7223. Phenethicillin Potassium

Nomenclature

CAS number: 132-93-4
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(1-oxo-2-phenoxypropyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid monopotassium salt; (α-phenoxyethyl)penicillin potassium; α-phenoxyethylpenicillinic acid potassium salt; 6-(α-phenoxypropionamido)penicillanic acid potassium salt; penicillin-152; penicillin MV; penicillin-152 potassium; potassium phenethicillin; Maxipen (Pfizer); Syncillin (Bayer).
C17H19KN2O5S; mol wt 402.51.
C 50.73%, H 4.76%, K 9.71%, N 6.96%, O 19.87%, S 7.97%.

Description and references

Semi-synthetic antibiotic related to penicillin. Prepn from 6-aminopenicillanic acid: Perron et al., Antibiot. Annu. 1959-1960, 107; J. Am. Chem. Soc. 82, 3934 (1960); Glombitza, Ann. 673, 166 (1964).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from acetone, dec 230-232°. Much less hygroscopic than benzylpenicillin sodium. Freely sol in water.

Derivative

l-Form.

Nomenclature

Epiphenethicillin potassium.

Properties

Crystals from 20% butanol, dec 238-239°. [α]D24 +218° (c = 0.01 in water).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins