1181. Betamipron

Nomenclature

CAS number: 3440-28-6
N-Benzoyl-β-alanine; 3-(benzoylamino)propionic acid; β-benzamidopropionic acid; CS-443.
C10H11NO3; mol wt 193.20.
C 62.17%, H 5.74%, N 7.25%, O 24.84%.

Description and references

Acyl amino acid that inhibits active transport of carbapenem antibiotics in the renal cortex. See also panipenem. Prepn: F. H. Holm, Arch. Pharm. 242, 590 (1904); C. C. Barker, J. Chem. Soc. 1954, 317; J. Barluenga et al., Tetrahedron 45, 2183 (1989). Use as renal protectant: T. Shiokari et al., EP 226304; eidem, US 4757066 (1987, 1988 both to Sankyo). Crystal structure: N. Feeder, W. Jones, Acta Crystallogr. C50, 813 (1994). Nephroprotective effect: Y. Hirouchi et al., Jpn. J. Pharmacol. 63, 487 (1993). Mode of action: eidem, ibid. 66, 1 (1994). Pharmacokinetics: A. Kurihara et al., Antimicrob. Agents Chemother. 36, 1810 (1992).

Chemical structure

Properties

Colorless prisms from hot water, mp 120° (Holm); also reported as crystals from water, mp 133° (Barker). Readily sol in warm water, chloroform. Very easily sol in alcohol, ether, acetone. LD50 in rats (mg/kg): >3000 i.v. (Hirouchi, 1994).

Therapeutic Category

Antibacterial adjunct (renal protectant).

Keywords

Antibacterial Adjuncts; Renal Protectant