Ampicillin
Title: Ampicillin
CAS Registry Number: 69-53-4
CAS Name: (2S,5R,6R)-6-[[(2R)-Aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: 6-[D(-)-a-aminophenylacetamido]penicillanic acid; D(-)-a-aminobenzylpenicillin
Manufacturers' Codes: AY-6108; BRL-1341; P-50
Trademarks: Albipen (Intervet); Amfipen (Yamanouchi); Ampitab (V oquinol); Amplital (Pharmacia); Omnipen (Wyeth); Pénicline (Sanofi-Aventis)
Molecular Formula: C16H19N3O4S
Molecular Weight: 349.40
Percent Composition: C 55.00%, H 5.48%, N 12.03%, O 18.32%, S 9.18%
Literature References: Orally active, semi-synthetic antibiotic; structurally related to penicillin. Prepn: Doyle et al., US 2985648 (1961); eidem, GB 902703 (1962 to Beecham); Doyle et al., J. Chem. Soc. 1962, 1440. Prepn of the trihydrate: D. A. Johnson, G. A. Hardcastle, US 3157640 (1964 to Bristol-Myers); of the anhydrous crystalline form: N. H. Grant, H. E. Alburn, US 3144445 (1964 to Am. Home Prods.). Alternate syntheses: Dane, Dockner, Ber. 98, 789 (1965); F. Kajfez et al., J. Heterocycl. Chem. 13, 561 (1976). LC determn: M. Margosis, J. Assoc. Off. Anal. Chem. 70, 206 (1987). Series of articles on pharmacology and antibacterial activity: Br. Med. J. 2, 193-206 (1961). Comprehensive description: E. Ivashkiv, Anal. Profiles Drug Subs. 2, 1-61 (1973). Review of pharmacology and clinical efficacy in combination with sulbactam, q.v.: D. M. Campoli-Richards, R. N. Brogden, Drugs 33, 577-609 (1987).
Properties: Crystals, dec 199-202°. [a]D23 +287.9° (c = 1 in water). Sparingly sol in water.
Optical Rotation: [a]D23 +287.9° (c = 1 in water)
 
Derivative Type: Monohydrate
Properties: Crystals from water, dec 202°. [a]D21 +281° (water). Sparingly sol in water at room temp.
Optical Rotation: [a]D21 +281° (water)
 
Derivative Type: Sesquihydrate
Properties: Dec 199-202°. [a]D20 +283.1° (water).
Optical Rotation: [a]D20 +283.1° (water)
 
Derivative Type: Trihydrate
CAS Registry Number: 7177-48-2
Trademarks: Amblosin (Hoechst); Amipenix (Toyo Jozo); Ampilar (Sandoz); Cymbi (Dolorgiet); Doktacillin (AstraZeneca); Penbritin (GSK); Polycillin (BMS); Principen (BMS); Rosampline (Tedis); Totapen (BMS); Vidopen (APS)
 
Derivative Type: Sodium salt
CAS Registry Number: 69-52-3
Trademarks: Ampicin (BMS); Binotal (Grñenthal); Cilleral (BMS); Penbristol (BMS); Pentrex (BMS); Pentrexyl (BMS); Polycillin-N (BMS); Synpenin (Sankyo); Totacillin N (GSK); Viccillin (Meiji)
Molecular Formula: C16H18NaN3O4S
Molecular Weight: 371.39
Percent Composition: C 51.74%, H 4.89%, Na 6.19%, N 11.31%, O 17.23%, S 8.63%
 
Derivative Type: L(+)-Form
Properties: Crystals, dec at about 205°. [a]D20 +209° (c = 0.2 in water). Less active as an antibiotic than D(-)-form.
Optical Rotation: [a]D20 +209° (c = 0.2 in water)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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