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

Details

Stereochemistry MIXED
Molecular Formula C26H26N2O6S
Molecular Weight 494.5615
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENICILLIN INDANYL

SMILES

CC1(C)[C@]([H])(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])S1)N=C(C([H])(c3ccccc3)C(=O)Oc4ccc5CCCc5c4)O

InChI

InChIKey=JIRBAUWICKGBFE-MNRDOXJOSA-N
InChI=1S/C26H26N2O6S/c1-26(2)20(24(31)32)28-22(30)19(23(28)35-26)27-21(29)18(15-7-4-3-5-8-15)25(33)34-17-12-11-14-9-6-10-16(14)13-17/h3-5,7-8,11-13,18-20,23H,6,9-10H2,1-2H3,(H,27,29)(H,31,32)/t18?,19-,20+,23-/m1/s1

HIDE SMILES / InChI

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

Carfecillin is a phenyl ester of the side-chain carboxyl group of carbenicillin, beta-lactam antibiotic, acting as a prodrug. Upon oral administration, is broken down in the intestinal mucosa to the active antibacterial. It is used for urinary tract infections.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.179999999999999993 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

88905600000
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

88905600000
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
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
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
Anicteric carbenicillin hepatitis. Eight episodes in four patients.
1975 May 26
Suppression of damping-off in maize seedlings by Pseudomonas corrugata.
2001
Generation of class-selective monoclonal antibodies against the penicillin group.
2001 Jul
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
Characterization of a putative RND-type efflux system in Agrobacterium tumefaciens.
2001 May 30
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.
2001 Oct
Calorimetric analysis of cephalosporins using an immobilized TEM-1 beta-lactamase on Ni2+ chelating sepharose fast flow.
2001 Sep 1
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia.
2002
Kinetic analysis of thermal decomposition for penicillin sodium salts: model-fitting and model-free methods.
2002 Aug 1
[Anti-Pseudomonas aerosol therapy in cystic fibrosis: improvement with tobramycin].
2002 Jun
Interaction of the Yersinia pestis type III regulatory proteins LcrG and LcrV occurs at a hydrophobic interface.
2002 Jun 28
[Evaluation of the influence of deep geomagnetic impacting on growth rate and sensitivity to antibiotics in Escherichia coli].
2002 May-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
On the mechanism of substrate specificity by resistance nodulation division (RND)-type multidrug resistance pumps: the large periplasmic loops of MexD from Pseudomonas aeruginosa are involved in substrate recognition.
2002 Nov
A novel assembly process of the multicomponent xenobiotic efflux pump in Pseudomonas aeruginosa.
2002 Nov
Sinorhizobium morelense sp. nov., a Leucaena leucocephala-associated bacterium that is highly resistant to multiple antibiotics.
2002 Sep
Establishment of a highly efficient transformation system for pepper (Capsicum annuum L.).
2003 Apr
Catalytic properties of an endogenous beta-lactamase responsible for the resistance of Azospirillum lipoferum to beta-lactam antibiotics.
2003 Feb
[Optimization of T-dNA insertional mutagenesis and analysis of mutants of Magnaporthe grisea].
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
Molecular characterisation and antimicrobial resistance of Vibrio vulnificus and Vibrio alginolyticus isolated from mussels (Mytilus galloprovincialis).
2003 Mar
Intravenous colistin in the treatment of sepsis from multiresistant Gram-negative bacilli in critically ill patients.
2003 Oct
Serovar determination, drug resistance patterns and plasmid profiles of Pseudomonas aeruginosa isolated from burn patients at two hospitals of Tehran (IRAN).
2003 Sep
Thermophile-specific proteins: the gene product of aq_1292 from Aquifex aeolicus is an NTPase.
2003 Sep 23
Evaluation of a simple carrier molecule to enhance drug penetration of dermal layers by utilizing multivariate methods, structure property correlations, and continuous system modeling.
2004
[Pseudomonas aeruginosa--a significant hospital pathogen and resistance to carbapenem].
2004
Interaction studies on proteins encoded by the phthiocerol dimycocerosate locus of Mycobacterium tuberculosis.
2004 Dec
Distribution and characterization of Campylobacter spp. from Russian poultry.
2004 Feb
Prevalence, antibiotic susceptibility, and virulence factors of Yersinia enterocolitica and related species from ready-to-eat vegetables available in Korea.
2004 Jun
Xylella fastidiosa subspecies: X. fastidiosa subsp. [correction] fastidiosa [correction] subsp. nov., X. fastidiosa subsp. multiplex subsp. nov., and X. fastidiosa subsp. pauca subsp. nov.
2004 May
Symbiotic innovation in the oxymonad Streblomastix strix.
2004 May-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
Efficient genetic transformation of Sorghum using a visual screening marker.
2005 Apr
New genes tied to endocrine, metabolic, and dietary regulation of lifespan from a Caenorhabditis elegans genomic RNAi screen.
2005 Jul
Characterization of Pseudomonas aeruginosa isolated from chronically infected children with cystic fibrosis in India.
2005 Jul 21
Cognate peptide-receptor ligand mapping by directed phage display.
2005 Jun 17
Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems.
2005 Mar
Antimicrobial responses of Yersinia enterocolitica isolates in comparison to other commonly encountered bacteria that causes diarrhoea.
2005 May
Infrared and Raman microspectroscopy of foreign materials in tissue specimens.
2005 May
Functional genomic analysis of C. elegans molting.
2005 Oct
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

Usual Adult Dose
Route of Administration: Oral
In Vitro Use Guide
The activity of carbenicillin against 200 strains of Pseudomonas aeruginosa was measured by a quantitative agar dilution method. Carbenicillin 300 mug. per ml. exerted appreciable bactericidal effect against nine of 15 strains of Ps. aeruginosa after a 24-hour contact period; after only six hours the bactericidal effect was very small. Quantitative sensitivity measurements for carbenicillin should include minimal inhibitory concentrations (M.I.C.'s) values for both complete inhibition (CI) and reduced growth (RG) criteria, using a range of inocula for testing. Such M.I.C. values may well be useful in monitoring carbenicillin therapy of tissue infections.
Name Type Language
CARBENICILLIN INDANYL
Common Name English
1-(5-INDANYL)(2S,5R,6R)-N-(2-CARBOXY-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-6-YL)-2-PHENYLMALONAMATE
Common Name English
INDANYL CARBENICILLIN
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((3-((2,3-DIHYDRO-1H-INDEN-5-YL)OXY)-1,3-DIOXO-2-PHENYLPROPYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S,5R,6R)-
Common Name English
CARINDACILLIN [MI]
Common Name English
CARINDACILLIN [WHO-DD]
Common Name English
CARINDACILLIN [INN]
Common Name English
CARINDACILLIN
INN   MI   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
WHO-ATC J01CA05
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
WHO-VATC QJ01CA05
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
NCI_THESAURUS C1500
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
Code System Code Type Description
MESH
C100244
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
EVMPD
SUB06629MIG
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
NCI_THESAURUS
C76219
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
MERCK INDEX
M3109
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY Merck Index
EPA CompTox
35531-88-5
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
PUBCHEM
93184
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
CAS
35531-88-5
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
DRUG CENTRAL
508
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
DRUG BANK
DB09319
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
INN
3405
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL1596
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY
FDA UNII
5V278481KE
Created by admin on Sat Jun 26 10:25:37 UTC 2021 , Edited by admin on Sat Jun 26 10:25:37 UTC 2021
PRIMARY