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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
The efficacy of amidantel, a new anthelmintic, on hookworms and ascarids in dogs.
1979 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In dogs amidantel is highly effective in a single oral dose of 25 mg/kg against both hookworm species, Ancylostoma caninum and Unicinaria stenocephala. In Toxascaris leonina infected dogs a complete cure rate was achieved with a single oral dose of 50 mg/kg. Similar results were obtained with 8 mg/kg administered three times per day. The most sensitive parasite to amidantel was found to be Toxocara canis with a 100 per cent cure rate after a single oral treatment with 10 mg/kg. https://www.ncbi.nlm.nih.gov/pubmed/295548
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
Created
by admin
on Sat Dec 16 15:51:28 GMT 2023
Edited
by admin
on Sat Dec 16 15:51:28 GMT 2023
Record UNII
C67IS11N0O
Record Status Validated (UNII)
Record Version
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Name Type Language
AMIDANTEL
INN  
INN  
Official Name English
amidantel [INN]
Common Name English
4'-((1-(DIMETHYLAMINO)ETHYLIDENE)AMINO)-2-METHOXYACETANILIDE
Systematic Name English
BAY-D 8815 FREE BASE
Code English
BAY D 8815 FREE BASE
Code English
BAY-D-8815 FREE BASE
Code English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
Code System Code Type Description
SMS_ID
100000087201
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105966
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
INN
4476
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
MESH
C019144
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
PUBCHEM
39521
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
EVMPD
SUB05425MIG
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
NCI_THESAURUS
C72152
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
FDA UNII
C67IS11N0O
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
CAS
49745-00-8
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID70198009
Created by admin on Sat Dec 16 15:51:28 GMT 2023 , Edited by admin on Sat Dec 16 15:51:28 GMT 2023
PRIMARY
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