CLIDANAC

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H19ClO2
Molecular Weight	278.774
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1CCC2=C1C=C(Cl)C(=C2)C3CCCCC3

InChI

InChIKey=OIRAEJWYWSAQNG-UHFFFAOYSA-N

InChI=1S/C16H19ClO2/c17-15-9-13-11(6-7-12(13)16(18)19)8-14(15)10-4-2-1-3-5-10/h8-10,12H,1-7H2,(H,18,19)

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Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4401197
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/6114148

Clidanac is an anti-inflammatory agent developed in Japan for the treatment of rheumatoid arthritis. The drug is mixture of two isomers, d- and l-, and the d-form is more active than the l-form. Therapeutic effect of clidanac is mediated by the inhibition of prostaglandin biosynthesis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin E synthase 2 2 Target ID: Q9H7Z7 Gene ID: 80142.0 Gene Symbol: PTGES2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/6114148	Inhibitor 8297		2.7 µM [IC50]
Prostamide/prostaglandin F synthase 1 Target ID: Q8TBF2\|\|\|J3KQD0 Gene ID: 127281.0 Gene Symbol: FAM213B Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/6114148	Inhibitor 8297		2.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: http://www.ncbi.nlm.nih.gov/pubmed/333619	Palliative		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284), a new antiinflammatory agent.	1971 Mar	5553051
Anti-inflammatory, analgesic and antipyretic activities of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284).	1971 Oct	4401197
Metabolism of 6-chloro-5-cyclohexylindane-1-carboxylic acid (TAI-284), a new non-steroidal anti-inflammatory agent. I. Absorption, distribution and excretion in rats.	1973 Oct	4774631
Biological activities of optical isomers of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284: anti-inflammatory agent).	1974 Oct	4455979
Biological activities of metabolites of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284: anti-inflammatory agent).	1974 Oct	4549085
Inhibition of prostaglandin biosynthesis by clidanac and related compounds: structural and conformational requirements for PG synthetase inhibition.	1981 Jan	6114148
[Influence of indomethacin and clidanac on the blood pressure lowering effect of beta-blockers].	1983 Jan	6133820
The effect of clidanac, a potent anti-inflammatory drug, on mitochondrial respiration: a consideration on the uncoupling activity of optical enantiomers.	1984 Sep	6334337

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Inhibitory effect of clidanac on ADP-induced rat platelet aggregation was tested in vitro. At concentrations 1*10(-3), 5*10(-4), 1*10(-4) M the drug produced 76, 16 and 0% of inhibition. At 10(-4) M the drug caused 61% of inhibition of the heat-induced erythrocyte lysis.

Name

Type

Language

CLIDANAC

Official Name

English

(±)-CLIDANAC

Common Name

English

(±)-TAI-284

Common Name

English

BRITAI

Brand Name

English

clidanac [INN]

Common Name

English

CLIDANAC [JAN]

Common Name

English

CLIDANAC [MI]

Common Name

English

(±)-6-CHLORO-5-CYCLOHEXYLINDANE-1-CARBOXYLIC ACID

Systematic Name

English

CLIDANAC, (±)-

Common Name

English

TAI-284

Code

English

INDANAL

Systematic Name

English

6-CHLORO-5-CYCLOHEXYL-1-INDANCARBOXYLIC ACID

Systematic Name

English

Clidanac [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257