Nitazoxanide

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Nitazoxanide
Nitazoxanide.svg
Nitazoxanide-from-xtal-Mercury-3D-balls.png
Clinical data
Trade names Alinia, Nizonide, others
AHFS/Drugs.com Monograph
MedlinePlus a603017
License data
Routes of
administration 		By mouth
Drug class Antiprotozoal
Broad-spectrum antiparasitic
Broad-spectrum antiviral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding Nitazoxanide: ?
Tizoxanide: over 99% [1] [2]
Metabolism Rapidly hydrolyzed to tizoxanide [1]
Metabolites tizoxanide [1] [2]
tizoxanide glucuronide [1] [2]
Elimination half-life 3.5 hours [3]
Excretion Kidney, bile duct, and fecal [1]
Identifiers
  • [2-[(5-Nitro-1,3-thiazol-2-yl)carbamoyl]phenyl]ethanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard 100.054.465 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H9N3O5S
Molar mass 307.28 g·mol−1
3D model (JSmol)
  • O=C(Nc1ncc(s1)[N+]([O-])=O)c2ccccc2OC(=O)C
  • InChI=1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17) Yes check.svgY
  • Key:YQNQNVDNTFHQSW-UHFFFAOYSA-N Yes check.svgY
   (verify)

Nitazoxanide, sold under the brand name Alinia among others, is a broad-spectrum antiparasitic and broad-spectrum antiviral medication that is used in medicine for the treatment of various helminthic, protozoal, and viral infections. [4] [5] [6] It is indicated for the treatment of infection by Cryptosporidium parvum and Giardia lamblia in immunocompetent individuals and has been repurposed for the treatment of influenza. [1] [6] Nitazoxanide has also been shown to have in vitro antiparasitic activity and clinical treatment efficacy for infections caused by other protozoa and helminths; [4] [7] evidence as of 2014 suggested that it possesses efficacy in treating a number of viral infections as well. [6]

Contents

Chemically, nitazoxanide is the prototype member of the thiazolides, a class of drugs which are synthetic nitrothiazolyl-salicylamide derivatives with antiparasitic and antiviral activity. [4] [6] [8] Tizoxanide, an active metabolite of nitazoxanide in humans, is also an antiparasitic drug of the thiazolide class. [4] [9]

Nitazoxanide tablets were approved as a generic medication in the United States in 2020. [10]

Uses

Nitazoxanide is an effective first-line treatment for infection by Blastocystis species [11] [12] and is indicated for the treatment of infection by Cryptosporidium parvum or Giardia lamblia in immunocompetent adults and children. [1] It is also an effective treatment option for infections caused by other protozoa and helminths (e.g., Entamoeba histolytica , [13] Hymenolepis nana , [14] Ascaris lumbricoides , [15] and Cyclospora cayetanensis [16] ). [7]

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 hepatitis C with nitazoxanide. [20] The drug garnered interest from the hepatology community after three phase II clinical trials involving the treatment of hepatitis C with nitazoxanide produced positive results for treatment efficacy and similar tolerability to placebo without any signs of toxicity. [20] A meta-analysis from 2014 concluded that the previous held trials were of low-quality and withheld with a risk of bias. The authors concluded that more randomized trials with low risk of bias are needed to determine if Nitazoxanide can be used as an effective treatment for chronic hepatitis C patients. [21]

Contraindications

Nitazoxanide is contraindicated only in individuals who have experienced a hypersensitivity reaction to nitazoxanide or the inactive ingredients of a nitazoxanide formulation. [1]

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. [1] [2] In various animals, the oral LD50 is higher than 10 g/kg. [1]

Interactions

Due to the exceptionally high plasma protein binding (>99.9%) of nitazoxanide's metabolite, tizoxanide, the concurrent use of nitazoxanide with other highly plasma protein-bound drugs with narrow therapeutic indices (e.g., warfarin) increases the risk of drug toxicity. [1] In vitro evidence suggests that nitazoxanide does not affect the CYP450 system. [1]

