586. Ampicillin

Nomenclature

CAS number: 69-53-4
(2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-[d()-α-aminophenylacetamido]penicillanic acid; d()-α-aminobenzylpenicillin; AY-6108; BRL-1341; P-50; Albipen (Intervet); Amfipen (Yamanouchi); Ampitab (Vétoquinol); Amplital (Pharmacia); Omnipen (Wyeth); Pénicline (Sanofi-Aventis).
C16H19N3O4S; mol wt 349.40.
C 55.00%, H 5.48%, N 12.03%, O 18.32%, S 9.18%.

Description and 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).

Chemical structure

Properties

Crystals, dec 199-202°. [α]D23 +287.9° (c = 1 in water). Slightly sol in water, methanol. Insol in benzene, carbon tetrachloride, chloroform.

Derivative

Monohydrate.

Properties

Crystals from water, dec 202°. [α]D21 +281° (water). Sparingly sol in water at room temp.

Derivative

Sesquihydrate.

Properties

Dec 199-202°. [α]D20 +283.1° (water).

Derivative

Trihydrate.

Nomenclature

CAS number: 7177-48-2
Amblosin (Hoechst); Amipenix (Toyo Jozo); Ampilar (Sandoz); Cymbi (Dolorgiet); Doktacillin (AstraZeneca); Penbritin (GSK); Polycillin (BMS); Principen (BMS); Rosampline (Tedis); Totapen (BMS); Vidopen (APS).

Derivative

Sodium salt.

Nomenclature

CAS number: 69-52-3
Ampicin (BMS); Binotal (Grünenthal); Cilleral (BMS); Penbristol (BMS); Pentrex (BMS); Pentrexyl (BMS); Polycillin-N (BMS); Synpenin (Sankyo); Totacillin N (GSK); Viccillin (Meiji).
C16H18NaN3O4S; mol wt 371.39.
C 51.74%, H 4.89%, Na 6.19%, N 11.31%, O 17.23%, S 8.63%.

Properties

White crystalline powder. Hygroscopic. Very sol in water, isotonic sodium chloride, dextrose solutions.

Derivative

l(+)-Form.

Properties

Crystals, dec at about 205°. [α]D20 +209° (c = 0.2 in water). Less active as an antibiotic than d()-form.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins