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    Also known as: 55981-09-4, Alinia, 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate, Nitazoxamide, Daxon, Nitazoxanidum [inn-latin]
    Molecular Formula
    C12H9N3O5S
    Molecular Weight
    307.28  g/mol
    InChI Key
    YQNQNVDNTFHQSW-UHFFFAOYSA-N
    FDA UNII
    SOA12P041N
    Nitazoxanide
    Nitazoxanide is a synthetic benzamide with antiprotozoal activity. Nitazoxanide exerts its antiprotozoal activity by interfering with the pyruvate ferredoxin/flavodoxin oxidoreductase dependent electron transfer reaction, which is essential to anaerobic energy metabolism. PFOR enzyme reduces nitazoxanide, thereby impairing the energy metabolism. However, interference with the PFOR enzyme-dependent electron transfer reaction may not be the only pathway by which nitazoxanide exhibits antiprotozoal activity. Nitazoxanide is active against Giardia lamblia and Cryptosporidium parvum.
    Nitazoxanide is an Antiprotozoal.
    1 2D Structure

    Nitazoxanide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate
    2.1.2 InChI
    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)
    2.1.3 InChI Key
    YQNQNVDNTFHQSW-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    SOA12P041N
    2.3 Synonyms
    2.3.1 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

    2.3.2 Depositor-Supplied Synonyms

    1. 55981-09-4

    2. Alinia

    3. 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl Acetate

    4. Nitazoxamide

    5. Daxon

    6. Nitazoxanidum [inn-latin]

    7. Nitazoxanida [inn-spanish]

    8. 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl Acetate

    9. Benzamide, 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)-

    10. [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] Acetate

    11. 2-(acetolyloxy)-n-(5-nitro-2-thiazolyl)benzamide

    12. Nsc 697855

    13. Nsc697855

    14. Ntz

    15. 2-acetyloxy-n-[(5-nitro-2-thiazolyl)]benzamide

    16. Nsc-697855

    17. Nsc-760057

    18. N-(5-nitrothiazol-2-yl)salicylamide Acetate Ester

    19. Ph 5776

    20. Ph-5776

    21. Nitazoxanide (alinia, Annita)

    22. Soa12p041n

    23. Nitazoxanida

    24. Cryptaz

    25. [2-[(5-nitrothiazol-2-yl)carbamoyl]phenyl] Acetate

    26. Ncgc00090774-01

    27. Nitazoxanid

    28. Nitazoxanidum

    29. Colufase

    30. Heliton

    31. Dsstox_cid_13757

    32. Dsstox_rid_79095

    33. Dsstox_gsid_33757

    34. Phavic-1

    35. Smr000466367

    36. Alinia (tn)

    37. Azt + Nitazoxanide

    38. Cas-55981-09-4

    39. Einecs 259-931-8

    40. Nitazoxanide (usan/inn)

    41. (2-((5-nitro-2-thiazolyl)carbamoyl)phenyl)acetat

    42. Brn 1225475

    43. Unii-soa12p041n

    44. N-(5-nitro-2-thiazolyl)salicylamide Acetate (ester)

    45. Nitrazoxanide

    46. Pacovanton

    47. Dexidex

    48. Kidonax

    49. Nitazox

    50. Paramix

    51. Nitax

    52. Toza

    53. Nitazoxanide [usan:inn:ban]

    54. Alinia(tm)

    55. Mfcd00416599

    56. O-(n-(5-nitrothiazol-2-yl)carbamoyl)phenyl Acetate

    57. Nitazoxanide- Bio-x

    58. Salicylamide, N-(5-nitro-2-thiazolyl)-, Acetate (ester)

    59. Cpd000466367

    60. Nitazoxanide [mi]

    61. Nitazoxanide [inn]

    62. Ncimech_000843

    63. Nitazoxanide [usan]

    64. Chembl1401

    65. Nitazoxanide [vandf]

    66. 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)benzamide

    67. Oprea1_263587

    68. Schembl40981

    69. Nitazoxanide [mart.]

    70. Mls000759492

    71. Mls001424074

    72. Mls006010127

    73. Nitazoxanide [usp-rs]

    74. Nitazoxanide [who-dd]

    75. Dtxsid5033757

    76. Chebi:94807

    77. Nitazoxanide [green Book]

    78. Nitazoxanide, >=98% (hplc)

    79. Ntz;nsc 697855

    80. Hms2051l04

    81. Hms3393l04

    82. Hms3655m11

