PIRBENICILLIN SODIUM

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/938027 | https://www.ncbi.nlm.nih.gov/pubmed/405363 | https://www.ncbi.nlm.nih.gov/pubmed/817665 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C66414

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	817665
Laboratory studies with a new broad-spectrum penicillin, pirbenicillin.	1976 Jun	938027
Pirbenicillin: pharmacokinetic parameters in mice.	1976 Sep	984791
Comparative in vitro activity of piribenicillin, ticarcillin, and carbenicillin against Pseudomonas aeruginosa.	1977 Jan	13704
Pirbenicillin: comparison with carbenicillin and BL-P1654, alone and with gentamicin, against Pseudomonas aeruginosa.	1977 Mar	404963
Pirbenicillin--a semi-synthetic penicillin with antipseudomonal activity.	1977 Mar	405363
Laboratory evaluation of pirbenicillin, a new penicillin with antipseudomonal activity.	1977 Mar	405364
Activity of azlocillin and mezlocillin against gram-negative organisms: comparison with other penicillins.	1978 Apr	96726
Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins.	1979 Apr	111613
Pseudomonas aeruginosa bacteremia: susceptibility of 100 blood culture isolates to seven antimicrobial agents and its clinical significance.	1979 Aug	110892
Activity of beta-lactam antibiotics against Pseudomonas aeruginosa carrying R plasmids determining different beta-lactamases.	1979 Aug	114107
Pharmacokinetics of the new broad spectrum penicillin CP-33994-2.	1980	7191297
Comparative "in vitro" activity of pirbenicillin and carbenicillin against clinical and environmental "Pseudomonas aeruginosa" isolates from hospitals.	1980 Nov-Dec	6794465
Susceptibility of pneumococci to 14 beta-lactam agents: comparison of strains resistant, intermediate-resistant, and susceptible to penicillin.	1981 Aug	6912777

Sample Use Guides

In Vivo Use Guide

Single dose - 1.0 g

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:20:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:20:44 GMT 2023`
Record UNII	638D8M316Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIRBENICILLIN SODIUM

Official Name

English

Sodium (2S,5R,6R)-6-[(R)-2-[2-(isonicotinimidoylamino)acetamido]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Systematic Name

English

CP-33,994-2

Code

English

CP-33994-2

Code

English

PIRBENICILLIN SODIUM [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500