CAS 188116-07-6|Imepitoin

Introduction：Basic information about CAS 188116-07-6|Imepitoin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Imepitoin BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	Imepitoin
CAS Number	188116-07-6	Molecular Weight	279.722
Density	1.4±0.1 g/cm3	Boiling Point	421.8±55.0 °C at 760 mmHg
Molecular Formula	C₁₃H₁₄ClN₃O₂	Melting Point	/
MSDS	/	Flash Point	208.9±31.5 °C

Names

Name	3-(4-chlorophenyl)-5-morpholin-4-yl-4H-imidazol-2-one
Synonym	More Synonyms

Imepitoin BiologicalActivity

Description	AWD 131-138(Imepitoin) is a new low-affinity partial benzodiazepine receptor agonist with potent anticonvulsant and anxiolytic properties in rodent models.IC50 Value: Target: GABA receptorin vitro: AWD 131-138 dose-dependently stimulated GABA currents(Recombinant gamma-aminobutyric acid A (GABA(A)) receptors of the subunit compositions alpha1beta2gamma2, alpha1beta3gamma2, alpha2beta2gamma2, alpha3beta2gamma2 and alpha5beta2gamma2). At 10 microM AWD 131-138, this allosteric stimulation amounted in average to about 12-21% of the maximal stimulation achieved using diazepam. The threshold of stimulation was about 0.3-1.0 microM [1]. in vivo: AWD 131-138 did not produce midazolam-like responding or alter response rates at cumulative doses up to 18.0 mg/kg i.m. (plasma levels over 2100 ng/ml). When AWD 131-138 (10-100 microg/kg/injection) was studied by substitution, responding declined to vehicle substitution levels within three sessions. At the dose of 100 microg/kg i.v. AWD 131-138, sufficient drug was self-administered during the first session (about 3.5 mg/kg) to produce plasma levels above 1000 ng/ml, yet responding over the next two sessions dropped to vehicle levels [2]. Prolonged oral administration with twice-daily dosing of ELB 138 with either 5 or 40 mg/kg over a 5-week period was not associated with loss of anticonvulsant efficacy in the PTZ dog model [3].
Related Catalog	Signaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorSignaling Pathways >>Neuronal Signaling >>GABA ReceptorResearch Areas >>Neurological Disease
References	[1]. Sigel E, et al. The antiepileptic drug AWD 131-138 stimulates different recombinant isoforms of the rat GABA(A) receptor through the benzodiazepine binding site. Neurosci Lett. 1998 Apr 3;245(2):85-8. [2]. Yasar S, et al. Evaluation of the novel antiepileptic drug, AWD 131-138, for benzodiazepine-like discriminative stimulus and reinforcing effects in squirrel monkeys. Eur J Pharmacol. 2003 Apr 4;465(3):257-65. [3]. Loscher W, et al. 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. Epilepsia. 2004 Oct;45(10):1228-39.

Description

AWD 131-138(Imepitoin) is a new low-affinity partial benzodiazepine receptor agonist with potent anticonvulsant and anxiolytic properties in rodent models.IC50 Value: Target: GABA receptorin vitro: AWD 131-138 dose-dependently stimulated GABA currents(Recombinant gamma-aminobutyric acid A (GABA(A)) receptors of the subunit compositions alpha1beta2gamma2, alpha1beta3gamma2, alpha2beta2gamma2, alpha3beta2gamma2 and alpha5beta2gamma2). At 10 microM AWD 131-138, this allosteric stimulation amounted in average to about 12-21% of the maximal stimulation achieved using diazepam. The threshold of stimulation was about 0.3-1.0 microM [1]. in vivo: AWD 131-138 did not produce midazolam-like responding or alter response rates at cumulative doses up to 18.0 mg/kg i.m. (plasma levels over 2100 ng/ml). When AWD 131-138 (10-100 microg/kg/injection) was studied by substitution, responding declined to vehicle substitution levels within three sessions. At the dose of 100 microg/kg i.v. AWD 131-138, sufficient drug was self-administered during the first session (about 3.5 mg/kg) to produce plasma levels above 1000 ng/ml, yet responding over the next two sessions dropped to vehicle levels [2]. Prolonged oral administration with twice-daily dosing of ELB 138 with either 5 or 40 mg/kg over a 5-week period was not associated with loss of anticonvulsant efficacy in the PTZ dog model [3].

Related Catalog

Signaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorSignaling Pathways >>Neuronal Signaling >>GABA ReceptorResearch Areas >>Neurological Disease

References

[1]. Sigel E, et al. The antiepileptic drug AWD 131-138 stimulates different recombinant isoforms of the rat GABA(A) receptor through the benzodiazepine binding site. Neurosci Lett. 1998 Apr 3;245(2):85-8.

[2]. Yasar S, et al. Evaluation of the novel antiepileptic drug, AWD 131-138, for benzodiazepine-like discriminative stimulus and reinforcing effects in squirrel monkeys. Eur J Pharmacol. 2003 Apr 4;465(3):257-65.

[3]. Loscher W, et al. 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. Epilepsia. 2004 Oct;45(10):1228-39.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	421.8±55.0 °C at 760 mmHg
Molecular Formula	C₁₃H₁₄ClN₃O₂
Molecular Weight	279.722
Flash Point	208.9±31.5 °C
Exact Mass	279.077454
PSA	45.14000
LogP	0.04
Appearance of Characters	white solid
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.664
InChIKey	IQHYCZKIFIHTAI-UHFFFAOYSA-N
SMILES	O=C1N=C(N2CCOCC2)CN1c1ccc(Cl)cc1
Storage condition	-20℃

Synonyms

2H-Imidazol-2-one, 1-(4-chlorophenyl)-1,5-dihydro-4-(4-morpholinyl)-

1-(4-Chlorophenyl)-1,5-dihydro-4-(4-morpholinyl)-2H-imidazol-2-one

1-(4-Chlorophenyl)-4-(4-morpholinyl)-1,5-dihydro-2H-imidazol-2-one

UNII-19V39682LI

1-(4-Chlorophenyl)-4-(morpholin-4-yl)-1,5-dihydro-2H-imidazol-2-one

AWD 131-138

Imepitoin

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