Details of the Drug

General Information of Drug (ID: DMB3JY8)

Drug Name
(+/-)-threo-N-(4-Nitrobenzyl)methylphenidate
Synonyms CHEMBL1253839; (+/-)-threo-N-(4-Nitrobenzyl)methylphenidate
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 368.4
Topological Polar Surface Area (xlogp) 4
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C21H24N2O4
IUPAC Name
methyl (2R)-2-[(2R)-1-[(4-nitrophenyl)methyl]piperidin-2-yl]-2-phenylacetate
Canonical SMILES
COC(=O)[C@@H]([C@H]1CCCCN1CC2=CC=C(C=C2)[N+](=O)[O-])C3=CC=CC=C3
InChI
InChI=1S/C21H24N2O4/c1-27-21(24)20(17-7-3-2-4-8-17)19-9-5-6-14-22(19)15-16-10-12-18(13-11-16)23(25)26/h2-4,7-8,10-13,19-20H,5-6,9,14-15H2,1H3/t19-,20-/m1/s1
InChIKey
WXZFAWFIMBPTEP-WOJBJXKFSA-N
Cross-matching ID
PubChem CID
52943636
TTD ID
D0P9MQ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine transporter (DAT) TTVBI8W SC6A3_HUMAN Inhibitor [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine transporter (DAT) DTT SLC6A3 1.08E-03 -3.08 -1.99
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Quantitative structure-activity relationship studies of threo-methylphenidate analogs. Bioorg Med Chem. 2010 Oct 15;18(20):7221-38.
2 Differential involvement of the norepinephrine, serotonin and dopamine reuptake transporter proteins in cocaine-induced taste aversion. Pharmacol Biochem Behav. 2009 Jul;93(1):75-81.
3 Dasotraline for the Treatment of Attention-Deficit/Hyperactivity Disorder: A Randomized, Double-Blind, Placebo-Controlled, Proof-of-Concept Trial in Adults. Neuropsychopharmacology. 2015 Nov;40(12):2745-52.
4 Imaging the effects of methylphenidate on brain dopamine: new model on its therapeutic actions for attention-deficit/hyperactivity disorder. Biol Psychiatry. 2005 Jun 1;57(11):1410-5.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain. Eur J Pharmacol. 2002 Jun 28;447(1):51-7.
7 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
8 Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate. J Med Chem. 2007 May 31;50(11):2718-31.
9 Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters. Synapse. 1998 Jun;29(2):128-41.
10 Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
11 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: 927).