Chemistry:Fidarestat

Fidarestat

Names
Preferred IUPAC name (2S,4S)-6-Fluoro-2′,5′-dioxo-2,3-dihydrospiro[[1]benzopyran-4,4′-imidazolidine]-2-carboxamide
Other names (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide
Identifiers
CAS Number	136087-85-9 Y 105300-43-4 (non specific) Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL84446
ChemSpider	140679
KEGG	D01842
PubChem CID	160024
UNII	8SH8T1164U Y
InChI InChI=1S/C12H10FN3O4/c13-5-1-2-7-6(3-5)12(4-8(20-7)9(14)17)10(18)15-11(19)16-12/h1-3,8H,4H2,(H2,14,17)(H2,15,16,18,19)/t8-,12-/m0/s1 Key: WAAPEIZFCHNLKK-UFBFGSQYSA-N
SMILES c1cc2c(cc1F)[C@@]3(C[C@H](O2)C(=O)N)C(=O)NC(=O)N3
Properties
Chemical formula	C12H10FN3O4
Molar mass	279.227 g·mol−1
Melting point	290–300 °C (554–572 °F; 563–573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracking categories (test):

• SizeSet

Fidarestat (SNK-860) is an aldose reductase inhibitor under investigation for treatment of diabetic neuropathy.

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).