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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL462605
CHEMBL462605
Compound Name PITOLISANT
ChEMBL Synonyms Wakix | BF2.649 | Tiprolisant | Pitolisant
Max Phase 4 (Approved)
Trade Names Wakix
Molecular Formula C17H26ClNO

Additional synonyms for CHEMBL462605 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Clc1ccc(CCCOCCCN2CCCCC2)cc1
Standard InChI InChI=1S/C17H26ClNO/c18-17-9-7-16(8-10-17)6-4-14-20-15-5-13- ...
Download InChI
Standard InChI Key NNACHAUCXXVJSP-UHFFFAOYSA-N

Sources

  • Clinical Candidates
  • Scientific Literature
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL462605

Molecule Features

CHEMBL462605 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Unknown

Mechanism of Action

Mechanism of Action ChEMBL Target References
Histamine H3 receptor inverse agonist Histamine H3 receptor PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
SchizophreniaD012559EFO:0000692schizophrenia2ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease3ClinicalTrials
Substance-Related DisordersD019966EFO:0003890drug dependence1ClinicalTrials
NarcolepsyD009290EFO:0000614narcolepsy with cataplexy3ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials

Clinical Data

ClinicalTrials.gov PITOLISANT
The Cochrane Collaboration PITOLISANT

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL462605. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL264 Histamine H3 receptor Homo sapiens 1.000
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 1.000
CHEMBL4124 Histamine H3 receptor Rattus norvegicus 1.000
CHEMBL4153 Sigma-1 receptor Cavia porcellus 1.000
CHEMBL287 Sigma opioid receptor Homo sapiens 1.000
CHEMBL5076 Histamine H3 receptor Cavia porcellus 1.000
CHEMBL3361 Dopamine D4 receptor Rattus norvegicus 1.000
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 1.000
CHEMBL4777 Neuropeptide Y receptor type 1 Homo sapiens 1.000
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 1.000
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.999
CHEMBL313 Serotonin transporter Rattus norvegicus 0.999
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 0.998
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.997
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.996
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.996
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.995
CHEMBL338 Dopamine transporter Rattus norvegicus 0.995
CHEMBL228 Serotonin transporter Homo sapiens 0.985



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL264 Histamine H3 receptor Homo sapiens 1.000
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 1.000
CHEMBL4124 Histamine H3 receptor Rattus norvegicus 1.000
CHEMBL4153 Sigma-1 receptor Cavia porcellus 1.000
CHEMBL287 Sigma opioid receptor Homo sapiens 1.000
CHEMBL5076 Histamine H3 receptor Cavia porcellus 1.000
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL3241 Histamine N-methyltransferase Rattus norvegicus 1.000
CHEMBL3361 Dopamine D4 receptor Rattus norvegicus 1.000
CHEMBL4777 Neuropeptide Y receptor type 1 Homo sapiens 1.000
CHEMBL219 Dopamine D4 receptor Homo sapiens 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.999
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 0.999
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 0.999
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.999
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.999
CHEMBL240 HERG Homo sapiens 0.998
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.997
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.996

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
295.9 295.1703 4.17 8 12.47 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 0 0 2 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.41 4.41 2.43 1 20 0.67

Structural Alerts

There are 3 structural alerts for CHEMBL462605. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N07 - OTHER NERVOUS SYSTEM DRUGS
N07X - OTHER NERVOUS SYSTEM DRUGS
N07XX - Other nervous system drugs
N07XX11 - pitolisant

ChemSpider ChemSpider:NNACHAUCXXVJSP-UHFFFAOYSA-N
Wikipedia Pitolisant

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL462605



BindingDB 50247053
ChEBI 134709
DrugBank DB11642
DrugCentral 5048
FDA SRS 4BC83L4PIY
Guide to Pharmacology 8924
IBM Patent System 8CA8E2A87C02F19C81D9B0D85B5C1123
MolPort MolPort-035-936-409
Nikkaji J1.574.747A
PubChem 9948102
PubChem: Thomson Pharma 14922700
SureChEMBL SCHEMBL117648
ZINC ZINC000034045468

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/NNACHAUCXXVJSP-UHFFFAOYSA-N spacer
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