    83. Hms3715f10

    84. Nitazoxanide [orange Book]

    85. Pharmakon1600-01503843

    86. Bcp13918

    87. Hy-b0217

    88. Zinc3956788

    89. Tox21_111018

    90. Tox21_201226

    91. Bdbm50075050

    92. Ccg-35851

    93. Mmv688991

    94. Nsc760057

    95. Stk395664

    96. Akos015915393

    97. Tox21_111018_1

    98. Ac-1302

    99. Db00507

    100. Ks-1160

    101. Nc00246

    102. Ncgc00090774-02

    103. Ncgc00090774-03

    104. Ncgc00090774-04

    105. Ncgc00090774-05

    106. Ncgc00258778-01

    107. Bn164151

    108. Nci60_034935

    109. Ft-0601547

    110. N1031

    111. Nitrazoxanide 100 Microg/ml In Acetonitrile

    112. S1627

    113. Sw197626-2

    114. 2-(5-nitrothiazol-2-ylcarbamoyl)phenyl Acetate

    115. D02486

    116. Ab00639988-07

    117. Ab00639988-09

    118. Ab00639988_10

    119. Ab00639988_11

    120. 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)-benzamide

    121. 981n094

    122. A830877

    123. Sr-01000759418

    124. Q-201475

    125. Q2943789

    126. Sr-01000759418-9

    127. Salicylamide, N-(5-nitro-2-thiazolyl)- Acetate (ester)

    128. Z1514087129

    129. Nitazoxanide, United States Pharmacopeia (usp) Reference Standard

    130. Acetic Acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] Ester

    131. Zox

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 307.28 g/mol
    Molecular Formula C12H9N3O5S
    XLogP32
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass307.02629157 g/mol
    Monoisotopic Mass307.02629157 g/mol
    Topological Polar Surface Area142 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity428
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAlinia
    PubMed HealthNitazoxanide (By mouth)
    Drug ClassesAntiprotozoal
    Drug LabelAlinia Tablets and Alinia for Oral Suspension contain the active ingredient, nitazoxanide, a synthetic antiprotozoal agent for oral administration. Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically ins...
    Active IngredientNitazoxanide
    Dosage FormTablet; For suspension
    Routeoral; Oral
    Strength100mg/5ml; 500mg
    Market StatusPrescription
    CompanyRomark

    2 of 2  
    Drug NameAlinia
    PubMed HealthNitazoxanide (By mouth)
    Drug ClassesAntiprotozoal
    Drug LabelAlinia Tablets and Alinia for Oral Suspension contain the active ingredient, nitazoxanide, a synthetic antiprotozoal agent for oral administration. Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically ins...
    Active IngredientNitazoxanide
    Dosage FormTablet; For suspension
    Routeoral; Oral
    Strength100mg/5ml; 500mg
    Market StatusPrescription
    CompanyRomark

    4.2 Drug Indication

    For the treatment of diarrhea in adults and children caused by the protozoa Giardia lamblia, and for the treatment of diarrhea in children caused by the protozoan, Cryptosporidium parvum. Nitazoxanide has not been shown to be superior to placebo medication for the management of diarrhea caused by Cryptosporidium parvum in patients with HIV/immunodeficiency.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    The general effect of this medication is the prevention of microbe activity through disruption of important energy pathways for survival and proliferation. Nitazoxanide exhibits antiprotozoal activity by interfering with the pyruvate ferredoxin/flavodoxin oxidoreductase dependent electron transfer reaction, an essential reaction need for anaerobic energy metabolism of various microorganisms. Sporozoites of Cryptosporidium parvum and trophozoites of Giardia lamblia are therefore inhibited, relieving symptoms of diahrrea. Interference with the PFOR enzyme-dependent electron transfer reaction may only be one of the many pathways by which nitazoxanide exhibits antiprotozoal activity.

