U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C17H18N2O6S
Molecular Weight 378.4
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C(O)=O)C3=CC=CC=C3)C(O)=O

InChI

InChIKey=FPPNZSSZRUTDAP-UWFZAAFLSA-N
InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H18N2O6S
Molecular Weight 378.4
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/21771 and http://www.ncbi.nlm.nih.gov/pubmed/789326

Geocillin, a trade name is the sodium salt of the indanyl ester of carbenicillin disodium, which used to treat acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria. In addition, Geocillin was also indicated in the treatment of prostatitis due to susceptible strains of the following organisms: Escherichia coli; Enterococcus (S. faecalis); Proteus mirabilis; Enterobacter sp. Free carbenicillin is the predominant pharmacologically active fraction of Geocillin. After absorption, Geocillin is rapidly converted to carbenicillin by hydrolysis of the ester linkage. Carbenicillin exerts its antibacterial activity by interference with final cell wall synthesis of susceptible bacteria. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. In 2008 Pfizer has decided to discontinue the manufacturing of Geocillin (carbenicillin indanyl sodium)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.18 µM [Ki]
Target ID: Escherichia coli growth
Target ID: Staphylococcus aureus growth
Target ID: Streptococcus pneumoniae growth
Target ID: Pseudomonas aeruginosa growth
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Uticillin

Approved Use

Indications: urinary tract infections
Curative
GEOCILLIN

Approved Use

Geocillin (carbenicillin indanyl sodium) is indicated in the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of the following organisms: Escherichia coli; Proteus mirabilis; Morganella morganii (formerly Proteus morganii); Providencia rettgeri (formerly Proteus rettgeri); Proteus vulgaris; Pseudomonas Enterobacter; Enterococci. Geocillin is also indicated in the treatment of prostatitis due to susceptible strains of the following organisms: Escherichia coli; Enterococcus (S. faecalis); Proteus mirabilis; Enterobacter sp. WHEN HIGH AND RAPID BLOOD AND URINE LEVELS OF ANTIBIOTIC ARE INDICATED, THERAPY WITH GEOPEN (CARBENICILLIN DISODIUM) SHOULD BE INITIATED BY PARENTERAL ADMINISTRATION FOLLOWED, AT THE PHYSICIAN’S DISCRETION, BY ORAL THERAPY. To reduce the development of drug-resistant bacteria and maintain effectiveness of Geocillin and other antibacterial drugs, Geocillin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

1972
Curative
GEOCILLIN

Approved Use

Geocillin (carbenicillin indanyl sodium) is indicated in the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of the following organisms: Escherichia coli; Proteus mirabilis; Morganella morganii (formerly Proteus morganii); Providencia rettgeri (formerly Proteus rettgeri); Proteus vulgaris; Pseudomonas Enterobacter; Enterococci. Geocillin is also indicated in the treatment of prostatitis due to susceptible strains of the following organisms: Escherichia coli; Enterococcus (S. faecalis); Proteus mirabilis; Enterobacter sp. WHEN HIGH AND RAPID BLOOD AND URINE LEVELS OF ANTIBIOTIC ARE INDICATED, THERAPY WITH GEOPEN (CARBENICILLIN DISODIUM) SHOULD BE INITIATED BY PARENTERAL ADMINISTRATION FOLLOWED, AT THE PHYSICIAN’S DISCRETION, BY ORAL THERAPY. To reduce the development of drug-resistant bacteria and maintain effectiveness of Geocillin and other antibacterial drugs, Geocillin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

1972
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.5 μg/mL
382 mg single, oral
dose: 382 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
16 μg × h/mL
382 mg single, oral
dose: 382 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
382 mg single, oral
dose: 382 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 g 4 times / day steady, intravenous
Dose: 5 g, 4 times / day
Route: intravenous
Route: steady
Dose: 5 g, 4 times / day
Sources:
unhealthy, 57 years
Health Status: unhealthy
Condition: interstitial nephritis
Age Group: 57 years
Sex: M
Sources:
Other AEs: Nephrotoxicity...
Other AEs:
Nephrotoxicity (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nephrotoxicity 1 patient
5 g 4 times / day steady, intravenous
Dose: 5 g, 4 times / day
Route: intravenous
Route: steady
Dose: 5 g, 4 times / day
Sources:
unhealthy, 57 years
Health Status: unhealthy
Condition: interstitial nephritis
Age Group: 57 years
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes (co-administration study)
Comment: When coadministrated with Probenecid (OAT inhibitor), Carbenicillin CLr was significantlly reduced.
PubMed

PubMed

TitleDatePubMed
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.
1975 Dec
Carbenicillin prodrugs: stability kinetics of alpha-phenyl and alpha-indanyl esters in aqueous solution.
1979 Oct
Val-237 for Ala substitution in the TEM-2 beta-lactamase dramatically alters the catalytic efficiencies towards carbenicillin and ticarcillin.
1994 Apr 15
Suppression of damping-off in maize seedlings by Pseudomonas corrugata.
2001
[Improvement of transformation frequency of rice mediated by Agrobacterium].
2001
Prevalence and antibiotic susceptibility pattern of bacterial isolates from blood culture in Tikur Anbassa Hospital, Addis Ababa, Ethiopia.
2001 Apr
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.
2001 Jan 16
Generation of class-selective monoclonal antibodies against the penicillin group.
2001 Jul
Rapid two-step purification of a recombinant mouse Fab fragment expressed in Escherichia coli.
2001 Jul
Antimicrobial sensitivity of Neisseria gonorrhoea in Gondar, Ethiopia.
2001 May
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase.
2001 May
Shewanella japonica sp. nov.
2001 May
Sterile preparation of antibiotic-selective LB agar plates using a microwave oven.
2001 May
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001 May
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs.
2001 May-Jun
Frequency of Pseudomonas aeruginosa serotypes in burn wound infections and their resistance to antibiotics.
2002 Jun
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
DNA-DNA reassociation and phenotypic data indicate synonymy between Aeromonas enteropelogenes Schubert et al. 1990 and Aeromonas trota Carnahan et al. 1991.
2002 Nov
A novel assembly process of the multicomponent xenobiotic efflux pump in Pseudomonas aeruginosa.
2002 Nov
Establishment of a highly efficient transformation system for pepper (Capsicum annuum L.).
2003 Apr
Changes in antibiotic resistance in equine bacterial ulcerative keratitis (1991-2000): 65 horses.
2003 Dec
Catalytic properties of an endogenous beta-lactamase responsible for the resistance of Azospirillum lipoferum to beta-lactam antibiotics.
2003 Feb
Deacetoxycephalosporin C synthase isozymes exhibit diverse catalytic activity and substrate specificity.
2003 Jan 28
[Optimization of T-dNA insertional mutagenesis and analysis of mutants of Magnaporthe grisea].
2003 Jul
Prevalence and antibiotic susceptibility of Salmonella isolated from foods in Korea from 1993 to 2001.
2003 Jul
Maturation of the Coxiella burnetii parasitophorous vacuole requires bacterial protein synthesis but not replication.
2003 Jul
Fusogenicity of the Coxiella burnetii parasitophorous vacuole.
2003 Jun
Shewanella waksmanii sp. nov., isolated from a sipuncula (Phascolosoma japonicum).
2003 Sep
[Pseudomonas aeruginosa--a significant hospital pathogen and resistance to carbapenem].
2004
Investigation of Burkholderia cepacia nosocomial outbreak with high fatality in patients suffering from diseases other than cystic fibrosis.
2004
Staphylococcus aureus and Escherichia hermanii in diabetes patient.
2004 Jul
Molecular dissection of the human antibody response to the structural repeat epitope of Plasmodium falciparum sporozoite from a protected donor.
2004 Jul 29
Prevalence, antibiotic susceptibility, and virulence factors of Yersinia enterocolitica and related species from ready-to-eat vegetables available in Korea.
2004 Jun
Functional characterization in Caenorhabditis elegans of transmembrane worm-human orthologs.
2004 Nov 8
Early detection of breast cancer based on gene-expression patterns in peripheral blood cells.
2005
Nuclear hormone receptor NHR-49 controls fat consumption and fatty acid composition in C. elegans.
2005 Feb
Cognate peptide-receptor ligand mapping by directed phage display.
2005 Jun 17
Infrared and Raman microspectroscopy of foreign materials in tissue specimens.
2005 May
Characterization of antimicrobial resistance and class 1 integrons found in Escherichia coli isolates from humans and animals in Korea.
2005 May
An improved method for rapid generation of unmarked Pseudomonas aeruginosa deletion mutants.
2005 May 23
Uncoupling of longevity and telomere length in C. elegans.
2005 Sep
Changes in patterns of antimicrobial susceptibility and class 1 integron carriage among Escherichia coli isolates.
2005 Sep
Patents

Sample Use Guides

In Vivo Use Guide
500 mg every 8 h for 7 days .
Route of Administration: Oral
In Vitro Use Guide
Carfecillin inhibited Staphylococcus aureus growth with MIC 0.25 ug/ml
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:55:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:48 GMT 2023
Record UNII
G42ZU72N5G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBENICILLIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Carbenicillin [WHO-DD]
Common Name English
CARBENICILLIN [VANDF]
Common Name English
CARBENICILLIN [HSDB]
Common Name English
carbenicillin [INN]
Common Name English
CARBENICILLIN [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175497
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NCI_THESAURUS C1558
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
WHO-ATC J01CA03
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
LIVERTOX 147
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
WHO-VATC QJ01CA03
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
Code System Code Type Description
WIKIPEDIA
CARBENICILLIN
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
DRUG BANK
DB00578
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
FDA UNII
G42ZU72N5G
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
NCI_THESAURUS
C343
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
225-171-0
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL1214
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
EVMPD
SUB06122MIG
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
CHEBI
3393
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
CAS
4697-36-3
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
DRUG CENTRAL
492
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
MERCK INDEX
m3063
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY Merck Index
INN
2516
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID6048464
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
MESH
D002228
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
HSDB
3020
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
RXCUI
2015
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY RxNorm
PUBCHEM
20824
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
SMS_ID
100000081338
Created by admin on Fri Dec 15 15:55:48 GMT 2023 , Edited by admin on Fri Dec 15 15:55:48 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC