Benznidazole

Names

[ Name ]:
Benznidazole

[Synonym ]:
MFCD00243089
N-benzyl-2-(2-nitroimidazol-1-yl)acetamide
1H-Imidazole-1-acetamide,2-nitro-N-(phenylmethyl)-

Biological Activity

[Description]:

Benznidazol (Ro 07-1051) is an antiparasitic medication, with an IC50 of 20.35 μM for Colombian T. cruzi strains, and has been used in the treatment of Chagas disease[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[In Vivo]

Benznidazole (100 mg/kg/day, p.o., 30 days) produces a decrease in electrocardiographic alterations, fewer modifications in the affinity and density of cardiac-receptors, and few isolated areas of fibrosis in the heart, in mice infected with Trypanosoma cruzi Tulahuen strain or SGO-Z12 isolate and treated at 180 days post infection (p.i.) (i.e. chronic phase) with Benznidazole[1]. Animal Model: Mice infected with Trypanosoma cruzi Tulahuen strain or SGO-Z12[1] Dosage: 100 mg/kg/day Administration: Orally for 30 days Result: Produced a decrease in electrocardiographic alterations, fewer modifications in the affinity and density of cardiac-receptors, and few isolated areas of fibrosis in the heart.

[References]

[1]. Bustamante JM, et al. Treatment with benznidazole or thioridazine in the chronic phase of experimental Chagas disease improves cardiopathy. Int J Antimicrob Agents. 2007 Jun;29(6):733-7.

[2]. Luna KP, et al. In vitro susceptibility of Trypanosoma cruzi strains from Santander, Colombia, to hexadecylphosphocholine (miltefosine), nifurtimox and benznidazole. Biomedica. 2009 Sep;29(3):448-55.

Chemical & Physical Properties

[ Density]:
1.35g/cm3

[ Melting Point ]:
189-192ºC(lit.)

[ Molecular Formula ]:
C₁₂H₁₂N₄O₃

[ Molecular Weight ]:
260.24900

[ Exact Mass ]:
260.09100

[ PSA ]:
92.74000

[ LogP ]:
2.02180

[ Index of Refraction ]:
1.643

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI3340000

CHEMICAL NAME :: Imidazole-1-acetamide, N-benzyl-2-nitro-

CAS REGISTRY NUMBER :: 22994-85-0

BEILSTEIN REFERENCE NO. :: 0551486

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C12-H12-N4-O3

MOLECULAR WEIGHT :: 260.28

WISWESSER LINE NOTATION :: T5N CNJ A1VM1R& BNW

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 8 gm/kg

SEX/DURATION :: male 8 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 50 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 320,305,1994

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
NI3340000

[ HS Code ]:
2933290090

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Targeting the substrate preference of a type I nitroreductase to develop antitrypanosomal quinone-based prodrugs.

Antimicrob. Agents Chemother. 56(11) , 5821-30, (2012)

Nitroheterocyclic prodrugs are used to treat infections caused by Trypanosoma cruzi and Trypanosoma brucei. A key component in selectivity involves a specific activation step mediated by a protein hom...

Microsatellite and mini-exon analysis of Mexican human DTU I Trypanosoma cruzi strains and their susceptibility to nifurtimox and benznidazole.

Vector Borne Zoonotic Dis. 13(3) , 181-7, (2013)

Chagas disease is caused by the protozoan parasite Trypanosoma cruzi, and it affects as many as 10 million people in North and South America, where it represents a major public health problem. T. cruz...

Immunosuppression and Chagas disease: a management challenge.

PLoS Negl. Trop. Dis. 7(1) , e1965, (2013)

Immunosuppression, which has become an increasingly relevant clinical condition in the last 50 years, modifies the natural history of Trypanosoma cruzi infection in most patients with Chagas disease. ...