You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCalcipotriol
Accession NumberDB02300  (EXPT02131)
TypeSmall Molecule
GroupsApproved
DescriptionCalcipotriol (INN) or calcipotriene (USAN) is a sythetic derivative of calcitriol or Vitamin D.
Structure
Thumb
Synonyms
Calcipotriene
Calcipotriol
Daivonex
Dovonex
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CalcipotrieneOintment50 ug/gTopicalPrasco Laboratories2013-07-01Not applicableUs
CalcipotrieneCream50 ug/gTopicalPrasco Laboratories1996-10-01Not applicableUs
DovonexCream50 ug/gTopicalWarner Chilcott (US), LLC2006-01-01Not applicableUs
DovonexCream50 ug/gTopicalPhysicians Total Care, Inc.2006-09-15Not applicableUs
DovonexSolution.05 mg/mLTopicalWarner Chilcott (US), LLC2006-01-01Not applicableUs
DovonexSolution.05 mg/mLTopicalPhysicians Total Care, Inc.2009-08-12Not applicableUs
DovonexCream50 ug/gTopicalLEO Pharma Inc.1996-10-01Not applicableUs
DovonexSolution.05 mg/mLTopicalLEO Pharma Inc.1997-06-01Not applicableUs
Dovonex - Crm 50mcg/gmCream50 mcgTopicalLeo Pharma Inc1995-12-31Not applicableCanada
Dovonex Ont 50mcg/gmOintment50 mcgTopicalLeo Pharma Inc1992-12-31Not applicableCanada
Dovonex Solution - Top 50mcg/mlSolution50 mcgTopicalLeo Pharma Inc1996-12-312016-03-16Canada
SoriluxAerosol, foam50 ug/gTopicalStiefel Laboratories Inc2010-10-26Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CalcipotrieneSolution.05 mg/mLTopicalImpax Generics2009-11-20Not applicableUs
CalcipotrieneSolution.05 mg/mLTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2008-05-06Not applicableUs
CalcipotrieneSolution.05 mg/mLTopicalG&W Laboratories, Inc.2011-04-04Not applicableUs
CalcipotrieneCream.05 mg/gTopicalSandoz Inc.2012-07-27Not applicableUs
CalcipotrieneOintment50 ug/gTopicalGlenmark Pharmaceuticals Inc., Usa2010-03-24Not applicableUs
CalcipotrieneSolution.05 mg/mLTopicalHi Tech Pharmacal Co., Inc.2014-10-06Not applicableUs
CalcipotrieneCream50 ug/gTopicalGlenmark Pharmaceuticals Inc.,Usa2015-06-10Not applicableUs
CalcipotrieneOintment.05 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2010-03-24Not applicableUs
CalcitreneOintment.05 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2010-03-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DaivonexNot Available
Brand mixtures
NameLabellerIngredients
Calcipotriene 0.005% and Betamethasone Dipropionate 0.064%Sandoz Inc.
Calcipotriene and Betamethasone DipropionatePerrigo New York Inc
Dovobet GelLeo Pharma Inc
Dovobet OintmentLeo Pharma Inc
EnstilarLEO Pharma Inc.
TaclonexWarner Chilcott (US), LLC
Taclonex ScalpWarner Chilcott (US), LLC
Salts
Name/CASStructureProperties
Calcipotriol hydrate
ThumbNot applicableDBSALT001386
Categories
UNII143NQ3779B
CAS number112965-21-6
WeightAverage: 412.6047
Monoisotopic: 412.297745146
Chemical FormulaC27H40O3
InChI KeyLWQQLNNNIPYSNX-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[[email protected]](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[[email protected]](O)C1=C)C1CC1
Pharmacology
IndicationFor the treatment of moderate plaque psoriasis in adults.
Structured Indications
PharmacodynamicsCalcipotriene 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 actionThe 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% as active as the calcitriol 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 it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.
