Title: Sorbinil
CAS Registry Number: 68367-52-2
CAS Name: (4¢S)-6-Fluoro-2,3-dihydrospiro[4H-1-benzopyran-4,4¢-imidazolidine]-2¢,5¢-dione
Additional Names: (+)-(4S)-6-fluorospiro[chroman-4,4¢-imidazolidine]-2¢,5¢-dione
Manufacturers' Codes: CP-45634
Molecular Formula: C11H9FN2O3
Molecular Weight: 236.20
Percent Composition: C 55.93%, H 3.84%, F 8.04%, N 11.86%, O 20.32%
Literature References: Spirohydantoin aldose reductase inhibitor. Prepn of racemate and resolution of isomers: R. Sarges, DE 2821966; idem, US 4130714 (both 1978 to Pfizer). Synthesis: R. Sarges et al., J. Org. Chem. 47, 4081 (1982); N. L. Dirlam et al., J. Org. Chem. 52, 3587 (1987). Absolute configuration: R. Sarges et al., J. Med. Chem. 28, 1716 (1985). Effect on polyol accumulation in diabetic rats: M. J. Peterson et al., Metabolism 28, Suppl. 1, 456 (1979). Pharmacokinetics in humans: G. Foulds et al., Clin. Pharmacol. Ther. 30, 693 (1981). HPLC determn in human lens and plasma: P. Lloyd, M. J. C. Crabbe, J. Chromatogr. 343, 402 (1985). Preliminary clinical trials in diabetic neuropathy: R. J. Young et al., Diabetes 32, 938 (1983); J. Jaspan et al., Lancet 2, 758 (1983). Symposium on pharmacology and clinical efficacy: Metabolism 35, Suppl 1, 1-121 (1986).
Properties: Crystals from ethanol, mp 241-243°. [a]D25 +54.0° (c = 1 in methanol).
Melting point: mp 241-243°
Optical Rotation: [a]D25 +54.0° (c = 1 in methanol) |