DIMINAZENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H15N7
Molecular Weight	281.3158
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0
Stereo Comments	Assumed E-isomer (MM2 minimum energy for E and Z-isomers are 7.8031 and 19.4013 kcal/mol respectively)

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XNYZHCFCZNMTFY-UHFFFAOYSA-N

InChI=1S/C14H15N7/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)

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

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
Developments in the treatment of leishmaniasis and trypanosomiasis.	2002 May	15989536
Application of field methods to assess isometamidium resistance of trypanosomes in cattle in western Ethiopia.	2004 Apr	15177142
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
Micronuclei induced by aneugens and clastogens in mononucleate and binucleate cells using the cytokinesis block assay.	2004 Jul	15215326
DNA minor groove binders as potential antitumor and antimicrobial agents.	2004 Jul	15170593
Gametocytogenesis: the puberty of Plasmodium falciparum.	2004 Jul 14	15253774
Efficacy of combined atovaquone and azithromycin for therapy of chronic Babesia gibsoni (Asian genotype) infections in dogs.	2004 Jul-Aug	15320586
Effect of diminazene block treatment on live redwater vaccine reactions.	2004 Jun	15373333
Lipid-drug conjugate nanoparticles of the hydrophilic drug diminazene-cytotoxicity testing and mouse serum adsorption.	2004 May 18	15120899
RNA-interference silencing of the adenosine transporter-1 gene in Trypanosoma evansi confers resistance to diminazene aceturate.	2004 May-Jun	15208037
Analysis of GAA/TTC DNA triplexes using nuclear magnetic resonance and electrospray ionization mass spectrometry.	2004 Nov 15	15494127
Efficacy of Trypan: a diminazene based drug as antileishmanial agent.	2004 Nov-Dec	15533297
Degradation of berenil (diminazene aceturate) in acidic aqueous solution.	2004 Oct	15482649
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
Trypanocidal failure suggested by PCR results in cattle field samples.	2004 Sep	15301970
The susceptibility of Trypanosoma congolense isolated in Zambézia Province, Mozambique, to isometamidium chloride, diminazene aceturate and homidium chloride.	2005 Dec	16562737
Comparative application of wavelet approaches to absorption and ratio spectra for the simultaneous determination of diminazene aceturate and phenazone in veterinary granules for injection.	2005 Dec	16398263
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
Anti-babesial compounds from Curcuma zedoaria.	2005 May	15977324
Diminazene aceturate resistance on the virulence of Trypanosoma brucei for rats.	2005 Nov	16271938
Thermodynamic evaluation and modeling of proton and water exchange associated with benzamidine and berenil binding to beta-trypsin.	2005 Nov	16258627
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
Study on the susceptibility of Sahel goats to experimental Trypanosoma vivax infection.	2006 Apr 30	16497441
Quantitative analysis of DNA-porphyrin interactions.	2006 Apr 5	16358258
Stability analysis for double-stranded DNA oligomers and their noncovalent complexes with drugs by laser spray.	2006 Aug	16830356
In vitro growth inhibition of bloodstream forms of Trypanosoma brucei and Trypanosoma congolense by iron chelators.	2006 Aug 16	16914038
Equine trypanosomosis in the Central River Division of The Gambia: a study of veterinary gate-clinic consultation records.	2006 Aug 17	16814418
Fumagillin, a new P-glycoprotein-interfering agent able to modulate moxidectin efflux in rat hepatocytes.	2006 Dec	17083452
Androgens differentially potentiate mouse intestinal smooth muscle by nongenomic activation of polyamine synthesis and Rho kinase activation.	2006 Dec	16946014
Combined contribution of TbAT1 and TbMRPA to drug resistance in Trypanosoma brucei.	2006 Dec	16935360
Drug-resistance of Trypanosoma b. rhodesiense isolates from Tanzania.	2006 Feb	16451338
Complexes of poly(ethylene oxide)-block-poly(L-glutamate) and diminazene.	2006 Feb 28	16489824
A diminazene-resistant strain of Trypanosoma brucei brucei isolated from a dog is cross-resistant to pentamidine in experimentally infected albino rats.	2006 Jan	16393361
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
Epidemiology of Trypanosoma vivax infection in cattle in the tse-tse free area of Lake Chad.	2006 May 17	16321453
Chemotherapy against babesiosis.	2006 May 31	16504402
SSCP analysis of the P2 purine transporter TcoAT1 gene of Trypanosoma congolense leads to a simple PCR-RFLP test allowing the rapid identification of diminazene resistant stocks.	2006 Nov	17083909
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
The pathogenesis of anaemia in goats experimentally infected with Trypanosoma congolense or Trypanosoma brucei: use of the myeloid:erythroid ratio.	2007 Feb 28	16982150
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 16:15:18 GMT 2023` Edited by `admin` on `Sat Dec 16 16:15:18 GMT 2023`
Record UNII	Y5G36EEA5Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMINAZENE

Official Name

English

4-(2-(4-CARBAMIMIDOYLPHENYL)IMINOHYDRAZINYL)BENZENECARBOXIMIDAMIDE

Systematic Name

English

diminazene [INN]

Common Name

English

Diminazene [WHO-DD]

Common Name

English

4,4'-(DIAZOAMINO)BENZAMIDINE

Common Name

English

DIMINAZEN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277