcipotrieneAerosol, foam50 ug/1gTopicalMayne Pharma2021-02-15Not applicableUS flag
Calcipotriene 0.005% 60 gram FoamAerosol, foam50 ug/1gTopicalTrifluent Pharma LLC2020-08-24Not applicableUS flag
Calcipotriene FoamAerosol, foam50 ug/1gTopicalAyurax2020-01-082020-05-07US flag
DovonexSolution0.05 mg/1mLTopicalAllergan2006-01-012012-03-31US flag
DovonexSolution0.05 mg/1mLTopicalPhysicians Total Care, Inc.2009-08-12Not applicableUS flag
DovonexCream50 ug/1gTopicalLEO Pharma Inc.1996-10-01Not applicableUS flag
DovonexOintment50 ug/1gTopicalPhysicians Total Care, Inc.2004-06-302010-12-29US flag
DovonexCream50 ug/1gTopicalAllergan2006-01-012012-03-31US flag
DovonexOintment50 ug/1gTopicalWarner Chilcott2006-01-012007-04-01US flag
DovonexOintment50 mcg / gTopicalLeo Pharma1992-12-31Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CalcipotrieneSolution0.05 mg/1mLTopicalHi-Tech Pharmacal Co., Inc.2014-10-06Not applicableUS flag
CalcipotrieneSolution0.05 mg/1mLTopicalSandoz2009-11-202013-10-31US flag
CalcipotrieneCream0.05 mg/1gTopicalSandoz Inc.2012-07-27Not applicableUS flag
CalcipotrieneCream50 ug/1gTopicalPrasco Laboratories1996-10-01Not applicableUS flag
CalcipotrieneSolution0.05 mg/1mLTopicalFougera Pharmaceuticals Inc.2008-05-06Not applicableUS flag
CalcipotrieneSolution.05 mg/1mLTopicalCosette Pharmaceuticals, Inc.2011-03-24Not applicableUS flag
CalcipotrieneSolution0.05 mg/1mLTopicalAmneal Pharmaceuticals of New York Llc2009-11-20Not applicableUS flag
CalcipotrieneSolution0.05 mg/1mLTopicalNovel Laboratories, Inc.2017-12-26Not applicableUS flag
CalcipotrieneOintment50 ug/1gTopicalPrasco Laboratories2013-07-01Not applicableUS flag
CalcipotrieneCream50 ug/1gTopicalGlenmark Pharmaceuticals Inc.,Usa2015-06-10Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Calcipotriene and Betamethasone DipropionateCalcipotriol (50 ug/1g) + Betamethasone dipropionate (.643 mg/1g)OintmentTopicalPadagis Israel Pharmaceuticals Ltd2020-01-30Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol (50 ug/1g) + Betamethasone dipropionate (50 mg/1g)SuspensionTopicalTaro Pharmaceuticals U.S.A., Inc.2020-09-02Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (.5 mg/1g)SuspensionTopicalbryant ranch prepack2020-10-09Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)SuspensionTopicalPrasco Laboratories2020-01-07Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)SuspensionTopicalTOLMAR Inc.2020-05-11Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (.5 mg/1g)SuspensionTopicalbryant ranch prepack2020-10-09Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)OintmentTopicalPrasco Laboratories2020-01-28Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol (50 ug/1g) + Betamethasone dipropionate (.643 mg/1g)OintmentTopicalbryant ranch prepack2020-01-30Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)OintmentTopicalSandoz Inc.2014-03-31Not applicableUS flag
Calcipotriene and Betamethasone DipropionateCalcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)OintmentTopicalPerrigo New York Inc2008-06-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Calcipotriene 0.005% / Clobetasol Propionate 0.05%Calcipotriol (0.005 g/100g) + Clobetasol propionate (0.05 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-20Not applicableUS flag
Calcipotriene 0.005% / Diclofenac Sodium 3% / Hyaluronic Acid Sodium Salt 2% / Niacinamide 2%Calcipotriol (0.005 g/100g) + Diclofenac sodium (3 g/100g) + Sodium hyaluronate (2 g/100g) + Nicotinamide (2 g/100g)CreamTopicalSincerus Florida, LLC2019-05-07Not applicableUS flag
Calcipotriene 0.005% / Niacinamide 4%Calcipotriol (0.005 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2019-05-14Not applicableUS flag
Calcipotriene 0.005% / Triamcinolone Acetonide 0.1%Calcipotriol (0.005 g/100g) + Triamcinolone acetonide (0.1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-11Not applicableUS flag

Categories

ATC Codes
D05AX52 — Calcipotriol, combinationsD05AX02 — Calcipotriol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Triterpenoid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
seco-cholestane, hydroxy seco-steroid (CHEBI:50749) / Vitamin D3 and derivatives (LMST03020106)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
143NQ3779B
CAS number
112965-21-6
InChI Key
LWQQLNNNIPYSNX-UROSTWAQSA-N
InChI
InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
IUPAC Name
(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
SMILES
O[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC1

References

Synthesis Reference

Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski, "Process for Preparation of Pharmaceutically Pure Anhydrous Calcipotriol." U.S. Patent US20080214876, issued September 04, 2008.

