Rifaximin

Last updated

Rifaximin
Rifaximin.svg
Rifaximin ball-and-stick.png
Clinical data
Trade names Xifaxan, others [1]
AHFS/Drugs.com Monograph
MedlinePlus a604027
License data
Pregnancy
category
  • AU:B1
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability < 0.4%
Metabolism Liver
Elimination half-life 6 hours
Excretion Fecal (97%)
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.111.624 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C43H51N3O11
Molar mass 785.891 g·mol−1
3D model (JSmol)
Melting point 200 to 205 °C (392 to 401 °F) (dec.)
  • 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=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 Yes check.svgY
  • Key:NZCRJKRKKOLAOJ-XRCRFVBUSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Rifaximin, sold under the brand name Xifaxan among others, 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 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 was developed by Salix Pharmaceuticals. [3] [5] [6]

Contents

Medical uses

Travelers' diarrhea

Rifaximin is used to treat travelers' diarrhea caused by E. coli bacteria in people aged twelve years of age and older. 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. [7]

Irritable bowel syndrome

Rifaximin is used for the treatment of irritable bowel syndrome (IBS). It possesses anti-inflammatory and antibacterial properties, and is a non-absorbable antibiotic that acts locally in the gut. These properties make it efficacious in relieving chronic functional symptoms of non-constipation type irritable bowel syndrome. [8] It appears to retain its therapeutic properties for this indication, even after repeated courses. [9] [10] It is particularly indicated where small intestine bacterial overgrowth is suspected of involvement in irritable bowel syndrome. Symptom relief or improvement can be obtained for global irritable bowel syndrome symptoms, including: abdominal pain, flatulence, bloating, and stool consistency. A drawback is that repeated courses may be necessary for relapse of symptoms. [10] [11]

Clostridioides difficile infection

Rifaximin may also be a useful addition to vancomycin when treating people with relapsing C. difficile infection. [12] [13] However, the quality of evidence of these studies was judged to be low. [14] Because exposure to rifamycins in the past may increase risk for resistance, rifaximin should be avoided in such cases. [15]

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 adults who have liver disease). It treats hepatic encephalopathy by stopping the growth of bacteria that produce toxins and that may worsen the liver disease. Although high-quality evidence is 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. [11] [16] 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. [17] The drawbacks are increased cost, and lack of robust clinical trials for hepatic encephalopathy without combination lactulose therapy. [18]

Other uses

Other uses include treatment of: infectious diarrhea, small intestinal bacterial overgrowth, inflammatory bowel disease, and diverticular disease. [19] [11] [20] [21] It is effective in treating small intestinal bacterial overgrowth regardless of whether it is associated with irritable bowel syndrome or not. [22] 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). [23]

Special caution

People should avoid rifaximin if they are allergic to any of rifabutin, rifampin, and rifapentine. It may cause attenuated vaccines (such as typhoid vaccine) not to work well. Health-care professionals should be informed about its usage before receiving immunization. [24] Pregnant or breastfeeding women should avoid rifaximin: it can harm the fetus. [25] Caution is required in people with cirrhosis who have a Child–Pugh score of C. [11]

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 rifaximin. There were no deaths while using it in the clinical trials. [9] [10] [26]

The most common side effects include nausea, stomach pain, dizziness, fatigue, headaches, muscle tightening, and joint pain. It may also cause reddish discoloration of urine. [27]

The most serious side effects of rifaximin are:

  1. Clostridioides difficile-associated diarrhea
  2. Drug-resistant bacterial superinfection
  3. Severe allergic reactions including hives, rashes and itching

Interactions

As rifaximin is not significantly absorbed from the gut, the great majority of this drug's interactions are negligible in people with healthy liver function, so healthcare providers usually do not worry about drug interactions unless liver impairment is present. [9] It may decrease the effectiveness of warfarin, a commonly prescribed anticoagulant, in people with liver problems. [28]

Pharmacology

Rifaximin is a semisynthetic broad spectrum antibacterial drug, derived through chemical modification of the natural antibiotic rifamycin. [29] 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 resistance 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. [30]

Mechanism of action

Rifaximin interferes with transcription by binding to the β-subunit of bacterial RNA polymerase. [11] 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. [31] 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 and aerobic bacteria. As a result of bile acid solubility, its antibacterial action is limited mostly to the small intestine and less so the colon. [11] A resetting of the bacterial composition has also been suggested as a possible mechanism of action for relief of irritable bowel syndrome symptoms. [32] Additionally, rifaximin may have a direct anti-inflammatory effect on gut mucosa via modulation of the pregnane X receptor. [32] 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. [33]

Availability

In the United States, Salix Pharmaceuticals holds a US Patent for rifaximin and markets it under the brand name Xifaxan. [3] In addition to receiving FDA approval for travelers' diarrhea and (marketing approved for) [34] hepatic encephalopathy, rifaximin received FDA approval for irritable bowel syndrome in May 2015. [35] 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. [34] In 2018, a patent dispute with Teva was settled which delayed a generic in the United States, with the patent set to expire in 2029. [36]

Rifaximin is approved in many countries for GI disorders. [37] In August 2013, Health Canada issued a Notice of Compliance to Salix Pharmaceuticals for the drug product Zaxine. [38] In India, it is available under the brand names Ciboz and Xifapill. [39] [40] In Russia and Ukraine the drug is sold under the name Alfa Normix (Альфа Нормикс), and under the name Flonorm in Mexico, produced by Alfa Wassermann S.p.A. (Italy). [41] In 2018, the FDA approved a similar drug by Cosmos Pharmaceuticals called Aemcolo for traveler's diarrhea. [42]

Related Research Articles

<span class="mw-page-title-main">Diarrhea</span> Loose or liquid bowel movements

Diarrhea, also spelled diarrhoea or diarrhœa, is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin with loss of the normal stretchiness of the skin and irritable behaviour. This can progress to decreased urination, loss of skin color, a fast heart rate, and a decrease in responsiveness as it becomes more severe. Loose but non-watery stools in babies who are exclusively breastfed, however, are normal.

<span class="mw-page-title-main">Irritable bowel syndrome</span> Functional gastrointestinal disorder

Irritable bowel syndrome (IBS) is a functional gastrointestinal disorder characterized by a group of symptoms that commonly include abdominal pain, abdominal bloating and changes in the consistency of bowel movements. These symptoms may occur over a long time, sometimes for years. IBS can negatively affect quality of life and may result in missed school or work or reduced productivity at work. Disorders such as anxiety, major depression, and myalgic encephalomyelitis/chronic fatigue syndrome (ME/CFS) are common among people with IBS.

<span class="mw-page-title-main">Diverticulitis</span> Digestive disease of the large intestine

Diverticulitis, also called colonic diverticulitis, is a gastrointestinal disease characterized by inflammation of abnormal pouches—diverticula—that can develop in the wall of the large intestine. Symptoms typically include lower abdominal pain of sudden onset, but the onset may also occur over a few days. There may also be nausea, diarrhea or constipation. Fever or blood in the stool suggests a complication. People may experience a single attack, repeated attacks, or ongoing "smoldering" diverticulitis.

<span class="mw-page-title-main">Gastroenteritis</span> Inflammation of the stomach and small intestine

Gastroenteritis, also known as infectious diarrhea, is an inflammation of the gastrointestinal tract including the stomach and intestine. Symptoms may include diarrhea, vomiting, and abdominal pain. Fever, lack of energy, and dehydration may also occur. This typically lasts less than two weeks. Although it is not related to influenza, in the U.S. and U.K., it is sometimes called the "stomach flu".

<span class="mw-page-title-main">Rifamycin</span> Group of antibiotics

The rifamycins are a group of antibiotics that are synthesized either naturally by the bacterium Amycolatopsis rifamycinica or artificially. They are a subclass of the larger family of ansamycins. Rifamycins are particularly effective against mycobacteria, and are therefore used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections.

Spontaneous bacterial peritonitis (SBP) is the development of a bacterial infection in the peritoneum, despite the absence of an obvious source for the infection. It is specifically an infection of the ascitic fluid – an increased volume of peritoneal fluid. Ascites is most commonly a complication of cirrhosis of the liver. It can also occur in patients with nephrotic syndrome. SBP has a high mortality rate.

<span class="mw-page-title-main">Achlorhydria</span> Lack of hydrochloric acid production in the digestive organs

Achlorhydria and hypochlorhydria refer to states where the production of hydrochloric acid in gastric secretions of the stomach and other digestive organs is absent or low, respectively. It is associated with various other medical problems.

<span class="mw-page-title-main">Travelers' diarrhea</span> Stomach and intestinal infection

Travelers' diarrhea (TD) is a stomach and intestinal infection. TD is defined as the passage of unformed stool while traveling. It may be accompanied by abdominal cramps, nausea, fever, headache and bloating. Occasionally dysentery may occur. Most travelers recover within three to four days with little or no treatment. About 12% of people may have symptoms for a week.

<span class="mw-page-title-main">Gastrointestinal disease</span> Illnesses of the digestive system

Gastrointestinal diseases refer to diseases involving the gastrointestinal tract, namely the esophagus, stomach, small intestine, large intestine and rectum; and the accessory organs of digestion, the liver, gallbladder, and pancreas.

<span class="mw-page-title-main">Hepatic encephalopathy</span> Brain disease resulting from liver failure

Hepatic encephalopathy (HE) is an altered level of consciousness as a result of liver failure. Its onset may be gradual or sudden. Other symptoms may include movement problems, changes in mood, or changes in personality. In the advanced stages, it can result in a coma.

<span class="mw-page-title-main">Small intestinal bacterial overgrowth</span> Medical condition

Small intestinal bacterial overgrowth (SIBO), also termed bacterial overgrowth, or small bowel bacterial overgrowth syndrome (SBBOS), is a disorder of excessive bacterial growth in the small intestine. Unlike the colon, which is rich with bacteria, the small bowel usually has fewer than 100,000 organisms per millilitre. Patients with bacterial overgrowth typically develop symptoms which may include nausea, bloating, vomiting, diarrhea, malnutrition, weight loss, and malabsorption by various mechanisms.

<span class="mw-page-title-main">Diverticular disease</span> Problems arising from pouch formations in the large intestinal wall

Diverticular disease is when problems occur due to diverticulosis, a benign condition defined by the formation of pouches (diverticula) from weak spots in the wall of the large intestine. This disease spectrum includes diverticulitis, symptomatic uncomplicated diverticular disease (SUDD), and segmental colitis associated with diverticulosis (SCAD). The most common symptoms across the disease spectrum are abdominal pain and bowel habit changes such as diarrhea or constipation. Otherwise, diverticulitis presents with systemic symptoms such as fever and elevated white blood cell count whereas SUDD and SCAD do not. Treatment ranges from conservative bowel rest to medications such as antibiotics, antispasmodics, acetaminophen, mesalamine, rifaximin, and corticosteroids depending on the specific conditions.

<span class="mw-page-title-main">Fecal microbiota transplant</span> Process of transplantation of fecal bacteria from a healthy individual into a recipient

Fecal microbiota transplant (FMT), also known as a stool transplant, is the process of transferring fecal bacteria and other microbes from a healthy individual into another individual. FMT is an effective treatment for Clostridioides difficile infection (CDI). For recurrent CDI, FMT is more effective than vancomycin alone, and may improve the outcome after the first index infection.

Dysbiosis is characterized by a disruption to the microbiome resulting in an imbalance in the microbiota, changes in their functional composition and metabolic activities, or a shift in their local distribution. For example, a part of the human microbiota such as the skin flora, gut flora, or vaginal flora, can become deranged (unbalanced), when normally dominating species become underrepresented and species that normally are outcompeted or contained increase to fill the void. Similar to the human gut microbiome, diverse microbes colonize the plant rhizosphere, and dysbiosis in the rhizosphere, can negatively impact plant health. Dysbiosis is most commonly reported as a condition in the gastrointestinal tract or plant rhizosphere.

<span class="mw-page-title-main">Lubiprostone</span> Medication used for constipation

Lubiprostone, sold under the brand name Amitiza among others, is a medication used in the management of chronic idiopathic constipation, predominantly irritable bowel syndrome-associated constipation in women and opioid-induced constipation. The drug is owned by Mallinckrodt and is marketed by Takeda Pharmaceutical Company.

<span class="mw-page-title-main">Ceftaroline fosamil</span> Chemical compound

Ceftaroline fosamil (INN), brand name Teflaro in the US and Zinforo in Europe, is a cephalosporin antibiotic with anti-MRSA activity. Ceftaroline fosamil is a prodrug of ceftaroline. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria. It retains some activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria, but its effectiveness is relatively much weaker. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection.

<span class="mw-page-title-main">Crofelemer</span> Pharmaceutical drug

Crofelemer is an antidiarrheal indicated for the symptomatic relief of non-infectious diarrhea in adult patients with HIV/AIDS on antiretroviral therapy. Other possible uses include diarrhea in children, acute infectious diarrhea, and diarrhea in patients with irritable bowel syndrome. It is a purified oligomeric proanthocyanidin from "dragon's blood", the sap of the South American tree Croton lechleri.

Bacteriotherapy is the purposeful use of bacteria or their products in treating an illness. Forms of bacteriotherapy include the use of probiotics, microorganisms that provide health benefits when consumed; fecal matter transplants (FMT) /intestinal microbiota transplant (IMT), the transfer of gut microorganisms from the fecal matter of healthy donors to recipient patients to restore microbiota; or synbiotics which combine prebiotics, indigestible ingredients that promote growth of beneficial microorganisms, and probiotics. Through these methods, the gut microbiota, the community of 300-500 microorganism species that live in the digestive tract of animals aiding in digestion, energy storage, immune function and protection against pathogens, can be recolonized with favorable bacteria, which in turn has therapeutic effects.

<i>Clostridioides difficile</i> Species of bacteria

Clostridioides difficile is a bacterium known for causing serious diarrheal infections, and may also cause colon cancer. It is known also as C. difficile, or C. diff, and is a Gram-positive species of spore-forming bacteria. Clostridioides spp. are anaerobic, motile bacteria, ubiquitous in nature and especially prevalent in soil. Its vegetative cells are rod-shaped, pleomorphic, and occur in pairs or short chains. Under the microscope, they appear as long, irregular cells with a bulge at their terminal ends. Under Gram staining, C. difficile cells are Gram-positive and show optimum growth on blood agar at human body temperatures in the absence of oxygen. C. difficile is catalase- and superoxide dismutase-negative, and produces up to three types of toxins: enterotoxin A, cytotoxin B and Clostridioides difficile transferase. Under stress conditions, the bacteria produce spores that are able to tolerate extreme conditions that the active bacteria cannot tolerate.

Serum-derived bovine immunoglobulin/protein isolate (SBI) is a medical food product derived from bovine serum obtained from adult cows in the United States. It is sold under the name EnteraGam.

References

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  42. ↑ "Cosmo to give Bausch Health a run for its money with FDA nod for Xifaxan rival". FiercePharma. 20 November 2018. Retrieved 14 May 2019.
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