CICLOPROFEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H14O2
Molecular Weight	238.2812
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC=C2C(CC3=C2C=CC=C3)=C1

InChI

InChIKey=LRXFKKPEBXIPMW-UHFFFAOYSA-N

InChI=1S/C16H14O2/c1-10(16(17)18)11-6-7-15-13(8-11)9-12-4-2-3-5-14(12)15/h2-8,10H,9H2,1H3,(H,17,18)

HIDE SMILES / InChI

Molecular Formula	C16H14O2
Molecular Weight	238.2812
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/626004 | https://www.ncbi.nlm.nih.gov/pubmed/602253 | https://www.ncbi.nlm.nih.gov/pubmed/6155392 | https://www.ncbi.nlm.nih.gov/pubmed/19370733

Cicloprofen is fluorene derivative patented by American pharmaceutical company E. R. Squibb as anti-inflammatory agents. Cicloprofen is potent cyclooxygenase inhibitor. Cicloprofen undergoes hydroxylation of the fluorene rings and conjugation with glucuronic acid or sulfate and metabolic transformation leading to stereospecific inversion of the ( - )-enantiomer of Cicloprofen to its (+)-antipode

Originator

Approval Year

PubMed

Title	Date	PubMed
Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs.	2009-09	19740398
Metabolism of alpha-methylfluorene-2-acetic acid (cicloprofen): isolation and identification of metabolites from rat urine.	1978-02	626004
Metabolism of the (+)-, (+/-)-, and (-)-enantiomers of alpha-methylfluorene-2-acetic acid (cicloprofen) in rats.	1977-09	602253
Inversion of optical configuration of alpha-methylfluorene-2-acetic acid (cicloprofen) in rats and monkeys.	1976-07-01	8287
Stereospecific inversion of l-alpha-methylfluorene-2-acetic acid to its d-enantiomer in the dog.	1976-03	1274380
Interactions of alpha-methylfluorene-2-acetic acid with adenylate cyclase.	1974-09-01	4154750

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:10 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:10 GMT 2025`
Record UNII	325708J22C
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CICLOPROFEN

Official Name

English

NSC-293916

Preferred Name

English

SQ 20824

Code

English

CICLOPROFEN [USAN]

Common Name

English

?-Methylfluorene-2-acetic acid

Systematic Name

English

SQ-20824

Code

English

9H-FLUORENE-2-ACETIC ACID, .ALPHA.-METHYL-

Common Name

English

cicloprofen [INN]

Common Name

English

Code System Code Type Description

EVMPD

SUB06247MIG