TargetKindPharmacological actionActionsOrganismUniProt ID
Vitamin D3 receptorProteinunknown
antagonist
HumanP11473 details
Related Articles
AbsorptionClinical 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 distributionNot Available
Protein bindingNot 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 eliminationThe 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 lifeNot Available
ClearanceNot Available
ToxicityTopically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Calcipotriol.Approved
AlfacalcidolThe risk or severity of adverse effects can be increased when Alfacalcidol is combined with Calcipotriol.Approved, Nutraceutical
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Calcipotriol.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Calcipotriol.Investigational
BendroflumethiazideBendroflumethiazide may increase the hypercalcemic activities of Calcipotriol.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Calcipotriol.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Calcipotriol.Approved
CalcidiolThe risk or severity of adverse effects can be increased when Calcidiol is combined with Calcipotriol.Approved, Nutraceutical
CalcitriolThe risk or severity of adverse effects can be increased when Calcitriol is combined with Calcipotriol.Approved, Nutraceutical
CalciumThe risk or severity of adverse effects can be increased when Calcium is combined with Calcipotriol.Nutraceutical
Calcium AcetateThe risk or severity of adverse effects can be increased when Calcium Acetate is combined with Calcipotriol.Approved
Calcium carbonateThe risk or severity of adverse effects can be increased when Calcium carbonate is combined with Calcipotriol.Approved
Calcium ChlorideThe risk or severity of adverse effects can be increased when Calcium Chloride is combined with Calcipotriol.Approved
Calcium citrateThe risk or severity of adverse effects can be increased when Calcium citrate is combined with Calcipotriol.Approved
Calcium glubionateThe risk or severity of adverse effects can be increased when Calcium glubionate is combined with Calcipotriol.Approved
Calcium GluceptateThe risk or severity of adverse effects can be increased when Calcium Gluceptate is combined with Calcipotriol.Approved
Calcium gluconateThe risk or severity of adverse effects can be increased when Calcium gluconate is combined with Calcipotriol.Approved, Vet Approved
ChlorothiazideChlorothiazide may increase the hypercalcemic activities of Calcipotriol.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypercalcemic activities of Calcipotriol.Approved
CholecalciferolThe risk or severity of adverse effects can be increased when Cholecalciferol is combined with Calcipotriol.Approved, Nutraceutical
CholestyramineThe serum concentration of Calcipotriol can be decreased when it is combined with Cholestyramine.Approved
ColesevelamThe serum concentration of Calcipotriol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Calcipotriol can be decreased when it is combined with Colestipol.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Calcipotriol.Approved, Investigational
DanazolDanazol may increase the hypercalcemic activities of Calcipotriol.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Calcipotriol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Calcipotriol.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Calcipotriol.Approved
DihydrotachysterolThe risk or severity of adverse effects can be increased when Dihydrotachysterol is combined with Calcipotriol.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Calcipotriol.Approved, Investigational
DoxercalciferolThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Doxercalciferol.Approved
ErgocalciferolThe risk or severity of adverse effects can be increased when Ergocalciferol is combined with Calcipotriol.Approved, Nutraceutical
HydrochlorothiazideHydrochlorothiazide may increase the hypercalcemic activities of Calcipotriol.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypercalcemic activities of Calcipotriol.Approved
IndapamideIndapamide may increase the hypercalcemic activities of Calcipotriol.Approved
MethyclothiazideMethyclothiazide may increase the hypercalcemic activities of Calcipotriol.Approved
MetolazoneMetolazone may increase the hypercalcemic activities of Calcipotriol.Approved
Mineral oilThe serum concentration of Calcipotriol can be decreased when it is combined with Mineral oil.Approved
OrlistatThe serum concentration of Calcipotriol can be decreased when it is combined with Orlistat.Approved, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Calcipotriol.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Calcipotriol.Approved, Vet Approved
ParicalcitolThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Paricalcitol.Approved, Investigational
PolythiazidePolythiazide may increase the hypercalcemic activities of Calcipotriol.Approved
QuinethazoneQuinethazone may increase the hypercalcemic activities of Calcipotriol.Approved
SucralfateThe serum concentration of Sucralfate can be increased when it is combined with Calcipotriol.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Calcipotriol.Approved, Investigational
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Calcipotriol.Approved, Vet Approved
Food InteractionsNot Available
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 ReferencesNot Available
External Links
ATC CodesD05AX02D05AX52
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical.05 mg/g
OintmentTopical.05 mg/g
OintmentTopical50 ug/g
SolutionTopical.05 mg/mL
GelTopical
CreamTopical50 ug/g
CreamTopical50 mcg
OintmentTopical50 mcg
SolutionTopical50 mcg
Aerosol, foamTopical
Aerosol, foamTopical50 ug/g
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)
US5763426 No1995-06-092015-06-09Us
US6753013 No2000-01-272020-01-27Us
US6787529 No2000-01-272020-01-27Us
US8263580 No2008-09-272028-09-27Us
US8629128 No2006-05-262026-05-26Us
US9119781 No2011-06-102031-06-10Us
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Steroid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
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/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
Gene Name:
VDR
Uniprot ID:
P11473
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
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. [PubMed:12928540 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity
Specific Function:
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can perform up to 6 rounds of hydroxylation of calcitriol leading to calcitroic acid. It also shows 23-hydroxylating activity leading to 1-alpha,25-dihydroxyvitamin D(3)-26,23-lactone as end product.
Gene Name:
CYP24A1
Uniprot ID:
Q07973
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. [PubMed:16886668 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on December 03, 2016 02:47