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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 = 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
| 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 | PubChem = 39849
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | 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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Latest revision as of 05:50, 9 December 2024

Chemical compound Pharmaceutical compound
Bacampicillin
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral
Drug classaminopenicillin
ATC code
Pharmacokinetic data
MetabolismRapidly hydrolyzed to ampicillin
Identifiers
IUPAC name
  • 1-Ethoxycarbonyloxyethyl (2S,5R)-6-amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H27N3O7S
Molar mass465.52 g·mol
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
  (what is this?)  (verify)

Bacampicillin (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.

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

  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. 13 October 2015. Retrieved 2022-07-29.
  4. DE 2311328, Ekström, Bertil; Kovacs, Ödön Kalman Jozsef & Sjöberg, Berndt Olof Harald, "Penicilline und Verfahren zu deren Herstellung ", 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 ", 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).
Antibacterials active on the cell wall and envelope (J01C-J01D)
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cell wall by binding
to and inhibiting
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