Rifaximin

• CAT Number: A001202
• CAS Number: 80621-81-4
• Molecular Formula: C43H51N3O11
• Molecular Weight: 785.9
• Purity: ≥95%
• Target: DNA Synthesis
• Solubility: >39.3mg/mL in DMSO
• Storage: 3 years -20C powder
• 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)/b
• InChIKey: NZCRJKRKKOLAOJ-XRCRFVBUSA-N
• SMILES: OC1=C(NC(/C(C)=CC=C[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)/C=C/O[C@@](C2=O)(C)O3)=O)C4=C(N=C5N4C=CC(C)=C5)C6=C2C3=C(C)C(O)=C61

Rifaximin is a semisynthetic antibiotic based on rifamycin. It has poor oral bioavailability, meaning that very little of the drug will be absorbed into the blood stream when it is taken orally. Rifaximin is used in the treatment of traveler/’s diarrhea, irritable bowel syndrome, and hepatic encephalopathy, for which it received orphan drug status from the U.S. Food and Drug Administration in 1998. Rifaximin interferes with transcription by binding to the β-subunit of bacterial RNA polymerase. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription process.

Reference

1:The influence of rifaximin on diverticulitis rate and quality of life in patients with diverticulosis. Banasiewicz T, Francuzik W, Bobkiewicz A, Krokowicz Ł, Borejsza-Wysocki M, Paszkowski J, Studniarek A, Krokowicz P, Grochowalski M, Szczepkowski M, Lorenc Z.Pol Przegl Chir. 2017 Feb 28;89(1):22-31. doi: 10.5604/01.3001.0009.6012. PMID: 28522790 2:A meta-analysis of the use of rifaximin to prevent travellers/’ diarrhoea. Ng QX, Ho CYX, Shin D, Venkatanarayanan N, Chan HW.J Travel Med. 2017 Sep 1;24(5). doi: 10.1093/jtm/tax025. PMID: 28498921 3:Response to: Improvement of sleep architecture parameters in cirrhotic patients with recurrent hepatic encephalopathy with the use of rifaximin: hepatic encephalopathy in association with zolpidem. Nevo ON, Brinker AD, Diak IL, Kortepeter CM.Eur J Gastroenterol Hepatol. 2017 May 3. doi: 10.1097/MEG.0000000000000894. [Epub ahead of print] No abstract available. PMID: 28471831 4:Diagnosis of symptomatic uncomplicated diverticular disease and the role of Rifaximin in management. Maconi G.Acta Biomed. 2017 Apr 28;88(1):25-32. doi: 10.23750/abm.v88i1.6360. PMID: 28467330 5:Rifaximin in Non-Alcoholic Steatohepatitis: An Open-Label Pilot Study. Cobbold JFL, Atkinson S, Marchesi JR, Smith A, Wai SN, Stove J, Shojaee-Moradie F, Jackson N, Umpleby AM, Fitzpatrick J, Thomas EL, Bell JD, Holmes E, Taylor-Robinson SD, Goldin RD, Yee MS, Anstee QM, Thursz MR.Hepatol Res. 2017 Apr 20. doi: 10.1111/hepr.12904. [Epub ahead of print] PMID: 28425154 6:Retrospective comparison of long-term ten-day/month rifaximin or mesalazine in prevention of relapse in acute diverticulitis. Festa V, Spila Alegiani S, Chiesara F, Moretti A, Bianchi M, Dezi A, Traversa G, Koch M.Eur Rev Med Pharmacol Sci. 2017 Mar;21(6):1397-1404. PMID: 28387885 Free Article7:Rifaximin in the Treatment of Patients With Diarrhea-Predominant Irritable Bowel Syndrome. Dai C, Jiang M, Sun MJ.Gastroenterology. 2017 May;152(6):1629-1630. doi: 10.1053/j.gastro.2016.09.068. Epub 2017 Apr 1. No abstract available. PMID: 28376323 8:The impact of rifaximin in the prevention of bacterial infections in cirrhosis. Mariani M, Zuccaro V, Patruno SF, Scudeller L, Sacchi P, Lombardi A, Vecchia M, Columpsi P, Marone P, Filice G, Bruno R.Eur Rev Med Pharmacol Sci. 2017 Mar;21(5):1151-1158. PMID: 28338174 Free Article9:Susceptibility to rifaximin and other antimicrobials of bacteria isolated in patients with acute gastrointestinal infections in Southeast Mexico. Novoa-Farias O, Frati-Munari AC, Peredo MA, Flores-Juárez S, Novoa-García O, Galicia-Tapia J, Romero-Carpio CE.Rev Gastroenterol Mex. 2017 Mar 12. pii: S0375-0906(17)30021-6. doi: 10.1016/j.rgmx.2016.10.006. [Epub ahead of print] English, Spanish. PMID: 28298258 Free Article10:Rifaximin (Xifaxan) for Irritable Bowel Syndrome. Karuppiah S, Pomianowski K.Am Fam Physician. 2017 Feb 15;95(4):258-259. No abstract available. PMID: 28290635