6171. Mezlocillin

Nomenclature

CAS number: 51481-65-3
(2S,5R,6R)-3,3-Dimethyl-6-[[(2R)-[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]phenylacetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6R-[2-[3-(methylsulfonyl)-2-oxo-1-imidazolidine carboxamido]-2-phenylacetamido]penicillanic acid; Bayf 1353.
C21H25N5O8S2; mol wt 539.58.
C 46.74%, H 4.67%, N 12.98%, O 23.72%, S 11.89%.

Description and references

Semisynthetic, broad-spectrum antibiotic related to penicillins and azlocillin, q.v. Prepn: H. B. Knig et al., DE 2152967; eidem, US 3974142 (1973, 1976 both to Bayer). In vitro study: G. P. Bodey, T. Pan, Antimicrob. Agents Chemother. 11, 74 (1977). Pharmacokinetics: H. Lode et al., Infection 5, 163 (1977); S. J. Pancoast, H. C. Neu, Clin. Pharmacol. Ther. 24, 108 (1978). Clinical pharmacology: B. F. Issell et al., Antimicrob. Agents Chemother. 13, 180 (1978). Tissue concentration and efficacy: E. Helwing et al., Med. Klin. 74, 112 (1979). Series of articles on antibacterial activity, pharmacology, and clinical trials: Arzneim.-Forsch. 29, 1915-2032 (1979); Infection 10, Suppl. 3, S121-S266 (1982); J. Antimicrob. Chemother. 11, Suppl. C, 1-108 (1983).

Chemical structure

Derivative

Sodium salt monohydrate.

Nomenclature

CAS number: 59798-30-0
Baycipen (Bayer); Baypen (Bayer); Mezlin (Miles).
C21H24N5NaO5S2.H2O; mol wt 531.58.
C 47.45%, H 4.93%, N 13.17%, Na 4.32%, O 18.06%, S 12.06%.

Properties

Pale yellow cryst; sol in water, methanol, DMF. Insol in acetone and ethanol.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins