PIRBENICILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H26N6O5S
Molecular Weight	510.565
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)CNC(=N)C3=CC=NC=C3)C4=CC=CC=C4)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=WRFCGBVLTRJBKN-QSNWEANLSA-N

InChI=1S/C24H26N6O5S/c1-24(2)18(23(34)35)30-21(33)17(22(30)36-24)29-20(32)16(13-6-4-3-5-7-13)28-15(31)12-27-19(25)14-8-10-26-11-9-14/h3-11,16-18,22H,12H2,1-2H3,(H2,25,27)(H,28,31)(H,29,32)(H,34,35)/t16-,17-,18+,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C24H26N6O5S
Molecular Weight	510.565
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/938027 | https://www.ncbi.nlm.nih.gov/pubmed/405363 | https://www.ncbi.nlm.nih.gov/pubmed/817665 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C66414

Pirbenicillin is a broad-spectrum semisynthetic penicillin with activity against both gram-positive cocci and gram-negative bacilli. Pirbenicillin is less active than either carbenicillin or ticarcillin against Proteus spp. It is as active as carbenicillin against Serratia spp. and Enterobacter spp. Pirbenicillin demonstrated eight- and fourfold better minimal bactericidal concentration values towards Pseudomonas isolates than those of carbenicillin and ticarcillin, respectively. Pirbenicillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. The drug is somewhat more stable in serum than carbenicillin. Pirbenicillin does not appear to inactivate gentamicin as rapidly as carbenicillin.

Originator

Approval Year

PubMed

Title	Date	PubMed
Susceptibility of pneumococci to 14 beta-lactam agents: comparison of strains resistant, intermediate-resistant, and susceptible to penicillin.	1981-08	6912777
Comparative "in vitro" activity of pirbenicillin and carbenicillin against clinical and environmental "Pseudomonas aeruginosa" isolates from hospitals.	1980-11-01	6794465
Pharmacokinetics of the new broad spectrum penicillin CP-33994-2.	1980	7191297
Pseudomonas aeruginosa bacteremia: susceptibility of 100 blood culture isolates to seven antimicrobial agents and its clinical significance.	1979-08	110892
Activity of beta-lactam antibiotics against Pseudomonas aeruginosa carrying R plasmids determining different beta-lactamases.	1979-08	114107
Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins.	1979-04	111613
Activity of azlocillin and mezlocillin against gram-negative organisms: comparison with other penicillins.	1978-04	96726
Pirbenicillin: comparison with carbenicillin and BL-P1654, alone and with gentamicin, against Pseudomonas aeruginosa.	1977-03	404963
Pirbenicillin--a semi-synthetic penicillin with antipseudomonal activity.	1977-03	405363
Laboratory evaluation of pirbenicillin, a new penicillin with antipseudomonal activity.	1977-03	405364
Comparative in vitro activity of piribenicillin, ticarcillin, and carbenicillin against Pseudomonas aeruginosa.	1977-01	13704
Pirbenicillin: pharmacokinetic parameters in mice.	1976-09	984791
Laboratory studies with a new broad-spectrum penicillin, pirbenicillin.	1976-06	938027
Pirbenicillin, a new semisynthetic penicillin with broad-spectrum activity.	1976-04	817665

Sample Use Guides

In Vivo Use Guide

Single dose - 1.0 g

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:24:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:39 GMT 2025`
Record UNII	8ARY01XRYU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

pirbenicillin [INN]

Preferred Name

English

PIRBENICILLIN

Official Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500