Compound ID | 517

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ABI-0299

Class: Rifamycin

Spectrum of activity: Gram-negative
Description: 1. Flamm RK, Karginova E, Rothstein DMDM, et al. In vitro potency and spectrum of novel rifamycins ABI-0043, ABI-0094 and ABI-0299. 45th-Intersci-Conf-Antimicrob-Agents-Chemother 2005;222-224 2. Rothstein DM, Sirokman K, Gwathmey JK, et al. Efficacy of rifalazil and related rifamycins in a mouse model of Helicobacter pylori infection is due to both a luminal and systemic component. 45th-Intersci-Conf-Antimicrob-Agents-Chemother 2005;224
Institute where first reported: ActivBiotics, Inc., USA
Year first mentioned: 2005
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Despite having low MICs, it failed to display efficacy unlike ABI-0043 which is now in pre-clinical studies (1)
Chemical structure(s):
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Molecular weight: 941.07
Iso. SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=C3C(=C4C(=C(C(=C5C4=C([C@](O5)(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)O)C)O)C2=O)N=C6C(=CC(=CC6=O)N7CCC(CC7)(C)N(C)C)O3)/C
InChI Key: ZNEAZPQILGZFPW-BDSYRQRVSA-N
Can. SMILES: C[C@H]1/C=C/C=C(/C)\C(=O)NC2=C3C(=C4C(=C(C(=C5C4=C([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)O5)O)C)O)C2=O)N=C6C(=O)C=C(C=C6O3)N7CCC(C)(CC7)N(C)C
InChI: InChI=1S/C51H64N4O13/c1-24-14-13-15-25(2)49(63)53-40-44(61)36-35(39-47(40)67-34-23-31(22-32(57)38(34)52-39)55-19-17-50(8,18-20-55)54(10)11)37-46(29(6)43(36)60)68-51(9,48(37)62)65-21-16-33(64-12)26(3)45(66-30(7)56)28(5)42(59)27(4)41(24)58/h13-16,21-24,26-28,33,41-42,45,58-60,62H,17-20H2,1-12H3,(H,53,63)/b14-13+,21-16+,25-15-/t24-,26+,27+,28+,33-,41-,42+,45+,51-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135466425
Citations:
  • https://journals.asm.org/doi/10.1128/aac.01567-07?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed

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