Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Rifaximin: Difference between pages

{{Short description|Antibiotic medication}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Use dmy dates|date=March 2024}}

| Verifiedfields = changed

| verifiedrevid = 464382444

| image = Rifaximin.svg

| width = 300

| alt =

| image2 = Rifaximin ball-and-stick.png

| width2 = 300

| alt2 =

| tradename = Xifaxan, Zaxine, Xifaxanta, Normix, others<ref>{{cite web | title=Rifaximin international | website=Drugs.com | date=2 November 2020 | url=https://www.drugs.com/international/rifaximin.html | access-date=11 November 2020}}</ref>

| Drugs.com = {{drugs.com|monograph|rifaximin}}

| MedlinePlus = a604027

| pregnancy_AU = B1

| routes_of_administration = [[Oral administration|By mouth]]

| ATC_prefix = A07

| ATC_suffix = AA11

| ATC_supplemental = {{ATC|D06|AX11}}, {{ATCvet|G51|AA06}}, {{ATCvet|J51|XX01}}

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref>

| legal_US = Rx-only

| legal_US_comment = <ref name="Xifaxan FDA label">{{cite web | title=Xifaxan- rifaximin tablet | website=DailyMed | date=1 October 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c5e8e2fd-7087-4b78-9181-cc259c0be2f1 | access-date=11 November 2020}}</ref>

| legal_status = Rx-only

| bioavailability = < 0.4%

| protein_bound =

| metabolism = [[Liver]]

| excretion = Fecal (97%)

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 80621-81-4

| PubChem = 6436173

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01220

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10482302

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L36O5T016N

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02554

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 75246

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1617

| IUPAC_name = (2''S'',16''Z'',18''E'',20''S'',21''S'',22''R'',23''R'',24''R'',25''S'',26''S'',27''S'',28''E'')-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<br />[4,5-e]pyrido[1,2-a]-benzimida-zole-1,15(2''H'')-dione,25-acetate

| C = 43

| H = 51

| N = 3

| O = 11

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NZCRJKRKKOLAOJ-XRCRFVBUSA-N

| melting_point = 200

| melting_high = 205

| melting_notes = (dec.)

'''Rifaximin,''' is a [[Bioavailability|non-absorbable]], [[Broad-spectrum antibiotic|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 (biology)|transcription.]]<ref>{{cite journal | vauthors = Koo HL, DuPont HL | title = Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases | journal = Current Opinion in Gastroenterology | volume = 26 | issue = 1 | pages = 17–25 | date = January 2010 | pmid = 19881343 | pmc = 4737517 | doi = 10.1097/MOG.0b013e328333dc8d }}</ref> It is marketed under the brand name Xifaxan by [[Salix Pharmaceuticals]].<ref>{{Cite web |title=Rifaximin |url=https://go.drugbank.com/drugs/DB01220 |access-date=26 June 2022 |website=go.drugbank.com}}</ref>

== Medical uses ==

=== Travelers' diarrhea ===

Rifaximin is used to treat [[travelers' diarrhea]] (TD) caused by ''[[Escherichia coli|E. coli]]'' bacteria in adults and children at least 12 years of age. It treats travelers' diarrhea by stopping the growth of the bacteria that cause diarrhea. Rifaximin will not work to treat travelers' diarrhea that is bloody or occurs with fever.<ref>{{cite journal | vauthors = DuPont HL | title = Therapy for and prevention of traveler's diarrhea | journal = Clinical Infectious Diseases | volume = 45 | issue = Suppl 1 | pages = S78–S84 | date = July 2007 | pmid = 17582576 | doi = 10.1086/518155 | author-link = Herbert L. DuPont | doi-access = free }}</ref>

