Rifaximin

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
Clinical data
Trade names	Xifaxan
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 Y
ATC code	A07AA11 D06AX11 QG51AA06 QJ51XX01
PubChem	CID 6436173
DrugBank	APRD01218
ChemSpider	10482302 Y
UNII	L36O5T016N N
KEGG	D02554 N
ChEMBL	CHEMBL1617 Y
Chemical data
Formula	C43H51N3O11
Mol. mass	785.879 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:NZCRJKRKKOLAOJ-XRCRFVBUSA-N Y
N(what is this?)  (verify)

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.

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] 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.^[5]

In the United States, rifaximin has orphan drug status for the treatment of hepatic encephalopathy.^[6] 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.^[7] The drawbacks to rifaximin are increased cost and lack of robust clinical trials for HE without combination lactulose therapy.

A recent study suggests that treatment with rifaximin relieves symptoms for some sufferers of irritable bowel syndrome. ^[8]

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, Rifacol and Colidur, and in India under the name Rixmin, Rcifax, Rifagut and Torfix.

References

1. ^ Xifaxan label informationPDF Retrieved November 15, 2008.
2. ^ 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. 
3. ^ 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. 
4. ^ 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. 
5. ^ 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.
6. ^ Wolf, David C. (2007-01-09). "Hepatic Encephalopathy". eMedicine. WebMD. http://www.emedicine.com/med/TOPIC3185.HTM. Retrieved 2007-02-15. 
7. ^ 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.
8. ^ Antibiotic May Help Ease Irritable Bowel, Businessweek, January 05, 2011

External links

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

This systemic antibacterial-related article is a stub. You can help Wikipedia by expanding it.v · Categories: Orphan drugs Rifamycin antibiotics Acetate esters Ethers Lactams Antibiotic stubs Wikimedia Foundation. 2010. Игры ⚽ Нужно решить контрольную? Marcgraviaceae Gangaridai Look at other dictionaries: Rifaximin — Strukturformel Allgemeines Freiname Rifaximin Andere Namen …   Deutsch Wikipedia rifaximin — rif·ax·i·min (rif akґsĭ min) a semisynthetic antibacterial compound, derived from rifamycin, that inhibits bacterial RNA synthesis, used for the treatment of traveler s diarrhea caused by noninvasive strains of Escherichia coli; administered …   Medical dictionary Irritable bowel syndrome — This article is about a functional disorder. For bowel inflammation, see Inflammatory bowel disease. Irritable bowel syndrome Classification and external resources ICD 10 K58 ICD 9 …   Wikipedia Hepatic encephalopathy — Classification and external resources Micrograph of Alzheimer type II astrocytes, as may be seen in hepatic encephalopathy. ICD 10 …   Wikipedia Neomycin — Systematic (IUPAC) name (1R,2R,3S,4R,6S) 4,6 diamino 2 Clinical data Trade names Neo rx …   Wikipedia Metronidazole — Systematic (IUPAC) name 2 (2 methyl 5 nitro 1H …   Wikipedia Clostridium difficile — C. difficile colonies on a blood agar plate …   Wikipedia Rifamycin — The rifamycins are a group of antibiotics which are synthesized either naturally by the bacterium Amycolatopsis mediterranei , or artificially. They are a subclass of the larger family, Ansamycin. Rifamycins are particularly effective against… …   Wikipedia Sulfanilamide — Systematic (IUPAC) name 4 aminobenzenesulfonamide Clinical data AHFS/Drugs.com …   Wikipedia Mafenide — Systematic (IUPAC) name 4 (aminomethyl)benzenesulfonamide Clinical data AHFS/Drugs.com …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”