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Chemical Structure| 22994-85-0 Chemical Structure| 22994-85-0

Structure of Benznidazole
CAS No.: 22994-85-0

Chemical Structure| 22994-85-0

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Benznidazole is an antiparasitic medication used in the treatment of Chagas disease.

Synonyms: Ro 71051; Ro 07-1051; Rochagan.

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Product Citations

Carla B. Hartman ; Phelelisiwe S. Dube ; Lesetja J. Legoabe ; Natascha Van Pelt ; An Matheeussen ; Guy Caljon , et al.

Abstract: Several quinoline derivatives incorporating arylnitro and aminochalcone moieties were synthesized and evaluated in vitro against a broad panel of trypanosomatid protozoan parasites responsible for sleeping sickness (Trypanosoma brucei rhodesiense), nagana (Trypanosoma brucei brucei), Chagas disease (Trypanosoma cruzi), and leishmaniasis (Leishmania infantum). Several of the compounds demonstrated significant antiprotozoal activity. Specifically, compounds 2c, 2d, and 4i displayed submicromolar activity against T. b. rhodesiense with half-maximal effective concentration (EC50) values of 0.68, 0.8, and 0.19 µM, respectively, and with a high selectivity relative to human lung fibroblasts and mouse primary macrophages (∼100-fold). Compounds 2d and 4i also showed considerable activity against T. b. brucei with EC50 values of 1.4 and 0.4 µM, respectively.

Keywords: anti‐infectives ; arylnitro ; chalcones ; protozoal ; quinoline

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Product Details of Benznidazole

CAS No. :22994-85-0
Formula : C12H12N4O3
M.W : 260.25
SMILES Code : O=C(NCC1=CC=CC=C1)CN2C=CN=C2[N+]([O-])=O
Synonyms :
Ro 71051; Ro 07-1051; Rochagan.
MDL No. :MFCD00243089
InChI Key :CULUWZNBISUWAS-UHFFFAOYSA-N
Pubchem ID :31593

