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Rifaximin

Rifaximin
Clinical data
Trade namesXifaxan, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa604027
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability< 0.4%
MetabolismLiver
Elimination half-life6 hours
ExcretionFecal (97%)
Identifiers
  • (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26S,27S,28E)-5,6,21,23,25-pentahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca-[1,11,13]trienimino)benzofuro
    [4,5-e]pyrido[1,2-a]-benzimida-zole-1,15(2H)-dione,25-acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.111.624 Edit this at Wikidata
Chemical and physical data
FormulaC43H51N3O11
Molar mass785.891 g·mol−1
3D model (JSmol)
Melting point200 to 205 °C (392 to 401 °F) (dec.)
  • CC(=O)O[C@H]3[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)Nc6c2c(nc1cc(C)ccn12)c5c4C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]3C)Oc4c(C)c(O)c5c6O
  • 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 checkY
  • Key:NZCRJKRKKOLAOJ-XRCRFVBUSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rifaximin, sold under the brand name Xifaxan among others, is a non-absorbable, broad-spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since its approval in Italy in 1987, it has been licensed in more than 30 countries for the treatment of a variety of gastrointestinal diseases like irritable bowel syndrome and hepatic encephalopathy. It acts by inhibiting RNA synthesis in susceptible bacteria by binding to the RNA polymerase enzyme. This binding blocks translocation, which stops transcription.[4] It was developed by Salix Pharmaceuticals.[3][5][6]

  1. ^ "Rifaximin international". Drugs.com. 2 November 2020. Retrieved 11 November 2020.
  2. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  3. ^ a b "Xifaxan- rifaximin tablet". DailyMed. 1 October 2019. Retrieved 11 November 2020.
  4. ^ Koo HL, DuPont HL (January 2010). "Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases". Current Opinion in Gastroenterology. 26 (1): 17–25. doi:10.1097/MOG.0b013e328333dc8d. PMC 4737517. PMID 19881343.
  5. ^ "Drug Approval Package: Xifaxan (Nfaximin) NDA #021361". U.S. Food and Drug Administration (FDA). Retrieved 28 December 2024.
  6. ^ "Drug Approval Package: Xifaxan (rifaximin) NDA #022554". U.S. Food and Drug Administration (FDA). 26 July 2011. Retrieved 28 December 2024.

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ريفاكسيمين Arabic ریفاوکسیمین AZB Rifaximina Catalan Rifaximin German Ριφαξιμίνη Greek Rifaximina Spanish ریفاکسیمین FA Rifaksimiini Finnish Rifaximine French Rifaximin Hungarian

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