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55981-09-4

Basic Information
CAS No.: 55981-09-4
Name: Nitazoxanide
Article Data: 5
Molecular Structure:
Molecular Structure of 55981-09-4 (Nitazoxanide)
Formula: C12H9N3O5S
Molecular Weight: 307.287
Synonyms: Alinia;BRN 1225475;Cryptaz;DRG 0242;N-(5-Nitro-2-thiazolyl)salicylamide acetate(ester);NSC 697855;NTX;Nitacure;Nitacure 500;Nitarid;Nitazox 500;
EINECS: 259-931-8
Density: 1.532 g/cm3
Melting Point: 202 °C
Appearance: Crystalline Solid
Hazard Symbols: Xn
Risk Codes: 22-36/37/38
Safety: 26-36
PSA: 142.35000
LogP: 2.82510
Synthetic route

C13H10N2O5S

55981-09-4

nitazoxanide

Conditions
ConditionsYield
With nitronium tetrafluoborate; silver carbonate In N,N-dimethyl acetamide at 90℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;71%
121-66-4

2-amino-5-nitro-1,3-thiazole

5538-51-2

O-acetylsalicyloyl chloride

55981-09-4

nitazoxanide

55981-09-4

nitazoxanide

tizoxanide

Conditions
ConditionsYield
With hydrogenchloride at 50℃; for 24h;98%
With hydrogenchloride; sulfuric acid; water at 50℃;92%
With hydrogenchloride In water at 50℃; for 24h;
With hydrogenchloride; water at 100℃; for 24h;
With water; lithium hydroxide In tetrahydrofuran
55981-09-4

nitazoxanide

108-24-7

acetic anhydride

1221683-29-9

C14H13N3O4S

Conditions
ConditionsYield
Stage #1: nitazoxanide; acetic anhydride With hydrogen for 0.5h;
Stage #2: With hydrogenchloride; water In acetone for 2h;
86%
55981-09-4

nitazoxanide

14516-54-2

bromopentacarbonylmanganese(I)

fac-[MnBr(CO)3(nitazoxanide)2]

Conditions
ConditionsYield
In acetone for 0.25h; Inert atmosphere; Darkness; Reflux;68%
55981-09-4

nitazoxanide

C10H6N3O4S(1-)

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 20℃;
55981-09-4

nitazoxanide

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol for 2h; Kinetics; Reflux;
55981-09-4

nitazoxanide

950832-38-9

(2-hydroxybenzoyl)-N-(5-acetamidothiazol-2-yl)amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogen / 0.5 h
1.2: 2 h
2.1: ammonia; water / acetone / 20 °C
View Scheme
55981-09-4

nitazoxanide

Reaxys ID: 23229670

Reaxys ID: 23229670

55981-09-4

nitazoxanide

7585-39-9

β‐cyclodextrin

1491140-58-9

C42H70O35*C12H9N3O5S

Conditions
ConditionsYield
In aq. phosphate buffer pH=7.4;
Downstream Products
130234-70-7
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Chemistry

The Molecular Structure of Nitazoxanide (CAS NO.55981-09-4):

 
Empirical Formula: C12H9N3O5S
Molecular Weight: 307.282 
EINECS: 259-931-8
Nominal Mass: 307 Da
Average Mass: 307.282 Da
Monoisotopic Mass: 307.02629 Da 
Index of Refraction: 1.673
Molar Refractivity: 75.19 cm3
Molar Volume: 200.4 cm3
Surface Tension: 70.6 dyne/cm
Density: 1.532 g/cm3 
Appearance: Crystalline Solid
IUPAC Name:  [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate   
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
InChI
InChI=1/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)
Smiles
c1(c(cccc1)OC(C)=O)C(Nc1sc([N+]([O-])=O)cn1)=O 
Synonyms: BRN 1225475 ; PH 5776 ; UNII-SOA12P041N  
Nitazoxanide(also known by the brand names Alinia and Annita),it's melting point is about  202°C,it is a light yellow crystalline powder ,poorly soluble in ETHANOL and practically insoluble in water.

Uses

 Nitazoxanide (CAS NO.55981-09-4) is a first-line choice for the treatment of illness caused by Cryptosporidium parvum or Giardia lamblia infection in immunocompetent adults and children, and is an option to be considered in the treatment of illness caused by other protozoa and/or helminths. It is used for the treatment of infectious diarrhea caused by Cryptosporidium parvum [7] and Giardia lamblia in patients 1 year of age and older.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD oral > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
JAT, Journal of Applied Toxicology. Vol. 5, Pg. 49, 1985.
 
dog LD oral > 10gm/kg (10000mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" JAT, Journal of Applied Toxicology. Vol. 5, Pg. 49, 1985.
 
mouse LD50 oral 1350mg/kg (1350mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS
JAT, Journal of Applied Toxicology. Vol. 5, Pg. 49, 1985.
 
rat LD50 oral > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS
JAT, Journal of Applied Toxicology. Vol. 5, Pg. 49, 1985.
 

Safety Profile

Adverse effects of Nitazoxanide (CAS NO.55981-09-4):
Side effects are mostly gastrointestinal,  include abdominal pain, headache, vomiting, nausea and diarrhea.

Specification

 Nitazoxanide (CAS NO.55981-09-4) can also be called as Nitazoxanide [USAN:INN] ; (2-((5-Nitro-2-thiazolyl)carbamoyl)phenyl)acetat ; 2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl) benzamide ; Alinia ; Benzamide, 2-(acetyloxy)-N-(5-nitro-2-thiazolyl)- ; N-(5-Nitro-2-thiazolyl)salicylamide acetate (ester) ; N-(5-Nitrothiazol-2-yl)salicylamide acetate ester ; Nitazoxanida ; Nitazoxanida [INN-Spanish] ; Nitazoxanidum ; Nitazoxanidum [INN-Latin] ; Salicylamide, N-(5-nitro-2-thiazolyl)-, acetate (ester) ; o-(N-(5-Nitrothiazol-2-yl)carbamoyl)phenyl acetate .

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