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Identification
NameCalcipotriol
Accession NumberDB02300  (EXPT02131)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
Calcipotriene
Calcipotriol
Daivonex
Dovonex
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Calcipotrienecream50 ug/gtopicalPrasco Laboratories1996-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrieneointment50 ug/gtopicalPrasco Laboratories2013-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonexsolution.05 mg/mLtopicalPhysicians Total Care, Inc.2009-08-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonexcream50 ug/gtopicalPhysicians Total Care, Inc.2006-09-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonexsolution.05 mg/mLtopicalLEO Pharma Inc.1997-06-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonexcream50 ug/gtopicalLEO Pharma Inc.1996-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonexsolution.05 mg/mLtopicalWarner Chilcott (US), LLC2006-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonexcream50 ug/gtopicalWarner Chilcott (US), LLC2006-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dovonex - Crm 50mcg/gmcream50 mcgtopicalLeo Pharma Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dovonex Ont 50mcg/gmointment50 mcgtopicalLeo Pharma Inc1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dovonex Solution - Top 50mcg/mlsolution50 mcgtopicalLeo Pharma Inc1996-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Soriluxaerosol, foam50 ug/gtopicalStiefel Laboratories Inc2010-10-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Calcipotrienesolution.05 mg/mLtopicalGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2009-11-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrieneointment50 ug/gtopicalGlenmark Pharmaceuticals Inc., Usa2010-03-24Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrieneointment.05 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2010-03-24Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrienesolution.05 mg/mLtopicalHi Tech Pharmacal Co., Inc.2014-10-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrienecream.05 mg/gtopicalSandoz Inc.2012-07-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrienesolution.05 mg/mLtopicalG&W Laboratories, Inc.2011-04-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrienesolution.05 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2008-05-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcipotrienecream50 ug/gtopicalGlenmark Pharmaceuticals Inc.,Usa2015-06-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Calcitreneointment.05 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2010-03-24Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot 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 KeyInChIKey=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
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
Pharmacology
IndicationFor the treatment of moderate plaque psoriasis in adults.
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.
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
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
Suspensiontopical
Spray, meteredtopical
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
CountryPatent NumberApprovedExpires (estimated)
United States57634261995-06-092015-06-09
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
SpectraNot 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 CodesD05AX02
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DigoxinCalcipotriol may increase the arrhythmogenic activities of Digoxin.
DihydrotachysterolThe risk or severity of adverse effects can be increased when Dihydrotachysterol is combined with Calcipotriol.
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Calcipotriol.
Food InteractionsNot Available

Targets

1. Vitamin D3 receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Vitamin D3 receptor P11473 Details

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
  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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Myeloperoxidase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Myeloperoxidase P05164 Details

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

2. 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial Q07973 Details

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

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Drug created on June 13, 2005 07:24 / Updated on November 27, 2015 15:01