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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 of PIRBENICILLIN

SMILES

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Pirbenicillin, a new semisynthetic penicillin with broad-spectrum activity.
1976 Apr
Pirbenicillin--a semi-synthetic penicillin with antipseudomonal activity.
1977 Mar
Laboratory evaluation of pirbenicillin, a new penicillin with antipseudomonal activity.
1977 Mar
Activity of azlocillin and mezlocillin against gram-negative organisms: comparison with other penicillins.
1978 Apr
Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins.
1979 Apr

Sample Use Guides

Single dose - 1.0 g
Route of Administration: Intramuscular
Name Type Language
PIRBENICILLIN
INN  
INN  
Official Name English
pirbenicillin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
Code System Code Type Description
EVMPD
SUB09899MIG
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MESH
C012497
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SMS_ID
100000081641
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INN
3937
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FDA UNII
8ARY01XRYU
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EPA CompTox
DTXSID70204553
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ChEMBL
CHEMBL2110979
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NCI_THESAURUS
C66414
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CAS
55975-92-3
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PUBCHEM
9871712
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
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