Compound ID | 360

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KP-736

Synonym(s): KP736  |  KP 736

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Pseudomonas
Description: Cephem-type
Institute where first reported: Kaken Pharmaceutical
Year first mentioned: 1989
Highest development stage: Phase 2/3
Development status: Inactive
Reason dropped: Catechol-containing compounds: MIC50s 0.008-0.39 mg/L against P. aeruginosa are superior to that of ceftazidime. These catecholic beta-lactams were expected to show superior therapeutic responses against pseudomonal infections in humans, but they were discontinued due to side effects or unfavourable pharmacokinetics in phase I/ II studies
Chemical structure(s):
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Molecular weight: 682.65
Iso. SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=N\OCC3=CC(=O)C(=CN3O)[O-])/C4=CSC(=N4)N)C(=O)[O-])CSC5=CN=NS5.[Na+].[Na+]
InChI Key: RNPRGWFDYQHVDK-PUZJMABTSA-L
Can. SMILES: C1=C(CO/N=C(/C2=CSC(=N2)N)\C(=O)N[C@@H]3C(=O)N4C(=C(CSC5=CN=NS5)CS[C@H]34)C(=O)[O-])N(C=C(C1=O)[O-])O.[Na+].[Na+]
InChI: InChI=1S/C21H18N8O8S4.2Na/c22-21-24-10(7-40-21)14(26-37-4-9-1-11(30)12(31)3-28(9)36)17(32)25-15-18(33)29-16(20(34)35)8(6-39-19(15)29)5-38-13-2-23-27-41-13;;/h1-3,7,15,19,31,36H,4-6H2,(H2,22,24)(H,25,32)(H,34,35);;/q;2*+1/p-2/b26-14-;;/t15-,19-;;/m1../s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9690114
Guide to Pharmacology: KP-736
Citations:
  • https://journals.asm.org/doi/epdf/10.1128/aac.35.1.104
  • https://journals.asm.org/doi/epdf/10.1128/aac.35.1.104

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