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QuickView for rifaximin (compound)
PubChem
| Name: | rifaximin |
|---|---|
| PubChem Compound ID: | 6436173 |
| Molecular formula: | C43H51N3O11 |
| Molecular weight: | 785.879 g/mol |
| Synonyms: |
Ritacol; Fatroximin; Xifaxan; 2,7-(Epoxypentadeca(1,11,13)trienimino)benzofuro(4,5-e)pyrido(1,2-a)benzimidazole-1,15(2H)-dione, 25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-, (2S-(2R*,16Z,18E,20R*,21R*,22S*,23S*,24S*,25R*,26S*,27R*,28E))-; (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)benzimidazole-1,15(2H)-dione, 25-acetate; Xifaxsan; Flonorm; 4-Deoxy-4'-methylpyrido(1',2'-1,2)imidazo(5,4-c)rifamycin SV; D02554; BRN 3584528.
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DrugBank
Identification
| Name: | rifaximin |
|---|---|
| Name (isomeric): | DB01220 |
| Drug Type: | small molecule |
| Synonyms: |
Rifamycin L 105SV; Rifaxidin; Rifamixin; Rifaximina [Spanish]; Rifaximine [French]; Rifaximinum [Latin]; Rifaximin [USAN:INN]; Rifamycin L 105
|
| Brand: | Fatroximin, Xifaxan, Rifacol, Ritacol, Normix |
| Category: | Anti-Infective Agents, Gastrointestinal Agents |
| CAS number: | 80621-81-4 |
Pharmacology
| Indication: | For the treatment of patients (≥12 years of age) with travelers' diarrhea caused by noninvasive strains of <i>Escherichia coli</i>. Rifaximin is also designated an orphan drug by the Food and Drug Administration for the adjunctive treatment of hepatic encephalopathy to reduce blood ammonia concentrations and decrease severity of neurological manifestations. |
|---|---|
| Pharmacology: |
Rifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. This non-systemic property of the drug is due to the addition of a pyridoimidazole ring, which renders it non-absorbable. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora...
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| Mechanism of Action: |
Rifaximin acts by inhibiting RNA synthesis in susceptible bacteria by binding to the beta-subunit of bacterial deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase enzyme. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription ...
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| Absorption: | Low absorption in both the fasting state and when administered within 30 minutes of a high-fat breakfast. |
| Biotransformation: | In vitro drug interactions studies have shown that rifaximin, at concentrations ranging from 2 to 200 ng/mL, did not inhibit human hepatic cytochrome P450 isoenzymes: 1A2, 2A6, 2B6, 2C9, 2C19, 2D6, 2E1, and 3A4. In an in vitro hepa-tocyte induction model, rifaximin was shown to induce cytochrome P450 3A4 (CYP3A4), an isoenzyme which rifampin is known to induce. |
| Route of elimination: | In a mass balance study, after administration of 400 mg 14C-rifaximin orally to healthy volunteers, of the 96.94% total recovery, 96.62% of the administered radioactivity was recovered in feces almost exclusively as the unchanged drug and 0.32% was recovered in urine mostly as metabolites with 0.03% as the unchanged drug.Rifaximin accounted for 18% of radioactivity in plasma. This suggests that the absorbed rifaximin undergoes metabolism with minimal renal excretion of the unchanged drug |
| Half Life: | Approximately 6 hours. |
| Toxicity: | LD50 > 2 g/kg (orally, in rats) |
| Affected organisms: | Enteric bacteria and other eubacteria |
Targets
Enzymes
