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
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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Pirbenicillin--a semi-synthetic penicillin with antipseudomonal activity. | 1977 Mar |
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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 |
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
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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
SALT/SOLVATE (PARENT)