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tribendimidine

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tribendimidine Basic information

Product Name:
tribendimidine
Synonyms:
  • tribendimidine
  • Ethanimidamide, N',N'''-[1,4-phenylenebis(methylidynenitrilo-4,1-phenylene)]bis[N,N-dimethyl-
  • N'-[4-[[4-[[4-[1-(dimethylamino)ethylideneamino]phenyl]iminomethyl]phenyl]methylideneamino]phenyl]-N,N-dimethylethanimidamide
  • N',N'''-(((1,4-Phenylenebis(methaneylylidene))bis(azaneylylidene))bis(4,1-phenylene))bis(N,N-dimethylacetimidamide)
  • N'-(4-{[(4-{[(4-{[1-(dimethylamino)ethylidene]amino}phenyl)imino]methyl}phenyl)methylidene]amino}phenyl)-N,N-dimethylethanimidamide
  • Tribendimidine, 10 mM in DMSO
  • N',N'''-(((1,4-Phenylenebis(methaneylylidene))bis(azaneylylidene))bis(4,1-phenylene))bis(N,N-dimethylacetimidamide)
CAS:
115103-15-6
MF:
C28H32N6
MW:
452.59
EINECS:
620-470-6
Mol File:
115103-15-6.mol
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tribendimidine Chemical Properties

Boiling point:
618.2±65.0 °C(Predicted)
Density 
1.04±0.1 g/cm3(Predicted)
form 
Solid
pka
12.31±0.15(Predicted)
color 
Light yellow to yellow
InChI
InChI=1S/C28H32N6/c1-21(33(3)4)31-27-15-11-25(12-16-27)29-19-23-7-9-24(10-8-23)20-30-26-13-17-28(18-14-26)32-22(2)34(5)6/h7-20H,1-6H3
InChIKey
XOIOGKHKNQYULW-UHFFFAOYSA-N
SMILES
C1(C=NC2=CC=C(N=C(N(C)C)C)C=C2)=CC=C(C=NC2=CC=C(N=C(N(C)C)C)C=C2)C=C1
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tribendimidine Usage And Synthesis

Uses

Tribendimidine is an orally active, broad-spectrum anthelmintic agent, with particularly high activity against A. lumbricoides and N. americanus. Tribendimidine is also an L-type nicotinic acetylcholine receptor (nAChR) agonist[1][2][3].

in vivo

Tribendimidine (75 and 150 mg/kg; p.o.; once) shows inhibition activity against C. sinensis in rats, and shows inhibition against O. viverrini at 400 mg/kg in hamsters[2].

Animal Model:C. sinensis infected Female Wistar rats[2]
Dosage:75 mg/kg and 150 mg/kg
Administration:Oral administration, once
Result:A 99.1% worm burden reduction was achieved at 150 mg/kg, and the worm burden reduction was still significant (68.9%) at 75 mg/kg.

References

[1] Xiao SH, et al. Tribendimidine: a promising, safe and broad-spectrum anthelmintic agent from China. Acta Trop. 2005 Apr;94(1):1-14. DOI:10.1016/j.actatropica.2005.01.013
[2] Keiser J, et al. Evaluation of the in vivo activity of tribendimidine against Schistosoma mansoni, Fasciola hepatica, Clonorchis sinensis, and Opisthorchis viverrini. Antimicrob Agents Chemother. 2007 Mar;51(3):1096-8. DOI:10.1128/AAC.01366-06
[3] Hu Y, et al. The new anthelmintic tribendimidine is an L-type (levamisole and pyrantel) nicotinic acetylcholine receptor agonist. PLoS Negl Trop Dis. 2009 Aug 11;3(8):e499. DOI:10.1371/journal.pntd.0000499

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