bacampicillin
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 458983047
| IUPAC_name = 1-Ethoxycarbonyloxyethyl (2S,5R)-6-
| image = Bacampicillin Structural Formula V2.svg
| class = aminopenicillin
| tradename =
| Drugs.com = {{drugs.com|CONS|bacampicillin}}
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = Oral
| bioavailability =
| protein_bound =
| metabolism = Rapidly hydrolyzed to ampicillin
| elimination_half-life =
| excretion =
| index2_label = HCL
| CAS_number_Ref = {{cascite|changed|??}}
| 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_suffix = CA06
| ATC_supplemental =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PFOLLRNADZZWEX-FFGRCDKISA-N
| PubChem = 39849
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01602
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390135
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1583
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = PM034U953T
| chemical_formula =
| C=21 | H=27 | N=3 | O=7 | S=1
}}
Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.{{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 }}
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.{{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 |archive-url=https://web.archive.org/web/20170430205002/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=050520 |url-status=dead |archive-date=April 30, 2017 |access-date=2022-07-29 |website=www.accessdata.fda.gov}} Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.{{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 }}
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|inventor1-last=Ekström|inventor1-first=Bertil|inventor2-last=Kovacs|inventor2-first=Ödön Kalman Jozsef|inventor3-last=Sjöberg|inventor3-first=Berndt Olof Harald}}Ekstrom BA, Kovacs OK, and Sjoberg BO, (1973). Chem. Abstr., 80, 14921q(1974).{{Cite patent|country=DE|number=2144457|pubdate=1972-03-30|title=α-Aminopenicilline und Verfahren zu deren Herstellung [α-aminopenicillins and processes for their preparation]|assign=Astra Läkemedel AB|inventor1-last=Ekström|inventor1-first=Bertil Ake
|inventor2-last=Sjöberg|inventor2-first=Berndt Olof Harald}}Ekstrom BA, Sjoberg BO, {{US patent|3873521}} and {{US patent|3939270}} (1975 and 1976 both to Astra).]]
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.{{cn|date=March 2023}}
References
{{Reflist}}
{{PenicillinAntiBiotics}}