===Irritable bowel syndrome===

Rifaximin is used for the treatment of [[irritable bowel syndrome]] (IBS). It possesses anti-inflammatory and antibacterial properties, and is a nonabsorbable antibiotic that acts locally in the gut. These properties make it efficacious in relieving chronic functional symptoms of non-[[constipation]] type IBS.<ref name="pmid26753693">{{cite journal | vauthors = Kane JS, Ford AC | title = Rifaximin for the treatment of diarrhea-predominant irritable bowel syndrome | journal = Expert Review of Gastroenterology & Hepatology | volume = 10 | issue = 4 | pages = 431–442 | date = 2016 | pmid = 26753693 | doi = 10.1586/17474124.2016.1140571 | s2cid = 13607138 }}</ref> It appears to retain its therapeutic properties for this indication, even after repeated courses.<ref name="pmid27149541">{{cite journal | vauthors = Ponziani FR, Pecere S, Lopetuso L, Scaldaferri F, Cammarota G, Gasbarrini A | title = Rifaximin for the treatment of irritable bowel syndrome - a drug safety evaluation | journal = Expert Opinion on Drug Safety | volume = 15 | issue = 7 | pages = 983–991 | date = July 2016 | pmid = 27149541 | doi = 10.1080/14740338.2016.1186639 | s2cid = 25426888 }}</ref><ref name="pmid29605976">{{cite journal |vauthors=Song KH, Jung HK, Kim HJ, Koo HS, Kwon YH, Shin HD, Lim HC, Shin JE, Kim SE, Cho DH, Kim JH, Kim HJ |date=April 2018 |title=Clinical Practice Guidelines for Irritable Bowel Syndrome in Korea, 2017 Revised Edition |journal=Journal of Neurogastroenterology and Motility |volume=24 |issue=2 |pages=197–215 |doi=10.5056/jnm17145 |pmc=5885719 |pmid=29605976}}</ref> It is particularly indicated where [[small intestine bacterial overgrowth]] is suspected of involvement in a person's IBS. Symptom relief or improvement can be obtained for global IBS symptoms, including: abdominal pain, [[flatulence]], [[bloating]], and [[Feces|stool]] consistency. A drawback is that repeated courses may be necessary for relapse of symptoms.<ref name="pmid29605976" /><ref name="pmid26089696" />

=== ''Clostridioides difficile'' infection ===

Rifaximin may also be a useful addition to [[vancomycin]] when treating patients with relapsing [[C. difficile infection|''C. difficile'' infection]] (CDI).<ref name="pmid17304459">{{cite journal | vauthors = Johnson S, Schriever C, Galang M, Kelly CP, Gerding DN | title = Interruption of recurrent Clostridium difficile-associated diarrhea episodes by serial therapy with vancomycin and rifaximin | journal = Clinical Infectious Diseases | volume = 44 | issue = 6 | pages = 846–848 | date = March 2007 | pmid = 17304459 | doi = 10.1086/511870 | doi-access = free }}</ref><ref name="pmid21948965">{{cite journal | vauthors = Garey KW, Ghantoji SS, Shah DN, Habib M, Arora V, Jiang ZD, DuPont HL | title = A randomized, double-blind, placebo-controlled pilot study to assess the ability of rifaximin to prevent recurrent diarrhoea in patients with Clostridium difficile infection | journal = The Journal of Antimicrobial Chemotherapy | volume = 66 | issue = 12 | pages = 2850–2855 | date = December 2011 | pmid = 21948965 | doi = 10.1093/jac/dkr377 | doi-access = free }}</ref> However, the quality of evidence of these studies was judged to be low.<ref name="pmid28257555">{{cite journal | vauthors = Nelson RL, Suda KJ, Evans CT | title = Antibiotic treatment for Clostridium difficile-associated diarrhoea in adults | journal = The Cochrane Database of Systematic Reviews | volume = 2017 | issue = 3 | pages = CD004610 | date = March 2017 | pmid = 28257555 | pmc = 6464548 | doi = 10.1002/14651858.CD004610.pub5 }}</ref> Because exposure to rifamycins in the past may increase risk for resistance, rifaximin should be avoided in such cases.<ref>{{cite journal | vauthors = Huang JS, Jiang ZD, Garey KW, Lasco T, Dupont HL | title = Use of rifamycin drugs and development of infection by rifamycin-resistant strains of Clostridium difficile | journal = Antimicrobial Agents and Chemotherapy | volume = 57 | issue = 6 | pages = 2690–2693 | date = June 2013 | pmid = 23545528 | pmc = 3716149 | doi = 10.1128/AAC.00548-13 }}</ref>

===Hepatic encephalopathy===

Rifaximin is used to prevent episodes of hepatic encephalopathy (changes in thinking, behavior, and personality caused by a build-up of toxins in the brain in people who have liver disease) in adults who have liver disease. It treats hepatic encephalopathy (HE) by stopping the growth of bacteria that produce toxins and that may worsen the liver disease. Although high-quality evidence is still lacking, it appears to be as effective as, or more effective than, other available treatments for hepatic encephalopathy (such as [[lactulose]]), is better tolerated, and may work faster.<ref name="pmid26089696" /><ref>{{cite journal | vauthors = Lawrence KR, Klee JA | title = Rifaximin for the treatment of hepatic encephalopathy | journal = Pharmacotherapy | volume = 28 | issue = 8 | pages = 1019–1032 | date = August 2008 | pmid = 18657018 | doi = 10.1592/phco.28.8.1019 | s2cid = 25662917 }} [http://www.medscape.com/viewarticle/578716 Free full text with registration] at [[Medscape]].</ref> It prevents reoccurring encephalopathy and is associated with high patient satisfaction. People are more compliant and satisfied to take this medication than any other due to minimal side effects, prolonged remission, and overall cost.<ref>{{cite journal | vauthors = Kimer N, Krag A, Gluud LL | title = Safety, efficacy, and patient acceptability of rifaximin for hepatic encephalopathy | journal = Patient Preference and Adherence | volume = 8 | pages = 331–338 | date = March 2014 | pmid = 24672227 | pmc = 3964161 | doi = 10.2147/PPA.S41565 | doi-access = free }}</ref> The drawbacks are increased cost, and lack of robust clinical trials for HE without combination lactulose therapy.<ref>{{cite journal | vauthors = Vilstrup H, Amodio P, Bajaj J, Cordoba J, Ferenci P, Mullen KD, Weissenborn K, Wong P | title = Hepatic encephalopathy in chronic liver disease: 2014 Practice Guideline by the American Association for the Study of Liver Diseases and the European Association for the Study of the Liver | journal = Hepatology | volume = 60 | issue = 2 | pages = 715–735 | date = August 2014 | pmid = 25042402 | doi = 10.1002/hep.27210 | s2cid = 3155213 | doi-access = free }}</ref>

===Other uses===

Other uses include treatment of: [[infectious diarrhea]], [[small intestinal bacterial overgrowth]], [[inflammatory bowel disease]], and [[diverticular disease]].<ref>{{cite journal | vauthors = Piccin A, Gulotta M, di Bella S, Martingano P, Crocè LS, Giuffrè M | title = Diverticular Disease and Rifaximin: An Evidence-Based Review | journal = Antibiotics | volume = 12 | issue = 3 | pages = 443 | date = February 2023 | pmid = 36978310 | pmc = 10044695 | doi = 10.3390/antibiotics12030443 | doi-access = free }}</ref><ref name="pmid26089696"/><ref>{{cite journal | vauthors = Bianchi M, Festa V, Moretti A, Ciaco A, Mangone M, Tornatore V, Dezi A, Luchetti R, De Pascalis B, Papi C, Koch M | title = Meta-analysis: long-term therapy with rifaximin in the management of uncomplicated diverticular disease | journal = Alimentary Pharmacology & Therapeutics | volume = 33 | issue = 8 | pages = 902–910 | date = April 2011 | pmid = 21366632 | doi = 10.1111/j.1365-2036.2011.04606.x }}</ref><ref>{{cite journal | vauthors = Kruse E, Leifeld L | title = Prevention and Conservative Therapy of Diverticular Disease | journal = Viszeralmedizin | volume = 31 | issue = 2 | pages = 103–106 | date = April 2015 | pmid = 26989379 | pmc = 4789966 | doi = 10.1159/000377651 }}</ref> It is effective in treating small intestinal bacterial overgrowth regardless of whether it is associated with irritable bowel syndrome or not.<ref name="pmid26202193">{{cite journal | vauthors = Triantafyllou K, Sioulas AD, Giamarellos-Bourboulis EJ | title = Rifaximin: The Revolutionary Antibiotic Approach for Irritable Bowel Syndrome | journal = Mini Reviews in Medicinal Chemistry | volume = 16 | issue = 3 | pages = 186–192 | date = 2015 | pmid = 26202193 | doi = 10.2174/1389557515666150722105340 }}</ref> It has also shown efficacy with [[rosacea]], ocular rosacea which also presents as [[dry eyes]] for patients with co-occurrence with [[small intestinal bacterial overgrowth]] (SIBO).<ref>{{cite journal | vauthors = Weinstock LB, Steinhoff M | title = Rosacea and small intestinal bacterial overgrowth: prevalence and response to rifaximin | journal = Journal of the American Academy of Dermatology | volume = 68 | issue = 5 | pages = 875–876 | date = May 2013 | pmid = 23602178 | doi = 10.1016/j.jaad.2012.11.038 }}</ref>

==Special caution==

Patients should avoid rifaximin if they are allergic to any of [[rifabutin]], [[Isoniazid/rifampicin|rifampin]], and [[rifapentine]]. It may cause [[attenuated vaccine]]s (such as typhoid vaccine) not to work well. Health-care professionals should be informed about its usage before receiving [[immunization]].<ref>{{Cite web |title=Rifaximin Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD |url=https://www.webmd.com/drugs/2/drug-91339/rifaximin-oral/details |access-date=27 June 2022 |website=www.webmd.com }}</ref> Pregnant or breastfeeding women should avoid rifaximin: it is a [[Pregnancy category|pregnancy category C]] drug and can harm the [[fetus]].<ref>{{cite journal | vauthors = Mahadevan U | title = Fertility and pregnancy in the patient with inflammatory bowel disease | journal = Gut | volume = 55 | issue = 8 | pages = 1198–1206 | date = August 2006 | pmid = 16849349 | pmc = 1856272 | doi = 10.1136/gut.2005.078097 }}</ref> Caution is required in persons with [[cirrhosis]] who have a [[Child–Pugh score]] of C.<ref name="pmid26089696" />

==Side effects==

Rifaximin has an excellent safety profile due to its lack of systemic absorption. Clinical trials did not show any serious adverse events while using the drug. There were no deaths while using it in the clinical trials.<ref name="pmid27149541"/><ref name="pmid29605976" /><ref>{{Citation | vauthors = Robertson KD, Nagalli S |title=Rifaximin |date=2022 |url=http://www.ncbi.nlm.nih.gov/books/NBK562329/ |work=StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=32966000 |access-date=28 June 2022 }}</ref>

The most common side effects includes [[nausea]], [[Abdominal pain|stomach pain]], [[dizziness]], [[fatigue]], [[headaches]], muscle tightening and [[Arthralgia|joint pain]]. It may also cause reddish discoloration of urine.<ref>{{cite web | title = Rifaximin Side Effects | url = https://medlineplus.gov/druginfo/meds/a604027.html#side-effects | work = MedlinePlus | publisher = U.S. National Library of Medicine }}</ref>

The most serious side effects of rifaximin are:

# [[Clostridioides difficile-associated diarrhea]] (CDAD)

# [[Antimicrobial resistance|Drug-resistant bacterial superinfection]]

# Severe allergic reactions including [[hives]], [[rash]]es and [[itch]]ing

== Interactions ==

As rifaximin is not significantly absorbed from the gut, the great majority of these drug interactions are negligible in people with healthy liver function, so healthcare providers usually do not worry about drug interactions unless liver impairment is present.<ref name="pmid27149541"/> It may decrease the effectiveness of [[warfarin]], a commonly prescribed anticoagulant, in people with liver problems.<ref>{{cite journal | vauthors = Hoffman JT, Hartig C, Sonbol E, Lang M | title = Probable interaction between warfarin and rifaximin in a patient treated for small intestine bacterial overgrowth | journal = The Annals of Pharmacotherapy | volume = 45 | issue = 5 | pages = e25 | date = May 2011 | pmid = 21505109 | doi = 10.1345/aph.1P578 | s2cid = 12214785 }}</ref>

==Pharmacology==

Rifaximin is a [[semisynthetic]] broad spectrum antibacterial drug, derived through chemical modification of the natural antibiotic [[rifamycin]].<ref name="pmid 6526730">{{cite journal | vauthors = Brufani M, Cellai L, Marchi E, Segre A | title = The synthesis of 4-deoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV derivatives | journal = The Journal of Antibiotics | volume = 37 | issue = 12 | pages = 1611–1622 | date = December 1984 | pmid = 6526730 | doi = 10.7164/antibiotics.37.1611 | doi-access = free }}</ref> It has very low [[bioavailability]] due to its poor absorption after oral administration. Because of this local action within the gut and the lack of horizontal transfer of resistant genes, the development of [[bacterial resistance]] is rare, and most of the drug taken orally stays in the [[gastrointestinal tract]] where the infection takes place.<ref>{{cite journal | vauthors = Taylor DN | title = Poorly absorbed antibiotics for the treatment of traveler's diarrhea | journal = Clinical Infectious Diseases | volume = 41 | issue = Supplement_8 | pages = S564–S570 | date = December 2005 | pmid = 16267720 | doi = 10.1086/432953 | doi-access = free }}</ref>

===Mechanism of action===

Rifaximin interferes with [[transcription (genetics)|transcription]] by binding to the β-subunit of bacterial [[RNA polymerase]].<ref name="pmid26089696">{{cite journal | vauthors = Iorio N, Malik Z, Schey R | title = Profile of rifaximin and its potential in the treatment of irritable bowel syndrome | journal = Clinical and Experimental Gastroenterology | volume = 8 | pages = 159–167 | date = 2015 | pmid = 26089696 | pmc = 4467648 | doi = 10.2147/CEG.S67231 | doi-access = free }}</ref> 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.<ref>{{cite web |url=http://www.drugbank.ca/drugs/DB01220 |title=Rifaximin | work =DrugBank |date=22 March 2017 }}</ref> This in turn results in a reduction of bacteria populations, including gas-producing bacteria, which may reduce [[mucosal]] inflammation, [[epithelial]] dysfunction, and [[visceral hypersensitivity]]. Rifaximin has broad spectrum antibacterial properties against both [[gram positive]] and [[gram negative]] [[anaerobic organism|anaerobic]] and [[aerobic bacteria]]. As a result of [[bile acid]] solubility, its antibacterial action is limited mostly to the [[small intestine]] and less so the [[Large intestine|colon]].<ref name="pmid26089696"/> A resetting of the bacterial composition has also been suggested as a possible mechanism of action for relief of IBS symptoms.<ref name="pmid26618924">{{cite journal | vauthors = Pimentel M | title = Review article: potential mechanisms of action of rifaximin in the management of irritable bowel syndrome with diarrhoea | journal = Alimentary Pharmacology & Therapeutics | volume = 43 | issue = Suppl 1 | pages = 37–49 | date = January 2016 | pmid = 26618924 | doi = 10.1111/apt.13437 | doi-access = free }}</ref> Additionally, rifaximin may have a direct anti-inflammatory effect on gut mucosa via modulation of the [[pregnane X receptor]].<ref name="pmid26618924"/> Other mechanisms for its therapeutic properties include inhibition of bacterial translocation across the [[epithelial lining]] of the [[intestine]], inhibition of adherence of bacteria to the [[epithelial cells]], and a reduction in the expression of [[proinflammatory cytokines]].<ref name="pmid26576135">{{cite journal | vauthors = Lee KJ | title = Pharmacologic Agents for Chronic Diarrhea | journal = Intestinal Research | volume = 13 | issue = 4 | pages = 306–312 | date = October 2015 | pmid = 26576135 | pmc = 4641856 | doi = 10.5217/ir.2015.13.4.306 }}</ref>

==Availability==

In the United States, Salix Pharmaceuticals holds a US Patent for rifaximin and markets the drug under the name Xifaxan.<ref>{{cite web|url=http://www.salix.com/products/xifaxan550.aspx|title=Xifaxan (Rifaximin) 550 mg - Reduce Overt Hepatic Encephalopathy Recurrences |publisher=Salix Pharmaceuticals}}</ref> In addition to receiving FDA approval for travelers' diarrhea and (marketing approved for)<ref name="accessdata.fda.gov">{{cite web |title=Product Details for NDA 022554 |url=https://www.accessdata.fda.gov/scripts/cder/ob/results_product.cfm?Appl_Type=N&Appl_No=022554 |work=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations |publisher=U.S. [[Food and Drug Administration]] (FDA)}}</ref> hepatic encephalopathy, rifaximin received FDA approval for IBS in May 2015.<ref>{{cite press release|url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm448328.htm|title=FDA approves two therapies to treat IBS-D|publisher=U.S. [[Food and Drug Administration]] (FDA)|access-date=16 December 2019|archive-date=26 January 2018|archive-url=https://web.archive.org/web/20180126023501/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm448328.htm|url-status=dead}}</ref> No generic formulation is available in the US and none has appeared due to the fact that the FDA approval process was ongoing. If rifaximin receives full FDA approval for hepatic encephalopathy it is likely that Salix will maintain marketing exclusivity and be protected from generic formulations until 24 March 2017.<ref name="accessdata.fda.gov"/> In 2018, a patent dispute with [[Teva Pharmaceutical Industries|Teva]] was settled which delayed a generic in the United States, with the patent set to expire in 2029.<ref>{{Cite web|url=https://www.marketwatch.com/story/bausch-health-stock-soars-86-premarket-on-news-of-patent-settlement-2018-09-12|title=Bausch Health stock soars 8.6% premarket on news of patent settlement| vauthors = Linnane C |website=MarketWatch|access-date=14 May 2019}}</ref>

Rifaximin is approved in 33 countries for GI disorders.<ref>{{Cite web|url=https://www.salix.com/about-us/investors/|title=Investors &#124; Salix Pharmaceuticals|website=www.salix.com}}</ref> On 13 August 2013, Health Canada issued a Notice of Compliance to Salix Pharmaceuticals Inc. for the drug product Zaxine.<ref>{{cite web|url=http://www.hc-sc.gc.ca/dhp-mps/prodpharma/sbd-smd/drug-med/sbd_smd_2013_zaxine_161256-eng.php|title=Summary Basis of Decision (SBD): Zaxine | date = 2013| publisher = Government of Canada, Health Canada, Health Products and Food Branch, Therapeutic Products Directorate, Bureau of Gastroenterology Infection and Viral Diseases }}</ref> In India, it is available under the brand names Ciboz and Xifapill.<ref>{{Cite web |title=Brands |url=https://www.zydushealthcare.com/brands/ |access-date=28 June 2022 |website=Zydus Healthcare Limited.}}</ref><ref>{{cite web|url=https://ipindia.gov.in/writereaddata/Portal/IPOJournal/1_451_1/CLASS_1-5.pdf|publisher=The Government of India, Trade Mark Registry|date=20 March 2017|title=Trade Marks Journal}}</ref> In Russia and Ukraine the drug is sold under the name Alfa Normix (Альфа Нормикс), produced by Alfa Wassermann S.p.A. (Italy).<ref>{{Cite web|url=http://www.rusmedserv.com/lekarstva/alfa-normiks.html|title=Alfa Normix | work = Russian medical server }}</ref> In 2018, the FDA approved a similar drug by [[Cosmos Pharmaceuticals]] called Aemcolo for traveler's diarrhea.<ref>{{Cite web|url=https://www.fiercepharma.com/marketing/cosmo-to-give-bausch-health-sales-a-run-latest-fda-nod-for-xifaxan-rival|title=Cosmo to give Bausch Health a run for its money with FDA nod for Xifaxan rival|website=FiercePharma|access-date=14 May 2019}}</ref>

== References ==

{{Reflist}}

{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}}

{{Antibiotics and chemotherapeutics for dermatological use}}

{{Nucleic acid inhibitors}}

{{Xenobiotic-sensing receptor modulators}}

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[[Category:CYP3A4 inducers]]

[[Category:Orphan drugs]]

[[Category:Rifamycin antibiotics]]

[[Category:Acetate esters]]

[[Category:Ethers]]

[[Category:Lactams]]

[[Category:Pregnane X receptor agonists]]