    5.2 MeSH Pharmacological Classification

    Antiparasitic Agents

    Drugs used to treat or prevent parasitic infections. (See all compounds classified as Antiparasitic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    NITAZOXANIDE
    5.3.2 FDA UNII
    SOA12P041N
    5.3.3 Pharmacological Classes
    Antiprotozoal [EPC]
    5.4 ATC Code

    P - Antiparasitic products, insecticides and repellents

    P01 - Antiprotozoals

    P01A - Agents against amoebiasis and other protozoal diseases

    P01AX - Other agents against amoebiasis and other protozoal diseases

    P01AX11 - Nitazoxanide

    5.5 Absorption, Distribution and Excretion

    Absorption

    The relative bioavailability of the suspension compared to the tablet was 70%. When administered with food the AUC and Cmax increased by two-fold and 50%, respectively, for the tablet and 45 to 50% and ≤ 10%, respectively, for the oral suspension.

    Route of Elimination

    Tizoxanide is excreted in the urine, bile and feces, and tizoxanide glucuronide is excreted in urine and bile. Approximately 2/3 of the oral dose of nitazoxanide is excreted in the faeces and 1/3 in the urine.

    Clearance

    Nitazoxanide is cleared in the urine and feces. The metabolite, tizoxanide, is also found in the urine, plasma, and breastmilk. The drug is not found unchanged in the urine.

    5.6 Metabolism/Metabolites

    The active metabolite of this drug is tizoxanide (desacetyl-nitazoxanide). The initial reaction in the metabolic pathway of Nitazoxanide is hydrolysis to tizoxanide, followed by conjugation, primarily by glucuronidation to tizoxanide glucuronide. The oral suspension bioavailability of this drug is not equivalent to that of the oral tablets. Compared to the to the tablet, the bioavailability of the suspension was 70%. When administered with food, the AUCt of tizoxanide and tizoxanide glucuronide in plasma is increased to almost two-fold and the maximum concentration is increased by almost 50% compared to when ingested without food. When the oral suspension was ingested with food, the AUC of tizoxanide and tizoxanide glucuronide increased by approximately 50% and the Cmax increased by less than 10%.

    5.7 Biological Half-Life

    7.3h

    5.8 Mechanism of Action

    The most widely accepted mechanism of NTZ is believed to be the disruption of the energy metabolism in anaerobic microbes by inhibition of the pyruvate: ferredoxin/flavodoxin oxidoreductase (PFOR) cycle. In parasitic-protozoa, Nitazoxanide also induces lesions in the cell membranes and depolarizes the mitochondrial membrane while inhibiting quinone oxidoreductase NQO1, nitroreductase-1 and protein disulphide isomerase enzymes. In addition, this drug also inhibits the glutathione-S-transferase (a major detoxifying enzyme) and modulates the Avr-14 gene, encoding for the alpha-type subunit of glutamate-gated chloride ion channel present in nematodes. Aside from its well understood non-competitive inhibition of the PFOR in anaerobic bacteria, NTZ also demonstrates various other antibacterial mechanisms. It inhibits pyruvate dehydrogenase in E Coli, disrupts the membrane potential and pH homeostasis in the Mycobacterium tuberculosis, suppresses the chaperone/usher (CU) pathway of the gram-negative bacteria, and stimulates host macrophage autophagy in tuberculosis patients. NTZ also suppresses viral replication by inhibiting the maturation of the viral hemagglutinin and the viral transcription factor immediate early 2 (IE2) as well as by activating the eukaryotic translation initiation factor 2 (an antiviral intracellular protein). Lastly, NTZ exhibits an inhibitory effect on tumor cell progression by altering drug detoxification (glutathione-S-transferase P1), unfolded protein response, autophagy, anti-cytokines activity, and c-Myc inhibition.

