CLOCORTOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28ClFO4
Molecular Weight	410.907
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(Cl)[C@@]2([H])C[C@H](F)C4=CC(=O)C=C[C@]34C

InChI

InChIKey=YMTMADLUXIRMGX-RFPWEZLHSA-N

InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/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 172 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 2678
Glucocorticoid receptor 172 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 2678

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 8429	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 270

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 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
[Experiences with clocortolone in treating of skin diseases in hospital and ambulatory care].	1969 Sep 27	5351072
[Clocortolone (Cl 68) versus fluocinolone, a double-blind, randomized lateral comparison].	1973 Jul	4269321
Clocortolone, a new topical steroid in dermatoses.	1973 Mar 24	4693153
[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
Safety and efficacy of clocortolone pivalate 0.1 percent cream in the treatment of atopic dermatitis, contact dermatitis, and seborrheic dermatitis.	1981 Jun	6453703
Clocortolone pivalate cream 0.1% used concomitantly with tacrolimus ointment 0.1% in atopic dermatitis.	2003 Aug	12953943
Adherence to clocortolone pivalate cream 0.1% in a pediatric population with atopic dermatitis.	2008 May	18543596
A Comprehensive Review of Clocortolone Pivalate 0.1% Cream: Structural Development, Formulation Characteristics, and Studies Supporting Treatment of Corticosteroid-responsive Dermatoses.	2012 Jul	22798972
Identification and characterization of three impurities in clocortolone pivalate.	2012 Mar 25	22264563
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 Feb	23377405

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

Official Name

English

CLOCORTOLONE [USP-RS]

Common Name

English

9-CHLORO-6.APLHA.-FLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE

Common Name

English

clocortolone [INN]

Common Name

English

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

Systematic Name

English

CLOCORTOLONE [VANDF]

Common Name

English

CLOCORTOLONE [MI]

Common Name

English

Clocortolone [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D07AB21