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Compound Detail

CHEMBL255044

FLUPIRTINE
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)nc1N

Basic Information

ChEMBL ID CHEMBL255044
Name FLUPIRTINE
Phase Approved
Structure Type MOL
InChI Key JUUFBMODXQKSTD-UHFFFAOYSA-N

Known Names

Flupirtina Flupirtine Flupirtinte W-2964
3
Targets
4
Activities
2
Assay Types
9
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

304.3
MW (Da)
2.98
ALogP
5
HBA
3
HBD
89.3
PSA (Ų)
0.79
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn
USAN Year 1984

Extended Properties

Molecular Formula C15H17FN4O2
MW 304.32
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -1.58

Indications

Fever Pain Multiple Sclerosis, Relapsing-Remitting

ATC Classification

N02BG07
flupirtine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

Withdrawn
hepatotoxicity
Risk of serious liver injury
Country: European Union   Year: 2018
Withdrawn
hepatotoxicity
Risk of serious liver injury
Country: European Union   Year: 2018

Activity Summary

IC50 3 meas. best 6.03
EC50 1 meas. best 6.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3)
CHEMBL2221348
EC50 6.25 6.25 560.0 1
Serine hydroxymethyltransferase, mitochondrial
CHEMBL4295747
IC50 6.03 6.03 933.2 1
Bile salt export pump
CHEMBL6020
IC50 4.45 4.45 35500.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 6074.23 ng.hr.mL-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
Fu 0.15 - Homo sapiens
Fu 0.15 - Homo sapiens
MRT 11.0 hr Homo sapiens
T1/2 8.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
29110485 10.1021/acs.jmedchem.7b01199 PC-12 8
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
29110485 10.1021/acs.jmedchem.7b01199 Unchecked 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
29110485 10.1021/acs.jmedchem.7b01199 Glutamate [NMDA] receptor 2
- 10.6019/CHEMBL4651402 Vero C1008 2
31416667 10.1016/j.bmcl.2019.08.007 Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
26988304 10.1016/j.bmcl.2016.03.028 PC-12 2
- 10.6019/CHEMBL3301361 ADMET 2
37468498 10.1038/s41467-023-40064-9 Beta-1 adrenergic receptor 2
31815462 10.1021/acs.jmedchem.9b00796 Potassium voltage-gated channel subfamily KQT member 2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19445515 10.1021/jm900403j Homo sapiens 2

Data from ChEMBL 36 via Core Engine