22994-85-0

Basic information

• Product Name: N-BENZYL-2-NITRO-1 H-IMIDAZOLE-1-ACETAMIDE
• Synonyms: n-benzyl-2-(nitroimidazol-1-yl)-acetamid;n-benzyl-2-nitro-1-imidazoleacetamide;n-benzyl-2-nitro-imidazole-1-acetamid;n-benzyl-2-nitroimidazole-1-acetamide;radanil;ro71051;N-BENZYL-2-NITRO-1 H-IMIDAZOLE-1-ACETAMIDE;BenznidazoleBenznidazole
• CAS NO: 22994-85-0
• Molecular Formula: C₁₂H₁₂N₄O₃
• Molecular Weight: 260.25
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Imidazoles
• Mol File: 22994-85-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 189-192 °C(lit.)
• Appearance: /
• Density: 1.35 g/cm³
• Refractive Index: 1.643
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: methanol: soluble50mg/mL, clear, colorless to yellow
• PKA: 14?+-.0.46(Predicted)
• Water Solubility: 0.4g/L(temperature not stated)
• Merck: 13,1085
• CAS DataBase Reference: N-BENZYL-2-NITRO-1 H-IMIDAZOLE-1-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-2-NITRO-1 H-IMIDAZOLE-1-ACETAMIDE(22994-85-0)
• EPA Substance Registry System: N-BENZYL-2-NITRO-1 H-IMIDAZOLE-1-ACETAMIDE(22994-85-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NI3340000
• Hazardous Substances Data: 22994-85-0(Hazardous Substances Data)

Usage

Description

N-Benzyl-2-nitro-1H-imidazole-1-acetamide, commonly known as Benznidazole, is a nitro-heterocyclic compound that is widely used in the treatment of Chagas disease. It is an orally bioavailable antiprotozoal agent and exhibits three polymorphic forms. Benznidazole is effective against the circulating form of Trypanosoma cruzi during the acute phase of the disease but is ineffective during the chronic stage. It is also known to inhibit the growth of various parasites and cancer cells under specific conditions.

Uses

1. Used in Chagas Disease Treatment:
Benznidazole is used as an antiprotozoal agent for the treatment of Chagas disease caused by Trypanosoma cruzi. It is effective during the acute phase of the disease and helps decrease T. cruzi blood parasitemia to below detectable levels in a mouse model of chronic stable Chagas disease.
2. Used in Extraction and Evaluation of Guaianolide:
Benznidazole may be used as a reference drug for the extraction of guaianolide from the aerial parts of Tanacetum parthenium and to evaluate its in vitro antiprotozoal activity.
3. Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, Benznidazole has been shown to inhibit clonogenic growth of human C33A cervical and KNS42 glioblastoma cancer cells under hypoxic conditions. This suggests potential applications in the field of cancer research and treatment.
4. Used in Drug Delivery Systems:
While not directly mentioned in the materials, the use of Benznidazole in drug delivery systems could be explored to improve its bioavailability, delivery, and therapeutic outcomes, similar to the approach taken with gallotannin.

Antimicrobial activity

It exhibits antiprotozoal activity, particularly against Trypanosoma cruzi.

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 :HighCmax 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.

InChI:InChI=1/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)

Synthetic route

benznidazole (22994-85-0) → N-benzyl-(2'-amino-4',5'-dihydro-4',5'-dihydroxy-1'-imidazoyl) acetamide (124762-95-4, 124762-96-5)

Conditions	Yield
With phosphate buffer; sodium chloride Mechanism; electrochemical reduction, pH=6.5-7.5;
With phosphate buffer; sodium chloride electrochemical reduction pH 6.5-7.5;

Relevant articles and documents

Chemical compounds having ion channel blocking activity for the treatment of immune dysfunction

The present invention relates to chemical compounds having inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca), and the use of such compounds for the treatment or alleviation of diseases or conditions relating to immune dysfunction. Moreover, the invention relates to a method of screening a chemical compound for inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca).