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Compound Detail

CHEMBL4164059

PITOLISANT HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.Clc1ccc(CCCOCCCN2CCCCC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4164059
Name PITOLISANT HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key XLFKECRRMPOAQS-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL462605
Active Moiety CHEMBL462605

Known Names

BF-2649 HYDROCHLORIDE Ciproxidine Ozawade Pitolisant hydrochloride Wakix
8
Targets
9
Activities
1
Assay Types
1
PK Parameters
20
Publications
5
Known Names
3
Indications
1
Mechanisms

Molecular Properties

295.9
MW (Da)
4.17
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.67
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2016
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -isant
USAN Year 2018

Extended Properties

Molecular Formula C17H27Cl2NO
MW 332.31
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -1.15

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histamine H3 receptor inverse agonist INVERSE AGONIST Histamine H3 receptor ✓ ✓

Indications

Disorders of Excessive Somnolence Narcolepsy Sleep Apnea, Obstructive

Activity Summary

Ki 9 meas. best 9.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 9.04 9.04 0.9 1
Histamine H3 receptor
CHEMBL264
 Ki 8.36 7.96 4.4 2
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 8.15 8.15 7.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 6.05 6.05 899.3 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 5.96 5.96 1100.4 1
Histamine H1 receptor
CHEMBL231
 Ki 5.92 5.92 1200.5 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.72 5.72 1919.1 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.7 5.7 1987.9 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 0.9043 nM 9.04 PDSP Secondary Binding target: SIGMAR1 - Compounds are tested at 10 uM concentra... -
Histamine H3 receptor Ki = 4.361 nM 8.36 PDSP Secondary Binding target: HRH3 - Compounds are tested at 10 uM concentratio... -
Sigma intracellular receptor 2 Ki = 7.014 nM 8.15 PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat... -
Histamine H3 receptor Ki = 27.6 nM 7.56 Displacement of [3]-RAMH from recombinant human histamine H3 receptor expressed ... 30629436
Muscarinic acetylcholine receptor M4 Ki = 899.29 nM 6.05 PDSP Secondary Binding target: CHRM4 - Compounds are tested at 10 uM concentrati... -
5-hydroxytryptamine receptor 7 Ki = 1100.4 nM 5.96 PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio... -
Histamine H1 receptor Ki = 1200.47 nM 5.92 PDSP Secondary Binding target: HRH1 - Compounds are tested at 10 uM concentratio... -
Sodium-dependent noradrenaline transporter Ki = 1919.11 nM 5.72 PDSP Secondary Binding target: SLC6A2 - Compounds are tested at 10 uM concentrat... -
5-hydroxytryptamine receptor 2C Ki = 1987.93 nM 5.7 PDSP Secondary Binding target: HTR2C - Compounds are tested at 10 uM concentrati... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724696 U2OS 24
- 10.6019/CHEMBL5724696 TERT-RPE1 24
- 10.6019/CHEMBL4689842 HEK-293T 9
- 10.6019/CHEMBL4689842 U2OS 6
- 10.6019/CHEMBL4689842 Fibroblast 4
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 2
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 2
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 2
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 2
- 10.6019/CHEMBL5060014 Peregrin 1

Data from ChEMBL 36 via Core Engine