Rifaximin
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| Systematic (IUPAC) name | |
| (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 |
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| Clinical data | |
| Trade names | Xifaxan, Xifaxanta |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a604027 |
| Pregnancy cat. | C (US) |
| Legal status | ℞ Prescription only |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | < 0.4% |
| Metabolism | Hepatic |
| Half-life | 6 hours |
| Excretion | Fecal (97%) |
| Identifiers | |
| CAS number | 80621-81-4  |
| ATC code | A07AA11 D06AX11 QG51AA06 QJ51XX01 |
| PubChem | CID 6436173 |
| DrugBank | APRD01218 |
| ChemSpider | 10482302 |
| UNII | L36O5T016N |
| KEGG | D02554 |
| ChEMBL | CHEMBL1617 |
| Chemical data | |
| Formula | C43H51N3O11 |
| Mol. mass | 785.879 g/mol |
| SMILES | eMolecules & PubChem |
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Rifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that very little of the drug will pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is used in the treatment of traveler's diarrhea and hepatic encephalopathy, for which it received orphan drug status from the U.S. Food and Drug Administration in 1998.
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[edit] Uses
Rifaximin is licensed by the U.S. Food and Drug Administration to treat traveler's diarrhea caused by E. coli.[1] Clinical trials have shown that rifaximin is highly effective at preventing and treating traveler's diarrhea among travelers to Mexico, with few side effects and low risk of developing antibiotic resistance.[2] [3] It is not effective against Campylobacter jejuni, and there is no evidence of efficacy against Shigella or Salmonella species.
It may be efficacious in relieving chronic functional symptoms of bloating and flatulence that are common in irritable bowel syndrome.[4][5]
There was recently a pilot-study done on the efficacy of rifaximin as a means of treatment for rosacea, according to the study, induced by the co-presence of small intestinal bacterial overgrowth.[6]
In the United States, rifaximin has orphan drug status for the treatment of hepatic encephalopathy.[7] Although high-quality evidence is still lacking, rifaximin appears to be as effective as or more effective than other available treatments for hepatic encephalopathy (such as lactulose), is better tolerated, and may work faster.[8] The drawbacks to rifaximin are increased cost and lack of robust clinical trials for HE without combination lactulose therapy.
[edit] Mechanism of action
Rifaximin interferes with transcription by binding to the β-subunit of bacterial RNA polymerase. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription process. [9]
[edit] References
- ^ Xifaxan label informationPDF Retrieved November 15, 2008.
- ^ DuPont, H (2007). "Therapy for and Prevention of Traveler's Diarrhea". Clinical Infectious Diseases 45 (45 (Suppl 1)): S78–S84. doi:10.1086/518155. PMID 17582576.
- ^ Ruiz J, Mensa L, Pons MJ, Vila J, Gascon J (May 2008). "Development of Escherichia coli rifaximin-resistant mutants: frequency of selection and stability". The Journal of antimicrobial chemotherapy 61 (5): 1016–9. doi:10.1093/jac/dkn078. PMID 18325895. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=18325895.
- ^ Sharara A, Aoun E, Abdul-Baki H, Mounzer R, Sidani S, ElHajj I. (2006). "A randomized double-blind placebo-controlled trial of rifaximin in patients with abdominal bloating and flatulence". Am J Gastroenterol 101 (2): 326–33. doi:10.1111/j.1572-0241.2006.00458.x. PMID 16454838.
- ^ Antibiotic May Help Ease Irritable Bowel, Businessweek, January 05, 2011
- ^ Small intestinal bacterial overgrowth in rosacea: clinical effectiveness of its eradication. Parodi A, Paolino S, Greco A, Drago F, Mansi C, Rebora A, Parodi A, Savarino V.
- ^ Wolf, David C. (2007-01-09). "Hepatic Encephalopathy". eMedicine. WebMD. http://www.emedicine.com/med/TOPIC3185.HTM. Retrieved 2007-02-15.
- ^ Lawrence KR, Klee JA (2008). "Rifaximin for the treatment of hepatic encephalopathy". Pharmacotherapy 28 (8): 1019–32. doi:10.1592/phco.28.8.1019. PMID 18657018. Free full text with registration at Medscape.
- ^ http://www.drugbank.ca/drugs/DB01220
[edit] External links
- FDA label approved for Xifaxan (PDF warning)
- Xifaxan (manufacturer's website)
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