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Compound Detail

CHEMBL827

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

Basic Information

ChEMBL ID CHEMBL827
Name DEXMETHYLPHENIDATE
Phase Approved
Structure Type MOL
InChI Key DUGOZIWVEXMGBE-CHWSQXEVSA-N
Therapeutic ✓ Yes

Known Names

Dexmethylphenidate Dexmetilfenidato Methylphenidate d-threo-form
4
Targets
13
Activities
2
Assay Types
1
PK Parameters
17
Publications
3
Known Names
1
Indications

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 Natural Product
USAN Stem -
USAN Year 2002

Extended Properties

Molecular Formula C14H19NO2
MW 233.31
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.18

Indications

Attention Deficit Disorder with Hyperactivity

ATC Classification

N06BA11
dexmethylphenidate
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 11 meas. best 7.62
Ki 2 meas. best 7.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 7.8 7.7 16.0 2
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 7.62 7.188 24.0 5
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.06 6.935 88.0 2
Rattus norvegicus
CHEMBL376
 IC50 6.89 6.83 128.0 2
Norepinephrine transporter
CHEMBL304
 IC50 6.0 6.0 989.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 16.0 nM 7.8 Displacement of [3H]WIN-35,428 from human DAT expressed in mouse N2A cells after... 23066448
Sodium-dependent dopamine transporter IC50 = 24.0 nM 7.62 Inhibitory potency against [3H]DA uptake using [3H]WIN-35428 (WIN-) binding assa... 10579846
Sodium-dependent dopamine transporter Ki = 25.0 nM 7.6 Displacement of [3H]WIN-35428 from human DAT stably expressed in mouse N2A cells... 21129986
Sodium-dependent dopamine transporter IC50 = 83.0 nM 7.08 The compound was tested for its affinity at the rat striatal dopamine transporte... -
Sodium-dependent dopamine transporter IC50 = 83.0 nM 7.08 Inhibitory potency against dopamine (DA) transporter using [3H]WIN-35428 (WIN-) ... 10579846
Sodium-dependent dopamine transporter IC50 = 83.0 nM 7.08 Displacement of [3H]WIN 35428 from Sprague-Dawley rat striatal tissue after 2 hr... 20846865
Sodium-dependent dopamine transporter IC50 = 83.18 nM 7.08 Displacement of [3H]WIN 35428 from Sprague-Dawley rat striatal tissue after 2 hr... 20846865
Sodium-dependent dopamine transporter IC50 = 88.0 nM 7.06 Inhibition of [3H]WIN-35428 Binding to the Dopamine Transporter in Rhesus (Macac... 12672255
Rattus norvegicus IC50 = 128.0 nM 6.89 Ability to inhibit the uptake of norepinephrine [3H]-NE in to rat brain synaptos... 9484508
Sodium-dependent dopamine transporter IC50 = 156.0 nM 6.81 Inhibition of [3H]dopamine uptake at human DAT expressed in mouse N2A cells 21129986
Rattus norvegicus IC50 = 171.0 nM 6.77 Ability to inhibit the uptake of dopamine [3H]DA in to rat brain synaptosomes 9484508
Norepinephrine transporter IC50 = 989.0 nM 6.0 Selectivity for the norepinephrine transporter using [3H]nisoxetine binding assa... 10579846

Literature References

PubMed DOI Target Context # Activities
- 10.1016/S0960-894X(97)00193-5 Unchecked 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
21129986 10.1016/j.bmc.2010.11.002 Sodium-dependent dopamine transporter 2
20846865 10.1016/j.bmc.2010.08.034 Sodium-dependent dopamine transporter 2
19932971 10.1016/j.bmc.2009.10.052 Liver carboxylesterase 1 2
9484508 10.1021/jm970620j Unchecked 2
9484508 10.1021/jm970620j Rattus norvegicus 2
10579846 10.1021/jm990306k Sodium-dependent dopamine transporter 2
10579846 10.1021/jm990306k Monoamine transporters; serotonin & dopamine 1
10579846 10.1021/jm990306k Monoamine transporters; Norepininephrine & dopamine 1
12672255 10.1021/jm0205292 Sodium-dependent dopamine transporter 1
10579846 10.1021/jm990306k Sodium-dependent serotonin transporter 1
10579846 10.1021/jm990306k Norepinephrine transporter 1
23066448 10.1021/ml3000098 Sodium-dependent dopamine transporter 1
- 10.1016/S0960-894X(97)00193-5 Sodium-dependent dopamine transporter 1
28731336 10.1021/acs.jmedchem.6b01827 Homo sapiens 1
28731336 10.1021/acs.jmedchem.6b01827 ADMET 1

Data from ChEMBL 36 via Core Engine