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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H40O3
Molecular Weight 412.6047
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of CALCIPOTRIOL, (7Z)-

SMILES

[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=LWQQLNNNIPYSNX-CZCKTKQUSA-N
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

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
Effects of 1 alpha,25-dihydroxy-vitamin D3 and calcipotriol on organotypic cultures of outer root sheath cells: a potential model to evaluate antipsoriatic drugs.
1993
Hypercalcaemia associated with calcipotriol (Dovonex) treatment.
1993 Apr 3
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.
1994 Aug
Calcipotriol inhibits rectal epithelial cell proliferation in ulcerative proctocolitis.
1994 Dec
Hypercalcaemia during treatment of psoriasis with calcipotriol.
1994 Jun
Hypercalcaemic crisis after excessive topical use of a vitamin D derivative.
1994 Mar
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3.
1995 Jan
Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line.
1996 Feb 27
Topical calcipotriene has no short-term effect on calcium and bone metabolism of patients with psoriasis.
1996 Mar
The use of topical calcipotriene/calcipotriol in conditions other than plaque-type psoriasis.
1997 Sep
Nonpsoriatic uses of calcipotriol.
2002 Sep-Oct
Severe hypercalcemia and hypernatremia associated with calcipotriol for treatment of psoriasis.
2004
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
Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis.
2006 Aug 1
Effect of topical vitamin D analogue on in vivo contact sensitization.
2006 Oct
Hypercalcemia caused by vitamin D3 analogs in psoriasis treatment.
2007 Dec
Calcipotriol induces autophagy in HeLa cells and keratinocytes.
2011 Apr
The atopic dermatitis-like symptoms induced by MC903 were alleviated in JNK1 knockout mice.
2013 Dec
Vitamin D analogs enhance the anticancer activity of 5-fluorouracil in an in vivo mouse colon cancer model.
2013 Jun 18
Synthesis and Biological Activity of Diastereomeric and Geometric Analogs of Calcipotriol, PRI-2202 and PRI-2205, Against Human HL-60 Leukemia and MCF-7 Breast Cancer Cells.
2013 Oct 31
Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.
2014 Mar
Vitamin D Analogs Potentiate the Antitumor Effect of Imatinib Mesylate in a Human A549 Lung Tumor Model.
2015 Nov 13
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
CALCIPOTRIOL, (7Z)-
Common Name English
(5Z,7Z,22E,24S)-24-CYCLOPROPYL-9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1.ALPHA.,3.BETA.,24-TRIOL
Common Name English
(7Z)-CALCIPOTRIENE
Common Name English
CALCIPOTRIOL MONOHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
CALCIPOTRIOL IMPURITY B [EP IMPURITY]
Common Name English
(7Z)-CALCIPOTRIOL
Common Name English
Code System Code Type Description
PUBCHEM
17754072
Created by admin on Sat Dec 16 01:39:51 GMT 2023 , Edited by admin on Sat Dec 16 01:39:51 GMT 2023
PRIMARY
FDA UNII
075Y05GJ7L
Created by admin on Sat Dec 16 01:39:51 GMT 2023 , Edited by admin on Sat Dec 16 01:39:51 GMT 2023
PRIMARY