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Details

Stereochemistry ACHIRAL
Molecular Formula C13H19N3O2
Molecular Weight 249.3089
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMIDANTEL

SMILES

COCC(=O)NC1=CC=C(C=C1)\N=C(/C)N(C)C

InChI

InChIKey=MKFMTNNOZQXQBP-GXDHUFHOSA-N
InChI=1S/C13H19N3O2/c1-10(16(2)3)14-11-5-7-12(8-6-11)15-13(17)9-18-4/h5-8H,9H2,1-4H3,(H,15,17)/b14-10+

HIDE SMILES / InChI

Molecular Formula C13H19N3O2
Molecular Weight 249.3089
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

N-(4-[(1-(Dimethylamino)-ethylidene)-amino]-phenyl)-2 methoxyacetamide hydrochloride (amidantel, BAY d 8815) is an aminophenylamidine with an interesting anthelminthic spectrum. In rodents the compound is active against nematodes, filariae and cestodes. Of special interest is the high efficacy in dogs against hookworms and large roundworms. Amidantel was well tolerated by all animals tested and did not show teratogenic effects. The drug was moderately potent inhibitor of both E. electricus and C. elegans acetylcholinesterase but at concentrations too high to account for its abilitiy to contract cut worms. The primary mode of action of amidantel appears to be as agonist at the level of the acetylcholine receptor, a view supported by the observation that its effect may be blocked by the nicotinic antagonists d-tubocurarine and gallamine. Amidantel was also investigated it clinical trials as the treatment against Ancylostoma duodenale infection. Amidantel proved to be very effective against A. duodenale as well as Ascaris lumbricoides. With regard to dosage, a single dose of 6.0 mg/kg body weight of amidantel was found to be the most effective and well tolerated than the other dosages employed.

Originator

Approval Year

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Amidantel was tried in 140 patients with Ancylostoma duodenale and other helminth infections. In the first trial, each 16 cases in 64 patients with A. duodenale were treated with 3.0, 6.0 and 9.0 or 10.0 mg/kg body weight of amidantel including placebo control. Another 76 patients infected with hookworms and other helminths were treated with 5.0, 6.0 and 8.0 mg/kg body weight of amidantel in the second trial. In the results, it was confirmed that amidantel is very effective against A. duodenale as well as Ascaris lumbricoides. With regard to dosage, a single dose of 6.0 mg/kg body weight of amidantel was found to be the most effective and well tolerated than the other dosages employed. In a single dose of 6.0 mg/kg body weight the cure rates were 93.8 and 96.6 per cent for A. duodenale infection and 90.9 and 93.1 per cent for ascariasis in the first and second trials respectivley.
Route of Administration: Oral
In Vitro Use Guide
After rendering the C. elegans worms permeable by cutting them at their approximate midsections, the minimum effective concentrations of amidantel was 0.30 uM.
Substance Class Chemical
Record UNII
C67IS11N0O
Record Status Validated (UNII)
Record Version