CALCIPOTRIENE MONOHYDRATE

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 Search

SMILES

O.C[C@H](\C=C\[C@@H](O)C1CC1)[C@H]2CC[C@@H]3[C@]2(C)CCC\C3=C/C=C4/C[C@@H](O)C[C@H](O)C4=C

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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
Sources: https://www.drugs.com/dovonex.html | https://www.ncbi.nlm.nih.gov/pubmed/22879719 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020554s006lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/16880407https://www.ncbi.nlm.nih.gov/pubmed/23777514https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19941115&CC=JP&NR=H06316558A&KC=A

7Z-Calcipotriol is an isomeric impurity in vitamin D analog calcipotriol. Synthesis of 7Z-Calcipotriol was disclosed by Japanese company Kuraray Co in a patent application JP 06316558.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin D receptor 25 Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16880407	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23777514	Palliative	Preclinical	Unknown Approved Use Unknown
Lung cancer 70 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26580599	Palliative	Preclinical	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24202449	Primary	Preclinical	Unknown Approved Use Unknown
Unknown 2596
Plaque psoriasis 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020554s006lbl.pdf	Curative	Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
55.9 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207589s000lbl.pdf	0.005 % 1 times / day multiple, topical dose: 0.005 % route of administration: Topical experiment type: MULTIPLE co-administered: BETAMETHASONE DIPROPIONATE	BETAMETHASONE DIPROPIONATE	CALCIPOTRIENE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
24.4 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207589s000lbl.pdf	0.005 % 1 times / day multiple, topical dose: 0.005 % route of administration: Topical experiment type: MULTIPLE co-administered: BETAMETHASONE DIPROPIONATE	BETAMETHASONE DIPROPIONATE	MC1080 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
82.5 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207589s000lbl.pdf	0.005 % 1 times / day multiple, topical dose: 0.005 % route of administration: Topical experiment type: MULTIPLE co-administered: BETAMETHASONE DIPROPIONATE	BETAMETHASONE DIPROPIONATE	CALCIPOTRIENE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
59.3 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207589s000lbl.pdf	0.005 % 1 times / day multiple, topical dose: 0.005 % route of administration: Topical experiment type: MULTIPLE co-administered: BETAMETHASONE DIPROPIONATE	BETAMETHASONE DIPROPIONATE	MC1080 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP1 116 P-gp 1741 BCRP 910

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30232176/	yes [IC50 20.8 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30232176/	yes [IC50 37.9 uM]
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30232176/	yes [IC50 6 uM]

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA007RGL	https://www.aablocks.com/goods/Goods/detail?id=AA007RGL
Aaron Chemicals	AR007S8D	http://www.aaronchem.com/112965-21-6
Achemtek	0104-005732	http://www.achemtek.com/112828-00-9
Acorn PharmaTech	ACN-032164	http://www.acornpharmatech.com/
AHH Chemical co.,ltd	MT-01143	http://www.ahhchemical.com/product/MT-01143.html
AK Scientific, Inc. (AKSCI)	O763	http://www.aksci.com/item_detail.php?cat=O763
Aurum Pharmatech LLC	W-5148	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5148
AvaChem Scientific	2206	http://www.avachem.com/productSearch.asp?2206
Capot Chemical	18810	http://www.capotchem.com/en/18810.htm
Capot Chemical	19334	http://www.capotchem.com/en/19334.htm
Capot Chemical	PubChem18810	http://www.capotchem.com/en/18810.htm
Capot Chemical	PubChem19334	http://www.capotchem.com/en/19334.htm
Chem Scene	CS-0387	http://www.chemscene.com/112965-21-6.html
ChemMol	97900692	http://www.chemmol.com/chemmol/97900692.html
Chemspace	CSSB00020656683	https://chem-space.com/CSSB00020656683
Clearsynth	CS-O-06254	https://www.clearsynth.com/en/CSO06254.html
eNovation Chemicals	D371144	https://www.enovationchem.com/ProductDetails.asp?ProductID=D371144
eNovation Chemicals	D675441	https://www.enovationchem.com/ProductDetails.asp?ProductID=D675441
eNovation Chemicals	D761746	https://www.enovationchem.com/ProductDetails.asp?ProductID=D761746
eNovation Chemicals	Y0975952	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0975952
Excenen	EX-A4430	https://www.excenen.com/searchresultlist.php?id=EX-A4430
Glentham Life Sciences	GP2043	http://www.glentham.com/products/product/GP2043/
iChemical	EBD7189	http://www.ichemical.com/products/112828-00-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01343326	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343326
MedChem Express	HY-10001	https://www.medchemexpress.com/Calcipotriol.html
OChem	7044	http://www.ocheminc.com/index.php?act=psearch&pid=828C009
Selleck Chemicals	S3739	http://www.selleckchem.com/products/calcipotriene.html
Smolecule	S800532	https://www.smolecule.com/products/s800532
Tocris	2700	https://www.tocris.com/products/calcipotriol_2700

PubMed

Title	Date	PubMed
Vitamin D Analogs Potentiate the Antitumor Effect of Imatinib Mesylate in a Human A549 Lung Tumor Model.	2015-11-13	26580599
Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.	2014-03	24039193
The atopic dermatitis-like symptoms induced by MC903 were alleviated in JNK1 knockout mice.	2013-12	24046278
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.	2013-10-31	24202449
Vitamin D analogs enhance the anticancer activity of 5-fluorouracil in an in vivo mouse colon cancer model.	2013-06-18	23777514
Calcipotriol induces autophagy in HeLa cells and keratinocytes.	2011-04	21228817
Hypercalcemia caused by vitamin D3 analogs in psoriasis treatment.	2007-12	18173537
Effect of topical vitamin D analogue on in vivo contact sensitization.	2006-10	17043189
Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis.	2006-08-01	16880407
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Vitamin D receptor gene polymorphisms, particularly the novel A-1012G promoter polymorphism, are associated with vitamin D3 responsiveness and non-familial susceptibility in psoriasis.	2005-05	15864137
Severe hypercalcemia and hypernatremia associated with calcipotriol for treatment of psoriasis.	2004	14999528
Nonpsoriatic uses of calcipotriol.	2002-08-28	12196891
The use of topical calcipotriene/calcipotriol in conditions other than plaque-type psoriasis.	1997-09	9344189
Topical calcipotriene has no short-term effect on calcium and bone metabolism of patients with psoriasis.	1996-03	8609254
Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line.	1996-02-27	8620449
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3.	1995-01	7530193
Calcipotriol inhibits rectal epithelial cell proliferation in ulcerative proctocolitis.	1994-12	7829008
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.	1994-08	7976510
Hypercalcaemia during treatment of psoriasis with calcipotriol.	1994-06	8011511
Hypercalcaemic crisis after excessive topical use of a vitamin D derivative.	1994-03	8120527
Hypercalcaemia associated with calcipotriol (Dovonex) treatment.	1993-04-03	8490416
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	7508215

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 18:00:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:44 GMT 2025`
Record UNII	S7499TYY6G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALCIPOTRIENE HYDRATE

Preferred Name

English

CALCIPOTRIENE MONOHYDRATE

Common Name

English

TACLONEX COMPONENT CALCIPOTRIENE HYDRATE

Common Name

English

CALCIPOTRIOL HYDRATE [JAN]

Common Name

English

MC-903 HYDRATE

Code

English

CALCIPOTRIENE HYDRATE [ORANGE BOOK]

Common Name

English

CALCIPOTRIOL MONOHYDRATE

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 MONOHYDRATE [USP MONOGRAPH]

Common Name

English

Code System Code Type Description

SMS_ID

100000090521