146362-70-1

146362-70-1 structure

Name: SR 48692
Chemical Name: 2-[[1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid
CAS Number: 146362-70-1
Molecular Formula: C₃₂H₃₁ClN₄O₅
Molecular Weight: 587.065
Catalog: Signaling Pathways GPCR/G Protein Neurotensin Receptor
Create Date: 2018-07-25 11:16:16
Modify Date: 2024-01-08 17:29:21
Meclinertant (SR 48692) is a potent, selective, nonpeptide and orally active neurotensin receptor 1 (NTS1) antagonist. In human colon carcinoma (HT-29) cells, Meclinertant competitively antagonizes neurotensin-induced intracellular Ca2+ mobilization with a pA2 values of 8.13. Meclinertant has anxiolytic, anti-addictive and memory-impairing effects[1][2][3].

Name	2-[[1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid
Synonyms	Reminertant merclinertant SR48692 2-({[1-(7-Chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazol-3-yl]carbonyl}amino)adamantane-2-carboxylic acid UNII-5JBP4SI96H 2-({[1-(7-Chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazol-3-yl]carbonyl}amino)-2-adamantanecarboxylic acid Meclinertant Tricyclo[3.3.1.1]decane-2-carboxylic acid, 2-[[[1-(7-chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazol-3-yl]carbonyl]amino]-

Description	Meclinertant (SR 48692) is a potent, selective, nonpeptide and orally active neurotensin receptor 1 (NTS1) antagonist. In human colon carcinoma (HT-29) cells, Meclinertant competitively antagonizes neurotensin-induced intracellular Ca2+ mobilization with a pA2 values of 8.13. Meclinertant has anxiolytic, anti-addictive and memory-impairing effects[1][2][3].
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Neurotensin Receptor Research Areas >> Neurological Disease
Target	Neurotensin receptor 1 (NTS1)[1]
In Vitro	In vitro, Meclinertant (SR 48692) competitively inhibits 125I-labeled neurotensin binding to the high-affinity binding site present in brain tissue from various species with IC50 values of 0.99 nM (guinea pig), 4.0 nM (rat mesencephalic cells), 7.6 nM (COS-7 cells transfected with the cloned high-affinity rat brain receptor), 13.7 nM (newborn mouse brain), 17.8 nM (newborn human brain), 8.7 nM (adult human brain), and 30.3 nM (HT-29 cells). Meclinertant also displaces 125I-labeled neurotensin from the low-affinity levocabastine-sensitive binding sites but at higher concentrations (34.8 nM for adult mouse brain and 82.0 nM for adult rat brain)[1]. In guinea pig striatal slices, Meclinertant blocks K+-evoked release of [3H]dopamine stimulated by neurotensin with a potency (IC50 = 0.46 nM) that correlates with its binding affinity[1].
In Vivo	Meclinertant (SR 48692) treatment reverses at 80 μg/kg the turning behavior induced by intrastriatal injection of neurotensin in mice and with a long duration of action (6 hours)[1].
References	[1]. Gully D, et al. Biochemical and pharmacological profile of a potent and selective nonpeptide antagonist of the neurotensin receptor. Proc Natl Acad Sci U S A. 1993 Jan 1;90(1):65-9. [2]. Griebel G, et al. Characterization of the profile of neurokinin-2 and neurotensin receptor antagonists in the mouse defense test battery. Neurosci Biobehav Rev. 2001 Dec;25(7-8):619-26. [3]. Felszeghy K, et al. Neurotensin receptor antagonist administered during cocaine withdrawal decreases locomotor sensitization and conditioned place preference. Neuropsychopharmacology. 2007 Dec;32(12):2601-10.

Density	1.5±0.1 g/cm3
Boiling Point	781.2±60.0 °C at 760 mmHg
Molecular Formula	C₃₂H₃₁ClN₄O₅
Molecular Weight	587.065
Flash Point	426.2±32.9 °C
Exact Mass	586.198303
PSA	119.06000
LogP	4.55
Vapour Pressure	0.0±2.8 mmHg at 25°C
Index of Refraction	1.729
Storage condition	-20°C

RTECS	YD1988500

1443991-23-8

~88%

146362-70-1

Literature: Battilocchio, Claudio; Deadman, Benjamin J.; Nikbin, Nikzad; Kitching, Matthew O.; Baxendale, Ian R.; Ley, Steven V. Chemistry - A European Journal, 2013 , vol. 19, # 24 p. 7917 - 7930

1443991-22-7

146362-70-1

Literature: Baxendale; Cheung; Kitching; Ley; Shearman Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 14 p. 4378 - 4387

2040-04-2

146362-70-1

Literature: Baxendale; Cheung; Kitching; Ley; Shearman Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 14 p. 4378 - 4387

42381-05-5

146362-70-1

Literature: Battilocchio, Claudio; Deadman, Benjamin J.; Nikbin, Nikzad; Kitching, Matthew O.; Baxendale, Ian R.; Ley, Steven V. Chemistry - A European Journal, 2013 , vol. 19, # 24 p. 7917 - 7930

703-23-1

146362-70-1

Literature: Battilocchio, Claudio; Deadman, Benjamin J.; Nikbin, Nikzad; Kitching, Matthew O.; Baxendale, Ian R.; Ley, Steven V. Chemistry - A European Journal, 2013 , vol. 19, # 24 p. 7917 - 7930

700-58-3

146362-70-1

Literature: Baxendale; Cheung; Kitching; Ley; Shearman Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 14 p. 4378 - 4387

111697-04-2

146362-70-1

Literature: Baxendale; Cheung; Kitching; Ley; Shearman Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 14 p. 4378 - 4387

Precursor 5
2040-04-2 42381-05-5 703-23-1 700-58-3
111697-04-2
DownStream 0

146362-70-1	2088135-12-8
1781628-88-3	1446715-47-4
303126-97-8	160162-42-5
709024-69-1	141561-41-3
227321-12-2	1816294-67-3
1040339-59-0	1308963-00-9
944521-07-7	1021258-76-3
1171940-05-8	1021258-87-6
1021133-78-7	1040656-11-8
1021259-18-6	1021133-90-3