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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, (5E)-

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-GMGGYIQASA-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

Molecular Formula C27H40O3
Molecular Weight 412.6047
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 3
Optical Activity UNSPECIFIED

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
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
Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.
2014 Mar
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:39:52 GMT 2023
Edited
by admin
on Sat Dec 16 01:39:52 GMT 2023
Record UNII
QRA3492A7Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CALCIPOTRIOL, (5E)-
Common Name English
PRI 2205
Code English
CALCIPOTRIENE RELATED COMPOUND C [USP IMPURITY]
Common Name English
9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1,3,24-TRIOL, 24-CYCLOPROPYL-, (1.ALPHA.,3.BETA.,5E,7E,22E,24S)-
Common Name English
CALCIPOTRIENE RELATED COMPOUND C [USP-RS]
Common Name English
1,3-CYCLOHEXANEDIOL, 5-((2E)-2-((1R,3AS,7AR)-1-((1R,2E,4S)-4-CYCLOPROPYL-4-HYDROXY-1-METHYL-2-BUTEN-1-YL)OCTAHYDRO-7A-METHYL-4H-INDEN-4-YLIDENE)ETHYLIDENE)-4-METHYLENE-, (1S,3S,5E)-
Common Name English
(5E)-CALCIPOTRIOL
Common Name English
PRI-2205
Code English
5,6-TRANS-CALCIPOTRIOL
Common Name English
(5E)-CALCIPOTRIENE
Common Name English
CALCIPOTRIOL IMPURITY C [EP IMPURITY]
Common Name English
(5E,7E,22E,24S)-24-CYCLOPROPYL-9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1.ALPHA.,3.BETA.,24-TRIOL
Common Name English
CALCIPOTRIOL MONOHYDRATE IMPURITY C [EP IMPURITY]
Common Name English
Code System Code Type Description
PUBCHEM
9801803
Created by admin on Sat Dec 16 01:39:52 GMT 2023 , Edited by admin on Sat Dec 16 01:39:52 GMT 2023
PRIMARY
FDA UNII
QRA3492A7Q
Created by admin on Sat Dec 16 01:39:52 GMT 2023 , Edited by admin on Sat Dec 16 01:39:52 GMT 2023
PRIMARY
CAS
113082-99-8
Created by admin on Sat Dec 16 01:39:52 GMT 2023 , Edited by admin on Sat Dec 16 01:39:52 GMT 2023
PRIMARY
RS_ITEM_NUM
1086152
Created by admin on Sat Dec 16 01:39:52 GMT 2023 , Edited by admin on Sat Dec 16 01:39:52 GMT 2023
PRIMARY
Related Record Type Details
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