CARBENICILLIN

First approved in 1970

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

[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
Sources: http://link.springer.com/chapter/10.1007%2F978-1-4684-3126-1_11https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf
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)

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Neprilysin 28 Target ID: CHEMBL1944 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1284433	Inhibitor 8228	0.18 µM [Ki]
Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8228
Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8228
Target ID: Streptococcus pneumoniae growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8228
Target ID: Pseudomonas aeruginosa growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21771	Inhibitor 8228
Bacterial penicillin-binding protein 232 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20974151	Inhibitor 8228

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 204 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7116379	Curative	Approved 8360	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 8360	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
Prostatitis 25 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf	Curative	Approved 8360	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

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 Condition: interstitial nephritis 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 Condition: interstitial nephritis 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 320

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 320	substrate 3326 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
MolPort	MolPort-006-116-396	https://www.molport.com/shop/molecule-link/MolPort-006-116-396
eMolecules	535811	https://www.emolecules.com/cgi-bin/more?vid=535811

PubMed

Title	Date	PubMed
Anicteric carbenicillin hepatitis. Eight episodes in four patients.	1975 May 26	1173185
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.	2001 Jan 16	11148033
Sterile preparation of antibiotic-selective LB agar plates using a microwave oven.	2001 May	11355358
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia.	2002	12237969
Kinetic analysis of thermal decomposition for penicillin sodium salts: model-fitting and model-free methods.	2002 Aug 1	12110388
Growth and differentiation of transgenic callus regulated by phytohormones and antibiotics in transformation of loblolly pine.	2002 Feb	11902001
Interaction of the Yersinia pestis type III regulatory proteins LcrG and LcrV occurs at a hydrophobic interface.	2002 Jun 28	12102728
Establishment of a highly efficient transformation system for pepper (Capsicum annuum L.).	2003 Apr	12789523
Fusogenicity of the Coxiella burnetii parasitophorous vacuole.	2003 Jun	12860689
Thermophile-specific proteins: the gene product of aq_1292 from Aquifex aeolicus is an NTPase.	2003 Sep 23	14503925
Genome-wide mutagenesis of Zea mays L. using RescueMu transposons.	2004	15461800
Distribution and characterization of Campylobacter spp. from Russian poultry.	2004 Feb	14968953
Early detection of breast cancer based on gene-expression patterns in peripheral blood cells.	2005	16168108
Development of ERK Activity Sensor, an in vitro, FRET-based sensor of Extracellular Regulated Kinase activity.	2005 Jul 5	15998468
Infrared and Raman microspectroscopy of foreign materials in tissue specimens.	2005 May	15820906
Characterization of antimicrobial resistance and class 1 integrons found in Escherichia coli isolates from humans and animals in Korea.	2005 May	15761064
An improved method for rapid generation of unmarked Pseudomonas aeruginosa deletion mutants.	2005 May 23	15907219
Uncoupling of longevity and telomere length in C. elegans.	2005 Sep	16151516
Changes in patterns of antimicrobial susceptibility and class 1 integron carriage among Escherichia coli isolates.	2005 Sep	16131822

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 `Wed Jul 05 23:24:03 UTC 2023` Edited by `admin` on `Wed Jul 05 23:24:03 UTC 2023`
Record UNII	G42ZU72N5G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBENICILLIN

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