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Compound Detail

CHEMBL54349

ALPIDEM
💊 Approved Drug
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💊 Approved Drug
CCCN(CCC)C(=O)Cc1c(-c2ccc(Cl)cc2)nc2ccc(Cl)cn12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL54349
Name ALPIDEM
Phase Approved
Structure Type MOL
InChI Key JRTIDHTUMYMPRU-UHFFFAOYSA-N

Known Names

Alpidem SL 80.0342-00 SL-80.0342-00
7
Targets
24
Activities
3
Assay Types
1
PK Parameters
20
Publications
3
Known Names
1
Mechanisms

Molecular Properties

404.3
MW (Da)
5.50
ALogP
3
HBA
0
HBD
37.6
PSA (Ų)
0.52
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn
USAN Stem -pidem
USAN Year 1987

Extended Properties

Molecular Formula C21H23Cl2N3O
MW 404.34
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.86

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Translocator protein partial agonist PARTIAL AGONIST Translocator protein ✓ ✓

Drug Warnings

Withdrawn
hepatotoxicity
Hepatitis
Country: France   Year: 1993
Withdrawn
hepatotoxicity
Hepatitis
Country: France   Year: 1993
Withdrawn
hepatotoxicity
Hepatitis
Country: France   Year: 1993

Activity Summary

IC50 13 meas. best 9.3
Ki 10 meas. best 9.3
Kd 1 meas. best 5.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Translocator protein
CHEMBL4552
 IC50 9.3 8.5167 0.5 3
Translocator protein
CHEMBL4552
 Ki 9.3 8.83 0.5 5
Translocator protein
CHEMBL5742
 Ki 9.3 9.3 0.5 3
Unchecked
CHEMBL612545
 IC50 9.0 8.29 1.0 2
Unchecked
CHEMBL612545
 Ki 9.0 9.0 1.0 2
Translocator protein
CHEMBL5742
 IC50 8.1 8.1 7.9 1
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 7.58 7.565 26.0 2
Albumin
CHEMBL3253
 Kd 5.7 5.7 2000.0 1
Bile salt export pump
CHEMBL6020
 IC50 5.04 5.04 9155.0 4
Bile salt export pump
CHEMBL2073674
 IC50 4.64 4.64 23000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 285.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Translocator protein IC50 = 0.5 nM 9.3 Displacement of [3H]PK11195 from TSPO receptor in rat brain cortex membrane incu... 34254805
Translocator protein Ki = 0.5 nM 9.3 Binding affinity to TSPO receptor (unknown origin) 34254805
Translocator protein Ki = 0.5 nM 9.3 Binding affinity to TSPO (unknown origin) 33081988
Translocator protein Ki = 0.5 nM 9.3 Inhibition of TSPO (unknown origin) 31404862
Translocator protein Ki = 0.5 nM 9.3 Displacement of [3H]PK11195 from TSPO in rat kidney mitochondrial membranes by c... 22489952
Translocator protein Ki = 0.5 nM 9.3 Displacement of [3H]PK11195 from translocator protein in rat kidney mitochondria... 18729350
Translocator protein Ki = 0.5 nM 9.3 Displacement of [3H]PK 11195 from peripheral-type benzodiazepine receptor in rat... 17228885
Unchecked IC50 = 1.0 nM 9.0 Displacement of [3H]flunitrazepam from CBR receptor in rat brain cortex membrane... 34254805
Unchecked Ki = 1.0 nM 9.0 Binding affinity to CBR (unknown origin) 34254805
Unchecked Ki = 1.0 nM 9.0 Binding affinity to CBR (unknown origin) 33081988
Translocator protein IC50 = 7.0 nM 8.15 Binding affinity against peripheral benzodiazepine receptor( PBR). 8863805
Translocator protein Ki = 7.0 nM 8.15 Binding affinity to peripheral benzodiazepine receptors using [3H]-PK11195 radio... 15027878
Translocator protein Ki = 7.9 nM 8.1 Displacement of [3H]-flunitrazepam from TSPO receptor in Wistar rat brain withou... 33081988
Translocator protein IC50 = 7.9 nM 8.1 Inhibition of TSPO (unknown origin) 31404862
Translocator protein IC50 = 7.9 nM 8.1 Displacement of Ro 5-4864 from peripheral (renal cell) Benzodiazepine receptor 9301675
Unchecked IC50 = 26.0 nM 7.58 Inhibition of CBR (unknown origin) 31404862
GABA-A receptor; anion channel IC50 = 26.0 nM 7.58 Displacement of [3H]flunitrazepam from rat brain GABA-A Benzodiazepine receptor 9301675
GABA-A receptor; anion channel IC50 = 28.0 nM 7.55 Binding affinity against central benzodiazepine receptor(CBR). 8863805
Albumin Kd = 2000.0 nM 5.7 Binding affinity to albumin (unknown origin) 32049517
Bile salt export pump IC50 = 9200.0 nM 5.04 Inhibition of human BSEP expressed in HEK293 cell membrane vesicles assessed as ... 32511920

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2

Data from ChEMBL 36 via Core Engine