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Details

Stereochemistry MIXED
Molecular Formula C26H25N2O6S.Na
Molecular Weight 516.541
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENICILLIN INDANYL SODIUM

SMILES

[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C(=O)OC3=CC=C4CCCC4=C3)C5=CC=CC=C5)C([O-])=O

InChI

InChIKey=QFWPXOXWAUAYAB-XZVIDJSISA-M
InChI=1S/C26H26N2O6S.Na/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);/q;+1/p-1/t18?,19-,20+,23-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C26H25N2O6S
Molecular Weight 493.552
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
0.18 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Uticillin
Curative
GEOCILLIN
Curative
GEOCILLIN

Cmax

ValueDoseCo-administeredAnalytePopulation
6.5 μg/mL
382 mg single, oral
CARBENICILLIN serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
16 μg × h/mL
382 mg single, oral
CARBENICILLIN serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
382 mg single, oral
CARBENICILLIN serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

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
Record UNII
4OUL81K2RT
Record Status Validated (UNII)
Record Version