Compound ID | 961

Update compound information

BRL 42715

Synonym(s): BRL-42715  |  BRL42715

Class: Beta-lactamase inhibitor

Agent Type: Semisynthetic; Small molecule; Direct acting; Antibiotic adjuvant;
Spectrum of activity: Gram-negative
Mechanism of action: TEM and SHV type plasmid beta-lactamases inhibitor and chromosomal cephalosporinases inhibitor
Combined with other compounds: No antimicrobial activity (2) so would need to have been paired with a β-lactam
Description: Triazolyl methylene penem
Institute where first reported: Beecham Pharmaceuticals (GSK, US)
Year first mentioned: 1987
Highest development stage: Phase 1
Development status: Inactive
Reason dropped: No antimicrobial activity - by 2004 it was no longer in clinical development but may well have been discontinued earlier. Whilst it is a very potent inhibitor, it is quickly eliminated with an extrapolated terminal of 31mins. BRL 42715, its development has been discontinued as a result of its low serum half-life
Chemical structure(s):
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Molecular weight: 286.24
Iso. SMILES: CN1C=C(N=N1)/C=C/2\[C@@H]3N(C2=O)C(=CS3)C(=O)[O-].[Na+]
InChI Key: OMJBLZMKGVWHQP-VKVLVNHFSA-M
Can. SMILES: CN1C=C(/C=C\2/C(=O)N3C(=CS[C@H]23)C(=O)[O-])N=N1.[Na+]
InChI: InChI=1S/C10H8N4O3S.Na/c1-13-3-5(11-12-13)2-6-8(15)14-7(10(16)17)4-18-9(6)14;/h2-4,9H,1H3,(H,16,17);/q;+1/p-1/b6-2-;/t9-;/m1./s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/23705463
Guide to Pharmacology: BRL-42715
Citations:
  • https://www.ncbi.nlm.nih.gov/pubmed/20141132
  • https://doi.org/10.1128/aac.33.9.1580
  • https://doi.org/10.1128/aac.35.9.1748
  • https://doi.org/10.1159/000238886

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