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+].CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)CNC(=N)C3=CC=NC=C3)C4=CC=CC=C4)C(=O)N2[C@H]1C([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
| Molecular Formula | C24H25N6O5S |
| Molecular Weight | 509.558 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Susceptibility of pneumococci to 14 beta-lactam agents: comparison of strains resistant, intermediate-resistant, and susceptible to penicillin. | 1981-08 |
|
| Comparative "in vitro" activity of pirbenicillin and carbenicillin against clinical and environmental "Pseudomonas aeruginosa" isolates from hospitals. | 1980-11-01 |
|
| Pharmacokinetics of the new broad spectrum penicillin CP-33994-2. | 1980 |
|
| Pseudomonas aeruginosa bacteremia: susceptibility of 100 blood culture isolates to seven antimicrobial agents and its clinical significance. | 1979-08 |
|
| Activity of beta-lactam antibiotics against Pseudomonas aeruginosa carrying R plasmids determining different beta-lactamases. | 1979-08 |
|
| Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. | 1979-04 |
|
| Activity of azlocillin and mezlocillin against gram-negative organisms: comparison with other penicillins. | 1978-04 |
|
| Pirbenicillin: comparison with carbenicillin and BL-P1654, alone and with gentamicin, against Pseudomonas aeruginosa. | 1977-03 |
|
| Pirbenicillin--a semi-synthetic penicillin with antipseudomonal activity. | 1977-03 |
|
| Laboratory evaluation of pirbenicillin, a new penicillin with antipseudomonal activity. | 1977-03 |
|
| Comparative in vitro activity of piribenicillin, ticarcillin, and carbenicillin against Pseudomonas aeruginosa. | 1977-01 |
|
| Pirbenicillin: pharmacokinetic parameters in mice. | 1976-09 |
|
| Laboratory studies with a new broad-spectrum penicillin, pirbenicillin. | 1976-06 |
|
| Pirbenicillin, a new semisynthetic penicillin with broad-spectrum activity. | 1976-04 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:54:43 GMT 2025
by
admin
on
Mon Mar 31 17:54:43 GMT 2025
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| Record UNII |
638D8M316Y
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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Official Name | English | ||
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Systematic Name | English | ||
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Code | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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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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