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Rifaximin
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
Identifiers
CAS number	80621-81-4
ATC code	A07AA11 D06AX11 QG51AA06 QJ51XX01
PubChem	6436173
DrugBank	APRD01218
Chemical data
Formula	C43H51N3O11
Mol. mass	785.879 g/mol
Pharmacokinetic data
Bioavailability	< 0.4%
Metabolism	Hepatic
Half life	6 hours
Excretion	Fecal (97%)
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	℞ Prescription only
Routes	Oral ;

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.

[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] 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.^[3] 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.^[4]

In the United States, rifaximin has orphan drug status for the treatment of hepatic encephalopathy.^[5] 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.^[6]

[edit] Availability

Rifaximin is currently sold in the U.S. under the brand name Xifaxan by Salix Pharmaceuticals. It is also sold in Europe under the names Spiraxin, Zaxine, Normix and Rifacol. There is no generic version of the drug due to patent protection.

[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.
^ 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. doi:10.1111/j.1572-0241.2006.00458.x.
^ 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.

[edit] External links

Micromedex information on rifaximin
FDA label approved for Xifaxan (PDF warning)
Xifaxan (manufacturer's website)

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[0] Xifaxan label informationPDF Retrieved November 15, 2008.

[1] DuPont, H (2007). "Therapy for and Prevention of Traveler's Diarrhea". Clinical Infectious Diseases 45 (45 (Suppl 1)): S78–S84. doi:10.1086/518155.

[2] 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. doi:10.1111/j.1572-0241.2006.00458.x.

[3] 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.

[4] Wolf, David C. (2007-01-09). "Hepatic Encephalopathy". eMedicine. WebMD. http://www.emedicine.com/med/TOPIC3185.HTM. Retrieved 2007-02-15.

[5] 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.

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Contents

[edit] Uses

[edit] Availability

[edit] References

[edit] External links