Structure

InChI Key DGBIGWXXNGSACT-UHFFFAOYSA-N
Smile O=C1CN=C(c2ccccc2Cl)c2cc([N+](=O)[O-])ccc2N1
InChI
InChI=1S/C15H10ClN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H10ClN3O3
Molecular Weight 315.72
AlogP 3.04
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 84.6
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
POSITIVE ALLOSTERIC MODULATOR GABA-A receptor; anion channel positive allosteric modulator PubMed PubMed PubMed Wikipedia
Primary Target
GABAA receptor α1 subunit
GABAA receptor α2 subunit
GABAA receptor α3 subunit
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor
- 2-2 - 1-1 100

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Panic Disorder 4 D016584 ClinicalTrials
Epilepsy 4 D004827 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Status Epilepticus 3 D013226 ClinicalTrials
Epilepsy, Tonic-Clonic 3 D004830 ClinicalTrials
Epilepsia Partialis Continua 3 D017036 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
REM Sleep Behavior Disorder 2 D020187 ClinicalTrials
Marijuana Abuse 2 D002189 ClinicalTrials
Neuralgia 1 D009437 ClinicalTrials
Burning Mouth Syndrome 0 D002054 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Somnolence 50.0
Nervous system disorders Somnolence 37.0
Nervous system disorders Ataxia 30.0
Psychiatric disorders Abnormal behaviour 25.0
Gastrointestinal disorders Salivary hypersecretion 10.0
Nervous system disorders Somnolence
General disorders and administration site conditions Asthenia 8.0
Cardiac disorders Dizziness 8.0
General disorders and administration site conditions Fatigue 8.0
Infections and infestations Upper respiratory tract infection 8.0
General disorders and administration site conditions Asthenia 7.0
Psychiatric disorders Depression 7.0
General disorders and administration site conditions Fatigue 7.0
Nervous system disorders Somnolence 7.0
Nervous system disorders Coordination abnormal 6.0
Nervous system disorders Ataxia 5.0
Nervous system disorders Muscular weakness 5.0
Ear and labyrinth disorders Vertigo 5.0
General disorders and administration site conditions Asthenia
Psychiatric disorders Depression 4.0
Cardiac disorders Dizziness
General disorders and administration site conditions Fatigue
Infections and infestations Influenza 4.0
Nervous system disorders Memory impairment 4.0
Infections and infestations Sinusitis 4.0
Infections and infestations Upper respiratory tract infection
Reproductive system and breast disorders Dysmenorrhoea 3.0
Infections and infestations Influenza
Psychiatric disorders Nervousness 3.0
Infections and infestations Sinusitis
Psychiatric disorders Tension 3.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 2.0
Respiratory, thoracic and mediastinal disorders Cough 2.0
Nervous system disorders Dysarthria 2.0
Reproductive system and breast disorders Dysmenorrhoea
Immune system disorders Hypersensitivity 2.0
Nervous system disorders Memory impairment
Psychiatric disorders Nervousness
Musculoskeletal and connective tissue disorders Osteoarthritis 2.0
Gastrointestinal disorders Pharyngitis 2.0
Infections and infestations Rhinitis 2.0
Psychiatric disorders Tension
Nervous system disorders Confusional state 1.9
General disorders and administration site conditions Feeling abnormal 1.9
Nervous system disorders Agitation 1.5
General disorders and administration site conditions Irritability 1.5
Psychiatric disorders Aggression 1.4
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 1.0
Psychiatric disorders Affect lability
Psychiatric disorders Affect lability 1.0
Nervous system disorders Ataxia 1.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 1.0
Nervous system disorders Confusional state 1.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 1.0
Psychiatric disorders Depression
Psychiatric disorders Disturbance in sexual arousal 1.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 1.0
Reproductive system and breast disorders Dysmenorrhoea
Reproductive system and breast disorders Dysmenorrhoea 1.0
Reproductive system and breast disorders Ejaculation delayed 1.0
Psychiatric disorders Erectile dysfunction 1.0
General disorders and administration site conditions Feeling abnormal 1.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 1.0
Immune system disorders Hypersensitivity
Psychiatric disorders Libido decreased 1.0
Psychiatric disorders Mood swings
Psychiatric disorders Mood swings 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 1.0
Psychiatric disorders Nervousness 1.0
Gastrointestinal disorders Pharyngitis
Renal and urinary disorders Pollakiuria 1.0
Infections and infestations Rhinitis
Nervous system disorders Somnolence
Psychiatric disorders Tension 1.0
Infections and infestations Urinary tract infection 1.0
Infections and infestations Vaginal infection
Infections and infestations Vaginal infection 1.0
Vaginal inflammation
Vaginal inflammation 1.0
Eye disorders Vision blurred
Eye disorders Vision blurred 1.0
Eye disorders Visual impairment
Eye disorders Visual impairment 1.0
Nervous system disorders Agitation 0.7

Adverse Reactions

System Organ Classification (SOC)
Relative Frequency (%)
Psychiatric disorders
19.27
Nervous system disorders
17.17
General disorders and administration site conditions
14.57
Injury, poisoning and procedural complications
7.69
Gastrointestinal disorders
5.3
Respiratory, thoracic and mediastinal disorders
4.62
Musculoskeletal and connective tissue disorders
4.41
Cardiac disorders
4.0
Investigations
3.34
Vascular disorders
3.13
Skin and subcutaneous tissue disorders
2.95

Cross References

Resources Reference
CAS NUMBER 1622-61-3
ChEBI 3756
ChEMBL CHEMBL452
DrugBank DB01068
DrugCentral 703
EPA CompTox DTXSID1022845
FDA SRS 5PE9FDE8GB
Human Metabolome Database HMDB0015201
Guide to Pharmacology 6963
KEGG D00280
PharmGKB PA449050
PubChem 2802
SureChEMBL SCHEMBL38899
ZINC ZINC000003813003