Compound Detail

CHEMBL276520

INDALPINE

💊 Approved Drug

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💊 Approved Drug

c1ccc2c(CCC3CCNCC3)c[nH]c2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL276520
Name	INDALPINE
Phase	Approved
Structure Type	MOL
InChI Key	SADQVAVFGNTEOD-UHFFFAOYSA-N

Known Names

Indalpina Indalpine LM-5008

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Mechanisms

Molecular Properties

228.3

MW (Da)

3.10

ALogP

HBA

HBD

27.8

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Withdrawn
Chirality	Achiral

Flags

Withdrawn Natural Product

USAN Stem

-pine

Extended Properties

Molecular Formula	C15H20N2
MW	228.34
Aromatic Rings	2
Heavy Atoms	17
NP-Likeness	0.12

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin transporter inhibitor	INHIBITOR	Sodium-dependent serotonin transporter	✓	✓

Drug Warnings

Withdrawn

hematological toxicity

Agranulocytosis

Country: France Year: 1985

Withdrawn

hematological toxicity

agranulocytosis and severe neutropenia

Country: France Year: 1985

Withdrawn

hematological toxicity

agranulocytosis and severe neutropenia

Country: France Year: 1985

Activity Summary

IC50 5 meas. best 9.0

Ki 3 meas. best 8.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Rattus norvegicus CHEMBL376	IC50	9.0	9.0	1.0	1
Sodium-dependent serotonin transporter CHEMBL313	Ki	8.7	8.6667	2.0	3
Sodium-dependent serotonin transporter CHEMBL313	IC50	8.0	8.0	10.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	7.52	7.52	30.0	1
Norepinephrine transporter CHEMBL304	IC50	5.8	5.8	1600.0	1
Sodium-dependent dopamine transporter CHEMBL338	IC50	4.75	4.75	18000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Rattus norvegicus	IC50	=	1.0	nM	9.0	[3H]5-HT reuptake inhibition in Rat brain synaptosomes.	10737747
Sodium-dependent serotonin transporter	Ki	=	2.0	nM	8.7	Effect of compound on Serotonin transporter uptake from rat cortex using [3H]cit...	7629808
Sodium-dependent serotonin transporter	Ki	=	2.0	nM	8.7	In vitro inhibitory constant against [3H]paroxetine binding to rat frontal corte...	16250644
Sodium-dependent serotonin transporter	Ki	=	2.5	nM	8.6	In vitro binding affinity for serotonin reuptake sites in rat frontal cortex mem...	12565939
Sodium-dependent serotonin transporter	IC50	=	10.0	nM	8.0	Inhibition of uptake of 5-HT in rat brain cortex	7452682
Sodium-dependent serotonin transporter	IC50	=	30.0	nM	7.52	In vivo inhibition of uptake of 5-HT in human platelets	7452682
Norepinephrine transporter	IC50	=	1600.0	nM	5.8	Inhibition of uptake of noradrenaline in rat brain hypothalamus	7452682
Sodium-dependent dopamine transporter	IC50	=	18000.0	nM	4.75	Inhibition of uptake of dopamine (DA) rat brain striatum	7452682

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
7452682	10.1021/jm00186a005	Sodium-dependent serotonin transporter	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
7452682	10.1021/jm00186a005	Norepinephrine transporter	1
7452682	10.1021/jm00186a005	Sodium-dependent dopamine transporter	1
7452682	10.1021/jm00186a005	Mus musculus	1
7452682	10.1021/jm00186a005	Rattus norvegicus	1
7629808	10.1021/jm00014a021	Sodium-dependent serotonin transporter	1
10737747	10.1021/jm9811054	Rattus norvegicus	1
12565939	10.1016/s0960-894x(02)00996-4	D(2) dopamine receptor	1
12565939	10.1016/s0960-894x(02)00996-4	Sodium-dependent serotonin transporter	1
16250644	10.1021/jm050148z	D(2) dopamine receptor	1
16250644	10.1021/jm050148z	Sodium-dependent serotonin transporter	1
22961681	10.1124/dmd.112.047068	Bile salt export pump	1

Data from ChEMBL 36 via Core Engine