Bacampicillin

Bacampicillin
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Oral
Drug class	aminopenicillin
ATC code	J01CA06 (WHO) ;
Pharmacokinetic data
Metabolism	Rapidly hydrolyzed to ampicillin
Identifiers
	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;
CAS Number	50972-17-3 ; HCL: 37661-08-8 ;
PubChem CID	39849;
DrugBank	DB01602 ;
ChemSpider	390135 ;
UNII	8GM2J22278; HCL: PM034U953T ;
ChEBI	CHEBI:2968 ;
ChEMBL	ChEMBL1583 ;
CompTox Dashboard (EPA)	DTXSID2048030 ;
Chemical and physical data
Formula	C21H27N3O7S
Molar mass	465.52 g·mol−1
	InChI InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1 ; Key:PFOLLRNADZZWEX-FFGRCDKISA-N ;
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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, CO₂ 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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[1] 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.

[2] "Drugs@FDA: FDA-Approved Drugs , BACAMPICILLIN HYDROCHLORIDE". www.accessdata.fda.gov. Retrieved 2022-07-29.

[3] "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.

[4] 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

[5] Ekstrom BA, Kovacs OK, and Sjoberg BO, (1973). Chem. Abstr., 80, 14921q(1974).

[6] 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

[7] 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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