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Revision as of 15:23, 4 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI', 'StdInChI', 'StdInChIKey', 'CAS_number').← Previous edit Latest revision as of 05:50, 9 December 2024 edit undoCitation bot (talk | contribs)Bots5,418,255 edits Added date. | Use this bot. Report bugs. | Suggested by Abductive | Category:Prodrugs | #UCB_Category 151/338 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 437166992 | verifiedrevid = 458983047
| IUPAC_name = 1-Ethoxycarbonyloxyethyl (2''S'',5''R'')-6-<nowiki>amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate | IUPAC_name = 1-Ethoxycarbonyloxyethyl (2''S'',5''R'')-6-<nowiki>amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate
| image = Bacampicillin.png | image = Bacampicillin Structural Formula V2.svg


<!--Clinical data--> <!--Clinical data-->
| class = ]
| tradename = | tradename =
| Drugs.com = {{drugs.com|CONS|bacampicillin}} | Drugs.com = {{drugs.com|CONS|bacampicillin}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
| routes_of_administration = Oral | routes_of_administration = Oral


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = Rapidly ] to ] | metabolism = Rapidly ] to ]
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| index2_label = HCL
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 37661-08-8 -->
| CAS_number = 50972-17-3
⚫ | CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 37661-08-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = 8GM2J22278
| ATC_prefix = J01 | ATC_prefix = J01
| ATC_suffix = CA06 | ATC_suffix = CA06
| ATC_supplemental = | ATC_supplemental =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2968 | ChEBI = 2968
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PFOLLRNADZZWEX-FFGRCDKISA-N | StdInChIKey = PFOLLRNADZZWEX-FFGRCDKISA-N
| PubChem = 39849 | PubChem = 39849
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01602 | DrugBank = DB01602
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390135 | ChemSpiderID = 390135
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = 8GM2J22278
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1583 | ChEMBL = 1583


| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = PM034U953T
<!--Chemical data--> <!--Chemical data-->
| chemical_formula = | chemical_formula =
| C=21 | H=27 | N=3 | O=7 | S=1 | C=21 | H=27 | N=3 | O=7 | S=1
| molecular_weight = 465.519 g/mol
}} }}
'''Bacampicillin''' (]) is a ] ]. It is a ] of ] with improved oral ].<ref>{{cite journal |author=Bodin NO |title=Bacampicillin: a New Orally Well-Absorbed Derivative of Ampicillin |journal=] |volume=8 |issue=5 |pages=518–25 |year=1975 |month=November |pmid=1211909 |doi= |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=1211909 |pmc=429411 |author-separator=, |author2=Ekström B |author3=Forsgren U |display-authors=3 |last4=Jalar |first4=LP |last5=Magni |first5=L |last6=Ramsay |first6=CH |last7=Sjöberg |first7=B}}</ref> '''Bacampicillin''' (]) is a ] ]. It is a ] of ] with improved oral ].<ref>{{cite journal | vauthors = Bodin NO, Ekström B, Forsgren U, Jalar LP, Magni L, Ramsay CH, Sjöberg B | title = Bacampicillin: a new orally well-absorbed derivative of ampicillin | journal = Antimicrobial Agents and Chemotherapy | volume = 8 | issue = 5 | pages = 518–25 | date = November 1975 | pmid = 1211909 | pmc = 429411 | doi = 10.1128/aac.8.5.518 }}</ref>


It was sold under the brand names '''Spectrobid''' (]) and '''Penglobe''' (]).In 2015, Pfizer discontinued Spectrobid, and no generic manufacturer has taken over production.<ref>{{Cite web |title=Drugs@FDA: FDA-Approved Drugs , BACAMPICILLIN HYDROCHLORIDE |url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=050520 |access-date=2022-07-29 |website=www.accessdata.fda.gov}}</ref> Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.<ref>{{Cite web |title=Organon USA Inc. et al.; Withdrawal of Approval of 67 New Drug Applications and 128 Abbreviated New Drug Applications |url=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 |access-date=2022-07-29 |website=unblock.federalregister.gov|date=13 October 2015 }}</ref>
It is sold under the brand names '''Spectrobid''' (]) and '''Penglobe''' (]).


==References== ==Synthesis==
Semi-synthetic antibiotic related to penicillin.

The relatively small chemical difference between ] and ] 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 ]. 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.
|assign=]|inventor1-last=Ekström|inventor1-first=Bertil|inventor2-last=Kovacs|inventor2-first=Ödön Kalman Jozsef|inventor3-last=Sjöberg|inventor3-first=Berndt Olof Harald}}</ref><ref>Ekstrom BA, Kovacs OK, and Sjoberg BO, (1973). Chem. Abstr., 80, 14921q(1974).</ref><ref>{{Cite patent|country=DE|number=2144457|pubdate=1972-03-30|title=α-Aminopenicilline und Verfahren zu deren Herstellung |assign=]|inventor1-last=Ekström|inventor1-first=Bertil Ake
|inventor2-last=Sjöberg|inventor2-first=Berndt Olof Harald}}</ref><ref>Ekstrom BA, Sjoberg BO, {{US patent|3873521}} and {{US patent|3939270}} (1975 and 1976 both to Astra).</ref>]]
An azidopenicillin sodium salt ('''1''') is reacted with mixed carbonate ester '''2''' (itself prepared from ] and ]) 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.{{cn|date=March 2023}}

== References ==
{{Reflist}} {{Reflist}}


{{PenicillinAntiBiotics}} {{PenicillinAntiBiotics}}


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{{antibiotic-stub}} {{antibiotic-stub}}

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