Penicillin O
Title: Penicillin O
CAS Registry Number: 87-09-2
CAS Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[[(2-propenylthio)acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: [(allylthio)methyl] penicillin; allylmercaptomethylpenicillin; allylmercaptomethylpenicillinic acid; penicillin AT
Molecular Formula: C13H18N2O4S2
Molecular Weight: 330.42
Percent Composition: C 47.25%, H 5.49%, N 8.48%, O 19.37%, S 19.41%
Literature References: Antibiotic produced by Penicillium chrysogenum. Biosynthesis of salts: Behrens et al., J. Biol. Chem. 175, 793 (1948); Rhodehamel, Behrens et al., US 2528175 and US 2623876 (1950, 1952, both to Lilly); Ford et al., Antibiot. Chemother. 3, 1149 (1953); Ford, US 2647894 (1953 to Upjohn); Palecková, Slechta, C.A. 50, 17309g (1956).
 
Derivative Type: 2-Chloroprocaine salt monohydrate
Additional Names: Chloroprocaine penicillin O; penicillin O 2-chloroprocaine
Trademarks: Depo-Cer-O-Cillin Chloroprocaine (Upjohn)
Molecular Formula: C26H37ClN4O6S2.H2O
Molecular Weight: 619.19
Percent Composition: C 50.43%, H 6.35%, Cl 5.73%, N 9.05%, O 18.09%, S 10.36%
Properties: Slender needles from hot water, mp 79-81°. Practically insol in cold water. Stable in dry form at room temp. Aq suspensions are stable at room temp for 1 week, at refrigerator temps for 3 weeks. Calculated activity: 949 units/mg. Solubilities: Weiss et al., Antibiot. Chemother. 7, 374 (1957).
Melting point: mp 79-81°
 
Derivative Type: Potassium salt
CAS Registry Number: 897-61-0
Additional Names: Potassium penicillin O; penicillin O potassium
Molecular Formula: C13H17KN2O4S2
Molecular Weight: 368.51
Percent Composition: C 42.37%, H 4.65%, K 10.61%, N 7.60%, O 17.37%, S 17.40%
Properties: Crystals from acetone. Soluble in water. Stable in dry form at room temp for at least 3 years. Requires no refrigeration when dry. Aq solns may be kept for 3 days at +10° without significant loss of activity. Behrens' prepn assayed 1630 units/mg. Less toxic than benzylpenicillin in exptl animals.
 
Derivative Type: Procaine salt
Molecular Formula: C26H38N4O6S2
Molecular Weight: 566.73
Percent Composition: C 55.10%, H 6.76%, N 9.89%, O 16.94%, S 11.32%
Properties: Crystals from water.
 
Derivative Type: Sodium salt
CAS Registry Number: 7177-54-0
Trademarks: Cer-O-Cillin Sodium (Upjohn)
Molecular Formula: C13H17N2NaO4S2
Molecular Weight: 352.40
Percent Composition: C 44.31%, H 4.86%, N 7.95%, Na 6.52%, O 18.16%, S 18.20%
Properties: Crystals from acetone.
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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