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Compound Detail

CHEMBL796

METHYLPHENIDATE
💊 Approved Drug
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💊 Approved Drug
COC(=O)C(c1ccccc1)C1CCCCN1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL796
Name METHYLPHENIDATE
Phase Approved
Structure Type MOL
InChI Key DUGOZIWVEXMGBE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Cotempla xr-odt Daytrana Methylphenidate Methylphenidate extended release Metilfenidato Prc-063 Threo-dl-methylphenidate
5
Targets
12
Activities
2
Assay Types
7
PK Parameters
20
Publications
7
Known Names
20
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 1955
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product
USAN Year 2003

Extended Properties

Molecular Formula C14H19NO2
MW 233.31
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 Narcolepsy Alzheimer Disease Anemia, Sickle Cell Asthenia Bipolar Disorder Brain Neoplasms Delirium Dementia Depressive Disorder Depressive Disorder, Major Fatigue Hematologic Neoplasms Multiple Sclerosis Neoplasms Tobacco Use Disorder Amphetamine-Related Disorders Brain Injuries Chronic Pain Cocaine-Related Disorders

ATC Classification

N06BA04
methylphenidate
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Black Box Warning
misuse
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 7 meas. best 7.77
Ki 5 meas. best 7.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.77 7.435 17.0 2
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 7.47 7.215 34.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 7.21 7.21 61.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 7.08 7.08 83.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.77 6.565 171.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 6.47 6.325 340.0 2
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 5.29 5.29 5100.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 4.19 4.19 65000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.55 mL.min-1.kg-1 Homo sapiens
CL 0.55 mL.min-1.kg-1 Homo sapiens
CL 11.1 mL.min-1.g-1 Homo sapiens
Fu 0.85 - Homo sapiens
MRT 4.5 hr Homo sapiens
T1/2 4.8 hr Homo sapiens
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter IC50 = 17.0 nM 7.77 Inhibition of [3H]WIN-35428 Binding to the Dopamine Transporter in Rhesus (Macac... 12672255
Sodium-dependent dopamine transporter Ki = 34.0 nM 7.47 Displacement of [3H]WIN 35,428 from human DAT expressed in HEK293E cells after 1... 25050161
Sodium-dependent noradrenaline transporter IC50 = 61.0 nM 7.21 Inhibition of [3H]NE uptake into human NET expressing HEK293 cells 17228864
Sodium-dependent dopamine transporter IC50 = 79.0 nM 7.1 Inhibition of [3H]DA uptake at human DAT expressing HEK293 cells 17228864
Sodium-dependent dopamine transporter IC50 = 83.0 nM 7.08 Tested for the ability to bind stereoselectively and enantioselectively to the d... 12672255
Sodium-dependent dopamine transporter Ki = 110.0 nM 6.96 Displacement of [125I]RTI-55 from human DAT expressing HEK293 cells 17228864
Rattus norvegicus IC50 = 171.0 nM 6.77 Ability to inhibit the uptake of norepinephrine [3H]-NE in to rat brain synaptos... 9484508
Sodium-dependent noradrenaline transporter Ki = 340.0 nM 6.47 Displacement of [3H]Nisoxetine from human NET expressed in HEK293E cells after 1... 25050161
Rattus norvegicus IC50 = 438.0 nM 6.36 Ability to inhibit the uptake of dopamine [3H]DA in to rat brain synaptosomes 9484508
Sodium-dependent noradrenaline transporter Ki = 660.0 nM 6.18 Displacement of [125I]RTI-55 from human NET expressing HEK293 cells 17228864
Sodium-dependent serotonin transporter IC50 = 5100.0 nM 5.29 Inhibition of [3H]5-HT uptake into human SERT expressing HEK293 cells 17228864
Sodium-dependent serotonin transporter Ki = 65000.0 nM 4.19 Displacement of [125I]RTI-55 from human SERT expressing HEK293 cells 17228864

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 51
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
6716406 10.1021/jm00371a023 Mus musculus 5
7265121 10.1021/jm00135a020 Mus musculus 5
18426954 10.1124/dmd.108.020479 ADMET 4
19256501 10.1021/jm801441s No relevant target 3
20014752 10.1021/tx900326k Hepatotoxicity 3
17228864 10.1021/jm0608614 Sodium-dependent noradrenaline transporter 2
17228864 10.1021/jm0608614 Monoamine transporters; Norepinephrine & dopamine 2
17725338 10.1021/jm070375w No relevant target 2
17228864 10.1021/jm0608614 Sodium-dependent serotonin transporter 2
17228864 10.1021/jm0608614 Sodium-dependent dopamine transporter 2
12672255 10.1021/jm0205292 Sodium-dependent dopamine transporter 2
19445515 10.1021/jm900403j Homo sapiens 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
9484508 10.1021/jm970620j Rattus norvegicus 2
19261477 10.1016/j.bmc.2008.11.045 Mus musculus 1

Data from ChEMBL 36 via Core Engine