Compound ID | 1860

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Rifamycin

Synonym(s): Rifamycin SV  |  Rifocin  |  Aemcolo

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: Streptomyces natural compound (Amycolatopsis rifamycinica). Used for traveler's diarrhea in oral formulation
Institute where first reported: Cosmo Technologies Ltd, Dr. Falk Pharma Gmbh;; Redhill
Year first mentioned: 1957
Highest development stage: Approved by FDA in 2018
Development status: Discontinued
Chemical structure(s):
Click here for structure editor
Molecular weight: 697.77
Iso. SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=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
InChI Key: HJYYPODYNSCCOU-ODRIEIDWSA-N
Can. SMILES: C[C@H]1/C=C/C=C(/C)\C(=O)NC2=C(C3=C(C(=C4C(=C3C(=C2)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/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6324616
Guide to Pharmacology: rifamycin
Citations:
  • https://journals.asm.org/doi/10.1128/ecosalplus.ESP-0017-2019
  • https://www.nature.com/articles/s41429-021-00462-x
  • https://pubs.acs.org/doi/10.1021/cr030112j

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