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Compound Detail

CHEMBL1722

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

Basic Information

ChEMBL ID CHEMBL1722
Name METHYLPHENIDATE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key JUMYIBMBTDDLNG-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL796
Active Moiety CHEMBL796

Known Names

Adhansia xr Aptensio Aptensio xr Concerta Delmosart Equasym Equasym xl Foquest Jornay pm Matoride xl Medikinet Medikinet xl +18 more
2
Targets
4
Activities
1
Assay Types
0
PK Parameters
7
Publications
30
Known Names
12
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

Flags

Black Box Warning

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 Depressive Disorder Fatigue Tobacco Use Disorder Apraxias Neoplasms Schizophrenia Sleep Wake Disorders Conduct Disorder Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Relapsing-Remitting Apathy

Drug Warnings

Black Box Warning
misuse
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 4 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.7 7.31 19.9 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 7.29 6.695 51.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter IC50 = 19.9 nM 7.7 Inhibition of [3H]dopamine uptake in HEK293 cells expressing human dopamine tran... 15828826
Sodium-dependent noradrenaline transporter IC50 = 51.0 nM 7.29 Inhibition of [3H]norepinephrine uptake in HEK293 cells expressing human norepin... 15828826
Sodium-dependent dopamine transporter IC50 = 121.7 nM 6.92 Displacement of [125I]-RTI-55 from Dopamine transporter expressed in HEK293 cell... 15828826
Sodium-dependent noradrenaline transporter IC50 = 788.0 nM 6.1 Displacement of [125I]RTI-55 from human Norepinephrine transporter expressed in ... 15828826

Literature References

PubMed DOI Target Context # Activities
15828826 10.1021/jm0490989 Sodium-dependent dopamine transporter 2
15828826 10.1021/jm0490989 Sodium-dependent noradrenaline transporter 2
15828826 10.1021/jm0490989 Sodium-dependent serotonin transporter 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine