Penicillin G Procaine
Title: Penicillin G Procaine
CAS Registry Number: 6130-64-9
CAS Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid compd with 2-(diethylamino)ethyl 4-aminobenzoate (1:1) monohydrate
Additional Names: penicillin G compd with 2-(diethylamino)ethyl p-aminobenzoate monohydrate; benzylpenicillin procaine; procaine benzylpenicillinate; procaine penicillin G
Trademarks: Abbocillin (Abbott); Cilicaine (Sigma); Crysticillin (BMS); Duracillin (Lilly); Farmaproina (CEPA); Mammacillin (Stricker); Monocillin (Chassot); Pfizerpen-AS (Roerig); Wycillin (Wyeth)
Molecular Formula: C29H38N4O6S.H2O
Molecular Weight: 588.72
Percent Composition: C 59.16%, H 6.85%, N 9.52%, O 19.02%, S 5.45%
Literature References: Semi-synthetic antibiotic. Prepn: N. P. Sullivan et al., Science 107, 169 (1948); C. J. Sullivan et al., J. Am. Chem. Soc. 70, 1287 (1948); H. W. Rhodehamel, Jr., US 2515898 (1950 to Eli Lilly). Crystal structure: Rose, Anal. Chem. 27, 1841 (1955). Toxicity: K. Soehring et al., Arzneim.-Forsch. 1, 28 (1951). Soly profile: P. J. Weiss et al., Antibiot. Chemother. 7, 374 (1957). Pharmacokinetics in horses: S. M. Stover et al., Am. J. Vet. Res. 42, 629 (1981); in humans: B. T. Goh et al., Br. J. Vener. Dis. 60, 371 (1984). Review of use in syphilis: M. W. Adler, Br. Med. J. 288, 551-553 (1984).
Properties: Monoclinic hemimorphic crystals from methanol-water, mp 106-110° (with decompn). d 1.255-1.256. Not appreciably affected by air or light. Aq solns are dextrorotatory. The pH of a satd aq soln is between 5 and 7.5. Soly in mg/ml at about 28°: water 6.8; methanol >20; isopropanol 6.5; benzene 0.075; toluene 1.05; petr ether 0.12; isooctane 0.0; carbon tetrachloride 0.12; ethyl acetate 3.35. LD50 s.c. in mice: 2.3 g/kg (Soehring).
Melting point: mp 106-110° (with decompn)
Density: d 1.255-1.256
Toxicity data: LD50 s.c. in mice: 2.3 g/kg (Soehring)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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