Bacampicillin

Title: Bacampicillin
CAS Registry Number: 50972-17-3
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 1-[(ethoxycarbonyl)oxy]ethyl ester
Additional Names: (2S,5R,6R)-6-[(R)-(2-amino-2-phenylacetamido)]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid ester with ethyl 1-hydroxyethyl carbonate; 6-[(R)-2-amino-2-phenylacetamido]penicillanic acid [1-(ethoxycarbonyloxy)ethyl] ester; 1¢-ethoxycarbonyloxyethyl 6-(D-a-aminophenylacetamido)penicillanate
Molecular Formula: C21H27N3O7S
Molecular Weight: 465.52
Percent Composition: C 54.18%, H 5.85%, N 9.03%, O 24.06%, S 6.89%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn: B. A. Ekstrom, B. O. H. Sjoberg, DE 2144457; eidem, US 3873521 and US 3939270 (1972, 1975 and 1976 all to Astra). In vitro and in vivo study: N. O. Bodin et al., Antimicrob. Agents Chemother. 8, 518 (1975). Pharmacokinetics: M. Rozencweig et al., Clin. Pharmacol. Ther. 19, 592 (1976); T. Bergan, Antimicrob. Agents Chemother. 13, 971 (1978). Animal studies: C. Carbon et al., Scand. J. Infect. Dis. Suppl. 14, 127 (1978); T. Bergan, I. Versland, ibid. 135; U. Forsgren et al., ibid. 207. Clinical studies: P. V. Maesen et al., J. Antimicrob. Chemother. 2, 279 (1976); J. Sjövall, J. Int. Med. Res. 5, 313 (1977); C. Ekedahl et al., Scand. J. Infect. Dis. Suppl. 14, 279 (1978). Toxicology: M. Edanaga et al., Chemotherapy (Tokyo) 27, Suppl. 4, 17 (1979).
Derivative Type: Hydrochloride
CAS Registry Number: 37661-08-8
Trademarks: Ambacamp (Pharmacia & Upjohn); Ambaxin (Pharmacia); Bacacil (Rottapharm); Bacampicine (Pharmacia & Upjohn); Penglobe (AstraZeneca)
Molecular Formula: C21H27N3O7S.HCl
Molecular Weight: 501.98
Percent Composition: C 50.25%, H 5.62%, N 8.37%, O 22.31%, S 6.39%, Cl 7.06%
Properties: White crystals from acetone-petr ether, mp 171-176° (dec). [a]D20 +161.5°, also reported as +173° (Bodin). Sol in water. LD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga).
Melting point: mp 171-176° (dec)
Optical Rotation: [a]D20 +161.5°
Toxicity data: LD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.
Bacillus thuringiensis Bacilysin Bacimethrin Bacitracin Bacitracin Methylenedisalicylate

Bacampicillin
Bacampicillin.png
Systematic (IUPAC) name
1-Ethoxycarbonyloxyethyl (2S,5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
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Routes Oral
Pharmacokinetic data
Metabolism Rapidly hydrolyzed to ampicillin
Identifiers
CAS number 37661-08-8 N
ATC code J01CA06
PubChem CID 39849
DrugBank DB01602
ChemSpider 390135 YesY
UNII 8GM2J22278 YesY
ChEBI CHEBI:2968 YesY
ChEMBL CHEMBL1583 YesY
Chemical data
Formula C21H27N3O7S 
Mol. mass 465.519 g/mol
 N (what is this?)  (verify)

Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.[1]

It is sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).