Bacampicillin
Chemical compound
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Oral |
Drug class | aminopenicillin |
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Pharmacokinetic data | |
Metabolism | Rapidly hydrolyzed to ampicillin |
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Chemical and physical data | |
Formula | C 21 H 27 N 3 O 7 S |
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
- ↑ Bodin NO, Ekström B, Forsgren U, Jalar LP, Magni L, Ramsay CH, Sjöberg B (November 1975). "Bacampicillin: a new orally well-absorbed derivative of ampicillin" . Antimicrobial Agents and Chemotherapy . 8 (5): 518–25. doi : 10.1128/aac.8.5.518 . PMC 429411 . PMID 1211909 .
- ↑ "Drugs@FDA: FDA-Approved Drugs , BACAMPICILLIN HYDROCHLORIDE" . www.accessdata.fda.gov . Retrieved 2022-07-29 .
- ↑ "Organon USA Inc. et al.; Withdrawal of Approval of 67 New Drug Applications and 128 Abbreviated New Drug Applications" . unblock.federalregister.gov . Retrieved 2022-07-29 .
- ↑ DE 2311328 , Ekström, Bertil; Kovacs, Ödön Kalman Jozsef & Sjöberg, Berndt Olof Harald, "Penicilline und Verfahren zu deren Herstellung [Penicillin and method for manufacturing thereof]", published 1973-10-18, assigned to Astra Läkemedel AB
- ↑ Ekstrom BA, Kovacs OK, and Sjoberg BO, (1973). Chem. Abstr., 80, 14921q(1974).
- ↑ DE 2144457 , Ekström, Bertil Ake & Sjöberg, Berndt Olof Harald, "α-Aminopenicilline und Verfahren zu deren Herstellung [α-aminopenicillins and processes for their preparation]", published 1972-03-30, assigned to Astra Läkemedel AB
- ↑ 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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