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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 of CLOCORTOLONE PIVALATE

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

Description
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

1977
44
Targets

Targets

Primary TargetPharmacologyConditionPotency
Glucocorticoid receptor
172
Target ID: P04150
Gene ID: 2908.0
Gene Symbol: NR3C1
Target Organism: Homo sapiens (Human)
Agonist
2678
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
270
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 likely
Sourcing

Sourcing

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

PubMed

TitleDatePubMed
[Experiences with clocortolone in treating of skin diseases in hospital and ambulatory care].
1969 Sep 27
[Clocortolone (Cl 68) versus fluocinolone, a double-blind, randomized lateral comparison].
1973 Jul
Clocortolone, a new topical steroid in dermatoses.
1973 Mar 24
[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
Clocortolone pivalate: a paired comparison clinical trial of a new topical steroid in eczema/atopic dermatitis.
1980 Jan
Safety and efficacy of clocortolone pivalate 0.1 percent cream in the treatment of atopic dermatitis, contact dermatitis, and seborrheic dermatitis.
1981 Jun
Clocortolone pivalate cream 0.1% used concomitantly with tacrolimus ointment 0.1% in atopic dermatitis.
2003 Aug
Clocortolone Pivalate.
2006
Adherence to clocortolone pivalate cream 0.1% in a pediatric population with atopic dermatitis.
2008 May
Clinical utility of clocortolone pivalate for the treatment of corticosteroid-responsive skin disorders: a systematic review.
2012
A Comprehensive Review of Clocortolone Pivalate 0.1% Cream: Structural Development, Formulation Characteristics, and Studies Supporting Treatment of Corticosteroid-responsive Dermatoses.
2012 Jul
Identification and characterization of three impurities in clocortolone pivalate.
2012 Mar 25
Clocortolone pivalate: a topical corticosteroid with a unique structure.
2013 Feb
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
Patents

Patents

JP2012500104A
107

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 PIVALATE
MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
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
MI  
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
Created by admin on Fri Dec 15 15:48:13 GMT 2023 , Edited by admin on Fri Dec 15 15:48:13 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C47455
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PRIMARY
PUBCHEM
5282493
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PRIMARY
LACTMED
Clocortolone Pivalate
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PRIMARY
FDA UNII
QBL8IZH14X
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PRIMARY
DRUG BANK
DB00838
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PRIMARY
ChEMBL
CHEMBL1200975
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PRIMARY
SMS_ID
100000090212
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PRIMARY
RXCUI
21250
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PRIMARY RxNorm
CAS
34097-16-0
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PRIMARY
ECHA (EC/EINECS)
251-826-5
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PRIMARY
CHEBI
59583
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PRIMARY
DRUG CENTRAL
4606
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PRIMARY
EVMPD
SUB13393MIG
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PRIMARY
DAILYMED
QBL8IZH14X
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PRIMARY
RS_ITEM_NUM
1138507
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PRIMARY
MERCK INDEX
m3633
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PRIMARY Merck Index
EPA CompTox
DTXSID0045460
Created by admin on Fri Dec 15 15:48:13 GMT 2023 , Edited by admin on Fri Dec 15 15:48:13 GMT 2023
PRIMARY
WIKIPEDIA
Clocortolone pivalate
Created by admin on Fri Dec 15 15:48:13 GMT 2023 , Edited by admin on Fri Dec 15 15:48:13 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of CLOCORTOLONE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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