CLOCORTOLONE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H30ClFO5
Molecular Weight	452.943
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=O)COC(C)=O

InChI

InChIKey=ARPLCFGLEYFDCN-CDACMRRYSA-N

InChI=1S/C24H30ClFO5/c1-12-7-15-16-9-18(26)17-8-14(28)5-6-23(17,4)24(16,25)20(30)10-22(15,3)21(12)19(29)11-31-13(2)27/h5-6,8,12,15-16,18,20-21,30H,7,9-11H2,1-4H3/t12-,15+,16+,18+,20+,21-,22+,23+,24+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22791998
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/22798972

Clocortolone (used in form of pivalate prodrug) is a topical glucocorticoid that was approved by FDA for the treatment of corticosteroid-responsive skin disorders. The drug exerts its anti-inflammatory action by binding to glucocorticoid receptor which results in regulation of the expression of proinflammatory cytokines and further antiproliferative, immunosuppressive, and initial vasoconstrictive effects.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 173 Target ID: P04150 Gene ID: 2908.0 Gene Symbol: NR3C1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22798972	Agonist 2752
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/17765scp024_cloderm_lbl.pdf \| https://www.drugbank.ca/drugs/DB00838 \| https://affygility.com/oel/clocortolone-pivalate.html	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatoses 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/17765scp024_cloderm_lbl.pdf	Primary		Approved 8583	CLODERM Approved Use Topical corticosteroids are indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Launch Date 1977

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/17765scp024_cloderm_lbl.pdf Page: 1.0	likely

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:59582	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59582
ZINC	ZINC000021981454	http://zinc15.docking.org/substances/ZINC000021981454

PubMed

Title	Date	PubMed
Clocortolone pivalate: a topical corticosteroid with a unique structure.	2013-02	23377404
The role of a midpotency topical corticosteroid and the clinical relevance of formulation characteristics in the management of commonly encountered eczematous and inflammatory dermatoses in adults and children: focus on the pharmacologic properties of clocortolone pivalate 0.1% cream.	2013-02	23377405
A Comprehensive Review of Clocortolone Pivalate 0.1% Cream: Structural Development, Formulation Characteristics, and Studies Supporting Treatment of Corticosteroid-responsive Dermatoses.	2012-07	22798972
Identification and characterization of three impurities in clocortolone pivalate.	2012-03-25	22264563
Clinical utility of clocortolone pivalate for the treatment of corticosteroid-responsive skin disorders: a systematic review.	2012	22791998
Adherence to clocortolone pivalate cream 0.1% in a pediatric population with atopic dermatitis.	2008-05	18543596
Clocortolone pivalate cream 0.1% used concomitantly with tacrolimus ointment 0.1% in atopic dermatitis.	2003-08	12953943
Safety and efficacy of clocortolone pivalate 0.1 percent cream in the treatment of atopic dermatitis, contact dermatitis, and seborrheic dermatitis.	1981-06	6453703
Clocortolone pivalate: a paired comparison clinical trial of a new topical steroid in eczema/atopic dermatitis.	1980-01	6986236
[Human-pharmacokinetic Studies on Penetration Kinetics of a 6 alpha-Fluoro-9 alpha-chloro-16 alpha-methyl-delta 1,4-pregnadiene-11 beta-dihydroxy-3,20-dione-21-trimethyl-acetic acid (Clocortolone Trimethyl-acetic acid) after e picutaneous application].	1978	582571
[Clocortolone (Cl 68) versus fluocinolone, a double-blind, randomized lateral comparison].	1973-07	4269321
Clocortolone, a new topical steroid in dermatoses.	1973-03-24	4693153
[Experiences with clocortolone in treating of skin diseases in hospital and ambulatory care].	1969-09-27	5351072

Patents

Sample Use Guides

In Vivo Use Guide

Apply Cloderm (clocortolone pivalate) 1% cream to the affected areas 3 times/day.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Name

Type

Language

CLOCORTOLONE 21-ACETATE

Preferred Name

English

CLOCORTOLONE ACETATE

Official Name

English

9-Chloro-6?-fluoro-11?,21-dihydroxy-16?-methylpregna-1,4-diene-3,20-dione 21-acetate

Systematic Name

English

CLOCORTOLONE ACETATE [USAN]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-9-CHLORO-6-FLUORO-11-HYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)-

Systematic Name

English

SH 818

Code

English

CLOCORTOLONE 21-ACETATE [MI]

Common Name

English

SH-818

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C521