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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

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

8.8905597E10
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

8.8905597E10
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
Anicteric carbenicillin hepatitis. Eight episodes in four patients.
1975 May 26
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
Prevalence and antibiotic susceptibility pattern of bacterial isolates from blood culture in Tikur Anbassa Hospital, Addis Ababa, Ethiopia.
2001 Apr
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
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase.
2001 May
Sterile preparation of antibiotic-selective LB agar plates using a microwave oven.
2001 May
Characterization of a putative RND-type efflux system in Agrobacterium tumefaciens.
2001 May 30
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs.
2001 May-Jun
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.
2001 Oct
Construction of a shuttle vector and transformation of Xylella fastidiosa with plasmid DNA.
2001 Sep
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia.
2002
Pseudomonas aeruginosa ventilator-associated pneumonia: comparison of episodes due to piperacillin-resistant versus piperacillin-susceptible organisms.
2002 Apr 15
[Anti-Pseudomonas aerosol therapy in cystic fibrosis: improvement with tobramycin].
2002 Jun
In vitro antimicrobial susceptibility of 183 Pseudomonas aeruginosa strains isolated from dogs to selected antipseudomonal agents.
2002 May
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
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
Antimicrobial susceptibility pattern of clinical isolates of non-fermentative bacteria.
2003 Jul
Intravenous colistin in the treatment of sepsis from multiresistant Gram-negative bacilli in critically ill patients.
2003 Oct
Shewanella waksmanii sp. nov., isolated from a sipuncula (Phascolosoma japonicum).
2003 Sep
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
Distribution and characterization of Campylobacter spp. from Russian poultry.
2004 Feb
Staphylococcus aureus and Escherichia hermanii in diabetes patient.
2004 Jul
Prevalence, antibiotic susceptibility, and virulence factors of Yersinia enterocolitica and related species from ready-to-eat vegetables available in Korea.
2004 Jun
Mycobacterium tuberculosis from chronic murine infections that grows in liquid but not on solid medium.
2004 Nov 17
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
Common antimicrobial resistance patterns, biotypes and serotypes found among Pseudomonas aeruginosa isolates from patient's stools and drinking water sources in Jordan.
2005 Apr
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
Development of ERK Activity Sensor, an in vitro, FRET-based sensor of Extracellular Regulated Kinase activity.
2005 Jul 5
Epidemic strain Shigella dysenteriae Type 1 Dt66 encodes several drug resistances by chromosome.
2005 Jul-Aug
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
[Antibiotic resistance of shigellae and rationale for etiotropic therapy of Shigella infections].
2005 Mar-Apr
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
Characterization of antimicrobial resistance and class 1 integrons found in Escherichia coli isolates from humans and animals in Korea.
2005 May
Occurrence of antibiotic and metal resistance in bacteria from organs of river fish.
2005 May
An improved method for rapid generation of unmarked Pseudomonas aeruginosa deletion mutants.
2005 May 23
A combined approach exploring gene function based on worm-human orthology.
2005 May 6
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

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
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