Rifaximin | CAS#80621-81-4 | antibiotics

MedKoo Cat#: 326762 | Name: Rifaximin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Rifaximin

CAS#80621-81-4

Theoretical Analysis

MedKoo Cat#: 326762

Name: Rifaximin

CAS#: 80621-81-4

Chemical Formula: C43H51N3O11

Exact Mass: 785.3524

Molecular Weight: 785.89

Elemental Analysis: C, 65.72; H, 6.54; N, 5.35; O, 22.39

Price and Availability

Size	Price	Availability
500mg	USD 350.00	2 weeks
1g	USD 550.00	2 weeks
5g	USD 1,250.00	2 weeks

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Related CAS #

No Data

Synonym

BRN 3584528; L105; L-105; Fatroximin; L 105SV; Normix; Rifacol; Rifamycin L 105; Rifaxidin; Rifaximin; Rifaxin; Ritacol; Rifaximin; trade names: RCIFAX, Rifagut, Xifaxan, Zaxine

IUPAC/Chemical Name

(2S,18E,28E)-25S-(acetyloxy)-5,6,21S,23R-tetrahydroxy-27S-methoxy-2,4,11,16Z,20S,22R,24R,26R-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione

InChi Key

NZCRJKRKKOLAOJ-XRCRFVBUSA-N

InChi Code

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

SMILES Code

OC1=C(NC(/C(C)=C\C=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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rifaximin growth of several Gram-positive and Gram-negative bacteria in vitro, including Staphylococcus, Streptococcus, Enterococcus, H. influenzae, and N. gonorrhoeae (MIC50s = ≤0.015, <0.12, 0.25-2, 0.25, and 0.25 μg/mL, respectively). It is a pregnane X receptor (PXR) agonist (EC50 = ~20 μM). Rifaximin exhibits minimal intestinal absorption after oral administration. Rifaximin is effective in eliminating bacteria in the gastrointestinal system.

In vitro activity:

Rifaximin exerts counter-regulatory activities at the interface between enteric bacteria and intestinal epithelial cells. The ability of rifaximin to activate PXR contributes to the maintenance of the intestinal immune homeostasis. Reference: Eur J Pharmacol. 2011 Oct 1;668(1-2):317-24. https://pubmed.ncbi.nlm.nih.gov/21806984/

In vivo activity:

Rifaximin exerted a neuroprotective effect on the transgenic Parkinson's disease mice by modulating gut microbiota. Patients with higher baseline inflammation possibly benefited from rifaximin treatment. Reference: Preclinical and Clinical Studies. Cells. 2022 Nov 2;11(21):3468. https://pubmed.ncbi.nlm.nih.gov/36359864/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	38.17
	DMSO	10.0	12.72
	Ethanol	30.0	38.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 785.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Mencarelli A, Renga B, Palladino G, Claudio D, Ricci P, Distrutti E, Barbanti M, Baldelli F, Fiorucci S. Inhibition of NF-κB by a PXR-dependent pathway mediates counter-regulatory activities of rifaximin on innate immunity in intestinal epithelial cells. Eur J Pharmacol. 2011 Oct 1;668(1-2):317-24. doi: 10.1016/j.ejphar.2011.06.058. Epub 2011 Jul 26. PMID: 21806984. 2. Brown EL, Xue Q, Jiang ZD, Xu Y, Dupont HL. Pretreatment of epithelial cells with rifaximin alters bacterial attachment and internalization profiles. Antimicrob Agents Chemother. 2010 Jan;54(1):388-96. doi: 10.1128/AAC.00691-09. Epub 2009 Oct 26. PMID: 19858255; PMCID: PMC2798526. 3. Goh BC, Larsson S, Dam LC, Ling YHS, Chua WLP, Abirami R, Singh S, Ong JLE, Teo JWP, Ho P, Ingham PW, Pethe K, Dedon PC. Rifaximin potentiates clarithromycin against Mycobacterium abscessus in vitro and in zebrafish. JAC Antimicrob Resist. 2023 May 8;5(3):dlad052. doi: 10.1093/jacamr/dlad052. PMID: 37168836; PMCID: PMC10164658. 4. Hong CT, Chan L, Chen KY, Lee HH, Huang LK, Yang YSH, Liu YR, Hu CJ. Rifaximin Modifies Gut Microbiota and Attenuates Inflammation in Parkinson's Disease: Preclinical and Clinical Studies. Cells. 2022 Nov 2;11(21):3468. doi: 10.3390/cells11213468. PMID: 36359864; PMCID: PMC9656351.

In vitro protocol:

In vivo protocol:

1. Goh BC, Larsson S, Dam LC, Ling YHS, Chua WLP, Abirami R, Singh S, Ong JLE, Teo JWP, Ho P, Ingham PW, Pethe K, Dedon PC. Rifaximin potentiates clarithromycin against Mycobacterium abscessus in vitro and in zebrafish. JAC Antimicrob Resist. 2023 May 8;5(3):dlad052. doi: 10.1093/jacamr/dlad052. PMID: 37168836; PMCID: PMC10164658. 2. Hong CT, Chan L, Chen KY, Lee HH, Huang LK, Yang YSH, Liu YR, Hu CJ. Rifaximin Modifies Gut Microbiota and Attenuates Inflammation in Parkinson's Disease: Preclinical and Clinical Studies. Cells. 2022 Nov 2;11(21):3468. doi: 10.3390/cells11213468. PMID: 36359864; PMCID: PMC9656351.

1: Rifaximin (Zaxine): For the Reduction in Risk of Overt Hepatic Encephalopathy (HE) Recurrence in Patients ≥ 18 Years of Age [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Jul. Available from http://www.ncbi.nlm.nih.gov/books/NBK362587/ PubMed PMID: 27227188. 2: Rivkin A, Rybalov S. Update on the Management of Diarrhea-Predominant Irritable Bowel Syndrome: Focus on Rifaximin and Eluxadoline. Pharmacotherapy. 2016 Mar;36(3):300-16. doi: 10.1002/phar.1712. Epub 2016 Mar 11. Review. PubMed PMID: 26971716. 3: Li J, Zhu W, Liu W, Wu Y, Wu B. Rifaximin for Irritable Bowel Syndrome: A Meta-Analysis of Randomized Placebo-Controlled Trials. Medicine (Baltimore). 2016 Jan;95(4):e2534. doi: 10.1097/MD.0000000000002534. Review. PubMed PMID: 26825893. 4: Pimentel M. Review article: potential mechanisms of action of rifaximin in the management of irritable bowel syndrome with diarrhoea. Aliment Pharmacol Ther. 2016 Jan;43 Suppl 1:37-49. doi: 10.1111/apt.13437. Review. PubMed PMID: 26618924. 5: Sartor RB. Review article: the potential mechanisms of action of rifaximin in the management of inflammatory bowel diseases. Aliment Pharmacol Ther. 2016 Jan;43 Suppl 1:27-36. doi: 10.1111/apt.13436. Review. PubMed PMID: 26618923. 6: Bajaj JS. Review article: potential mechanisms of action of rifaximin in the management of hepatic encephalopathy and other complications of cirrhosis. Aliment Pharmacol Ther. 2016 Jan;43 Suppl 1:11-26. doi: 10.1111/apt.13435. Review. PubMed PMID: 26618922. 7: DuPont HL. Review article: the antimicrobial effects of rifaximin on the gut microbiota. Aliment Pharmacol Ther. 2016 Jan;43 Suppl 1:3-10. doi: 10.1111/apt.13434. Review. PubMed PMID: 26618921. 8: Ponziani FR, Gerardi V, Pecere S, D'Aversa F, Lopetuso L, Zocco MA, Pompili M, Gasbarrini A. Effect of rifaximin on gut microbiota composition in advanced liver disease and its complications. World J Gastroenterol. 2015 Nov 21;21(43):12322-33. doi: 10.3748/wjg.v21.i43.12322. Review. PubMed PMID: 26604640; PubMed Central PMCID: PMC4649116. 9: Cash BD, Lacy BE, Rao T, Earnest DL. Rifaximin and eluxadoline - newly approved treatments for diarrhea-predominant irritable bowel syndrome: what is their role in clinical practice alongside alosetron? Expert Opin Pharmacother. 2016;17(3):311-22. doi: 10.1517/14656566.2016.1118052. Epub 2015 Dec 8. Review. PubMed PMID: 26559529. 10: Rifaximin (Xifaxan) for irritable bowel syndrome with diarrhea. Med Lett Drugs Ther. 2015 Aug 3;57(1474):109-11. Review. PubMed PMID: 26218792. 11: DuPont HL. Therapeutic Effects and Mechanisms of Action of Rifaximin in Gastrointestinal Diseases. Mayo Clin Proc. 2015 Aug;90(8):1116-24. doi: 10.1016/j.mayocp.2015.04.016. Epub 2015 Jul 8. Review. PubMed PMID: 26162610. 12: Iorio N, Malik Z, Schey R. Profile of rifaximin and its potential in the treatment of irritable bowel syndrome. Clin Exp Gastroenterol. 2015 Jun 8;8:159-67. doi: 10.2147/CEG.S67231. eCollection 2015. Review. PubMed PMID: 26089696; PubMed Central PMCID: PMC4467648. 13: Laterza L, Ianiro G, Scoleri I, Landi R, Bruno G, Scaldaferri F, Gaetani E, Campanale M, Gasbarrini A. Rifaximin for the treatment of diarrhoea-predominant irritable bowel syndrome. Expert Opin Pharmacother. 2015 Mar;16(4):607-15. doi: 10.1517/14656566.2015.1007951. Epub 2015 Feb 1. Review. PubMed PMID: 25641072. 14: Scott LJ. Rifaximin: a review of its use in reducing recurrence of overt hepatic encephalopathy episodes. Drugs. 2014 Dec;74(18):2153-60. doi: 10.1007/s40265-014-0300-y. Review. PubMed PMID: 25352391. 15: Calanni F, Renzulli C, Barbanti M, Viscomi GC. Rifaximin: beyond the traditional antibiotic activity. J Antibiot (Tokyo). 2014 Sep;67(9):667-70. doi: 10.1038/ja.2014.106. Epub 2014 Aug 6. Review. PubMed PMID: 25095806. 16: Kimer N, Krag A, Møller S, Bendtsen F, Gluud LL. Systematic review with meta-analysis: the effects of rifaximin in hepatic encephalopathy. Aliment Pharmacol Ther. 2014 Jul;40(2):123-32. doi: 10.1111/apt.12803. Epub 2014 May 21. Review. PubMed PMID: 24849268. 17: Kimer N, Krag A, Gluud LL. Safety, efficacy, and patient acceptability of rifaximin for hepatic encephalopathy. Patient Prefer Adherence. 2014 Mar 18;8:331-8. doi: 10.2147/PPA.S41565. eCollection 2014. Review. PubMed PMID: 24672227; PubMed Central PMCID: PMC3964161. 18: Belous SS, Khalif IL, Golovenko OV. [Role of rifaximin in correction of IBS-like symptoms in patients with inflammatory bowel disease]. Eksp Klin Gastroenterol. 2013;(3):63-8. Review. Russian. PubMed PMID: 24294774. 19: Farrell DJ. Rifaximin in the treatment of irritable bowel syndrome: is there a high risk for development of antimicrobial resistance? J Clin Gastroenterol. 2013 Mar;47(3):205-11. doi: 10.1097/MCG.0b013e31827559a3. Review. PubMed PMID: 23340064. 20: Gluud LL, Dam G, Borre M, Les I, Cordoba J, Marchesini G, Aagaard NK, Vilstrup H. Lactulose, rifaximin or branched chain amino acids for hepatic encephalopathy: what is the evidence? Metab Brain Dis. 2013 Jun;28(2):221-5. doi: 10.1007/s11011-012-9372-0. Epub 2012 Dec 29. Review. PubMed PMID: 23275147.