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Rifaximin information


Rifaximin
Clinical data
Trade namesXifaxan, Zaxine, Xifaxanta, Normix, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa604027
Pregnancy
category
  • AU: B1
Routes of
administration
By mouth
ATC code
  • A07AA11 (WHO) D06AX11 (WHO), QG51AA06 (WHO), QJ51XX01 (WHO)
Legal status
Legal status
  • CA: ℞-only[2]
  • US: ℞-only[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability< 0.4%
MetabolismLiver
Elimination half-life6 hours
ExcretionFecal (97%)
Identifiers
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
CAS Number
  • 80621-81-4 checkY
PubChem CID
  • 6436173
DrugBank
  • DB01220 checkY
ChemSpider
  • 10482302 checkY
UNII
  • L36O5T016N
KEGG
  • D02554 checkY
ChEBI
  • CHEBI:75246 ☒N
ChEMBL
  • ChEMBL1617 checkY
CompTox Dashboard (EPA)
  • DTXSID7045998 Edit this at Wikidata
ECHA InfoCard100.111.624 Edit this at Wikidata
Chemical and physical data
FormulaC43H51N3O11
Molar mass785.891 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point200 to 205 °C (392 to 401 °F) (dec.)
SMILES
  • CC(=O)O[C@H]3[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)Nc6c2c(nc1cc(C)ccn12)c5c4C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]3C)Oc4c(C)c(O)c5c6O
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 checkY
  • Key:NZCRJKRKKOLAOJ-XRCRFVBUSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rifaximin, is a non-absorbable, broad spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since its approval in Italy in 1987, it has been licensed in over more than 30 countries for the treatment of a variety of gastrointestinal diseases like irritable bowel syndrome, and hepatic encephalopathy. It acts by inhibiting RNA synthesis in susceptible bacteria by binding to the RNA polymerase enzyme. This binding blocks translocation, which stops transcription.[4] It is marketed under the brand name Xifaxan by Salix Pharmaceuticals.[5]

  1. ^ "Rifaximin international". Drugs.com. 2 November 2020. Retrieved 11 November 2020.
  2. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  3. ^ "Xifaxan- rifaximin tablet". DailyMed. 1 October 2019. Retrieved 11 November 2020.
  4. ^ Koo HL, DuPont HL (January 2010). "Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases". Current Opinion in Gastroenterology. 26 (1): 17–25. doi:10.1097/MOG.0b013e328333dc8d. PMC 4737517. PMID 19881343.
  5. ^ "Rifaximin". go.drugbank.com. Retrieved 26 June 2022.

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Rifaximin

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Rifaximin, is a non-absorbable, broad spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since...

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Hepatic encephalopathy

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frequently used to decrease ammonia levels. Certain antibiotics (such as rifaximin) and probiotics are other potential options. A liver transplant may improve...

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Diverticulitis

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risk factors such as obesity, inactivity, and smoking. Mesalazine and rifaximin appear useful for preventing attacks in those with diverticulosis. Avoiding...

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Diverticular disease

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medications such as antibiotics, antispasmodics, acetaminophen, mesalamine, rifaximin, and corticosteroids depending on the specific conditions. The signs and...

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Rifamycin

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derivatives rifampicin (or rifampin), rifabutin, rifapentine, rifalazil and rifaximin. Rifamycin, sold under the trade name Aemcolo, is approved in the United...

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Escherichia coli

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are fluoroquinolones or azithromycin, with an emerging role for rifaximin. Rifaximin, a semisynthetic rifamycin derivative, is an effective and well-tolerated...

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Cirrhosis

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conversion of ammonia into ammonium, which is then excreted from the body. Rifaximin, an antibiotic that inhibits the function of ammonia-producing bacteria...

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Bausch Health

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which blocks the FDA from approving Norwich Pharmaceuticals' 550 mg rifaximin generic until October 2029. Judge Andrews' decision bolsters his previous...

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Timeline of antibiotics

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sultamicillin 1987 – ciprofloxacin, the first 2nd-gen fluoroquinolone 1987 – rifaximin, the first ansamycin 1988 – azithromycin 1988 – flomoxef 1988 – isepamycin...

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Inflammatory bowel disease

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may benefit from antibiotic therapy, such as with rifaximin. The evidence for a benefit of rifaximin is mostly limited to Crohn's disease with less convincing...

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Spontaneous bacterial peritonitis

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antibiotics if: They have bleeding esophageal varices Studies on the use of rifaximin in cirrhotic patients, have suggested that its use may be effective in...

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Flucloxacillin

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Fenbendazole

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Achlorhydria

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metronidazole, amoxicillin/clavulanate potassium, ciprofloxacin, and rifaximin, can be used to treat bacterial overgrowth. Achlorhydria resulting from...

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Fentanyl

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Spironolactone

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Mifepristone

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Erythromycin

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Dysbiosis

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antibiotics to treat dysbiosis. However, the broad-spectrum antibiotic rifaximin has been shown to have a favorable response in several of the ailments...

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Hypericum perforatum

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Flatulence

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individually or in combination blends, in commercial products. The antibiotic rifaximin, often used to treat diarrhea caused by the microorganism E. coli, may...

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Portal hypertension

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treatment plan may involve lactulose, enemas, and use of antibiotics such as rifaximin, neomycin, vancomycin, and the quinolones. Restriction of dietary protein...

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Levothyroxine

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Dexamethasone

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Clotrimazole

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Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine...

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Progesterone

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Amlodipine

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Nicotine

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Irritable bowel syndrome

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aluminum silicates and alverine citrate drugs can be effective for IBS. Rifaximin may be useful as a treatment for IBS symptoms, including abdominal bloating...

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