Safety of Benznidazole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Vero cells 2000-50 μM 48 h To determine the cytotoxicity of Benznidazole PMC8480776
RAW 264.7 macrophages 15 µM 30 min To study the effect of Bzl on macrophage polarization, results showed Bzl inhibits M1 markers (NOx, IL-6, TNF-α, IL-17A) and increases M2 markers (Arginase I, MR, TGF-β, VEGF-A, PPAR-γ, PPAR-α). PMC8675942
neonatal mouse primary cardiomyocytes 15 µM 30 min To study the anti-inflammatory effect of Bzl on LPS-stimulated cardiomyocytes, results showed Bzl inhibits NF-κB pathway by increasing SOCS3 expression and reduces NOx release. PMC8675942
cardiomyocytes 15 µM 30 min To study the anti-inflammatory mechanisms of Benznidazole, it was found to inhibit the NF-κB pathway via the IL-10/STAT3/SOCS3 axis, reducing the expression of inflammatory mediators. PMC6558013
Bloodstream trypomastigotes (BT) 8.82 µM 24 h Assess the direct trypanocidal effect of Benznidazole on bloodstream trypomastigotes, demonstrating significant activity of Bz MT. PMC9452897
Heart cells (HCs) 5.4 µM 72 h Evaluate the trypanocidal effect of Benznidazole on intracellular T. cruzi, showing that Bz MT partially restored the cytoskeleton structure of infected cells after 72 h of treatment. PMC9452897
Vero-C76 cells 0.51 µM 5 days Evaluate the in vitro activity of Benznidazole against Trypanosoma cruzi, showing inhibitory effects on intracellular amastigotes. PMC9294734
LN-18 glioma cells 100 μM 24 h To evaluate the inhibitory effect of Benznidazole on clonogenic potential under hypoxic conditions. Results showed that Benznidazole significantly inhibited the clonogenic potential of LN-18 cells under severe hypoxia (approximately 0% O2). PMC5199162
KNS42 glioma cells 100 μM 24 h To evaluate the inhibitory effect of Benznidazole on clonogenic potential under hypoxic conditions. Results showed that Benznidazole significantly inhibited the clonogenic potential of KNS42 cells under severe hypoxia (approximately 0% O2). PMC5199162
C33A cervical cancer cells 100 μM 24 h To evaluate the inhibitory effect of Benznidazole on clonogenic potential under hypoxic conditions. Results showed that Benznidazole significantly inhibited the clonogenic potential of C33A cells under severe hypoxia (approximately 0% O2). PMC5199162
HCT116 colon cancer cells 100 μM 24 h To evaluate the inhibitory effect of Benznidazole on clonogenic potential under hypoxic conditions. Results showed that Benznidazole significantly inhibited the clonogenic potential of HCT116 cells under severe hypoxia (approximately 0% O2). PMC5199162
MDA-MB-231 breast cancer cells 500 μM 24 h To evaluate the inhibitory effect of Benznidazole on clonogenic potential under hypoxic conditions. Results showed that Benznidazole significantly inhibited the clonogenic potential of MDA-MB-231 cells under severe hypoxia (approximately 0% O2). PMC5199162
SK-N-ER neuroblastoma cells 500 μM 24 h To evaluate the inhibitory effect of Benznidazole on clonogenic potential under hypoxic conditions. Results showed that Benznidazole significantly inhibited the clonogenic potential of SK-N-ER cells under severe hypoxia (approximately 0% O2). PMC5199162
T. cruzi Y strain bloodstream trypomastigotes ≤8 μM 24 h Evaluate the activity of Benznidazole against T. cruzi Y strain bloodstream trypomastigotes, all quinolines except DB2171 and DB2192 were more effective than Bz PMC5786769
L929 cells 0.1 to 2.05 μM 96 h Evaluate the activity of Benznidazole against T. cruzi Tulahuen strain, all quinolines were more potent than Bz PMC5786769
Trypanosoma cruzi bloodstream trypomastigotes 50-0.1 μM 24 h To evaluate the trypanocidal activity of Benznidazole against T. cruzi bloodstream trypomastigotes PMC8480776
Trypanosoma cruzi amastigotes 50-0.1 μM 72 h To evaluate the trypanocidal activity of Benznidazole against T. cruzi amastigotes PMC8480776
Trypanosoma cruzi epimastigotes 50-0.5 μM 48 h To evaluate the trypanocidal activity of Benznidazole against T. cruzi epimastigotes PMC8480776

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice Acute Chagas disease model 200 mg/Kg To evaluate the inhibitory effect of Benznidazole on inflammatory responses in vivo, it was found to reduce parasite load and inflammatory reaction in heart tissue. PMC6558013
BALB/cJ mice Acute Trypanosoma cruzi infection model Oral 100 mg/kg Once daily for 20 days Evaluate the in vivo efficacy of Benznidazole alone or in combination with Miltefosine against Trypanosoma cruzi infection, showing significant reduction in parasitemia and mortality. PMC9294734
Mice Chronic Chagas cardiomyopathy model Gavage 25 mg/kg Daily administration for 30 days To evaluate the therapeutic effects of Benznidazole in a mouse model of chronic Chagas cardiomyopathy. Results showed that Bz treatment partially reversed ECG abnormalities and controlled parasite load. PMC8351877
BALB/c mice T. cruzi Arequipa strain infection model Intraperitoneal injection 20 mg/kg Once daily for 5 consecutive days To evaluate the therapeutic effect of Benznidazole in acute and chronic Chagas disease PMC8480776
Mice Acute infection model with T. cruzi Ninoa strain Intragastric administration 100 mg/kg body weight Single dose, monitored for 8 hours Evaluation of Gliquidone monotherapy on clearance of T. cruzi infection in mice, reducing infection by 40-60% PMC11768481

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02625974 Chagas Disease Phase 3 Active, not recruiting August 9, 2021 Argentina ... More >> La Plata, Buenos Aires, Argentina, 1900 Buenos Aires, Ciudad Auton. De Buenos Aires, Argentina, 1281 Buenos Aires, Ciudad Auton. De Buenos Aires, Argentina, C1270AAN Buenos Aires, Ciudad Auton. De Buenos Aires, Argentina, C1425AGP Buenos Aires, Ciudad Auton. De Buenos Aires, Argentina, C1425EFD San Salvador de Jujuy, Jujuy, Argentina, 4600 Posadas, Misiones, Argentina Rosario, Santa Fe, Argentina, 2000 Corrientes, Argentina, W3400CBI Formosa, Argentina, P3600HZL La Rioja, Argentina Mendoza, Argentina, 5500 Mendoza, Argentina, 5535 Salta, Argentina, 4400 Salta, Argentina, A4400ESE San Juan, Argentina, 5400 Santiago del Estero, Argentina, 4202 Tucuman, Argentina, 4000 Bolivia Cochabamba, Bolivia Punata, Bolivia Tarija, Bolivia Colombia Barranquilla, Atlántico, Colombia Yopal, Casanare, Colombia, 0 Santa Marta, Magdalena, Colombia, 0 Floridablanca, Santander, Colombia Less <<
NCT01377480 Chagas Disease Phase 2 Completed - -
NCT01377480 - Completed - -
NCT01755377 Chagas Disease COMPLETED 2025-06-16 International Health Departmen... More >>t, Hospital Clinic, Barcelona, Barcelona, Catalu?a, 08036, Spain Less <<
NCT02369978 Chagas Disease Phase 2 Phase 3 Recruiting February 2019 Colombia ... More >> Fundación Oftalmológica de Santander - Clínica Ardila Lulle (FOSCAL) Recruiting Bucaramanga, Santander, Colombia Contact: Gustavo A Parra, MD       guparra@unab.edu.co    Contact: Skarlet M Vásquez, RN, MSc       svasquez196@unab.edu.co Less <<
NCT01489228 Chronic Chagas Disease, Indete... More >>rminate Less << Phase 2 Unknown December 2013 Bolivia ... More >> Plataforma de Atención Integral a los Pacientes con Enfermidad de Chagas Recruiting Cochabamba, Bolivia Contact: Faustino Torrico, PhD          Contact: Cristina Alonso, MD          Principal Investigator: Faustino Torrico, PhD          Plataforma de Atención Integral a los Pacientes con Enfermidad de Chagas Recruiting Tarija, Bolivia Contact: Lourdes Ortiz, MSc          Sub-Investigator: Lourdes Ortiz, MSc Less <<
NCT01678599 Chagas Disease PHASE4 COMPLETED 2025-04-13 Medicin Sans Frontièrs (MSF), ... More >>Aiquile, Bolivia Less <<
NCT01162967 Chagas Disease Phase 2 Completed - Spain ... More >> International Health Unit Metropolitana Nord Santa Coloma, Barcelona, Spain Infectious Disease Department Vall d'Hebron Hospital Barcelona, Spain International Health Unit Drassanes Barcelona, Spain Less <<
NCT03378661 Chagas Disease Phase 2 Active, not recruiting July 27, 2018 Bolivia ... More >> Plataforma de Atención Integral de Pacientes con Enfermedad de Chagas. Sucre, Chuquisaca, Bolivia Plataforma de Atención Integral de Pacientes con Enfermedad de Chagas. Cochabamba, Bolivia Plataforma de Atención Integral de Pacientes con Enfermedad de Chagas. Tarija, Bolivia Less <<
NCT01549236 Chagas' Disease Phase 4 Completed - Argentina ... More >> Hospital General de Niños Ricardo Gutierrez Buenos Aires, Argentina, C1425 Hospital de Niños "Doctor Héctor Quintana" Jujuy, Argentina, CP4600 Hospital Público Materno Infantil Salta, Argentina, CP3400 Less <<
NCT00123916 Chagas Disease ... More >> Trypanosomiasis Heart Disease Less << Phase 3 Unknown July 2013 -
NCT01755403 Chagas Disease PHASE4 COMPLETED 2025-11-13 International Health Departmen... More >>t, Hospital Clinic, Barcelona, Barcelona, Catalu?a, 08036, Spain Less <<
NCT03672487 Chagas Disease Phase 3 Not yet recruiting May 31, 2023 United States, California ... More >> University of California at San Diego Not yet recruiting San Diego, California, United States, 92093 Contact: Edmund Capparelli, PharmD    858-246-0009    ecapparelli@ucsd.edu    Principal Investigator: Edmund Capparelli, PharmD          Sub-Investigator: Jeremiah Momper, PhD          United States, Louisiana Tulane School of Public Health and Tropical Medicine Not yet recruiting New Orleans, Louisiana, United States, 70112 Contact: Pierre Buekens, MD, PhD    504-988-8803    pbuekens@tulane.edu    Principal Investigator: Pierre Buekens, MD, PhD          Sub-Investigator: Eric Dumonteil, PhD          Sub-Investigator: Claudia Herrera, PhD          Sub-Investigator: Jeffrey Shaffer, PhD          Argentina Institute for Clinical Effectiveness and Health Policy Not yet recruiting Buenos Aires, Argentina Contact: Fernando Althabe, MD, MSc       falthabe@gmail.com    Principal Investigator: Fernando Althabe, MD, MSc          Sub-Investigator: Maria Luisa Cafferata, MD          Sub-Investigator: Eduardo Bergel, MSc, PhD          Sub-Investigator: Mabel Berrueta, MD          Sub-Investigator: Jose Belizan, MD, PhD          Sub-Investigator: Sergio Sosa-Estani, MD, PhD          Sub-Investigator: Alejandro Schijman, DSc Less <<
NCT01547533 - Completed - Argentina ... More >> Parasitology and Chagas Service, Buenos Aires Children´s Hospital Ricardo Gutierrez Buenos Aires, Argentina, 1425 Less <<
NCT03739541 Healthy Male Subjects Phase 1 Completed - United Kingdom ... More >> Covance Leeds, United Kingdom, LS2 9LH Less <<
NCT03191162 Chagas Disease|Trypanosoma Cru... More >>zi Infection Less << PHASE2 COMPLETED 2021-03-16 Instituto Nacional de Parasito... More >>logía Dr. Mario Fatala Chaben (ANLIS), Buenos Aires, Argentina|Instituto de Cardiología de Corrientes Juana Francisca Cabral, Corrientes, Argentina|Centro de Pesquisas René Rachou - Funda??o Oswaldo Cruz. (FIOCRUZ), Belo Horizonte, Brazil|Hospital Universitário Clemente de Faria, Montes Claros, Brazil|Fundación Cardioinfantil - Instituto de Cardiología, Bogotá, Colombia|Centro Atencion y Diagnóstico de Enfermedades Infecciosas, Bucaramanga, Colombia|Infectious Disease Department Vall d'Hebron Hospital, Barcelona, Spain Less <<
NCT00699387 Chagas Disease COMPLETED 2025-05-11 Parasitology Division, Childre... More >>n's Hospital "R Gutierrez" of Buenos Aires, Buenos Aires, 1425, Argentina Less <<
NCT02386358 Chagas Disease Phase 3 Completed - Argentina ... More >> Instituto Nacional de Parasitología Dr Mario Fatala Chaben Ciudad Autónoma de Buenos Aires, Buenos Aires, Argentina, 1063 Less <<
NCT04024163 Chagas Disease PHASE3 ACTIVE_NOT_RECRUITING 2028-03-30 Hospital de Ninos "Dr. Ricardo... More >> Gutierrez", Ciudad Autónoma de Buenos Aires, Argentina|Hospital "Luis Carlos Lagomaggiore", Mendoza, Argentina|Hospital Pediatrico "Dr. Humberto Notti", Mendoza, Argentina|Hospital Público Descentralizado Dr. Guillermo Rawson, San Juan, Argentina|Centro de Enfermedad de Chagas y Patologías Regionales, Santiago Del Estero, Argentina|Antigua Hospital Viedma, Cochabamba, Bolivia|CEADES - Plataforma de Chagas Sucre, Sucre, Bolivia|Fundación Salud para el Trópico, Santa Marta, Colombia|Centro de Atención e Investigación Médica (CAIMED), Yopal, Colombia Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.84mL

0.77mL

0.38mL

19.21mL

3.84mL

1.92mL

38.42mL

7.68mL

3.84mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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