Compound ID | 891

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Rifaquizinone

Synonym(s): CBR-2092  |  TNP-2092

Class: Rifamycin-quinolone hybrid

Spectrum of activity: Gram-negative
Details of activity: Combined effects on RNA polymerase, DNA gyrase and DNA topoisomerase IV; potential for the treatment of biofilm associated infections such as Staphylococcal induced.
Description: Robertson GT, Bonventre EJ, Doyle TB, Du Q, Duncan L, Roche ED, et al. Comparative in vitro activity of CBR-2092, a novel rifamycin-quinolone hybrid antibiotic, and rifampin+quinolone combinations. 47th-ICAAC-2007 2007
Institute where first reported: Cumbre Pharmaceuticals, USA
Year first mentioned: 2007
Highest developmental phase: Phase 2 (NCT03964493)
Development status: Inactive
Chemical structure(s):
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Molecular weight: 1205.37
Iso. SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N5CCC(CC5)N(C)C6(CC6)[C@@H]7CCN(C7)C8=C(C9=C(C=C(C(=O)N9C=C8F)C(=O)O)C%10CC%10)C)/C
InChI Key: OPZFMLLAJBIKAN-YSBZUPOXSA-N
Can. SMILES: C[C@H]1/C=C/C=C(/C)\C(=O)NC2=C(C3=C(C(=C4C(=C3C(=C2/C=N/N5CCC(CC5)N(C)C6(CC6)[C@@H]7CCN(C7)C8=C(C)C9=C(C=C(C(=O)N9C=C8F)C(=O)O)C%10CC%10)O)C(=O)[C@@](C)(O/C=C/[C@@H]([C@H](C)[C@H]([C@@H](C)[C@@H]([C@H](C)[C@H]1O)O)OC(=O)C)OC)O4)C)O)O
InChI: InChI=1S/C65H81FN6O15/c1-31-13-12-14-32(2)61(80)68-50-44(56(77)47-48(57(50)78)55(76)37(7)59-49(47)60(79)64(9,87-59)85-26-20-46(84-11)33(3)58(86-38(8)73)36(6)54(75)35(5)53(31)74)28-67-71-24-18-41(19-25-71)69(10)65(21-22-65)40-17-23-70(29-40)52-34(4)51-42(39-15-16-39)27-43(63(82)83)62(81)72(51)30-45(52)66/h12-14,20,26-28,30-31,33,35-36,39-41,46,53-54,58,74-78H,15-19,21-25,29H2,1-11H3,(H,68,80)(H,82,83)/b13-12+,26-20+,32-14-,67-28+/t31-,33-,35+,36-,40+,46-,53-,54+,58+,64-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/145722022
Guide to Pharmacology: rifaquizinone
Citation: https://journals.asm.org/doi/10.1128/aac.01649-07

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