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Details

Stereochemistry ACHIRAL
Molecular Formula C13H14ClN3O2
Molecular Weight 279.722
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMEPITOIN

SMILES

ClC1=CC=C(C=C1)N2CC(=NC2=O)N3CCOCC3

InChI

InChIKey=IQHYCZKIFIHTAI-UHFFFAOYSA-N
InChI=1S/C13H14ClN3O2/c14-10-1-3-11(4-2-10)17-9-12(15-13(17)18)16-5-7-19-8-6-16/h1-4H,5-9H2

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24357084

Imepitoin (AWD 131–138 or ELB 138; 1-(4-chlorophenyl)-4-morpholino-imidazolin-2-one) is a new anti-epileptic drug recently approved in the European Union for the treatment of canine idiopathic epilepsy. It was developed from a series of imidazolinones due to its pronounced ant seizure activity in a large variety of rodent models of epileptic seizures, combined with a high tolerability in these models. Imepitoin is a centrally acting antiepileptic substance, which crosses the blood brain barrier without involvement of active transport or active clearance, resulting in immediate equilibrium between plasma and brain. Imepitoin acts as low-affinity partial agonists at the benzodiazepine (BZD) site of the GABAA receptor. Hopefully, that the favorable profile of imepitoin for the treatment of epilepsy in dogs will reactivate the interest in partial BZD site agonists as new treatments for human epilepsy.

CNS Activity

Curator's Comment: Known to be CNS penetrant in dog. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Imepitoin

Approved Use

For the reduction of the frequency of generalised seizures due to idiopathic epilepsy in dogs for use after careful evaluation of alternative treatment options.
PubMed

PubMed

TitleDatePubMed
Anticonvulsant efficacy of the low-affinity partial benzodiazepine receptor agonist ELB 138 in a dog seizure model and in epileptic dogs with spontaneously recurrent seizures.
2004 Oct
Patents

Sample Use Guides

for dog: Oral administration at a dose range of 10 mg to 30 mg imepitoin per kg body weight twice daily, approximately 12 hours apart. Each tablet can be halved for appropriate dosing according to the individual body weight of the dog. The required dose will vary between dogs and will depend on the severity of the disorder. The recommended initial dose of imepitoin is 10 mg per kg body weight twice daily. Initiate therapy using the bodyweight in kg and the dosing table. If seizures are not adequatey reduced following a minimum of 1 week of treatment at the current dose the supervising veterinary surgeon should re-assess the dog. Assuming that the veterinary medicinal product is well tolerated by the dog, the dose can be increased by 50 to 100% increments up to a maximum dosage of 30 mg per kg administered twice daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
IMEPITOIN
INN  
INN  
Official Name English
IMEPITION
Common Name English
IMEPITOIN [EMA EPAR VETERINARY]
Common Name English
1-(4-CHLOROPHENYL)-4-(MORPHOLIN-4-YL)-1,5-DIHYDRO-2H-IMIDAZOL-2-ONE
Systematic Name English
PEXION
Brand Name English
IMEPITOIN [MI]
Common Name English
imepitoin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C264
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EMA VETERINARY ASSESSMENT REPORTS PEXION [AUTHORIZED]
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WHO-VATC QN03AX90
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Code System Code Type Description
WIKIPEDIA
Imepitoin
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EPA CompTox
DTXSID50172160
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MERCK INDEX
m11975
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RXCUI
2600779
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NCI_THESAURUS
C87608
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FDA UNII
19V39682LI
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DAILYMED
19V39682LI
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CAS
188116-07-6
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INN
8794
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SMS_ID
100000183681
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PUBCHEM
3083511
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