Rifaximin

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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 D06 AX11
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 the drug will not pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is licensed for use to treat diarrhea caused by E. coli. 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.^[1]

In 2005, it received orphan drug status for the treatment of hepatic encephalopathy.^[2]

It is currently sold in the U.S. under the brand name Xifaxan by Salix Pharmaceuticals.

[edit] References

^ 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.
^ Wolf, David C. (2007-01-09). Hepatic Encephalopathy. eMedicine. WebMD. Retrieved on 2007-02-15.

Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. National Committee for Clinical Laboratory Standards, Sixth Edition, Wayne PA. — January 2003
Micromedex information on rifaximin
FDA label approved for Xifaxan (PDF warning)