CARBENICILLIN

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 Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)C(C(O)=O)C3=CC=CC=C3)C(=O)N2[C@H]1C(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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdfhttp://link.springer.com/chapter/10.1007%2F978-1-4684-3126-1_11
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Neprilysin 29 Target ID: CHEMBL1944 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1284433	Inhibitor 8504	0.18 µM [Ki]
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8504
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8504
Streptococcus pneumoniae growth 20 Target ID: Streptococcus pneumoniae growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8504
Pseudomonas aeruginosa growth 10 Target ID: Pseudomonas aeruginosa growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8504
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20974151	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7116379	Curative	Approved 8583	Uticillin Approved Use Indications: urinary tract infections
Acute and chronic infections of the upper and lower urinary tract 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf	Curative	Approved 8583	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
Prostatitis 25 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf	Curative	Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
6.5 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
16 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/622610/	unhealthy, 57 years Health Status: unhealthy Age Group: 57 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/622610/	Other AEs: Nephrotoxicity... Other AEs: Nephrotoxicity (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/622610/

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/622610/	unhealthy, 57 years Health Status: unhealthy Age Group: 57 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/622610/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OAT1 395

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8285614/, https://pubmed.ncbi.nlm.nih.gov/12697641/	yes		yes (co-administration study) Comment: When coadministrated with Probenecid (OAT inhibitor), Carbenicillin CLr was significantlly reduced. Sources: https://pubmed.ncbi.nlm.nih.gov/8285614/, https://pubmed.ncbi.nlm.nih.gov/12697641/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3393	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3393
ChemicalBook	CB0243304	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0243304
eMolecules	535811	https://www.emolecules.com/cgi-bin/more?vid=535811
MolPort	MolPort-006-116-396	https://www.molport.com/shop/molecule-link/MolPort-006-116-396