US20080214876
General References
Not Available
Human Metabolome Database
HMDB0015567
KEGG Drug
D01125
PubChem Compound
5288783
PubChem Substance
46507122
ChemSpider
4450880
BindingDB
50369964
RxNav
29365
ChEBI
50749
ChEMBL
CHEMBL1200666
ZINC
ZINC000003921872
Therapeutic Targets Database
DAP000292
PharmGKB
PA448714
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
MC9
RxList
RxList Drug Page
Wikipedia
Calcipotriol
PDB Entries
1s19

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
4CompletedOtherPsoriasis Vulgaris (Plaque Psoriasis)1
4CompletedSupportive CareAdherence1
4CompletedTreatmentPsoriasis (PsO)5
4CompletedTreatmentPsoriasis (PsO) / Psoriasis Vulgaris (Plaque Psoriasis)1
4CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)7
4Not Yet RecruitingTreatmentPsoriasis Nail1
4Not Yet RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
4RecruitingTreatmentPsoriasis (PsO)3
4TerminatedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Contract Pharm
  • Dispensing Solutions
  • E. Fougera and Co.
  • Glenmark Generics Ltd.
  • Hi Tech Pharmacal Co. Inc.
  • LEO Pharma Inc.
  • Nycomed Inc.
  • Physicians Total Care Inc.
  • Sandoz
  • Warner Chilcott Co. Inc.
  • WC Pharmaceuticals
Dosage Forms
FormRouteStrength
GelTopical
CreamTopical0.05 mg/1g
SolutionTopical.05 mg/1mL
SolutionTopical
CreamTopical
OintmentCutaneous0.05 MG/G
SolutionCutaneous; Topical0.05 MG/ML
OintmentTopical0.05 mg/1g
Gel
Ointment
GelTopical0.5 mg/g
OintmentTopical0.5 mg/g
CreamTopical0005 %
Ointment
OintmentCutaneous0005 %
SolutionCutaneous50 mcg/ml
SolutionTopical50 MICROGRAMMI/ML
CreamTopical5 mg
LotionTopical5 mg
OintmentTopical50 mcg/g
OintmentTopical0.005 g
GelCutaneous
OintmentCutaneous
CreamTopical50 ug/1g
OintmentTopical50 ug/1g
OintmentTopical50 mcg / g
SolutionTopical0.05 mg/1mL
CreamTopical50 mcg / g
SolutionTopical50 mcg / mL
Aerosol, foamTopical
Aerosol, foamCutaneous
KitTopical
SolutionTopical
CreamTopical
OintmentTopical
Aerosol, foamTopical50 ug/1g
OintmentTopical
Spray, meteredTopical
SuspensionTopical
Prices
Unit descriptionCostUnit
Dovonex 0.005% Cream 120 gm Tube607.03USD tube
Dovonex 0.005% Solution 60ml Bottle323.98USD bottle
Dovonex 0.005% Cream 60 gm Tube303.51USD tube
Dovonex 0.005% cream4.23USD g
Dovonex 50 mcg/ml Solution0.84USD ml
Dovonex 50 mcg/g Cream0.83USD g
Dovonex 50 mcg/g Ointment0.81USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5763426No1998-06-092015-06-09US flag
US6753013No2004-06-222020-01-27US flag
US6787529No2004-09-072020-01-27US flag
US8263580No2012-09-112028-09-27US flag
US8629128No2014-01-142026-05-26US flag
US9119781Yes2015-09-012031-12-10US flag
US10130640Yes2018-11-202031-12-10US flag
US9566286No2017-02-142031-06-10US flag
US10617698No2020-04-142031-06-10US flag
US10660908No2020-05-262031-06-10US flag
US10688108No2020-06-232031-06-10US flag
US10682364No2020-06-162031-06-10US flag
US10716799No2020-07-212031-06-10US flag
US10265265No2019-04-232027-09-27US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0135 mg/mLALOGPS
logP4.63ALOGPS
logP3.84ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.45 m3·mol-1ChemAxon
Polarizability49.59 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9945
Blood Brain Barrier+0.8426
Caco-2 permeable+0.7643
P-glycoprotein substrateSubstrate0.7718
P-glycoprotein inhibitor INon-inhibitor0.7297
P-glycoprotein inhibitor IINon-inhibitor0.9687
Renal organic cation transporterNon-inhibitor0.813
CYP450 2C9 substrateNon-substrate0.8383
CYP450 2D6 substrateNon-substrate0.8975
CYP450 3A4 substrateSubstrate0.7113
CYP450 1A2 substrateNon-inhibitor0.7455
CYP450 2C9 inhibitorNon-inhibitor0.7898
CYP450 2D6 inhibitorNon-inhibitor0.9336
CYP450 2C19 inhibitorNon-inhibitor0.7994
CYP450 3A4 inhibitorNon-inhibitor0.8014
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7475
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9332
BiodegradationNot ready biodegradable0.9871
Rat acute toxicity3.9699 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9198
hERG inhibition (predictor II)Non-inhibitor0.8018
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Details
1. Vitamin D3 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Sato H, Ogino Y, Takagi H, Hata J, Asano S, Ohta T, Komoriya K: Pharmacological profiles of high-concentration (20 microg/g) tacalcitol ointment: effects on cutaneous inflammation, epidermal proliferation, and differentiation in mice. J Dermatol. 2003 Jul;30(7):510-24. [Article]
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. Jones G, Byford V, West S, Masuda S, Ibrahim G, Kaufmann M, Knutson JC, Strugnell S, Mehta R: Hepatic activation and inactivation of clinically-relevant vitamin D analogs and prodrugs. Anticancer Res. 2006 Jul-Aug;26(4A):2589-95. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 26, 2021 21:40