ChemicalBook > CAS DataBase List > Nitazoxanide

Nitazoxanide

Product Name
Nitazoxanide
CAS No.
55981-09-4
Chemical Name
Nitazoxanide
Synonyms
nitazoxamide;Nitazoxanid;2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide;Nizonide;NSC 697855;BRN 1225475;NITAZOXANIDE;AURORA KA-645;Nitrazolamide;Nitrozantinib
CBNumber
CB7219063
Molecular Formula
C12H9N3O5S
Formula Weight
307.28
MOL File
55981-09-4.mol
More
Less

Nitazoxanide Property

Melting point:
202°C
Density 
1.629 g/cm3
storage temp. 
2-8°C
solubility 
Soluble in DMSO (>50 mg/ml)
pka
6.18±0.50(Predicted)
form 
solid
color 
Off-white
λmax
416nm(Phosphate buffer sol.)(lit.)
Merck 
14,6567
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
CAS DataBase Reference
55981-09-4(CAS DataBase Reference)
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
VN7830000
HS Code 
2934100000
Toxicity
LD50 orally in male, female mice: 1350, 1380 mg/kg; in rats: >10 g/kg (Murphy, Friedmann)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N0290
Product name
Nitazoxanide
Purity
≥98% (HPLC)
Packaging
10mg
Price
$84.1
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2888
Product name
Nitazoxanide
Purity
pharmaceutical secondary standard, certified reference material
Packaging
400MG
Price
$172
Updated
2024/03/01
Sigma-Aldrich
Product number
1463960
Product name
Nitazoxanide
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$174.4
Updated
2024/03/01
TCI Chemical
Product number
N1031
Product name
Nitazoxanide
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$241
Updated
2024/03/01
TCI Chemical
Product number
N1031
Product name
Nitazoxanide
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$638
Updated
2024/03/01
More
Less

Nitazoxanide Chemical Properties,Usage,Production

Description

Nitazoxanide (NT Z) has been approved as an orphan drug for the treatment of diarrhea in children (age, 1–11 years) and is associated with giardiasis, but it also is approved for diarrhea caused by crytosporidiosis in patients with AIDS. Crytosporidiosis is a protozoal infection caused by Cryptosporidi um parvum. The condition is uncommon in healthy individuals but can be life-threatening in immunosuppressed patients and those with HIV infections.

Chemical Properties

Crystalline Solid

Originator

Alinia,Romark Laboratories, L.C.

Uses

Nitazoxanide has been used:

  • to test its anti-viral activity against chikungunya virus
  • as an antiprotozoal agent to test its effect on cell viability in various cancer cell lines
  • to test its effect on human cytomegalovirus (HCMV) infected human fibroblast HFF cells

Uses

An anthelmintic (cestodes), antiprotozoal (cryptosporidium). Kills Mycobacterium tuberculosis.

Uses

antihypertensive

Uses

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 protozoa Cryptosporidium parvum.

Definition

ChEBI: 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.

Manufacturing Process

To a solution containing one mole p-metoxy-benzoyl chloride and one mole of carefully purified 2-amino-5-nitro-triazole in 200 ml of anhydrous tetrahydrofuran, one mole of triethylamine has been slowly added (about 10 minutes) while stirring. The reaction mixture, which became slightly warm, was stirred during 45 minutes and then poured under agitation, into 2 liters of distilled water. The stirring was continued until the precipitation of salicylamide, N-(5-nitro-2-thiazolyl)-, acetate (ester) was complete. The obtained precipitate was dried, washed with water, dried again and recrystallized from methanol. The yield about 60%; melting point 202°C.

brand name

Alinia (Romark).

Therapeutic Function

Anthelmintic

Antimicrobial activity

In vitro Cryptosporidium parvum sporocytes and oocysts are inhibited by <33 μm, and Giardia lamblia (intestinalis) trophozoites by <10 μm. The metabolite tizoxanide is more active than the parent compound against some isolates. E. histolytica is inhibited by 6–23 μm (parent compound) and 5.6– 28 μm (metabolite), and T. vaginalis by 0.5–15.5 μm (parent compound) and 0.3–12.2 μm (metabolite). Activity against other micro- organisms, including some helminths, bacteria (Clostridium difficile) and viruses (hepatitis C) has also been demonstrated.

Acquired resistance

Resistance caused by altered expression of genes involved in stress response has been demonstrated in experimental studies with G. lamblia.

General Description

Nitazoxanide (NTZ), a thiazolide compound is a antiparasitic drug with structure similar to niclosamide.

Pharmaceutical Applications

A synthetic broad-spectrum antiparasitic nitroheterocycle (2-acetyloxy- N-(5-nitro-2-thiazolyl) benzamide), formulated for oral use.

Biochem/physiol Actions

Nitazoxanide is an inhibitor of pyruvate-ferredoxin oxidoreductase (PFOR); Antimicrobial recently found to kill both non-replicating and replicating mycobacteria. FDA approved anti-parasitic drug (2002). Recent work (C & EN Sept. 14, 2009, p. 28) highlights that NTZ kills non-replicating and replicating TB bacteria and no apparent resistance is detected.

Mechanism of action

Nitazoxanide is a pro-drug that is metabolically converted into the deactylated drug tizoxanide (TIZ). The TIZ then undergoes a four-electron reduction of the 5-nitro group giving various short-lived intermediates, which may include the hydroxylamine derivative. It is these reduced products that represent the active form of NTZ. Whereas these intermediates would suggest that NTZ has the same mechanism of action as metronidazole, this does not appear to be the case. Nitazoxanide is thought to inhibit the enzyme pyruvate:ferredoxin oxidoreductase in Trichomonas vaginali s, Entamoeba histolytica, and Cl ostridium perfingens. The results of this inhibition is disruption of the bioenergetics of these organisms. Unlike metronidazole and tinidazole, which fragment DNA and are suspected mutagenic agents, NTZ and TIZ do not cause DNA fragmentation and are not considered to be mutagenic. This might be associated with the higher redox potential found for NTZ, a nitrothiazole, in comparison with very low redox potential found for the nitroimidazoles, such as metronidazole and tinidazole. Additional metabolites of TIZ also includes the glucuronide, which shows some biological activity, and small amounts of an aromatic hydroxylation product.

Pharmacokinetics

After oral administration the major circulating metabolites are tizoxanide (desacetyl nitazoxanide) and its glucuronide. Minor metabolites include salicyluric acid and tizoxanide sulfate. Maximum concentrations of the active metabolites tizoxanide and tizoxanide glucuronide are observed within 1–4 h. Following a single oral dose of 500 mg given with food, the Cmax of both metabolites was around 10 mg/L. Tizoxanide has a halflife of around 1–2 h and is >99.9% bound to plasma proteins.

Clinical Use

It is indicated for the treatment of diarrhea caused by G. lamblia or C. parvum.

Side effects

Nitazoxanide appears well tolerated. Side effects may include abdominal pain diarrhea, headache and nausea.

Veterinary Drugs and Treatments

Nitazoxanide oral paste is indicated for the treatment of horses with equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona.
In humans, nitazoxanide is approved (in the USA) for use in treating diarrhea caused by Cryptosporidium parvum and Giardia lamblia in pediatric patients from ages 1 to 11 years old.
Because of the drug’s spectrum of activity and apparent safety, there is considerable interest in using it in a variety of companion animal species, but data is lacking for specific indications and dosages.

Metabolism

Nitazoxanide is available as powder that is reconstituted and dispensed as an oral suspension. The drug is well absorbed from the GI tract and rapidly metabolized, with elimination products appearing in the urine and feces. The only identified products in the plasma are TIZ and its glucuronide. The product can be taken with food.

storage

Store at -20°C

References

References/Citations:

Nitazoxanide Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Nitazoxanide Suppliers

Jinan Wald Chemical Co., Ltd.
Tel
0531-88773586 13210588999
Fax
053188773586
Email
304264064@qq.com
Country
China
ProdList
195
Advantage
58
ELSA BIOTECHNOLOGY CO.,LTD.
Tel
15261860116
Fax
86-025-84106591
Email
sales@elsa-biotech.com
Country
China
ProdList
99
Advantage
55
Hubei huizepu Pharmaceutical Technology Co., Ltd
Tel
18507139096
Fax
QQ:2462856504
Email
17762444226@163.com
Country
China
ProdList
645
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
Fax
+86 351 7031519
Email
sales@RHFChem.com
Country
China
ProdList
2341
Advantage
56
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44751
Advantage
61
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10194
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
70
More
Less

View Lastest Price from Nitazoxanide manufacturers

Henan Fengda Chemical Co., Ltd
Product
Nitazoxanide 55981-09-4
Price
US $34.00-1.40/kg
Min. Order
1kg
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-03-26
Sigma Audley
Product
Nitazoxanide 55981-09-4
Price
US $35.00-25.00/kg
Min. Order
1kg
Purity
99.8%
Supply Ability
200tons/year
Release date
2024-03-12
Hebei Duling International Trade Co. LTD
Product
Nitazoxanide 55981-09-4
Price
US $100.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100 tons
Release date
2023-05-29

55981-09-4, NitazoxanideRelated Search:


  • 2-(acetolyloxy)-n-(5-nitro-2-thiazolyl)benzamide
  • 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)-benzamid
  • BRN 1225475
  • n-(5-nitro-2-thiazolyl)-salicylamidacetate(ester)
  • n-(5-nitro-2-thiazolyl)salicylamideacetate(ester)
  • AURORA KA-645
  • o-[n-(5-nitrothiazol-2-yl)carbamoyl]phenyl acetate
  • NITAZOXANIDE
  • nitazoxamide
  • PH-5776, Cryptaz, 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide
  • 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide
  • [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate
  • [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] ethanoate
  • acetic acid [2-[(5-nitrothiazol-2-yl)carbamoyl]phenyl] ester
  • Nitazoxanide (200 mg)
  • Nitazoxanide(Alinia, Annita)
  • Nitazoxanide API
  • 2-((5-nitrothiazol-2-yl)carbaMoyl)phenyl acetate
  • Benzamide, 2-(acetyloxy)-N-(5-nitro-2-thiazolyl)-
  • NSC 697855
  • Nitazoxanide USP/EP/BP
  • Nitazoxanid
  • Nitazoxanide (NTZ
  • NitazoxanideQ: What is Nitazoxanide Q: What is the CAS Number of Nitazoxanide Q: What is the storage condition of Nitazoxanide
  • Nitazoxanide (1463960)
  • Indications nita
  • Nitazoxanide,Nitazoxinide
  • Nitrazolamide
  • Nizonide
  • Nitrozantinib
  • 55981-09-4
  • C12H9N3O5S
  • Pyridines
  • API
  • Isotope labeled API
  • ENDURON
  • Aromatics
  • Heterocycles
  • Sulfur & Selenium Compounds
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • 55981-09-4