9005. Suprofen

Nomenclature

CAS number: 40828-46-4
α-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid; p-(2-thenoyl)hydratropic acid; sutoprofen; R-25061; Masterfen (Dompé); Srendam (Kayaku); Sulprotin (Taiyo); Supranol (Cilag); Suprocil (Cilag); Suprol (Cilag); Topalgic (Nippon Shoji).
C14H12O3S; mol wt 260.31.
C 64.60%, H 4.65%, O 18.44%, S 12.32%.

Description and references

Prostaglandin biosynthesis inhibitor. Prepn: P. A. Janssen et al., DE 2353357; eidem, US 4035376 (1974, 1977 both to Janssen); P. G. H. Van Daele et al., Arzneim.-Forsch. 25, 1495 (1975). Pharmacology: C. J. E. Niemegeers et al., ibid. 1537. HPLC determn in plasma and urine: H. Muller et al., ibid. 32, 257 (1982). Series of articles on pharmacology, toxicology and clinical trials: ibid. 25, 1501-1542 (1975); ibid. 33, 1322-1338 (1983); on pharmacology, efficacy and safety: Pharmacology 27, Suppl. 1, 1-96 (1983); on pharmacokinetics and clinical efficacy: Arzneim.-Forsch. 35, 738-759 (1985); ibid. 36, 941-971 (1986).

Chemical structure

Properties

White to slightly yellow microcryst powder, mp 124.3°. pKa 3.91. uv max (0.01N HCl-90% 2-propanol): 266, 292 nm (ε 15700, 15600). Freely sol in methanol, ethanol, chloroform, acetone, polyethylene glycol, 1.0N NaOH. Sol in ether. Slightly sol in 0.1N NaOH. Practically insol in n-hexane. Very slightly sol in water. LD50 (7 days post-drug) in mice, rats, guinea pigs, dogs (mg/kg): 590, 353, 280, 160 orally (Niemegeers).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives