RXM

(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-1,1 5-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)furo[2'',3'':7',8']naphtho[1',2':4,5]imidazo[1,2-a]pyridin-2 5-yl acetate


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Chemical Component Summary

Name(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-1,1 5-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)furo[2'',3'':7',8']naphtho[1',2':4,5]imidazo[1,2-a]pyridin-2 5-yl acetate
SynonymsRifaximin
Identifiersn/a
FormulaC43 H51 N3 O11
Molecular Weight785.879
TypeNON-POLYMER
Isomeric SMILESCc1ccn2c(c1)nc3c2c4c(c5c3c6c(c(c5O)C)O[C@@](C6=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(\C(=O)N4)/C)C)O)C)O)C)OC(=O)C)C)OC)C)O
InChIInChI=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
InChIKeyNZCRJKRKKOLAOJ-XRCRFVBUSA-N

Chemical Details

Formal Charge0
Atom Count108
Chiral Atom Count9
Bond Count113
Aromatic Bond Count20

Drug Info: DrugBank

DrugBank IDDB01220 
NameRifaximin
Groups
  • approved
  • investigational
DescriptionRifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that the drug will not pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It has multiple indications and is used in treatment of traveller's diarrhea caused by E. coli; reduction in risk of overt hepatic encephalopathy recurrence; as well as diarrhea-predominant irritable bowel syndrome (IBS-D) in adult women and men. It is marketed under the brand name Xifaxan by Salix Pharmaceuticals.
Synonyms
  • Rifamycin L 105SV
  • Rifaximinun
  • Rifamycin L 105
  • Rifaximina
  • Rifaxidin
Brand Names
  • Xifaxan
  • Zaxine
IndicationRifaximin has multiple indications by the FDA: for the treatment of patients (≥12 years of age) with traveller's diarrhea caused by noninvasive strains of Escherichia coli; for the reduction of overt hepatic encephalopathy recurrence in patients ≥18 years of age; and in May 2015 it was approved for irritable bowel syndrome with diarrhea (IBS-D) treatment in adult men and women.
Categories
  • Alimentary Tract and Metabolism
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics for Topical Use
  • Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
ATC-Code
  • A07AA11
  • D06AX11
CAS number80621-81-4

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA-directed RNA polymerase subunit betaMVYSYTEKKRIRKDFGKRPQVLDVPYLLSIQLDSFQKFIEQDPEGQYGLE...unknowninhibitor
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknownagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inducer
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninducer
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknowninducer
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 6436173
ChEMBL CHEMBL1617
ChEBI CHEBI:75246