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    06-Jan-2022
    29-May-2025
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    DOSAGE - TABLET;ORAL - 500MG

    USFDA APPLICATION NUMBER - 21497

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    DOSAGE - FOR SUSPENSION;ORAL - 100MG/5ML

    USFDA APPLICATION NUMBER - 21498

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    ABOUT THIS PAGE

    Looking for 55981-09-4 / Nitazoxanide API manufacturers, exporters & distributors?

    Nitazoxanide manufacturers, exporters & distributors 1

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    PharmaCompass offers a list of Nitazoxanide API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Nitazoxanide manufacturer or Nitazoxanide supplier for your needs.

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    PharmaCompass also assists you with knowing the Nitazoxanide API Price utilized in the formulation of products. Nitazoxanide API Price is not always fixed or binding as the Nitazoxanide Price is obtained through a variety of data sources. The Nitazoxanide Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

    API | Excipient name

    Nitazoxanide

    Synonyms

    55981-09-4, Alinia, 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate, Nitazoxamide, Daxon, Nitazoxanidum [inn-latin]

    Cas Number

    55981-09-4

    Unique Ingredient Identifier (UNII)

    SOA12P041N

    About Nitazoxanide

    Nitazoxanide is a synthetic benzamide with antiprotozoal activity. Nitazoxanide exerts its antiprotozoal activity by interfering with the pyruvate ferredoxin/flavodoxin oxidoreductase dependent electron transfer reaction, which is essential to anaerobic energy metabolism. PFOR enzyme reduces nitazoxanide, thereby impairing the energy metabolism. However, interference with the PFOR enzyme-dependent electron transfer reaction may not be the only pathway by which nitazoxanide exhibits antiprotozoal activity. Nitazoxanide is active against Giardia lamblia and Cryptosporidium parvum.

    Daxon Manufacturers

    A Daxon manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Daxon, including repackagers and relabelers. The FDA regulates Daxon manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Daxon API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Daxon manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Daxon Suppliers

    A Daxon supplier is an individual or a company that provides Daxon active pharmaceutical ingredient (API) or Daxon finished formulations upon request. The Daxon suppliers may include Daxon API manufacturers, exporters, distributors and traders.

    click here to find a list of Daxon suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Daxon USDMF

    A Daxon DMF (Drug Master File) is a document detailing the whole manufacturing process of Daxon active pharmaceutical ingredient (API) in detail. Different forms of Daxon DMFs exist exist since differing nations have different regulations, such as Daxon USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Daxon DMF submitted to regulatory agencies in the US is known as a USDMF. Daxon USDMF includes data on Daxon's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Daxon USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Daxon suppliers with USDMF on PharmaCompass.

    Daxon WC

    A Daxon written confirmation (Daxon WC) is an official document issued by a regulatory agency to a Daxon manufacturer, verifying that the manufacturing facility of a Daxon active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Daxon APIs or Daxon finished pharmaceutical products to another nation, regulatory agencies frequently require a Daxon WC (written confirmation) as part of the regulatory process.

    click here to find a list of Daxon suppliers with Written Confirmation (WC) on PharmaCompass.

    Daxon NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Daxon as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Daxon API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Daxon as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Daxon and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Daxon NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Daxon suppliers with NDC on PharmaCompass.

    Daxon GMP

    Daxon Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Daxon GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Daxon GMP manufacturer or Daxon GMP API supplier for your needs.

    Daxon CoA

    A Daxon CoA (Certificate of Analysis) is a formal document that attests to Daxon's compliance with Daxon specifications and serves as a tool for batch-level quality control.

    Daxon CoA mostly includes findings from lab analyses of a specific batch. For each Daxon CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Daxon may be tested according to a variety of international standards, such as European Pharmacopoeia (Daxon EP), Daxon JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Daxon USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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