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Compound Detail

CHEMBL904

DEXMETHYLPHENIDATE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
COC(=O)[C@H](c1ccccc1)[C@H]1CCCCN1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL904
Name DEXMETHYLPHENIDATE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key JUMYIBMBTDDLNG-OJERSXHUSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL827
Active Moiety CHEMBL827

Known Names

Dex-methylphenidate hydrochloride Dexmethylphenidate hcl Dexmethylphenidate hydrochloride Dexmethylphenidate hydrochloride component of azstarys Focalin Focalin xr Methylphenidate d-threo-form hydrochloride
3
Targets
5
Activities
2
Assay Types
0
PK Parameters
8
Publications
7
Known Names
1
Indications
2
Mechanisms

Molecular Properties

233.3
MW (Da)
2.09
ALogP
3
HBA
1
HBD
38.3
PSA (Ų)
0.81
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -
USAN Year 2002

Extended Properties

Molecular Formula C14H20ClNO2
MW 269.77
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine transporter inhibitor INHIBITOR Sodium-dependent dopamine transporter ✓ ✓
Norepinephrine transporter inhibitor INHIBITOR Sodium-dependent noradrenaline transporter ✓ ✓

Indications

Attention Deficit Disorder with Hyperactivity

Drug Warnings

Black Box Warning
misuse
Country: United States

Activity Summary

IC50 3 meas. best 7.08
Ki 2 meas. best 7.13

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 7.13 7.13 74.6 1
Dopamine receptor
CHEMBL2093868
 IC50 7.08 6.935 83.0 2
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 6.64 6.64 230.0 1
Norepinephrine transporter
CHEMBL304
 Ki 6.57 6.57 270.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 74.6 nM 7.13 Displacement of [3H]WIN-35428 from DAT in Sprague-Dawley rat striatum 17489581
Dopamine receptor IC50 = 83.0 nM 7.08 Potency of inhibiting [3H]WIN-35428 binding to dopamine receptor in rat striatal... 15026075
Dopamine receptor IC50 = 164.0 nM 6.79 Potency of inhibiting 10 pM [125I]-RTI-55 binding to dopamine receptor in rat st... 15026075
Sodium-dependent dopamine transporter IC50 = 230.0 nM 6.64 Inhibition of [3H]DA uptake at DAT in Sprague-Dawley rat striatum 17489581
Norepinephrine transporter Ki = 270.0 nM 6.57 Displacement of [3H]nisoxetine from NET in Sprague-Dawley rat cortical tissue 17489581

Literature References

PubMed DOI Target Context # Activities
15026075 10.1016/j.bmcl.2003.12.097 Dopamine receptor 2
17489581 10.1021/jm061354p Sodium-dependent dopamine transporter 2
15026075 10.1016/j.bmcl.2003.12.097 Unchecked 1
17489581 10.1021/jm061354p Norepinephrine transporter 1
17489581 10.1021/jm061354p Sodium-dependent serotonin transporter 1
17489581 10.1021/jm061354p Monoamine transporters; serotonin & dopamine 1
17489581 10.1021/jm061354p Monoamine transporters; Norepininephrine & dopamine 1
17489581 10.1021/jm061354p Monoamine transporters; Norepinephrine & serotonin 1

Data from ChEMBL 36 via Core Engine