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.[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

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://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=Ahttps://www.ncbi.nlm.nih.gov/pubmed/23777514

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.

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 1430

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23777514	Palliative	Preclinical	Unknown Approved Use Unknown
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26580599	Palliative	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24202449	Primary	Preclinical	Unknown Approved Use Unknown
Unknown 2578
Plaque psoriasis 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020554s006lbl.pdf	Curative	Approved 8429	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

Doses

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022563Orig1s000MedR.pdf	unhealthy, 48 n = 473 Health Status: unhealthy Condition: psoriasis Age Group: 48 Sex: M+F Population Size: 473 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022563Orig1s000MedR.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022563Orig1s000MedR.pdf
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: https://pubmed.ncbi.nlm.nih.gov/22587791/	unhealthy, 48.2 n = 437 Health Status: unhealthy Condition: psoriasis Age Group: 48.2 Sex: M+F Population Size: 437 Sources: https://pubmed.ncbi.nlm.nih.gov/22587791/	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: https://pubmed.ncbi.nlm.nih.gov/22587791/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP1 106 P-gp 1461 BCRP 699

Drug as perpetrator

Target	Modality	Activity
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30232176/	yes [IC50 20.8 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30232176/	yes [IC50 37.9 uM]
MRP1 172	inhibitor 3277 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
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
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/
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	PubChem18810	http://www.capotchem.com/en/18810.htm
Capot Chemical	19334	http://www.capotchem.com/en/19334.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
Excenen	EX-A4430	https://www.excenen.com/searchresultlist.php?id=EX-A4430
Glentham Life Sciences	GP2043	http://www.glentham.com/products/product/GP2043/
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
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
iChemical	EBD7189	http://www.ichemical.com/products/112828-00-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Hypercalcaemia associated with calcipotriol (Dovonex) treatment.	1993 Apr 3	8490416
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.	1994 Aug	7976510
Calcipotriol inhibits rectal epithelial cell proliferation in ulcerative proctocolitis.	1994 Dec	7829008
The use of topical calcipotriene/calcipotriol in conditions other than plaque-type psoriasis.	1997 Sep	9344189
Severe hypercalcemia and hypernatremia associated with calcipotriol for treatment of psoriasis.	2004	14999528
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	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 May	15864137
Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis.	2006 Aug 1	16880407
The atopic dermatitis-like symptoms induced by MC903 were alleviated in JNK1 knockout mice.	2013 Dec	24046278
Vitamin D Analogs Potentiate the Antitumor Effect of Imatinib Mesylate in a Human A549 Lung Tumor Model.	2015 Nov 13	26580599

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 `Fri Dec 15 15:32:51 GMT 2023` Edited by `admin` on `Fri Dec 15 15:32:51 GMT 2023`
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

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

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