Compound ID | 1859

Update compound information

Rifaximin

Class: Rifamycin

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: RNA synthesis inhibitor. DNA-dependent RNA polymerase inhibitor
Propensity to select resistant mutants: Yes
Description: Semisynthetic, derived from rifampicin, nonabsorbable. Used for the treatment of gastrointestinal infections (approved for traveler's diarrhea caused only by noninvasive E. coli, overt hepatic encephalopathy recurrence, irritable bowel syndrome with diarrhea)
Institute where first reported: Salix Pharmaceuticals
Year first mentioned: 1980
Highest development stage: Approved by FDA in 2004
Development status: Approved
Chemical structure(s):
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Molecular weight: 785.88
Iso. SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(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)C5=C2N6C=CC(=CC6=N5)C)O)/C
InChI Key: NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Can. SMILES: CC1=CC2=NC3=C(C4=C(C5=C(C(=C6C(=C53)C(=O)[C@@](C)(O/C=C/[C@@H]([C@@H](C)[C@H]([C@H](C)[C@@H]([C@H](C)[C@H]([C@@H](C)/C=C/C=C(/C)\C(=O)N4)O)O)OC(=O)C)OC)O6)C)O)O)N2C=C1
InChI: InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6436173
Guide to Pharmacology: rifaximin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9099111/
  • https://www.nejm.org/doi/full/10.1056/nejmoa0907893
  • https://www.nature.com/articles/ja2014106

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