Title: Fidarestat
CAS Registry Number: 136087-85-9; 105300-43-4 (unspecified)
CAS Name: (2S,4S)-6-Fluoro-2,3-dihydro-2¢,5¢-dioxospiro[4H-1-benzopyran-4,4¢-imidazolidine]-2-carboxamide
Additional Names: (2S,4S)-6-fluoro-2¢,5¢-dioxospiro[chroman-4,4¢-imidazolidine]-2-carboxamide
Manufacturers' Codes: SNK-860
Molecular Formula: C12H10FN3O4
Molecular Weight: 279.22
Percent Composition: C 51.62%, H 3.61%, F 6.80%, N 15.05%, O 22.92%
Literature References: Aldose reductase inhibitor for treatment of diabetic complications. Prepn (stereo unspec): M. Kurono, et al., EP 193415; eidem, US 4740517 (1986, 1988 both to Sanwa). Prepn of isomers: T. Yamaguchi et al., Arzneim.-Forsch. 44, 344 (1994). Pharmacological profile: K. Mizuno et al. in Current Concepts of Aldose Reductase and Its Inhibitions, N. Sakamoto et al., Eds. (Elsevier, Amsterdam, 1990) pp 89-96. Configuration and crystal structure of complex with aldose reductase: M. Oka et al., J. Med. Chem. 43, 2479 (2000). Clinical efficacy in diabetic peripheral neuropathy: N. Hotta et al., Diabetes Care 24, 1776 (2001). Clinical suppression of sorbitol accumulation in erythrocytes of diabetic patients: T. Asano et al., J. Diabetes Complications 16, 133 (2002); eidem, ibid. 18, 336 (2004). Review of clinical development: N. Giannoukakis, Curr. Opin. Invest. Drugs 4, 1233-1239 (2003).
Properties: Crystals from methanol, mp 290-300° (dec). [a]D27 +168° (c = 1.0 in methanol). LD50 in rats, dogs (mg/kg): >2000 orally (Yamaguchi).
Melting point: mp 290-300° (dec)
Optical Rotation: [a]D27 +168° (c = 1.0 in methanol)
Toxicity data: LD50 in rats, dogs (mg/kg): >2000 orally (Yamaguchi)
Therap-Cat: Treatment of diabetic neuropathy.
Keywords: Aldose Reductase Inhibitor. |