Nitazoxanide
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Trade names | Alinia, Nizonide, others |
AHFS/Drugs.com | Monograph |
MedlinePlus | a603017 |
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Broad-spectrum antiviral | |
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Nitazoxanide, sold under the brand name Alinia among others, is a
Chemically, nitazoxanide is the prototype member of the
Nitazoxanide tablets were approved as a
Uses
Nitazoxanide is an effective first-line treatment for infection by
Chronic hepatitis B
Nitazoxanide alone has shown preliminary evidence of efficacy in the treatment of chronic hepatitis B over a one-year course of therapy.[17] Nitazoxanide 500 mg twice daily resulted in a decrease in serum HBV DNA in all of 4 HBeAg-positive patients, with undetectable HBV DNA in 2 of 4 patients, loss of HBeAg in 3 patients, and loss of HBsAg in one patient. Seven of 8 HBeAg-negative patients treated with nitazoxanide 500 mg twice daily had undetectable HBV DNA and 2 had loss of HBsAg. Additionally, nitazoxanide monotherapy in one case and nitazoxanide plus adefovir in another case resulted in undetectable HBV DNA, loss of HBeAg and loss of HBsAg.[18] These preliminary studies showed a higher rate of HBsAg loss than any currently licensed therapy for chronic hepatitis B. The similar mechanism of action of interferon and nitazoxanide suggest that stand-alone nitazoxanide therapy or nitazoxanide in concert with nucleos(t)ide analogs have the potential to increase loss of HBsAg, which is the ultimate end-point of therapy. A formal phase 2 study is being planned for 2009.[19]
Chronic hepatitis C
Romark initially decided to focus on the possibility of treating chronic
Contraindications
Nitazoxanide is
Adverse effects
The side effects of nitazoxanide do not significantly differ from a placebo treatment for giardiasis;[1] these symptoms include stomach pain, headache, upset stomach, vomiting, discolored urine, excessive urinating, skin rash, itching, fever, flu syndrome, and others.[1][22] Nitazoxanide does not appear to cause any significant adverse effects when taken by healthy adults.[1][2]
Overdose
Information on nitazoxanide overdose is limited. Oral doses of 4 grams in healthy adults do not appear to cause any significant adverse effects.
Interactions
Due to the exceptionally high
Pharmacology
Pharmacodynamics
The anti-protozoal activity of nitazoxanide is believed to be due to interference with the
It has also been shown to have activity against
Nitazoxanide modulates a variety of other pathways in vitro, including glutathione-S-transferase and glutamate-gated chloride ion channels in nematodes, respiration and other pathways in bacteria and cancer cells, and viral and host transcriptional factors.[23]
Pharmacokinetics
Following oral administration, nitazoxanide is rapidly
Roughly 2⁄3 of an oral dose of nitazoxanide is excreted as its metabolites in feces, while the remainder of the dose excreted in urine.[1] Tizoxanide is excreted in the urine, bile and feces.[1] Tizoxanide glucuronide is excreted in urine and bile.[1]
Chemistry
This section needs expansion. You can help by adding to it. (January 2016) |
Acetic acid [2-[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl ester is a carboxylic ester and a member of benzamides. It is functionally related to a salicylamide. Nitazoxanide[25] is the prototype member of the thiazolides, which is a drug class of structurally-related broad-spectrum antiparasitic compounds. Nitazoxanide belongs to the class of drugs known as thiazolides. It is a broad-spectrum anti-infective drug that significantly modulates the survival, growth, and proliferation of a range of extracellular and intracellular protozoa, helminths, anaerobic and microaerophilic bacteria, in addition to viruses.[4] Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically insoluble in water. The molecular formula of Nitazoxanide is C12H9N3O5S and its molecular weight is 307.28 g/mol2. Tizoxanide, an active metabolite of nitazoxanide in humans, is also an antiparasitic drug of the thiazolide class.
IUPAC Name: [[[2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate2]][26]
Canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)N+[O-]2[27]
MeSH Synonyms:
1) 2-(acetolyloxy)-n-(5-nitro-2-thiazolyl)benzamide 2) Alinia 3) Colufase 4) Cryptaz 5) Daxon 6) Heliton 7) Ntz 8) Taenitaz[28]
History
Nitazoxanide was originally discovered in the 1980s by
Subsequently, Romark launched a series of controlled trials. A placebo-controlled study of nitazoxanide in cryptosporidiosis demonstrated significant clinical improvement in adults and children with mild illness. Among malnourished children in Zambia with chronic cryptosporidiosis, a three-day course of therapy led to clinical and parasitologic improvement and improved survival. In Zambia and in a study conducted in Mexico, nitazoxanide was not successful in the treatment of cryptosporidiosis in advanced infection with human immunodeficiency virus at the doses used. However, it was effective in patients with higher CD4 counts. In treatment of giardiasis, nitazoxanide was superior to placebo and comparable to
Pharmaceutical products
Dosage forms
Nitazoxanide is currently available in two oral dosage forms: a tablet (500 mg) and an oral suspension (100 mg per 5 ml when reconstituted).[1]
An
Brand names
Nitazoxanide is sold under the brand names Adonid, Alinia, Allpar, Annita, Celectan, Colufase, Daxon, Dexidex, Diatazox, Kidonax, Mitafar, Nanazoxid, Parazoxanide, Netazox, Niazid, Nitamax, Nitax, Nitaxide, Nitaz, Nizonide, NT-TOX, Pacovanton, Paramix, Toza, and Zox.[citation needed]
Research
As of September 2015[update], nitazoxanide was in
References
- ^ a b c d e f g h i j k l m n o p q r s t u v w x "Alinia- nitazoxanide tablet Alinia- nitazoxanide powder, for suspension". DailyMed. Retrieved 13 February 2021.
- ^ PMID 12051573.
- ^ "Nitazoxanide". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 3 January 2016.
- ^ PMID 24202339.
Nitazoxanide [NTZ: 2-acetyloxy-N-(5-nitro-2-thiazolyl)benzamide] is a thiazolide antiparasitic agent with excellent activity against a wide variety of protozoa and helminths. ... Nitazoxanide (NTZ) is a main compound of a class of broad-spectrum anti-parasitic compounds named thiazolides. It is composed of a nitrothiazole-ring and a salicylic acid moiety which are linked together by an amide bond ... NTZ is generally well tolerated, and no significant adverse events have been noted in human trials [13]. ... In vitro, NTZ and tizoxanide function against a wide range of organisms, including the protozoal species Blastocystis hominis, C. parvum, Entamoeba histolytica, G. lamblia and Trichomonas vaginalis [13]
- S2CID 219184877.
- ^ S2CID 260860340.
Nitazoxanide is effective in the treatment of protozoal and helminthic infections ... Nitazoxanide is a first-line choice for the treatment of illness caused by C. parvum or G. lamblia infection in immunocompetent adults and children, and is an option to be considered in the treatment of illnesses caused by other protozoa and/or helminths.
- ^ PMID 12069963.
Nitazoxanide (NTZ) is a redox-active nitrothiazolyl-salicylamide
- ^ PMID 17888524.
- ^ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). Retrieved 13 February 2021.
- ^ "Blastocystis: Resources for Health Professionals". United States Centers for Disease Control and Prevention. 2017-05-02. Retrieved 4 January 2016.
- PMID 24883113.
Blastocystis is one of the most common intestinal protists of humans. ... A recent study showed that 100% of people from low socio-economic villages in Senegal were infected with Blastocystis sp. suggesting that transmission was increased due to poor hygiene sanitation, close contact with domestic animals and livestock, and water supply directly from well and river [10]. ...
- S2CID 23861504.
Nitazoxanide: intestinal amoebiasis: 500 mg po bid x 3 days
- ^ "Hymenolepiasis: Resources for Health Professionals". United States Centers for Disease Control and Prevention. 2017-05-02. Retrieved 4 January 2016.
- S2CID 15403331.
new anthelmintic alternatives such as tribendimidine and Nitazoxanide have proved to be safe and effective against A. lumbricoides and other soil-transmitted helminthiases in human trials.
- ^ Shoff WH (5 October 2015). Chandrasekar PH, Talavera F, King JW (eds.). "Cyclospora Medication". Medscape. WebMD. Retrieved 11 January 2016.
Nitazoxanide, a 5-nitrothiazole derivative with broad-spectrum activity against helminths and protozoans, has been shown to be effective against C cayetanensis, with an efficacy 87% by the third dose (first, 71%; second 75%). Three percent of patients had minor side effects.
- PMID 19070525.
- ^ PMID 17962058.
- ^ World Journal of Gastroenterology 2009 April 21, Emmet B Keeffe MD, Professor, Jean-François Rossignol The Romark Institute for Medical Research, Tampa
- ^ PMID 19370775.
- PMID 24706397.
- ^ "Nitazoxanide". MedlinePlus. Retrieved 9 April 2014.
- ^ S2CID 19244282.
- PMID 19638339.
- ^ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7113776/figure/f0005/
- ^ https://pubchem.ncbi.nlm.nih.gov/compound/nitazoxanide
- ^ https://pubchem.ncbi.nlm.nih.gov/compound/nitazoxanide
- ^ https://www.pharmacompass.com/chemistry-chemical-name/nitazoxanide
- PMID 12875283.
- PMID 26389935.
Oral nitazoxanide is an available, approved antiparasitic agent (e.g., against cryptosporidium, giardia) with established safety profiles. Recently, it has been shown (together with its active metabolite tizoxanide) to possess anti-influenza activity by blocking haemagglutinin maturation/trafficking, and acting as an interferon-inducer [97]. ... A large, multicenter, Phase 3 randomized-controlled trial comparing nitazoxanide, oseltamivir, and their combination in uncomplicated influenza is currently underway (NCT01610245).
Figure 1: Molecular targets and potential antiviral treatments against influenza virus infection - PMID 32405422.
Further reading
- "Parasitic infections". American Journal of Transplantation. 4 (Suppl 10): 142–155. November 2004. S2CID 5742723.
External links
- "Nitazoxanide". Drug Information Portal. U.S. National Library of Medicine.