Nitazoxanide

Structural formula
General
Surname	Nitazoxanide
other names	2- (Acetyloxy) - N - (5-nitrothiazol-2-yl) benzamide; Alinia® (preparation);
Molecular formula	C 12 H 9 N 3 O 5 S
External identifiers / databases
EC number	259-931-8
ECHA InfoCard	100.054.465
PubChem	41684
DrugBank	DB00507
Wikidata	Q2943789
Drug information
ATC code	P01 AX11
properties
Molar mass	307.28 g · mol -1
Physical state	firmly
Melting point	202 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 251-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitazoxanide is a drug from the class of anti-parasitic drugs . It is a synthetic 5-nitrothiazolyl salicylamide derivative used to treat parasitic infestation . In the body, it is quickly converted to its active metabolite, tizoxanide , by splitting off the acetyl group .

Nitazoxanide is not approved in Germany.

effect

The effect is based on the non-competitive inhibition of pyruvate ferredoxin oxidoreductase (PFOR), which catalyzes the oxidative decarboxylation of pyruvate to acetate . The electron transfer in the redox system and thus the energy metabolism of the pathogens is interrupted.

pharmacology

When given orally, fatty foods potentiate the effectiveness. Nitazoxanide is hydrolyzed gastrointestinally to tizoxanide with almost complete protein binding . The maximum tizoxanide plasma level is reached after 1–4 hours. Excretion takes place via bile and deconjugation in the feces, as well as glucuronide and unchanged tizoxanide via the kidneys and urine.

application areas

Treatment of infestations with:

Giardia intestinalis
Cryptosporidia .

Therapeutic effectiveness in infestation with:

Nitazoxanide shows antibacterial activity in:

Antiviral activity in:

chronic hepatitis C / hepatitis B
Rotavirus , norovirus

Contraindications

A risk-benefit assessment of possible reproductive toxicity is necessary.

Side effects

Possible side effects include:

nausea
Vomit
stomach pain
diarrhea
Hives
itching

Therapy control

During therapy with nitazoxanide, infestation control by detecting cysts in the stool is indicated.

Web links

Entry on nitazoxanide in Flexikon , a Wiki of the DocCheck company

Individual evidence

↑ ^a ^b ^c ^d Entry on nitazoxanide. In: Römpp Online . Georg Thieme Verlag, accessed on August 15, 2016.
↑ ^a ^b Data sheet Nitazoxanide from Sigma-Aldrich , accessed on August 16, 2016 ( PDF ).
↑ Martin Schlitzer, Regina Ortmann, Imke Form: Active ingredients against worm and protozoal diseases and the antiviral agent ribavirin. Medicinal chemistry of some “exotic species” . In: Pharmacy in our time . tape 39 , no. 1 , January 2010, p. 18–26 , doi : 10.1002 / pauz.201000348 .
↑ Thomas Löscher: Tropical medicine in clinic and practice: with travel and migration medicine . Georg Thieme Verlag, Stuttgart 2010, ISBN 978-3-13-785804-1 , p. 1049 ( limited preview in Google Book search).

[Römpp-1] Entry on nitazoxanide. In: Römpp Online . Georg Thieme Verlag, accessed on August 15, 2016.

[Sigma-2] Data sheet Nitazoxanide from Sigma-Aldrich , accessed on August 16, 2016 ( PDF ).

[3] Martin Schlitzer, Regina Ortmann, Imke Form: Active ingredients against worm and protozoal diseases and the antiviral agent ribavirin. Medicinal chemistry of some “exotic species” . In: Pharmacy in our time . tape 39 , no. 1 , January 2010, p. 18–26 , doi : 10.1002 / pauz.201000348 .

[4] Thomas Löscher: Tropical medicine in clinic and practice: with travel and migration medicine . Georg Thieme Verlag, Stuttgart 2010, ISBN 978-3-13-785804-1 , p. 1049 ( limited preview in Google Book search).