| Identification | Back Directory | [Name]
Benznidazole | [CAS]
22994-85-0 | [Synonyms]
radanil
ro71051
Rochagan
Aids007909
NSC 299972
Ro 07-1051
Aids-007909
Benznidazol
Benzonidazol
benznidazole
benzonidazole
Benznidazol (Ro 07-1051
BenznidazoleBenznidazole
BENZNIDAZOLE (Ro 07-1051)
Benznidazol (Synonyms: Ro 07-1051
n-benzyl-2-nitro-1-imidazoleacetamide
n-benzyl-2-nitro-imidazole-1-acetamid
n-benzyl-2-nitroimidazole-1-acetamide
N-Benzyl-2-nitroiMidazol-1-yl-acetaMide
n-benzyl-2-(nitroimidazol-1-yl)-acetamid
N-BENZYL-2-NITRO-1 H-IMIDAZOLE-1-ACETAMIDE
N-Benzyl-2-nitro-1H-imidazole-1-acetamide 97%
2-nitro-n-(phenylmethyl)-1h-imidazole-1-acetamid
2-nitro-n-(phenylmethyl)-1h-imidazole-1-acetamide
1H-IMidazole-1-acetaMide, 2-nitro-N-(phenylMethyl)- | [EINECS(EC#)]
200-659-6 | [Molecular Formula]
C12H12N4O3 | [MDL Number]
MFCD00243089 | [MOL File]
22994-85-0.mol | [Molecular Weight]
260.25 |
| Chemical Properties | Back Directory | [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 | [InChI]
1S/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) | [InChIKey]
CULUWZNBISUWAS-UHFFFAOYSA-N | [SMILES]
[O-][N+](=O)c1nccn1CC(=O)NCc2ccccc2 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3
| [RTECS ]
NI3340000
| [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
Benznidazole is an orally bioavailable antiprotozoal agent.1 It is a 2-nitroimidazole prodrug that becomes active when the nitro group is reduced within the parasite.2 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).3,4 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.5 Benznidazole (100 mg/kg per day) decreases T. cruzi blood parasitemia to below detectable levels in a mouse model of chronic stable Chagas disease.1 Formulations containing benznidazole have been used in the treatment of Chagas disease caused by T. cruzi. | [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. | [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]
Benznidazole is used in treatment of South American trypanosomiasis (Chagas disease). | [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. | [Side effects]
Adverse effects are more common in the elderly and include nausea, vomiting, abdominal pain, peripheral neuropathy and severe skin reactions. | [Enzyme inhibitor]
This SSRI antidepressant (FW = 260.25 g/mol; CAS 22994-85-0;
Abbreviation: PXT), known by its trade name Aropax®, Paxil®, Pexeva®, Seroxat®, Sereupin® and Brisdelle® as well as its systematic name (3S,4R) -
3-[ (2H-1,3-benzodioxol-5-yloxy) methyl]-4- (4-fluorophenyl) piperidine, is a
selective serotonin reuptake inhibitor (IC50 = 33 μM) that is indicated for
the treatment of major depression, obsessive-compulsive disorder, panic
disorder, posttraumatic stress disorder, generalized anxiety disorder and
vasomotor symptoms, such as hot flashes and night sweats, that are
associated with menopause (1-4). Significantly, Antidepressant responses to
selective serotonin reuptake inhibitors (citalopram or paroxetine) are
abolished in mice unable to synthesize histamine due to either targeted
disruption of histidine decarboxylase gene (or HDC–/–) or injection of a-
fluoromethylhistidine, a suicide inhibitor of this enzyme. Such findings
demonstrate that SSRIs selectively require the integrity of the brain
histamine system to exert their preclinical responses. (See also
Citalopram; a-Fluoromethyl histidine) Pharmacokinetic Properties: Plasma
concentration and time-curves fit a two-compartment open model, with
the oral route giving a longer t1/2 (30 hours) than by the intravenous route
(12 hours). Deviations probably reflect saturated elimination kinetics during
first-pass metabolism. Co-administration of lipoic acid and PXT may
improve anxiolytic and antidepressant responses, suggesting that PXT
may deplete lipoic acid stores or that PXT interferes with some lipoic acid-
requiring metabolic pathway. Somewhat surprisingly, Paroxetine (20-40
μM) induces growth inhibition and apoptosis in prostate cancer cells in vitro
. Paroxetine is metabolized by CYP2D6 via demethylenation of the
methylenedioxy group, yielding a catechol metabolite and formic acid.
Paroxetine is also a potent inhibitor of cytochrome P450 2D6 (CYP2D6).
Time- dependent inhibition was demonstra–t1ed with an apparent Ki of 4.8
μM and an apparent kinact value of 0.17 min. Paroxetine has critical but
differential effects on IL-6 and TNFα production in macrophages and likely
regulates their formation by different mechanisms. Key
Pharmacokinetic Parameters: See Appendix II in Goodman & Gilman’s THE
PHARMACOLOGICAL BASIS OF THERAPEUTICS, 12th Edition (Brunton, Chabner
& Knollmann, eds.) McGraw-Hill Medical, New York. | [References]
[1] SHILPI KHARE. Antitrypanosomal Treatment with Benznidazole Is Superior to Posaconazole Regimens in Mouse Models of Chagas Disease.[J]. Antimicrobial Agents and Chemotherapy, 2015: 6385-6394. DOI: 10.1128/aac.00689-15
[2] ANDREA TROCHINE. Benznidazole biotransformation and multiple targets in Trypanosoma cruzi revealed by metabolomics.[J]. PLoS Neglected Tropical Diseases, 2014, 8 5: e2844. DOI: 10.1371/journal.pntd.0002844
[3] JULIANA COGO . Trypanocidal activity of guaianolide obtained from Tanacetum parthenium (L.) Schultz-Bip. and its combinational effect with benznidazole[J]. Phytomedicine, 2012, 20 1: Pages 59-66. DOI: 10.1016/j.phymed.2012.09.011
[4] EMANUEL HERNáNDEZ-Nú?EZ. Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents.[J]. Molecules, 2017. DOI: 10.3390/molecules22040579
[5] QUHUAN LI Z Y Q Lin. Hypoxia-activated cytotoxicity of benznidazole against clonogenic tumor cells[J]. Cancer Biology & Therapy, 2016, 17 1: 1266-1273. DOI: 10.1080/15384047.2016.1250988 |
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