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Details

Stereochemistry EPIMERIC
Molecular Formula C23H22N2O6S
Molecular Weight 454.496
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENICILLIN PHENYL

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C(=O)OC3=CC=CC=C3)C4=CC=CC=C4)C(O)=O

InChI

InChIKey=NZDASSHFKWDBBU-KVMCETHSSA-N
InChI=1S/C23H22N2O6S/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29)/t15?,16-,17+,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula C23H22N2O6S
Molecular Weight 454.496
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
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
Record UNII
9UU4XDB74X
Record Status Validated (UNII)
Record Version