AMBRISENTAN

Search structure
Trade Names:
Synonyms:
Status: Approved (2007)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: C02KX02
UNII: HW6NV07QEC

Structure
InChI Key OUJTZYPIHDYQMC-LJQANCHMSA-N
Smile COC(c1ccccc1)(c1ccccc1)[C@H](Oc1nc(C)cc(C)n1)C(=O)O
InChI
InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H22N2O4
Molecular Weight 378.43
AlogP 3.52
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 81.54
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Endothelin receptor, ET-A/ET-B antagonist DailyMed
Primary Target
ETA receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Slow voltage-gated potassium channel accessory protein family
- 63096 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 63096 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor
- 1-22 81-2344 - 43
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
31600-31600 - - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Vascular Diseases 3 D014652 ClinicalTrials
Hypoplastic Left Heart Syndrome 2 D018636 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Altitude Sickness 2 D000532 ClinicalTrials
Anemia, Sickle Cell 1 D000755 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Cardiac disorders Oedema peripheral 28.4
Nervous system disorders Headache 19.4
Cardiac disorders Oedema peripheral 18.5
Cardiac disorders Oedema peripheral 17.2
Nervous system disorders Headache 15.4
Nervous system disorders Headache 14.6
Nervous system disorders Headache
Cardiac disorders Right ventricular failure
Cardiac disorders Oedema peripheral
Respiratory, thoracic and mediastinal disorders Nasal congestion 10.4
Cardiac disorders Dizziness
Gastrointestinal disorders Nausea
Cardiac disorders Dizziness 8.96
Cardiac disorders Dyspnoea 7.69
Respiratory, thoracic and mediastinal disorders Cough 7.46
Infections and infestations Upper respiratory tract infection 7.46
Cardiac disorders Dizziness 6.92
Respiratory, thoracic and mediastinal disorders Cough
Cardiac disorders Dyspnoea
Infections and infestations Upper respiratory tract infection
Infections and infestations Urinary tract infection
Gastrointestinal disorders Constipation 5.97
Respiratory, thoracic and mediastinal disorders Epistaxis 5.97
Respiratory, thoracic and mediastinal disorders Nasal congestion 5.75
General disorders and administration site conditions Asthenia 5.38
Respiratory, thoracic and mediastinal disorders Cough 5.38
Cardiac disorders Dyspnoea 5.38
General disorders and administration site conditions Fatigue 5.38
Respiratory, thoracic and mediastinal disorders Nasal congestion 5.38
Infections and infestations Nasopharyngitis 5.38
Respiratory, thoracic and mediastinal disorders Pulmonary hypertension
Infections and infestations Bronchitis 4.62
Cardiac disorders Chest pain 4.62
Cardiac disorders Right ventricular failure 4.62
Infections and infestations Upper respiratory tract infection 4.62
Cardiac disorders Palpitations 4.6
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Asthenia 4.48
Cardiac disorders Dyspnoea 4.48
General disorders and administration site conditions Fatigue 4.48
Gastrointestinal disorders Nausea 4.48
Cardiac disorders Palpitations 4.48
Infections and infestations Sinusitis 4.48
Cardiac disorders Dyspnoea 4.21
General disorders and administration site conditions Flushing 3.85
Gastrointestinal disorders Nausea 3.85
Cardiac disorders Palpitations 3.85
Gastrointestinal disorders Constipation 3.83
General disorders and administration site conditions Flushing 3.83
Musculoskeletal and connective tissue disorders Arthralgia
Investigations Aspartate aminotransferase increased
Infections and infestations Bronchitis
Respiratory, thoracic and mediastinal disorders Epistaxis
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Infections and infestations Nasopharyngitis 3.45
Gastrointestinal disorders Abdominal pain 3.08
Gastrointestinal disorders Constipation 3.08
Gastrointestinal disorders Gastrointestinal pain 3.08
Infections and infestations Sinusitis 3.08
Gastrointestinal disorders Abdominal pain 3.07
Gastrointestinal disorders Gastrointestinal pain 3.07
Infections and infestations Sinusitis 3.07
Cardiac disorders Dyspnoea
Nervous system disorders Insomnia
Gastrointestinal disorders Abdominal pain 2.99
Musculoskeletal and connective tissue disorders Arthralgia 2.99
Investigations Aspartate aminotransferase increased 2.99
Gastrointestinal disorders Gastrointestinal pain 2.99
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.99
Infections and infestations Nasopharyngitis 2.99
Nervous system disorders Insomnia 2.31
Cardiac disorders Chest pain
Cardiac disorders Palpitations
Investigations Aspartate aminotransferase increased 1.54
Respiratory, thoracic and mediastinal disorders Epistaxis 1.54
Infections and infestations Urinary tract infection 1.54
Gastrointestinal disorders Constipation
Respiratory, thoracic and mediastinal disorders Nasal congestion
Infections and infestations Bronchitis 1.49
Cardiac disorders Chest pain 1.49
Cardiac disorders Dyspnoea 1.49
General disorders and administration site conditions Flushing 1.49
Nervous system disorders Insomnia 1.49
Respiratory, thoracic and mediastinal disorders Pulmonary hypertension 1.49
Cardiac disorders Right ventricular failure 1.49
Infections and infestations Urinary tract infection 1.49
Musculoskeletal and connective tissue disorders Arthralgia 0.769
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.769
Respiratory, thoracic and mediastinal disorders Pulmonary hypertension 0.769
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Flushing
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Nasopharyngitis

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Respiratory, thoracic and mediastinal disorders
16.37
General disorders and administration site conditions
15.89
Cardiac disorders
13.3
Nervous system disorders
7.03
Vascular disorders
6.92
Gastrointestinal disorders
5.51
Metabolism and nutrition disorders
5.41
Infections and infestations
5.39
Investigations
3.58
Injury, poisoning and procedural complications
3.51
Musculoskeletal and connective tissue disorders
3.21
Skin and subcutaneous tissue disorders
3.08
Renal and urinary disorders
2.37

Cross References

Resources Reference
CAS NUMBER 177036-94-1
ChEBI 135949
ChEMBL CHEMBL1111
DrugBank DB06403
DrugCentral 4337
EPA CompTox DTXSID4046282
FDA SRS HW6NV07QEC
Guide to Pharmacology 3951
KEGG D07077
PubChem 6918493
SureChEMBL SCHEMBL3679
ZINC ZINC000000538627
CONTENTS