6352. Nafcillin

Nomenclature

CAS number: 147-52-4
(2S,5R,6R)-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(2-ethoxy-1-naphthamido)penicillin.
C21H22N2O5S; mol wt 414.47.
C 60.85%, H 5.35%, N 6.76%, O 19.30%, S 7.74%.

Description and references

Semi-synthetic antibiotic related to penicillin. Prepn: F. P. Doyle et al., GB 880400; F. P. Doyle, J. H. C. Nayler, US 3157639 (1961, 1964 both to Beecham). Prepn of crystalline monohydrate: D. Flitter et al., US 3506645 (1970 to American Home Prod.). HPLC determn: P. Fan-Havard, M. C. Nahata, Ther. Drug Monit. 11, 105 (1989). Antibacterial activity: J. M. Steckelberg et al., Antimicrob. Agents Chemother. 37, 554 (1993). Clinical efficacy: D. L. Palmer et al., Ann. Thorac. Surg. 59, 626 (1995).

Chemical structure

Derivative

Sodium salt monohydrate.

Nomenclature

CAS number: 7177-50-6; 985-16-0 (anhydrous)
Sodium 6-(2-ethoxy-1-naphthamido)penicillanate; Wy-3277; Nafcil (Apothecon); Nallpen (SKB); Unipen (Wyeth-Ayerst).
C21H21N2NaO5S.H2O; mol wt 454.47.
C 55.50%, H 5.10%, N 6.16%, Na 5.06%, O 21.12%, S 7.06%.

Properties

Sol in water. Insol in acetone, chloroform.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins