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]

^ 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. Archived from the original on April 30, 2017. 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. 13 October 2015. Retrieved 2022-07-29.

[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. Archived from the original on April 30, 2017. 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. 13 October 2015. Retrieved 2022-07-29.

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