Trade Names:
Synonyms:
Status: Approved (2014)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: N05CM19
UNII: 081L192FO9

Structure

InChI Key JYTNQNCOQXFQPK-MRXNPFEDSA-N
Smile Cc1ccc(-n2nccn2)c(C(=O)N2CCN(c3nc4cc(Cl)ccc4o3)CC[C@H]2C)c1
InChI
InChI=1S/C23H23ClN6O2/c1-15-3-5-20(30-25-8-9-26-30)18(13-15)22(31)29-12-11-28(10-7-16(29)2)23-27-19-14-17(24)4-6-21(19)32-23/h3-6,8-9,13-14,16H,7,10-12H2,1-2H3/t16-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H23ClN6O2
Molecular Weight 450.93
AlogP 4.11
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 80.29
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 32.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Orexin receptor antagonist FDA
Primary Target
OX1 receptor
OX2 receptor

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Delirium 3 D003693 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Restless Legs Syndrome 2 D012148 ClinicalTrials
Sleep Wake Disorders 2 D012893 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Smoking Cessation 2 D016540 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Sleep Apnea Syndromes 1 D012891 ClinicalTrials
Tobacco Use Disorder 1 D014029 ClinicalTrials

Side Effects from Label

Adverse Reactions

System Organ Classification (SOC)
Relative Frequency (%)
Psychiatric disorders
26.5
General disorders and administration site conditions
24.43
Nervous system disorders
22.81
Injury, poisoning and procedural complications
6.17
Gastrointestinal disorders
3.42
Cardiac disorders
2.72
Musculoskeletal and connective tissue disorders
2.17
Vascular disorders
2.08
Respiratory, thoracic and mediastinal disorders
2.02

Cross References

Resources Reference
CAS NUMBER 1030377-33-3
ChEBI 82698
ChEMBL CHEMBL1083659
DrugBank DB09034
DrugCentral 4881
EPA CompTox DTXSID90145616
FDA SRS 081L192FO9
Guide to Pharmacology 2890
PDB SUV
PubChem 24965990
SureChEMBL SCHEMBL1586289
ZINC ZINC000049036447