Pharmacology

Pharmacodynamics

The anti-protozoal activity of nitazoxanide is believed to be due to interference with the pyruvate:ferredoxin oxidoreductase (PFOR) enzyme-dependent electron-transfer reaction that is essential to anaerobic energy metabolism. [1] [8] PFOR inhibition may also contribute to its activity against anaerobic bacteria. [23]

It has also been shown to have activity against influenza A virus in vitro. [24] The mechanism appears to be by selectively blocking the maturation of the viral hemagglutinin at a stage preceding resistance to endoglycosidase H digestion. This impairs hemagglutinin intracellular trafficking and insertion of the protein into the host plasma membrane.[ citation needed ]

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 hydrolyzed to the pharmacologically active metabolite, tizoxanide, which is 99% protein bound. [1] [9] Tizoxanide is then glucuronide conjugated into the active metabolite, tizoxanide glucuronide. [1] Peak plasma concentrations of the metabolites tizoxanide and tizoxanide glucuronide are observed 1–4 hours after oral administration of nitazoxanide, whereas nitazoxanide itself is not detected in blood plasma. [1]

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

Nitazoxanide is the prototype member of the thiazolides, which is a drug class of structurally-related broad-spectrum antiparasitic compounds. [4] Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically insoluble in water.[ citation needed ]

History

Nitazoxanide was originally discovered in the 1980s by Jean-François Rossignol at the Pasteur Institute. Initial studies demonstrated activity versus tapeworms. In vitro studies demonstrated much broader activity. Dr. Rossignol co-founded Romark Laboratories, with the goal of bringing nitazoxanide to market as an anti-parasitic drug. Initial studies in the USA were conducted in collaboration with Unimed Pharmaceuticals, Inc. (Marietta, GA) and focused on development of the drug for treatment of cryptosporidiosis in AIDS. Controlled trials began shortly after the advent of effective anti-retroviral therapies. The trials were abandoned due to poor enrollment and the FDA rejected an application based on uncontrolled studies.[ citation needed ]

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 metronidazole. Nitazoxanide was successful in the treatment of metronidazole-resistant giardiasis. Studies have suggested efficacy in the treatment of cyclosporiasis, isosporiasis, and amebiasis. [25] Recent studies have also found it to be effective against beef tapeworm(Taenia saginata). [18]

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 extended release tablet (675 mg) has been used in clinical trials for chronic hepatitis C; however, this form is not currently marketed or available for prescription. [20]

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, nitazoxanide was in phase 3 clinical trials for the treatment influenza due to its inhibitory effect on a broad range of influenza virus subtypes and efficacy against influenza viruses that are resistant to neuraminidase inhibitors like oseltamivir. [6] [26] Nitazoxanide is also being researched as a potential treatment for COVID-19, [27] chronic hepatitis B, chronic hepatitis C, rotavirus and norovirus gastroenteritis. [6]

Related Research Articles

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References

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  24. ↑ Rossignol JF, La Frazia S, Chiappa L, Ciucci A, Santoro MG (October 2009). "Thiazolides, a new class of anti-influenza molecules targeting viral hemagglutinin at the post-translational level". The Journal of Biological Chemistry. 284 (43): 29798–29808. doi: 10.1074/jbc.M109.029470 . PMC   2785610 . PMID   19638339.
  25. ↑ White AC (April 2003). "Nitazoxanide: an important advance in anti-parasitic therapy". The American Journal of Tropical Medicine and Hygiene. 68 (4): 382–383. doi: 10.4269/ajtmh.2003.68.382 . PMID   12875283.
  26. ↑ Li TC, Chan MC, Lee N (September 2015). "Clinical Implications of Antiviral Resistance in Influenza". Viruses. 7 (9): 4929–4944. doi: 10.3390/v7092850 . PMC   4584294 . 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
  27. ↑ Pepperrell T, Pilkington V, Owen A, Wang J, Hill AM (April 2020). "Review of safety and minimum pricing of nitazoxanide for potential treatment of COVID-19". Journal of Virus Eradication. 6 (2): 52–60. doi: 10.1016/S2055-6640(20)30017-0 . PMC   7332204 . PMID   32405422.

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