13-02374. Clidanac [Archived]

Nomenclature

CAS number: 28968-07-2
6-Chloro-5-cyclohexyl-2,3-dihydro-1H-indene-1-carboxylic acid; (±)-6-chloro-5-cyclohexylindan-1-carboxylic acid; TAI-284; Britai (BMS); Indanal (Takeda).
C16H19ClO2; mol wt 278.77.
C 68.94%, H 6.87%, Cl 12.72%, O 11.48%.

Description and references

Prepn: P. F. Juby et al., DE 2004038; eidem, US 3565943 (1970, 1971 both to Bristol-Myers); S. Noguchi et al., Chem. Pharm. Bull. 19, 646 (1971). Synthesis and anti-inflammatory activity: eidem, ibid. 22, 529 (1974); G. R. Allen et al., J. Med. Chem. 15, 934 (1972); and toxicity data: P. F. Juby et al., ibid. 1297. Pharmacology: S. Kuzuna et al., Jpn. J. Antibiot. 24, 695 (1974), C.A. 82, 80297h (1976). X-ray crystallographic study: K. Kamiya et al., Chem. Pharm. Bull. 23, 1589 (1975). Metabolism: S. Tanayama, Y. Kanai, Xenobiotica 7, 145 (1977). Immunogenicity study: S. Kuzuna et al., Oyo Yakuri 19, 951 (1980), C.A. 94, 76682 (1981). Inhibition of prostaglandin biosynthesis: S. Tamura et al., J. Pharm. Pharmacol. 33, 29 (1981). Antipyretic effect in cancer patients: H. Furue, Curr. Ther. Res. 30, 71 (1981).

Chemical structure

Properties

Colorless crystals from petr ether, mp 150.5-152.5°. LD50 orally in rats: 41 mg/kg (Juby, 1972).

Derivative

(S)-(+)-Form.

Properties

Colorless needles from petr ether, mp 135-136°. [α]D25 28.7°; [α]25365 +87.7° (c = 2 in ethanol). LD50 orally in rats: 35 mg/kg (Juby, 1972).

Derivative

(R)-()-Form.

Properties

Colorless cryst from petr ether, mp 134-135°. [α]D25 28.2°; [α]25365 87.5° (c = 2 in ethanol).

Therapeutic Category

Anti-inflammatory; antipyretic.

Keywords

Anti-inflammatory (Nonsteroidal); Arylcarboxylic Acids; Antipyretic

Status

This monograph has been retired and is no longer subject to revision or update.