1122. Benzydamine

Nomenclature

CAS number: 642-72-8
N,N-Dimethyl-3-[[1-(phenylmethyl)-1H-indazol-3-yl]oxy]-1-propanamine; 1-benzyl-3-[3-(dimethylamino)propoxy]-1H-indazole; 1-benzyl-1H-indazol-3-yl 3-(dimethylamino)propyl ether; benzindamine.
C19H23N3O; mol wt 309.41.
C 73.75%, H 7.49%, N 13.58%, O 5.17%.

Description and references

Prepn: FR 1382855; Palazzo, US 3318905 (1964, 1967 both to Angelini Francesco); Palazzo et al., J. Med. Chem. 9, 38 (1966). Pharmacology: Lisciani et al., Eur. J. Pharmacol. 3, 157 (1968). Metabolism: Catanese et al., Arzneim.-Forsch. 16, 1354 (1966); Kataoka et al., Chem. Pharm. Bull. 19, 1511 (1971). Toxicology: B. Silvestrini et al., Toxicol. Appl. Pharmacol. 10, 148 (1967). Series of articles on pharmacology: Arzneim.-Forsch. 37, 587-646 (1987).

Chemical structure

Properties

bp0.05 160°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 132-69-4
Afloben (Esseti); Andolex (3M Pharma); Benzyrin (Yoshitomi); Difflam (3M Pharma); Enzamin (Kowa); Imotryl (Cassenne); Opalgyne (Innothéra); Riripen (Daiichi); Salyzoron (Hishiyama); Saniflor (Esseti); Tamas (Schering); Tantum (Angelini); Verax (Tosi).
C19H23N3O.HCl; mol wt 345.87.
C 65.98%, H 6.99%, N 12.15%, O 4.63%, Cl 10.25%.

Properties

Crystals, mp 160°. uv max: 306 nm (E1%1cm 160). Very sol in water; rather sol in ethanol, chloroform, n-butanol. LD50 in mice, rats (mg/kg): 110, 100 i.p.; 515, 1050 orally (Silvestrini).

Therapeutic Category

Analgesic; anti-inflammatory.

Therapeutic Category (Veterinary)

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Analgesic; Non-opioids