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
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
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Pirbenicillin, a new semisynthetic penicillin with broad-spectrum activity. | 1976 Apr |
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Laboratory studies with a new broad-spectrum penicillin, pirbenicillin. | 1976 Jun |
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Pirbenicillin: pharmacokinetic parameters in mice. | 1976 Sep |
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Comparative in vitro activity of piribenicillin, ticarcillin, and carbenicillin against Pseudomonas aeruginosa. | 1977 Jan |
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Laboratory evaluation of pirbenicillin, a new penicillin with antipseudomonal activity. | 1977 Mar |
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Activity of azlocillin and mezlocillin against gram-negative organisms: comparison with other penicillins. | 1978 Apr |
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Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. | 1979 Apr |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7191297
Single dose - 1.0 g
Route of Administration:
Intramuscular
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:18:29 GMT 2023
by
admin
on
Fri Dec 15 16:18:29 GMT 2023
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Record UNII |
8ARY01XRYU
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Record Status |
Validated (UNII)
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Record Version |
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-
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Official Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1500
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SUB09899MIG
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C012497
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100000081641
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3937
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8ARY01XRYU
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DTXSID70204553
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CHEMBL2110979
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C66414
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55975-92-3
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9871712
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ACTIVE MOIETY |