Compound ID | 1859

Update compound information

Rifaximin

Class: Rifamycin

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Inhibits bacterial DNA-dependent RNA polymerase, thus inhibiting bacterial RNA synthesis
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 developmental phase: Approved by FDA in 2004
Development status: Approved, off-patent
Chemical structure(s):
Click here for structure editor
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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