Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H25N6O5S.Na |
Molecular Weight | 532.547 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[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=LWRGPIPUJPCPAY-HSRLECSKSA-M
InChI=1S/C24H26N6O5S.Na/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);/q;+1/p-1/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 |
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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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Pirbenicillin: comparison with carbenicillin and BL-P1654, alone and with gentamicin, against Pseudomonas aeruginosa. | 1977 Mar |
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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 |
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Pseudomonas aeruginosa bacteremia: susceptibility of 100 blood culture isolates to seven antimicrobial agents and its clinical significance. | 1979 Aug |
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Activity of beta-lactam antibiotics against Pseudomonas aeruginosa carrying R plasmids determining different beta-lactamases. | 1979 Aug |
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Pharmacokinetics of the new broad spectrum penicillin CP-33994-2. | 1980 |
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Comparative "in vitro" activity of pirbenicillin and carbenicillin against clinical and environmental "Pseudomonas aeruginosa" isolates from hospitals. | 1980 Nov-Dec |
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Susceptibility of pneumococci to 14 beta-lactam agents: comparison of strains resistant, intermediate-resistant, and susceptible to penicillin. | 1981 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
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NCI_THESAURUS |
C1500
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C76226
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638D8M316Y
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55162-26-0
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DTXSID50970502
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CHEMBL2110979
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23684409
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ACTIVE MOIETY
SUBSTANCE RECORD