CLOCORTOLONE PIVALATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H36ClFO5
Molecular Weight	495.023
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)COC(=O)C(C)(C)C)[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=SXYZQZLHAIHKKY-GSTUPEFVSA-N

InChI=1S/C27H36ClFO5/c1-14-9-16-17-11-19(29)18-10-15(30)7-8-26(18,6)27(17,28)21(32)12-25(16,5)22(14)20(31)13-34-23(33)24(2,3)4/h7-8,10,14,16-17,19,21-22,32H,9,11-13H2,1-6H3/t14-,16+,17+,19+,21+,22-,25+,26+,27+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H36ClFO5
Molecular Weight	495.023
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Clocortolone pivalate: a paired comparison clinical trial of a new topical steroid in eczema/atopic dermatitis.	1980 Jan	6986236
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
Clocortolone Pivalate.	2006	29999716
Adherence to clocortolone pivalate cream 0.1% in a pediatric population with atopic dermatitis.	2008 May	18543596
Clinical utility of clocortolone pivalate for the treatment of corticosteroid-responsive skin disorders: a systematic review.	2012	22791998
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
Clocortolone pivalate: a topical corticosteroid with a unique structure.	2013 Feb	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 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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:13 GMT 2023`
Record UNII	QBL8IZH14X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CLOCORTOLONE PIVALATE

Official Name

English

CLOCORTOLONE 21-PIVALATE [MI]

Common Name

English

CLOCORTOLONE PIVALATE [USP MONOGRAPH]

Common Name

English

SH 863

Code

English

CLOCORTOLONE PIVALATE [VANDF]

Common Name

English

CLOCORTOLONE PIVALATE [USAN]

Common Name

English

9-Chloro-6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-pivalate

Common Name

English

SH-863

Code

English

CLODERM

Brand Name

English

CLOCORTOLONE PIVALATE [USP-RS]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 9-CHLORO-21-(2,2-DIMETHYL-1-OXOPROPOXY)-6-FLUORO-11-HYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)-

Common Name

English

CLOCORTOLONE 21-PIVALATE

Common Name

English

CLOCORTOLONE PIVALATE [MART.]

Common Name

English

Clocortolone pivalate [WHO-DD]

Common Name

English

CLOCORTOLONE PIVALATE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C521