Compound ID | 1048

Update compound information

Pirbenicillin

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Propensity to select resistant mutants: Yes
Institute where first reported: Pfizer Inc
Year first mentioned: 1975
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Disappointing clinical results-only found mention of this once however
Chemical structure(s):
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Molecular weight: 510.57
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)CN=C(C4=CC=NC=C4)N)C(=O)O)C
InChI Key: WRFCGBVLTRJBKN-QSNWEANLSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)CN=C(C4=CC=NC=C4)N
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9871712
Guide to Pharmacology: pirbenicillin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC429777/
  • https://doi.org/10.1128/aac.9.4.668

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