U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H40O3.H2O
Molecular Weight 430.62
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of CALCIPOTRIENE MONOHYDRATE

SMILES

O.[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)\C=C\[C@@H](O)C4CC4

InChI

InChIKey=XBKHACNRWFKJNC-MANNPBRJSA-N
InChI=1S/C27H40O3.H2O/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;1H2/b13-6+,19-7+,21-10-;/t17-,22-,23-,24+,25-,26+,27-;/m1./s1

HIDE SMILES / InChI
5E-Calcipotriol is a geometric analog of vitamin D derivative calcipotriol. It was shown to enhance anticancer activity of 5-fluorouracil in an in vivo mouse colon cancer model and anticancer activity of imatinib in an in vivo lung cancer model. The compound also demonstrated activity in a subcutaneous MCF-7 model of breast cancer in vivo. The detailed mechanism of action for 5E-calcipotriol is not known.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Curative
DOVONEX

Approved Use

Calcipotriene Cream, 0.005%, is indicated for the treatment of plaque psoriasis. The safety and effectiveness of topical calcipotriene in dermatoses other than psoriasis have not been established.

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
55.9 pg/mL
0.005 % 1 times / day multiple, topical
dose: 0.005 %
route of administration: Topical
experiment type: MULTIPLE
co-administered: BETAMETHASONE DIPROPIONATE
CALCIPOTRIENE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
24.4 pg/mL
0.005 % 1 times / day multiple, topical
dose: 0.005 %
route of administration: Topical
experiment type: MULTIPLE
co-administered: BETAMETHASONE DIPROPIONATE
MC1080 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
82.5 pg × h/mL
0.005 % 1 times / day multiple, topical
dose: 0.005 %
route of administration: Topical
experiment type: MULTIPLE
co-administered: BETAMETHASONE DIPROPIONATE
CALCIPOTRIENE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
59.3 pg × h/mL
0.005 % 1 times / day multiple, topical
dose: 0.005 %
route of administration: Topical
experiment type: MULTIPLE
co-administered: BETAMETHASONE DIPROPIONATE
MC1080 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Disc. AE: Application site bleeding, Application site erythema...
Other AEs: Dental caries, Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Application site bleeding (1 patient)
Application site erythema (6 patients)
Application site exfoliation (1 patient)
Application site irritation (5 patients)
Application site pruritus (6 patients)
Application site swelling (1 patient)
Application site folliculitis (1 patient)
Other AEs:
Dental caries (1 patient)
Hypersensitivity (1 patient)
Musculoskeletal pain (1 patient)
Migraine (1 patient)
Atrial fibrillation (1 patient)
Cardiac failure congestive (1 patient)
Sources:
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Disc. AE: Application site erythema, Application site irritation...
Other AEs: Nausea, Toothache...
AEs leading to
discontinuation/dose reduction:
Application site erythema (9 patients)
Application site irritation (9 patients)
Application site pruritus (7 patients)
Other AEs:
Nausea (1 patient)
Toothache (2 patients)
Nasopharyngitis (7 patients)
Upper respiratory tract infection (2 patients)
Headache (3 patients)
Cough (1 patient)
Hypertension (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Atrial fibrillation 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Cardiac failure congestive 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Dental caries 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Hypersensitivity 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Migraine 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Musculoskeletal pain 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site bleeding 1 patient
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site exfoliation 1 patient
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site folliculitis 1 patient
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site swelling 1 patient
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site irritation 5 patients
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site erythema 6 patients
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Application site pruritus 6 patients
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48
n = 473
Health Status: unhealthy
Condition: psoriasis
Age Group: 48
Sex: M+F
Population Size: 473
Sources:
Cough 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Nausea 1 patient
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Hypertension 2 patients
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Toothache 2 patients
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Upper respiratory tract infection 2 patients
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Headache 3 patients
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Nasopharyngitis 7 patients
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Application site pruritus 7 patients
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Application site erythema 9 patients
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Application site irritation 9 patients
Disc. AE
0.005 % 2 times / day multiple, topical
Recommended
Dose: 0.005 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.005 %, 2 times / day
Sources:
unhealthy, 48.2
n = 437
Health Status: unhealthy
Condition: psoriasis
Age Group: 48.2
Sex: M+F
Population Size: 437
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 20.8 uM]
yes [IC50 37.9 uM]
yes [IC50 6 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The use of topical calcipotriene/calcipotriol in conditions other than plaque-type psoriasis.
1997 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Vitamin D receptor gene polymorphisms, particularly the novel A-1012G promoter polymorphism, are associated with vitamin D3 responsiveness and non-familial susceptibility in psoriasis.
2005 May
Effect of topical vitamin D analogue on in vivo contact sensitization.
2006 Oct
Patents

Sample Use Guides

Apply a thin layer of Dovonex Cream to the affected skin twice daily and rub in gently and completely. The safety and efficacy of Dovonex Cream have been demonstrated in patients treated for eight weeks.
Route of Administration: Topical
The immune modulatory effects of betamethasone, calcipotriol and the combination in ex vivo cultures of psoriatic skin and in vitro cultures of primary human cells that recapitulate key cellular activities of psoriatic inflammation were investigated and compared.
Name Type Language
CALCIPOTRIENE HYDRATE
ORANGE BOOK  
Preferred Name English
CALCIPOTRIENE MONOHYDRATE
Common Name English
TACLONEX COMPONENT CALCIPOTRIENE HYDRATE
Common Name English
CALCIPOTRIENE HYDRATE COMPONENT OF TACLONEX
Common Name English
CALCIPOTRIOL HYDRATE [JAN]
Common Name English
MC-903 HYDRATE
Code English
CALCIPOTRIENE HYDRATE [ORANGE BOOK]
Common Name English
CALCIPOTRIOL MONOHYDRATE
EP   WHO-DD  
EP  
Official Name English
Calcipotriol monohydrate [WHO-DD]
Common Name English
CALCIPOTRIOL HYDRATE
Common Name English
ENSTILAR COMPONENT CALCIPOTRIENE HYDRATE
Brand Name English
CALCIPOTRIOL MONOHYDRATE [EP MONOGRAPH]
Common Name English
9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1,3,24-TRIOL, 24-CYCLOPROPYL-, (1.ALPHA.,3.BETA.,5Z,7E,22E,24S)-, MONOHYDRATE
Common Name English
CALCIPOTRIENE HYDRATE COMPONENT OF ENSTILAR
Brand Name English
CALCIPOTRIENE MONOHYDRATE [USP MONOGRAPH]
Common Name English
Code System Code Type Description
SMS_ID
100000090521
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
RXCUI
1299898
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY RxNorm
DAILYMED
S7499TYY6G
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200666
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
EVMPD
SUB26081
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
PUBCHEM
49800068
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
CHEBI
90861
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
CAS
147657-22-5
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
FDA UNII
S7499TYY6G
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY
DRUG BANK
DBSALT001386
Created by admin on Fri Dec 15 15:32:51 GMT 2023 , Edited by admin on Fri Dec 15 15:32:51 GMT 2023
PRIMARY