PubMed

Title	Date	PubMed
Functional genomic analysis of C. elegans molting.	2005-10	16122351
Uncoupling of longevity and telomere length in C. elegans.	2005-09	16151516
Changes in patterns of antimicrobial susceptibility and class 1 integron carriage among Escherichia coli isolates.	2005-09	16131822
Characterization of Pseudomonas aeruginosa isolated from chronically infected children with cystic fibrosis in India.	2005-07-21	16033658
Development of ERK Activity Sensor, an in vitro, FRET-based sensor of Extracellular Regulated Kinase activity.	2005-07-05	15998468
New genes tied to endocrine, metabolic, and dietary regulation of lifespan from a Caenorhabditis elegans genomic RNAi screen.	2005-07	16103914
Cognate peptide-receptor ligand mapping by directed phage display.	2005-06-17	15963231
An improved method for rapid generation of unmarked Pseudomonas aeruginosa deletion mutants.	2005-05-23	15907219
[Antibiotic resistance of shigellae and rationale for etiotropic therapy of Shigella infections].	2005-05-11	15881945
A combined approach exploring gene function based on worm-human orthology.	2005-05-06	15877817
Antimicrobial responses of Yersinia enterocolitica isolates in comparison to other commonly encountered bacteria that causes diarrhoea.	2005-05	16119753
Infrared and Raman microspectroscopy of foreign materials in tissue specimens.	2005-05	15820906
Characterization of antimicrobial resistance and class 1 integrons found in Escherichia coli isolates from humans and animals in Korea.	2005-05	15761064
Occurrence of antibiotic and metal resistance in bacteria from organs of river fish.	2005-05	15721889
Common antimicrobial resistance patterns, biotypes and serotypes found among Pseudomonas aeruginosa isolates from patient's stools and drinking water sources in Jordan.	2005-04	15920903
Efficient genetic transformation of Sorghum using a visual screening marker.	2005-04	15838555
Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems.	2005-03	15705643
Nuclear hormone receptor NHR-49 controls fat consumption and fatty acid composition in C. elegans.	2005-02	15719061
Early detection of breast cancer based on gene-expression patterns in peripheral blood cells.	2005	16168108
Interaction studies on proteins encoded by the phthiocerol dimycocerosate locus of Mycobacterium tuberculosis.	2004-12	15668773
Mycobacterium tuberculosis from chronic murine infections that grows in liquid but not on solid medium.	2004-11-17	15548322
Functional characterization in Caenorhabditis elegans of transmembrane worm-human orthologs.	2004-11-08	15533247
Dictyostelium myosin bipolar thick filament formation: importance of charge and specific domains of the myosin rod.	2004-11	15492777
Incorporation of different antibiotics into carbonated hydroxyapatite coatings on titanium implants, release and antibiotic efficacy.	2004-09-14	15342186
Resistance to beta-lactam antibiotics in Aeromonas hydrophila isolated from rainbow trout (Oncorhynchus mykiss).	2004-09	15492935
Epidemic strain Shigella dysenteriae Type 1 Dt66 encodes several drug resistances by chromosome.	2004-08-27	15950082
Vibrio vulnificus in Taiwan.	2004-08	15496235
Molecular dissection of the human antibody response to the structural repeat epitope of Plasmodium falciparum sporozoite from a protected donor.	2004-07-29	15283866
Staphylococcus aureus and Escherichia hermanii in diabetes patient.	2004-07	15338542
Symbiotic innovation in the oxymonad Streblomastix strix.	2004-06-29	15218697
Serratia marcescens internalization and replication in human bladder epithelial cells.	2004-06-09	15189566
Prevalence, antibiotic susceptibility, and virulence factors of Yersinia enterocolitica and related species from ready-to-eat vegetables available in Korea.	2004-06	15222537
Xylella fastidiosa subspecies: X. fastidiosa subsp. [correction] fastidiosa [correction] subsp. nov., X. fastidiosa subsp. multiplex subsp. nov., and X. fastidiosa subsp. pauca subsp. nov.	2004-05	15214634
Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation.	2004-04	14727052
Bacterial variations on the methionine salvage pathway.	2004-03-04	15102328
Distribution and characterization of Campylobacter spp. from Russian poultry.	2004-02	14968953
Molecular characterization of plasmids with antimicrobial resistant genes in avian isolates of Pasteurella multocida.	2004-01-08	14708986
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	15789972
[Pseudomonas aeruginosa--a significant hospital pathogen and resistance to carbapenem].	2004	15700688
Genome-wide mutagenesis of Zea mays L. using RescueMu transposons.	2004	15461800
Investigation of Burkholderia cepacia nosocomial outbreak with high fatality in patients suffering from diseases other than cystic fibrosis.	2004	15119360
Self-transmissible antibiotic resistance to ampicillin, streptomycin, and tetracyclin found in Escherichia coli isolates from contaminated drinking water.	2004	15055932
Changes in antibiotic resistance in equine bacterial ulcerative keratitis (1991-2000): 65 horses.	2003-12	14641828
Intravenous colistin in the treatment of sepsis from multiresistant Gram-negative bacilli in critically ill patients.	2003-10	12974973
The susceptibility of ionophore-resistant Clostridium aminophilum F to other antibiotics.	2003-10	12951349
Thermophile-specific proteins: the gene product of aq_1292 from Aquifex aeolicus is an NTPase.	2003-09-23	14503925
Shewanella waksmanii sp. nov., isolated from a sipuncula (Phascolosoma japonicum).	2003-09	13130035
Serovar determination, drug resistance patterns and plasmid profiles of Pseudomonas aeruginosa isolated from burn patients at two hospitals of Tehran (IRAN).	2003-09	12927978
[Optimization of T-dNA insertional mutagenesis and analysis of mutants of Magnaporthe grisea].	2003-07	15969057
Antimicrobial susceptibility pattern of clinical isolates of non-fermentative bacteria.	2003-07	15025332

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose URINARY TRACT INFECTIONS: Escherichia coli, Proteus species and Enterobacter: 1–2 tablets 4 times daily Pseudomonas and Enterococcus: 2 tablets 4 times daily PROSTATITIS Escherichia coli, Proteus mirabilis, Enterobacter and Enterococcus: 2 tablets 4 times daily

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:13:32 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:32 GMT 2025`
Record UNII	G42ZU72N5G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBENICILLIN

Official Name

English

CARBENICILLIN [HSDB]

Preferred Name

English

Carbenicillin [WHO-DD]

Common Name

English

CARBENICILLIN [VANDF]

Common Name

English

carbenicillin [INN]

Common Name

English

CARBENICILLIN [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175497