TREPROSTINIL

Search structure
Trade Names:
Synonyms:
Status: Approved (2002)
Entry Type: Small molecule
Molecule Category: Parent
ATC: B01AC21
UNII: RUM6K67ESG

Structure
InChI Key PAJMKGZZBBTTOY-ZFORQUDYSA-N
Smile CCCCC[C@H](O)CC[C@@H]1[C@H]2Cc3cccc(OCC(=O)O)c3C[C@H]2C[C@H]1O
InChI
InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H34O5
Molecular Weight 390.52
AlogP 3.58
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 10.0
Polar Surface Area 86.99
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Prostanoid IP receptor agonist PubMed
Primary Target
IP receptor

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Familial Primary Pulmonary Hypertension 3 D065627 ClinicalTrials
Peripheral Vascular Diseases 2 D016491 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Ischemia 2 D007511 ClinicalTrials
Hernias, Diaphragmatic, Congenital 2 D065630 ClinicalTrials
Persistent Fetal Circulation Syndrome 2 D010547 ClinicalTrials
Respiratory Distress Syndrome 2 D012128 ClinicalTrials
Diabetic Foot 1 D017719 ClinicalTrials
Scleroderma, Systemic 1 D012595 ClinicalTrials
Reperfusion Injury 1 D015427 ClinicalTrials
Raynaud Disease 0 D011928 ClinicalTrials

Related Entries

Scaffolds

Salt
Salt
UNKNOWN

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Infusion site pain 85.0
General disorders and administration site conditions Infusion site reaction 83.0
Nervous system disorders Headache 63.0
Respiratory, thoracic and mediastinal disorders Cough 53.9
Nervous system disorders Headache 40.9
Gastrointestinal disorders Diarrhoea 30.0
Gastrointestinal disorders Nausea 30.0
Respiratory, thoracic and mediastinal disorders Cough
Nervous system disorders Headache 27.0
General disorders and administration site conditions Infusion site pain
General disorders and administration site conditions Infusion site reaction
Respiratory, thoracic and mediastinal disorders Laryngeal pain 25.2
Gastrointestinal disorders Throat irritation 25.2
Gastrointestinal disorders Diarrhoea 25.0
Nervous system disorders Headache
Nervous system disorders Headache
Gastrointestinal disorders Nausea 22.0
Gastrointestinal disorders Nausea 19.1
Nervous system disorders Headache
Gastrointestinal disorders Nausea
Gastrointestinal disorders Diarrhoea
General disorders and administration site conditions Flushing 15.0
General disorders and administration site conditions Flushing 14.8
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Gastrointestinal disorders Throat irritation
Skin and subcutaneous tissue disorders Dermatitis 14.0
Musculoskeletal and connective tissue disorders Pain in extremity 14.0
Skin and subcutaneous tissue disorders Rash 14.0
Musculoskeletal and connective tissue disorders Pain in jaw 13.0
Skin and subcutaneous tissue disorders Dermatitis
Musculoskeletal and connective tissue disorders Pain in jaw 11.0
Skin and subcutaneous tissue disorders Rash
Gastrointestinal disorders Nausea
Cardiac disorders Dizziness 9.0
Metabolism and nutrition disorders Hypokalaemia 9.0
General disorders and administration site conditions Oedema 9.0
Cardiac disorders Dizziness
Musculoskeletal and connective tissue disorders Pain in extremity
Skin and subcutaneous tissue disorders Pruritus 8.0
Cardiac disorders Dizziness 6.09
Nervous system disorders Loss of consciousness 6.09
Vascular disorders Shock 6.09
Cardiac disorders Syncope 6.09
Gastrointestinal disorders Abdominal discomfort 6.0
General disorders and administration site conditions Flushing
Skin and subcutaneous tissue disorders Pruritus
Musculoskeletal and connective tissue disorders Pain in jaw
Vascular disorders Hypotension 4.0
Musculoskeletal and connective tissue disorders Pain in jaw
Metabolism and nutrition disorders Hypokalaemia
General disorders and administration site conditions Oedema
Vascular disorders Hypotension
Renal and urinary disorders Haematuria
Renal and urinary disorders Haematuria 0.847
Cardiac disorders Dizziness
General disorders and administration site conditions Flushing
Nervous system disorders Loss of consciousness
Vascular disorders Shock
Cardiac disorders Syncope
Gastrointestinal disorders Nausea 0.0909
Gastrointestinal disorders Vomiting 0.0909
Respiratory, thoracic and mediastinal disorders Epistaxis 0.0904
General disorders and administration site conditions Decreased appetite 0.0592
Metabolism and nutrition disorders Hypokalaemia 0.0316
Gastrointestinal disorders Melaena 0.0316
Gastrointestinal disorders Diarrhoea 0.0091
General disorders and administration site conditions Oedema 0.0026
Musculoskeletal and connective tissue disorders Pain in jaw 0.001
General disorders and administration site conditions Infusion site pain 0.0001
General disorders and administration site conditions Infusion site reaction 0.0001

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
18.66
Injury, poisoning and procedural complications
10.87
Respiratory, thoracic and mediastinal disorders
10.6
Cardiac disorders
9.18
Gastrointestinal disorders
6.96
Vascular disorders
6.85
Infections and infestations
5.92
Nervous system disorders
5.54
Skin and subcutaneous tissue disorders
5.17
Metabolism and nutrition disorders
3.77
Musculoskeletal and connective tissue disorders
3.48
Investigations
3.06

Cross References

Resources Reference
CAS NUMBER 81846-19-7
ChEBI 50861
ChEMBL CHEMBL1237119
DrugBank DB00374
DrugCentral 2720
FDA SRS RUM6K67ESG
Human Metabolome Database HMDB0014518
Guide to Pharmacology 5820
PubChem 6918140
SureChEMBL SCHEMBL4349618
ZINC ZINC000003800475
CONTENTS