DIMINAZENE DIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H15N7.2ClH
Molecular Weight	354.238
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.NC(=N)C1=CC=C(N\N=N\C2=CC=C(C=C2)C(N)=N)C=C1

InChI

InChIKey=QTFXIVUZEWTIAR-UHFFFAOYSA-N

InChI=1S/C14H15N7.2ClH/c15-13(16)9-1-5-11(6-2-9)19-21-20-12-7-3-10(4-8-12)14(17)18;;/h1-8H,(H3,15,16)(H3,17,18)(H,19,20);2*1H

HIDE SMILES / InChI

Molecular Formula	C14H15N7
Molecular Weight	281.3158
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7902657 | https://www.ceva-africa.com/en/Products/Product-list/VERIBEN-R | http://www.inchem.org/documents/jecfa/jecmono/v25je09.htm

Diminazene is an aromatic diamidine derived from Surfen C. Diminazene is used as aceturate salt. Diminazene is highly active against both Trypanosoma and Babesia spp. It is also of value in the treatment of theileriosis due to Theileria annulata. Diminazene has become the most commonly used therapeutic agent for trypanosomiasis in animals. It is said to be effective in canine, ovine and bovine babesiosis and, unlike some drugs, is less susceptible to relapse. It may also possess antibacterial properties. Diminazene binds to trypanosomal kDNA. This binding does not occur by intercalation but via specific interaction with sites rich in adenine-thymine (A-T) base pairs. Diminazene specifically inhibits mitochondrial type II topoisomerase in viable trypanosomes. Thus, inhibition of DNA replication may also occur via this interaction. Diminazene is extensively distributed in the body of treated animals. Residues of the compound may persist for several weeks, principally in the liver and kidneys, and also, to a lesser extent, in the gastrointestinal tract, lungs, muscle, brain and fat.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Kinetoplast DNA 4 Target ID: CHEMBL2366047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23144931	Binding Agent 1064		1.0 µM [Kd]
DNA topoisomerase 2 5 Target ID: P30190 Gene ID: NA Gene Symbol: TOP2 Target Organism: Trypanosoma cruzi Sources: https://www.ncbi.nlm.nih.gov/pubmed/2153980	Inhibitor 8297

PubMed

Title	Date	PubMed
Bioassay-guided studies on the cytotoxic and in vitro trypanocidal activities of a sesquiterpene (Muzigadial) derived from a Ugandan medicinal plant (Warburgia ugandensis).	2001 Aug	12789127
Inhibition of DNA replication by berenil of bacterial plasmids containing poly(dA)-poly(dT) sequences. 2D gel analysis of replicative intermediates.	2002	12643445
Lipid-drug-conjugate (LDC) nanoparticles as novel carrier system for the hydrophilic antitrypanosomal drug diminazenediaceturate.	2002 Aug	12442809
Electron paramagnetic resonance dynamic signatures of TAR RNA-small molecule complexes provide insight into RNA structure and recognition.	2002 Dec 17	12475232
Developments in the treatment of leishmaniasis and trypanosomiasis.	2002 May	15989536
Financial implications of rearing sheep and goats under natural trypanosomosis challenge at Galana ranch, Kenya.	2002 Nov	12537388
A competitive enzyme-linked immunosorbent assay for diminazene.	2002 Nov	12429424
The rare human fragile site 16B.	2003	14526167
Field studies of drug-resistant cattle trypanosomes in Kénédougou Province, Burkina Faso.	2003 Apr	12711108
Changes in adenosine transport associated with melaminophenyl arsenical (Mel CY) resistance in Trypanosoma evansi: down-regulation and affinity changes of the P2 transporter.	2003 Dec	14700190
The effect of inducing agents on the metabolism of trypanocidal diamidines by isolated rat hepatocytes.	2003 Dec 15	14642741
The pathogenicity of diminazene aceturate-resistant Trypanosoma brucei in rats after treatment with the drug.	2003 Feb-Apr	12634097
Chemotherapy of surra in horses and mules with diminazene aceturate.	2003 Jan 2	12482651
Clinical and neuroinflammatory responses to meningoencephalitis in substance P receptor knockout mice.	2003 Jul	12805119
Intra-uterine Infection with Babesia bovis in a 2-day-old Calf.	2003 Mar	12675895
The leucocytic and parasitaemic profiles and immune response of rats treated with retinyl palmitate before infection with Trypanosoma brucei.	2003 Nov	14554122
Mechanisms of arsenical and diamidine uptake and resistance in Trypanosoma brucei.	2003 Oct	14555482
The effects of diminazene aceturate on systemic blood pressure in clinically healthy adult dogs.	2003 Sep	15029949
Liquid chromatographic determination of diminazene diaceturate (Berenil) in raw bovine milk.	2003 Sep-Oct	14632393
Application of field methods to assess isometamidium resistance of trypanosomes in cattle in western Ethiopia.	2004 Apr	15177142
Bloodstream form-specific up-regulation of silent vsg expression sites and procyclin in Trypanosoma brucei after inhibition of DNA synthesis or DNA damage.	2004 Apr 2	14726511
Knowledge and attitudes of cattle owners regarding trypanosomosis control in tsetse-infested areas of Uganda.	2004 Dec	15830601
Transition models to assess risk factors for new and persistent trypanosome infections in cattle-analysis of longitudinal data from the Ghibe Valley, southwest Ethiopia.	2004 Dec	15715217
Characterization of a novel DNA minor-groove complex.	2004 Feb	14747338
A large-scale trial to evaluate the efficacy of a 1% pour-on formulation of cyfluthrin (Cylence, Bayer) in controlling bovine trypanosomosis in Eastern Zambia.	2004 Jan	14979556
The effects of diminazene aceturate and ceftriaxone on ram sperm.	2004 Jan 15	14662149
Trypanocidal drug resistance in eastern province of Zambia.	2004 Jan 30	14746972
Micronuclei induced by aneugens and clastogens in mononucleate and binucleate cells using the cytokinesis block assay.	2004 Jul	15215326
Gametocytogenesis: the puberty of Plasmodium falciparum.	2004 Jul 14	15253774
Effect of diminazene block treatment on live redwater vaccine reactions.	2004 Jun	15373333
RNA-interference silencing of the adenosine transporter-1 gene in Trypanosoma evansi confers resistance to diminazene aceturate.	2004 May-Jun	15208037
Efficacy of Trypan: a diminazene based drug as antileishmanial agent.	2004 Nov-Dec	15533297
Protective efficacy of isometamidium chloride and diminazene aceturate against natural Trypanosoma brucei, Trypanosoma congolense and Trypanosoma vivax infections in cattle under a suppressed tsetse population in Uganda.	2004 Sep	15580773
The susceptibility of Trypanosoma congolense isolated in Zambézia Province, Mozambique, to isometamidium chloride, diminazene aceturate and homidium chloride.	2005 Dec	16562737
Semicarbazide-functionalized Si(111) surfaces for the site-specific immobilization of peptides.	2005 Feb 15	15697299
Identification of anti-babesial activity for four ethnoveterinary plants in vitro.	2005 Jun 10	15893064
Susceptibility of West African Dwarf goats and WAD x Saanen crosses to experimental infection with Trypanosoma congolense.	2005 Jun 10	15893063
Synthesis of a novel PEG-block-poly(aspartic acid-stat-phenylalanine) copolymer shows potential for formation of a micellar drug carrier.	2005 Jun 13	15907607
Acquired resistance to berenil in a cloned isolate of Trypanosoma evansi is associated with upregulation of a novel gene, TeDR40.	2005 Nov	16255822
The pharmacokinetics of diminazene aceturate after intramuscular administration in healthy dogs.	2005 Sep	16300182
RNA aptamers as potential pharmaceuticals against infections with African trypanosomes.	2006	16594626
Drug-resistance of Trypanosoma b. rhodesiense isolates from Tanzania.	2006 Feb	16451338
Leishmania donovani: differential activities of classical topoisomerase inhibitors and antileishmanials against parasite and host cells at the level of DNA topoisomerase I and in cytotoxicity assays.	2006 Jan	16293247
Excitability scores of goats administered ascorbic acid and transported during hot-dry conditions.	2006 Jun	16645336
Chemotherapy against babesiosis.	2006 May 31	16504402
Confirmation of diminazene diaceturate in bovine plasma using electrospray liquid chromatography-mass spectrometry.	2006 Nov 21	16891161
Porcine eperythrozoonosis in China.	2006 Oct	17135527
Response of four indigenous cattle breeds to natural tsetse and trypanosomosis challenge in the Ghibe valley of Ethiopia.	2006 Oct 10	16797843
The effectivity analysis of accumulation of liposomal, micellar, and water-soluble forms of diminazene in cells and in organs.	2006 Sep-Oct	16877310
Trypanosomiasis by Trypanosoma vivax in cattle in the Brazilian semiarid: Description of an outbreak and lesions in the nervous system.	2007 Jan 31	16965857

Sample Use Guides

In Vivo Use Guide

The recommended dosage is 3.5 mg of diminazene aceturate per kg body weight in a single injection.

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Sat Dec 16 12:48:24 GMT 2023` Edited by `admin` on `Sat Dec 16 12:48:24 GMT 2023`
Record UNII	V40X8767D1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMINAZENE DIHYDROCHLORIDE

Common Name

English

BERENIL DIHYDROCHLORIDE

Common Name

English

NSC-357775

Code

English

BENZENECARBOXIMIDAMIDE, 4,4'-(1-TRIAZENE-1,3-DIYL)BIS-, DIHYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

PUBCHEM

147381