Chemistry:Bacampicillin
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| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration | Oral |
| Drug class | aminopenicillin |
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| Pharmacokinetic data | |
| Metabolism | Rapidly hydrolyzed to ampicillin |
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| Chemical and physical data | |
| Formula | C21H27N3O7S |
| Molar mass | 465.52 g·mol−1 |
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Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.[1]
It was sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).In 2015, Pfizer discontinued Spectrobid, and no generic manufacturer has taken over production.[2] Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.[3]
Synthesis
Semi-synthetic antibiotic related to penicillin.
The relatively small chemical difference between ampicillin and benzylpenicillin not only allows for substantial oral activity but also results in a substantial broadening of antimicrobial spectrum so as to allow for use against many Gram-negative bacteria. Many devices have been employed in order to enhance still further the oral absorption of ampicillin. Bacampicillin is a prodrug of ampicillin designed for this purpose.
An azidopenicillin sodium salt (1) is reacted with mixed carbonate ester 2 (itself prepared from acetaldehyde and ethyl chloroformate) to give ester 3. Reduction of the azido linkage with hydrogen and a suitable catalyst produces bacampillin (4). Both enantiomers are active. The drug is rapidly absorbed from the gastrointestinal tract and is quickly cleaved by serum esterases to bioactive ampicillin, acetaldehyde, CO
2 and ethanol.[citation needed]
References
- ↑ "Bacampicillin: a new orally well-absorbed derivative of ampicillin". Antimicrobial Agents and Chemotherapy 8 (5): 518–25. November 1975. doi:10.1128/aac.8.5.518. PMID 1211909.
- ↑ "Drugs@FDA: FDA-Approved Drugs , BACAMPICILLIN HYDROCHLORIDE". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=050520.
- ↑ "Organon USA Inc. et al.; Withdrawal of Approval of 67 New Drug Applications and 128 Abbreviated New Drug Applications". https://www.federalregister.gov/documents/2015/10/13/2015-25922/organon-usa-inc-et-al-withdrawal-of-approval-of-67-new-drug-applications-and-128-abbreviated-new.
- ↑ Ekström, Bertil; Ödön Kalman Jozsef Kovacs & Berndt Olof Harald Sjöberg, "Penicilline und Verfahren zu deren Herstellung [Penicillin and method for manufacturing thereof]", DE patent 2311328, published 1973-10-18
- ↑ Ekstrom BA, Kovacs OK, and Sjoberg BO, (1973). Chem. Abstr., 80, 14921q(1974).
- ↑ Ekström, Bertil Ake & Berndt Olof Harald Sjöberg, "α-Aminopenicilline und Verfahren zu deren Herstellung [α-aminopenicillins and processes for their preparation]", DE patent 2144457, published 1972-03-30
- ↑ Ekstrom BA, Sjoberg BO, U.S. Patent 3,873,521 and U.S. Patent 3,939,270 (1975 and 1976 both to Astra).
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