Chemical compound
 ;templatestyles src="Infobox drug/styles.css"/ ;
 | vaccine = Vaccine description
 | combo = Combination of
 | mab = Monoclonal antibody
 | #default =
 |inactivated |killed = Inactivated
 |attenuated = Attenuated
 |live = Live bacteria
 |viral = Viral vector
 |toxoid = Toxoid
 |subunit = Subunit
 |protein |protein subunit = Protein subunit
 |peptide |peptide subunit = Peptide subunit
 |polysaccharide = Polysaccharide
 |vlp = Virus-like particles
 |conjugate = Conjugate
 |recombinant = Recombinant vector
 |dna = DNA
 |rna = RNA
 |mrna = mRNA
 |heterologous = Heterologous
 | mab = Whole antibody
 | fab = Fab fragment
 | f(ab')2 = F(ab')2 fragment
 | fab' = Fab' fragment
 | scfv = Single-chain variable fragment
 | discfv = Di-single-chain variable fragment
 | sdab = Single domain antibody
 | 3funct = Trifunctional antibody
 | clfab = Chemically linked Fab
 | bite = Bi-specific T-cell engager
 |INN_EMA=
 | _EMA_use_INN={{ParameterUseFirst
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 |3=
 |licence_US=
 |DailyMedID=
 |licence_CA=
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 | label71 = [[Bioavailability]]
 | data71 = 
 | label72 = [[Plasma protein binding|Protein binding]]
 | data72 = 
 | label73 = [[Drug metabolism|Metabolism]]
 | data73 = {{#if: |Rapidly [[hydrolysis|{{#if:
 | label74 = [[Metabolite]]s
 | data74 = 
 | label75 = [[Onset of action]]
 | data75 = 
 | label76 = [[Biological half-life|Elimination {{nowrap|half-life}}]]
 | data76 = 
 | label77 = [[Pharmacodynamics#Duration_of_action|Duration of action]]
 | data77 = 
 | label78 = [[Excretion]]
 | data78 = 
 | data81 = {{#switch:{{lc:}} |mab|combo|vaccine= |#default={{#if:1-Ethoxycarbonyloxyethyl (2"S",5"R")-6-[[(2"R")-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
 | label102 = [[Chemical formula|Formula]]
 | data102 = {{Infobox drug/chemical formula
 | label103 = [[Molar mass]]
 | data103 = {{Chem molar mass
 | label104 = 3D model ([[JSmol]])
 | data104 = {{#ifeq:|none||{{unbulleted list
 | label106 = [[Chirality (chemistry)|Chirality]]
 | data106 = 
 | label107 = [[Specific rotation]]
 | data107 = 
 | label111 = [[Density]]
 | data111 = {{#if: |  g/cm3}} 
 | label112= [[Melting point]]
 | data112 = {{#if:|{{convert| {{#if:|to |}}|C|F}} }} 
 | label113 = [[Boiling point]]
 | data113 = {{#if:|{{convert| {{#if:|to |}}|C|F}} }} 
 | label114 = [[Aqueous solution|Solubility in water]]
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 {{Collapsible list
 |liststyle=word-break:break-all;
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Oral
 [[aminopenicillin]]
J01
Bacampicillin ([[International Nonproprietary Name|INN]]) is a [[penicillin]] [[antibiotic]]. It is a [[prodrug]] of [[ampicillin]] with improved oral [[bioavailability]].
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. Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.
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.
[[File:Bacampicillin synthesis.svg|thumb|center|700px|Bacampicillin synthesis:]]
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.
References.
 ;templatestyles src="Reflist/styles.css" / ;
[[Category:Penicillins]]
[[Category:Carboxylate esters]]
[[Category:Prodrugs]]
[[Category:Ethyl esters]]