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Compound Detail

CHEMBL1177

PEMOLINE
💊 Approved Drug
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💊 Approved Drug
NC1=NC(=O)C(c2ccccc2)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1177
Name PEMOLINE
Phase Approved
Structure Type MOL
InChI Key NRNCYVBFPDDJNE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Azoksodon Azoxodon Azoxodone Centramin Cylert Dantromin Deltamin Deltamine Fenoxazol Hyton Hyton asa Kethamed +18 more
1
Targets
2
Activities
2
Assay Types
0
PK Parameters
20
Publications
30
Known Names
2
Indications
1
Mechanisms

Molecular Properties

176.2
MW (Da)
0.60
ALogP
3
HBA
1
HBD
64.7
PSA (Ų)
0.68
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product
USAN Year 1966

Extended Properties

Molecular Formula C9H8N2O2
MW 176.18
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness 0.12

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Attention Deficit Disorder with Hyperactivity Cocaine-Related Disorders

ATC Classification

N06BA05
pemoline
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Withdrawn
hepatotoxicity
Liver toxicity
Country: United States; United Kingdom; Canada   Year: 1997
Withdrawn
hepatotoxicity
Hepatic toxicity
Country: United States; United Kingdom; Canada   Year: 1997
Withdrawn
hepatotoxicity
Liver toxicity
Country: United States; United Kingdom; Canada   Year: 1997
Withdrawn
hepatotoxicity
Hepatic toxicity
Country: United States; United Kingdom; Canada   Year: 1997
Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 1 meas. best 6.28
Ki 1 meas. best 6.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.38 6.38 414.2 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 6.28 6.28 521.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 414.2 nM 6.38 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter IC50 = 521.3 nM 6.28 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1422
- 10.6019/CHEMBL3885881 Rattus norvegicus 432
16472241 10.2174/1570163043334794 Hepatotoxicity 18
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
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
1271419 10.1021/jm00227a600 Mus musculus 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine