Benznidazole Property

Melting point:

189-192 °C (lit.)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: soluble50mg/mL, clear, colorless to yellow

form 

Solid

pka

14?+-.0.46(Predicted)

color 

White to Off-White

Water Solubility 

0.4g/L(temperature not stated)

Merck 

13,1085

BCS Class

3

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

NI3340000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

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.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

Benznidazole Chemical Properties,Usage,Production

Description

Benznidazole is the second of the drugs approved for treatment of Chagas' disease. Like nifurtimox, it is effective against the circulating form of Trypanosoma cruzi during the acute phase of the disease, but also like nifurtimox, it is ineffective during the chronic stage of the disease.

Description

Benznidazole is an orally bioavailable antiprotozoal agent. It is a 2-nitroimidazole prodrug that becomes active when the nitro group is reduced within the parasite. It inhibits the growth of the parasites T. cruzi, T. vaginalis, G. lamblia, and E. histolytica (IC₅₀s = 8.1, 18.62, 22.58, and 4.27 μM, respectively). It also inhibits clonogenic growth of human C33A cervical and KNS42 glioblastoma cancer cells under hypoxic, but not normoxic, conditions when used at a concentration of 100 μM. Benznidazole (100 mg/kg per day) decreases T. cruzi blood parasitemia to below detectable levels in a mouse model of chronic stable Chagas disease. Formulations containing benznidazole have been used in the treatment of Chagas disease caused by T. cruzi.

Uses

N-Benzyl-2-nitro-1H-imidazole-1-acetamide (Benznidazole) may be used as reference drug for the extraction of guaianolide from the aerial parts of Tanacetum parthenium and to evaluate its in vitro antiprotozoal activity.

Uses

Benznidazole (BNZ) is traditionally used to treat Chagas disease caused by Trypanosoma cruzi. The drugs used for the treatment of this disease, Nifurtimox and Benznidazole, are toxic and present sever e side effects.

Definition

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.

Antimicrobial activity

It exhibits antiprotozoal activity, particularly against Trypanosoma cruzi.

General Description

N-Benzyl-2-nitro-1H-imidazole-1-acetamide (Benznidazole) is a nitro-heterocyclic compound. It is widely employed drug for the treatment of Chagas disease. It exhibits three polymorphic forms..

Pharmaceutical Applications

A synthetic 2-nitroimidazole, formulated for oral administration. Solubility in water 400 mg/L.

Mechanism of action

Studies suggest that benznidazole does not catalyze the formation of ROS and, therefore, has a mechanism of action different from that of nifurtimox. It has been proposed that benznidazole undergoes an one-electron transfer to the nitro group, which in turn dismutates to give back the nitroimidazole and a nitrosoimidazole. The latter product may then undergo an electrophilic addition to trypanothione, which leads to depletion of trypanothione, an essential enzyme system in the Trypanosoma cruzi.

Pharmacokinetics

Oral bioavailability :High
Cmax 100 mg oral ：2.2–2.8 mg/L after 3–4 h
Plasma half-life：10.5–13.6 h
Volume of distribution：c. 0.56 L/kg
Plasma protein binding： c. 44%
The 2-nitro group undergoes reduction to the amine and hydrolysis to the hydroxy derivative.

Clinical Use

N-Benzyl-2-nitroimidazole-1-acetamide (Radanil, Rochagan)is a nitroimidazole derivative that is used for the treatment ofChagas disease. It is not available in the United States but isused extensively in South America. The effectiveness of benznidazoleis similar to that of nifurtimox. Therapy forAmerican trypanosomiasis with oral benznidazole requiresseveral weeks and is frequently accompanied by adverse effectssuch as peripheral neuropathy, bone marrow depression,and allergic-type reactions.

Clinical Use

Benznidazole is used in treatment of South American trypanosomiasis (Chagas disease).

Side effects

Adverse effects are more common in the elderly and include nausea, vomiting, abdominal pain, peripheral neuropathy and severe skin reactions.