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Details

Stereochemistry MIXED
Molecular Formula C26H26N2O6S
Molecular Weight 494.559
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENICILLIN INDANYL

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)OC3=CC4=C(CCC4)C=C3)C5=CC=CC=C5)C(=O)N2[C@H]1C(O)=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

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)

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia.
2002
[Anti-Pseudomonas aerosol therapy in cystic fibrosis: improvement with tobramycin].
2002 Jun
[Evaluation of the influence of deep geomagnetic impacting on growth rate and sensitivity to antibiotics in Escherichia coli].
2002 May-Jun
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
Changes in antibiotic resistance in equine bacterial ulcerative keratitis (1991-2000): 65 horses.
2003 Dec
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
The susceptibility of ionophore-resistant Clostridium aminophilum F to other antibiotics.
2003 Oct
Molecular characterization of plasmids with antimicrobial resistant genes in avian isolates of Pasteurella multocida.
2003 Oct-Dec
Shewanella waksmanii sp. nov., isolated from a sipuncula (Phascolosoma japonicum).
2003 Sep
Thermophile-specific proteins: the gene product of aq_1292 from Aquifex aeolicus is an NTPase.
2003 Sep 23
[Pseudomonas aeruginosa--a significant hospital pathogen and resistance to carbapenem].
2004
Genome-wide mutagenesis of Zea mays L. using RescueMu transposons.
2004
Self-transmissible antibiotic resistance to ampicillin, streptomycin, and tetracyclin found in Escherichia coli isolates from contaminated drinking water.
2004
Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation.
2004 Apr
Vibrio vulnificus in Taiwan.
2004 Aug
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
Staphylococcus aureus and Escherichia hermanii in diabetes patient.
2004 Jul
Serratia marcescens internalization and replication in human bladder epithelial cells.
2004 Jun 9
Bacterial variations on the methionine salvage pathway.
2004 Mar 4
Dictyostelium myosin bipolar thick filament formation: importance of charge and specific domains of the myosin rod.
2004 Nov
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
Resistance to beta-lactam antibiotics in Aeromonas hydrophila isolated from rainbow trout (Oncorhynchus mykiss).
2004 Sep
Incorporation of different antibiotics into carbonated hydroxyapatite coatings on titanium implants, release and antibiotic efficacy.
2004 Sep 14
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
Nuclear hormone receptor NHR-49 controls fat consumption and fatty acid composition in C. elegans.
2005 Feb
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 Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
WHO-VATC QJ01CA05
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
NCI_THESAURUS C1500
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
Code System Code Type Description
MESH
C100244
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
EVMPD
SUB06629MIG
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
NCI_THESAURUS
C76219
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
MERCK INDEX
M3109
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY Merck Index
EPA CompTox
35531-88-5
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
PUBCHEM
93184
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
CAS
35531-88-5
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
INN
3405
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY
ChEMBL
CHEMBL1596
Created by admin on Tue Oct 22 00:34:38 UTC 2019 , Edited by admin on Tue Oct 22 00:34:38 UTC 2019
PRIMARY