ELB-139

ELB-139

Identifiers
IUPAC name 1-(4-Chlorophenyl)-4-piperidin-1-yl-1,5-dihydro-imidazol-2-one
CAS Number	188116-08-7  Y
PubChem CID	11277418
ChemSpider	9452418
UNII	BKP2A5554F
CompTox Dashboard (EPA)	DTXSID40877536
Chemical and physical data
Formula	C14H16ClN3O
Molar mass	277.75 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc3ccc(cc3)N1CC(=NC1=O)N2CCCCC2
InChI InChI=1S/C14H16ClN3O/c15-11-4-6-12(7-5-11)18-10-13(16-14(18)19)17-8-2-1-3-9-17/h4-7H,1-3,8-10H2 Key:YGXIELIREXEJQN-UHFFFAOYSA-N
(verify)

ELB-139 (LS-191,811) is an anxiolytic drug with a novel chemical structure, which is used in scientific research. It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic. ^{[1] [2]}

ELB-139 is a subtype-selective partial agonist at GABA_A receptors, with highest affinity for the α3 subtype, but highest efficacy at α1 and α2. ^[3] It has primarily anxiolytic and anticonvulsant effects, but produces little sedative effects or ataxia, ^[4] and has also been demonstrated in rats to increase serotonin levels in the striatum and prefrontal cortex, without affecting dopamine levels. ^[5] It has been proposed as a possible candidate for a novel non-sedating anxiolytic or anticonvulsant drug for use in humans ^[6] The sponsor elbion AG registered a clinical trial in ClinicalTrials.gov for the treatment of anxiety associated with panic disorder but the results have not been reported. ^[7] It was developed by Arzneimittelwerk Dresden in the 1990s. ^[8]

References

1. Langen B, Egerland U, Bernöster K, Dost R, Unverferth K, Rundfeldt C (August 2005). "Characterization in rats of the anxiolytic potential of ELB139 [1-(4-chlorophenyl)-4-piperidin-1-yl-1,5-dihydro-imidazol-2-on], a new agonist at the benzodiazepine binding site of the GABAA receptor". The Journal of Pharmacology and Experimental Therapeutics. 314 (2): 717–24. doi:10.1124/jpet.105.084681. PMID   15860576. S2CID   21967108.
2. Atack JR (May 2005). "The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics". Expert Opinion on Investigational Drugs. 14 (5): 601–18. doi:10.1517/13543784.14.5.601. PMID   15926867. S2CID   22793644.
3. Rabe H, Kronbach C, Rundfeldt C, Lüddens H (March 2007). "The novel anxiolytic ELB139 displays selectivity to recombinant GABA(A) receptors different from diazepam". Neuropharmacology. 52 (3): 796–801. doi:10.1016/j.neuropharm.2006.09.013. PMID   17087982. S2CID   21598180.
4. Grunwald C, Rundfeldt C, Lankau HJ, Arnold T, Höfgen N, Dost R, et al. (March 2006). "Synthesis, pharmacology, and structure-activity relationships of novel imidazolones and pyrrolones as modulators of GABAA receptors". Journal of Medicinal Chemistry. 49 (6): 1855–66. doi:10.1021/jm0509400. PMID   16539371.
5. Langen B, Rundfeldt C (January 2007). "ELB139 an agonist at the benzodiazepine binding site increases 5-HT in the striatum and prefrontal cortex of rats: a microdialysis study". Pharmacology, Biochemistry, and Behavior. 86 (1): 79–85. doi:10.1016/j.pbb.2006.12.010. PMID   17257662. S2CID   22862432.
6. Rogawski MA (June 2006). "Diverse mechanisms of antiepileptic drugs in the development pipeline". Epilepsy Research. 69 (3): 273–94. doi:10.1016/j.eplepsyres.2006.02.004. PMC   1562526 . PMID   16621450.
7. Whiting PJ (February 2006). "GABA-A receptors: a viable target for novel anxiolytics?". Current Opinion in Pharmacology. 6 (1): 24–9. doi:10.1016/j.coph.2005.08.005. PMID   16359919.
8. US 5869481,"Anticonvulsive 1-ar(alk)ylimidazolin-2-ones and process for making"