Compound ID | 961

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BRL-42715

Class: Beta-lactamase inhibitor (penem)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Triazolyl methylene penem that is a potent inhibitor of TEM and SHV type plasmid β-lactamases and also chromosomal Cephalosporinases of Enterobacter and Citrobacter. In combination with amoxycillin alowed activity against resistant (β-lactamase producing) bacteria such as Xanthamonas maltophilia, B. fragilis and more
Combined with other compounds: No antimicrobial activity (2) so would need to have been paired with a β-lactam
Institute where first reported: Beecham Pharmaceuticals (GSK, US)
Year first mentioned: 1987
Highest developmental phase: Phase 1
Development status: Inactive
Reason Dropped: No antimicrobial activity (2)-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 t½ of 31mins (1). BRL 42715, its development has been discontinued as a result of its low serum half-life (2)
Chemical structure(s):
Click here for structure editor
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:
  • http://aac.asm.org/content/35/9/1748.long
  • https://books.google.co.uk/books?id=GgPoCAAAQBAJ&pg=PA308&lpg=PA308&dq=LY173013&source=bl&ots=spuNwNoFKJ&sig=jTjiVJirHIj6GLgqaVt76y91ThA&hl=en&sa=X&ei=4ct2Vc6bLMOBU_e3gHA&ved=0CDcQ6AEwBg#v=onepage&q=LY173013&f=false
  • https://www.ncbi.nlm.nih.gov/pubmed/20141132
  • https://www.ncbi.nlm.nih.gov/pubmed/1760938/

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