Details of the Drug

General Information of Drug (ID: DMMRY0Z)

Drug Name
NPS-2390
Synonyms
N-(Adamantan-1-yl)quinoxaline-2-carboxamide; NPS 2390; 226878-01-9; NPS2390; N-(1-adamantyl)quinoxaline-2-carboxamide; CHEMBL399160; N-(adamantan-1-yl)quinoxaline-2-carboxamide; quinoxaline-2-carboxylic acid adamantan-1-ylamide; N-tricyclo[33113,7]dec-1-yl-2-quinoxalinecarboxamide; AC1OF2ZL; SCHEMBL659603; GTPL1384; NPS-239; DTXSID10427729; MolPort-003-351-281; ZKFVOZCCAXQXBU-UHFFFAOYSA-N; ZINC3966256; PDSP2_001301; BDBM50231744; PDSP1_001317; AKOS001304198; NPS-2390 solution, 30 mM in DMSO; N-(1-Adamantyl)-2-quinoxalinecarboxamide; Quinoxaline-2-carboxylic acid adamantan-1-ylamide
Indication
Disease Entry ICD 11 Status REF
Cerebrovascular ischaemia 8B1Z Preclinical [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 307.4
Topological Polar Surface Area (xlogp) 4.1
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C19H21N3O
IUPAC Name
N-(1-adamantyl)quinoxaline-2-carboxamide
Canonical SMILES
C1C2CC3CC1CC(C2)(C3)NC(=O)C4=NC5=CC=CC=C5N=C4
InChI
InChI=1S/C19H21N3O/c23-18(17-11-20-15-3-1-2-4-16(15)21-17)22-19-8-12-5-13(9-19)7-14(6-12)10-19/h1-4,11-14H,5-10H2,(H,22,23)
InChIKey
ZKFVOZCCAXQXBU-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
7067728
CAS Number
226878-01-9
TTD ID
D0W0XM

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Extracellular calcium-sensing receptor (CASR) TTBUYHA CASR_HUMAN Modulator [3]
Metabotropic glutamate receptor 1 (mGluR1) TTVBPDM GRM1_HUMAN Inhibitor [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Cerebrovascular ischaemia
ICD Disease Classification 8B1Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Metabotropic glutamate receptor 1 (mGluR1) DTT GRM1 2.31E-01 -0.05 -0.2
Metabotropic glutamate receptor 1 (mGluR1) DTT GRM1 2.46E-02 0.11 0.74
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1384).
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800014988)
3 The Extracellular Calcium-Sensing Receptor (CASR) Regulates Gonadotropins-Induced Meiotic Maturation of Porcine Oocytes.Biol Reprod.2015 Dec;93(6):131.
4 Positive and negative modulation of group I metabotropic glutamate receptors. J Med Chem. 2008 Feb 14;51(3):634-47.
5 Pfizer. Product Development Pipeline. March 31 2009.
6 Clinical pipeline report, company report or official report of AstraZeneca (2009).
7 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
8 Comparison of the mGluR1 antagonist A-841720 in rat models of pain and cognition. Behav Pharmacol. 2007 Jul;18(4):273-81.
9 Anticonvulsant actions of LY 367385 ((+)-2-methyl-4-carboxyphenylglycine) and AIDA ((RS)-1-aminoindan-1,5-dicarboxylic acid). Eur J Pharmacol. 1999 Feb 26;368(1):17-24.
10 Mutational analysis and molecular modeling of the allosteric binding site of a novel, selective, noncompetitive antagonist of the metabotropic glut... J Biol Chem. 2003 Mar 7;278(10):8340-7.
11 Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections. J Neurochem. 2000 Dec;75(6):2590-601.
12 [3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists. Mol Pharmacol. 2003 May;63(5):1082-93.
13 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 289).
14 Clinical pipeline report, company report or official report of Amgen (2009).
15 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
16 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800035616)
17 Antagonist for calcium-sensing receptor. JTT-305/MK-5442. Clin Calcium. 2011 Jan;21(1):89-93.
18 ATF936, a novel oral calcilytic, increases bone mineral density in rats and transiently releases parathyroid hormone in humans. Bone. 2011 Aug;49(2):233-41.
19 AXT914 a novel, orally-active parathyroid hormone-releasing drug in two early studies of healthy volunteers and postmenopausal women. Bone. 2014 Jul;64:204-10.
20 Mixed-effects modeling of the pharmacodynamic response to the calcimimetic agent R-568. Clin Pharmacol Ther. 1999 Jan;65(1):40-9.
21 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
22 Calcium-sensing receptor antagonist (calcilytic) NPS 2143 specifically blocks the increased secretion of endogenous Abeta42 prompted by exogenous fibrillary or soluble Abeta25-35 in human cortical astrocytes and neurons-therapeutic relevance to Alzheimer's disease. Biochim Biophys Acta. 2013 Oct;1832(10):1634-52.
23 N2-benzyl-N1-(1-(1-naphthyl)ethyl)-3-phenylpropane-1,2-diamines and conformationally restrained indole analogues: development of calindol as a new calcimimetic acting at the calcium sensing receptor.Bioorg Med Chem Lett. 2004 Jun 21;14(12):3345-9.