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Rifaximin
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Systematic (IUPAC) name
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(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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Identifiers
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CAS number
| 80621-81-4
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ATC code
| A07AA11 D06AX11
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PubChem
| 6436173
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DrugBank
| APRD01218
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Chemical data
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Formula | C43H51N3O11
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Mol. mass | 785.879 g/mol
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Pharmacokinetic data
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Bioavailability | < 0.4%
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Metabolism | Hepatic
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Half life | 6 hours
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Excretion | Fecal (97%)
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Therapeutic considerations
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Pregnancy cat.
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C(US)
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Legal status
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℞ Prescription only
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Routes
| Oral
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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.
Additional recommended knowledge
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.
It's also sold in Europe under the name Spiraxin and Zaxine, both of which seem to be cheaper solutions. There isn't a generic version of the drug.
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)
Antidiarrheals, intestinal anti-inflammatory/anti-infective agents (A07) |
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Intestinal anti-infectives | Antibiotics (Neomycin, Nystatin, Natamycin, Streptomycin, Polymyxin B, Paromomycin, Amphotericin B, Kanamycin, Vancomycin, Colistin, Rifaximin)
Sulfonamides (Phthalylsulfathiazole, Sulfaguanidine, Succinylsulfathiazole)
other (Miconazole, Broxyquinoline, Acetarsol, Nifuroxazide, Nifurzide) |
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Intestinal adsorbents | Charcoal - Bismuth - Pectin - Kaolin - Crospovidone - Attapulgite - Diosmectite |
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Antipropulsives | Diphenoxylate - Opium - Loperamide - Difenoxin |
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Intestinal anti-inflammatory agents | corticosteroids acting locally (Prednisolone, Hydrocortisone, Prednisone, Betamethasone, Tixocortol, Budesonide, Beclometasone)
antiallergic agents, excluding corticosteroids (Cromoglicic acid)
aminosalicylic acid and similar agents (Sulfasalazine, Mesalazine, Olsalazine, Balsalazide) |
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Antidiarrheal micro-organisms | Saccharomyces boulardii |
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Other antidiarrheals | Albumin tannate - Ceratonia - Racecadotril |
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