7085. Penethamate Hydriodide

Nomenclature

CAS number: 808-71-9
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 2-(diethylamino)ethyl ester monohydriodide; penicillin G 2-diethylaminoethyl ester hydriodide; benzylpenicillin β-diethylaminoethyl ester hydriodide; β-diethylaminoethyl benzylpenicillinate hydriodide; ephicillin hydriodide; penethecillin; Bronchocillin (Bellon); Estopen; Leocillin (Leo Pharm); Mamyzin (Boehringer, Ing.); Neo-Penil.
C22H32IN3O4S; mol wt 561.48.
C 47.06%, H 5.74%, I 22.60%, N 7.48%, O 11.40%, S 5.71%.

Description and references

Prepn: K. A. Jensen et al., Ugeskr. Laeg. 112, 1043, 1075 (1950); E. K. Frederiksen, E. J. Nielsen, US 2694061; A. B. A. Jansen, J. C. Hamlet, US 2880203 (1954, 1959 both to L"ovens). Selective concentration in lung: A. G. S. Heathcote, E. Nassau, Lancet 260, 1255 (1951). Properties: W. A. Woodard, J. Pharm. Pharmacol. 4, 1009 (1952). Veterinary trial in cows: G. Ziv, M. Storper, J. Vet. Pharmacol. Ther. 8, 276 (1985).

Chemical structure

Properties

Crystals, mp 178-179°. Slightly soluble in water (0.96% at 20°). pH of satd aq soln 4.5-5.2. Aq solns are unstable, the ester is hydrolyzed to free penicillin and diethylaminoethanol, the velocity of the reaction increasing with rise in temperature and pH.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins