Tribendimidine A broad spectrum, orally bioactive anthelmintic with particularly high activity against A. lumbricoides and N. americanus. Tribendimidine is also an L-type nicotinic acetylcholine receptor (nAChR) agonist.

Physicochemical Properties

Molecular Formula	C28H32N6
Molecular Weight	452.59388
Exact Mass	452.269
Elemental Analysis	C, 74.30; H, 7.13; N, 18.57
CAS #	115103-15-6
PubChem CID	3086564
Appearance	Light yellow to yellow solid powder
Density	1.04g/cm3
Boiling Point	618.2ºC at 760mmHg
Flash Point	327.7ºC
Vapour Pressure	3.26E-15mmHg at 25°C
Index of Refraction	1.575
LogP	6.41
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	8
Heavy Atom Count	34
Complexity	651
Defined Atom Stereocenter Count	0
SMILES	CN(/C(=N/C1C=CC(/N=C/C2C=CC(/C=N/C3C=CC(/N=C(/N(C)C)\C)=CC=3)=CC=2)=CC=1)/C)C
InChi Key	XOIOGKHKNQYULW-UHFFFAOYSA-N
InChi Code	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
Chemical Name	N'-[4-[[4-[[4-[1-(dimethylamino)ethylideneamino]phenyl]iminomethyl]phenyl]methylideneamino]phenyl]-N,N-dimethylethanimidamide
Synonyms	Tribendimidine
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	C exhibits intoxication with 100 μg/mL of trimethidine for a 24-hour period. elegans [3]. With an LC50 value of 54.4 μg/mL, which indicates the concentration at which half of the animals die, triphenyldiamidine (0-100 μg/mL; 6 days) exhibits toxicity [3]. Levoamisole-resistant mutants are resistant to tribendimidine, while trb mutant hermaphrodites are resistant to infertility produced by tribendimidine (0-200 μg/mL; 64 h). [3].
ln Vivo	Tribendimidine (75 and 150 mg/kg; oral; one time) has demonstrated C-inhibitory action. sinensis against O and in rats. 400 mg/kg of viverrini in hamsters [2].
Animal Protocol	Animal/Disease Models: C. sinensis infected female Wistar rats [2] Doses: 75 mg/kg and 150 mg/kg Route of Administration: Orally once. Experimental Results: 99.1% reduction in worm load at 150 mg/kg and 99.1% reduction in worm load at 75 mg /kg dose, the reduction remained significant (68.9%).
References	[1]. Tribendimidine: a promising, safe and broad-spectrum anthelmintic agent from China. Acta Trop. 2005 Apr;94(1):1-14. [2]. 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. [3]. 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.

Solubility Data

Solubility (In Vitro)

DMSO : ~50 mg/mL (~110.48 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.52 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.2095 mL	11.0475 mL	22.0951 mL
	5 mM	0.4419 mL	2.2095 mL	4.4190 mL
	10 mM	0.2210 mL	1.1048 mL	2.2095 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.