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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

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

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
Pseudomonas aeruginosa bacteremia: susceptibility of 100 blood culture isolates to seven antimicrobial agents and its clinical significance.
1979 Aug
Activity of beta-lactam antibiotics against Pseudomonas aeruginosa carrying R plasmids determining different beta-lactamases.
1979 Aug

Sample Use Guides

Single dose - 1.0 g
Route of Administration: Intramuscular
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:18:29 GMT 2023
Edited
by admin
on Fri Dec 15 16:18:29 GMT 2023
Record UNII
8ARY01XRYU
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
MESH
C012497
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
SMS_ID
100000081641
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
INN
3937
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
FDA UNII
8ARY01XRYU
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID70204553
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110979
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
NCI_THESAURUS
C66414
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
CAS
55975-92-3
Created by admin on Fri Dec 15 16:18:29 GMT 2023 , Edited by admin on Fri Dec 15 16:18:29 GMT 2023
PRIMARY
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
PRIMARY
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