7463. Piperacillin

Nomenclature

CAS number: 61477-96-1
(2S,5R,6R)-6-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[(R)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-d(-)-α-(4-ethyl-2,3-dioxo-1-piperazinylcarbonylamino)-α-phenylacetamidopenicillanic acid; 4-ethyl-2,3-dioxopiperazine carbonyl ampicillin.
C23H27N5O7S; mol wt 517.55.
C 53.38%, H 5.26%, N 13.53%, O 21.64%, S 6.20%.

Description and references

Broad spectrum semi-synthetic antibiotic related to pencillin. Prepn: I. Saikawa et al., DE 2519400; eidem, US 4087424 (1976, 1978 both to Toyama). In vitro studies: G. P. Bodey, B. LeBlanc, Antimicrob. Agents Chemother. 14, 78 (1978); R. Wise et al., ibid. 549. In vitro and in vivo: N. A. Kuck, G. S. Redin, J. Antibiot. 31, 1175 (1978). Pharmacokinetics: M. A. Evans et al., J. Antimicrob. Chemother. 4, 255 (1978). Metabolism: K. Iida et al., Antimicrob. Agents Chemother. 14, 257 (1978). Clinical study: T. Saito, Y. Yamada, Jpn. J. Antibiot. 30, 835 (1977). Toxicity study: A. Takai et al., Chemotherapy (Tokyo) 25, 816 (1977). Review of antibacterial activity, pharmacokinetics: G. L. Mandell, Clin. Ther. 7, Suppl. B, 28-35 (1985). Review of clinical experience in urinary tract infections: S. J. Childs, ibid. 36-45. Series of articles on antibacterial activity and clinical use: Chemotherapy (Tokyo) 36, Suppl. 7, 1-85 (1988).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 59703-84-3
CL-227193; T-1220; Isipen (Krka); Pentcillin (Toyama-Sankyo); Pipracil (Wyeth); Pipril (Wyeth).
C23H26N5NaO7S; mol wt 539.54.
C 51.20%, H 4.86%, N 12.98%, Na 4.26%, O 20.76%, S 5.94%.

Properties

mp 183-185° (dec). LD50 in mice, rats, dogs, monkeys (g/kg): 5, 2.7, >6, >4 i.v. (Takai).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins