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
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)
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)
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..…
N-Bromosuccinimide Price
- Product number
- N0290
- Product name
- Nitazoxanide
- Purity
- ≥98% (HPLC)
- Packaging
- 10mg
- Price
- $84.1
- Updated
- 2024/03/01
- Product number
- PHR2888
- Product name
- Nitazoxanide
- Purity
- pharmaceutical secondary standard, certified reference material
- Packaging
- 400MG
- Price
- $172
- Updated
- 2024/03/01
- Product number
- 1463960
- Product name
- Nitazoxanide
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 200mg
- Price
- $174.4
- Updated
- 2024/03/01
- Product number
- N1031
- Product name
- Nitazoxanide
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $241
- Updated
- 2024/03/01
- Product number
- N1031
- Product name
- Nitazoxanide
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 5g
- Price
- $638
- Updated
- 2024/03/01
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
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View Lastest Price from Nitazoxanide manufacturers
- Product
- Nitazoxanide 55981-09-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99.0%
- Supply Ability
- 10tons
- Release date
- 2024-04-26
- Product
- Nitazoxanide 55981-09-4
- Price
- US $50.00/kg
- Min. Order
- 1kg
- Purity
- 99.10%
- Supply Ability
- 5000kg
- Release date
- 2024-04-19
- Product
- Nitazoxanide 55981-09-4
- Price
- US $50.00/kg
- Min. Order
- 1kg
- Purity
- 99.10%
- Supply Ability
- 5000kg
- Release date
- 2024-04-19