TRANDOLAPRIL

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: C09AA10
UNII: 1T0N3G9CRC

Structure
InChI Key VXFJYXUZANRPDJ-WTNASJBWSA-N
Smile CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@@H]21
InChI
InChI=1S/C24H34N2O5/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29)/t16-,18+,19-,20-,21-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H34N2O5
Molecular Weight 430.55
AlogP 2.77
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 95.94
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 31.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Angiotensin-converting enzyme inhibitor DailyMed
Primary Target
Angiotensin-converting enzyme
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M2 family
- 1 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 102

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Heart Failure 4 D006333 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Respiratory, thoracic and mediastinal disorders Cough 35.0
Cardiac disorders Dizziness 23.0
Respiratory, thoracic and mediastinal disorders Cough
Cardiac disorders Dizziness
Vascular disorders Hypotension 11.0
Investigations Blood urea increased 9.0
Investigations Blood urea increased
Vascular disorders Hypotension
Gastrointestinal disorders Dyspepsia 6.4
Gastrointestinal disorders Dyspepsia
Cardiac disorders Dizziness 5.9
Nervous system disorders Loss of consciousness 5.9
Vascular disorders Shock 5.9
Cardiac disorders Syncope 5.9
Metabolism and nutrition disorders Hyperkalaemia 5.3
Nervous system disorders Headache 4.9
Respiratory, thoracic and mediastinal disorders Cough 4.8
Investigations Blood creatinine increased 4.7
Cardiac disorders Bradycardia 4.7
Metabolism and nutrition disorders Hypocalcaemia 4.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.7
Musculoskeletal and connective tissue disorders Myalgia 4.7
Cardiac disorders Bradycardia
Gastrointestinal disorders Gastritis 4.2
Infections and infestations Bronchitis 3.9
Respiratory, thoracic and mediastinal disorders Cough 3.9
Metabolism and nutrition disorders Hypocalcaemia
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 3.9
Cardiac disorders Cardiogenic shock 3.8
Vascular disorders Intermittent claudication 3.8
Gastrointestinal disorders Gastritis
Infections and infestations Upper respiratory tract infection 3.4
General disorders and administration site conditions Asthenia 3.3
Nervous system disorders Cerebrovascular accident 3.3
Cardiac disorders Dizziness
Nervous system disorders Loss of consciousness
Vascular disorders Shock
Cardiac disorders Syncope
Nervous system disorders Cerebrovascular accident
General disorders and administration site conditions Asthenia 3.1
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Metabolism and nutrition disorders Hyperkalaemia
General disorders and administration site conditions Asthenia
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 2.6
Cardiac disorders Dizziness 2.6
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 2.6
Investigations Blood creatinine increased
Cardiac disorders Dizziness 2.4
Nervous system disorders Headache 2.31
Nervous system disorders Nervous system disorder 2.31
Nervous system disorders Headache 2.3
Vascular disorders Angiopathy 2.1
General disorders and administration site conditions Asthenia 2.1
Vascular disorders Hypotension 2.1
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 2.01
Cardiac disorders Cardiogenic shock
Vascular disorders Intermittent claudication
Cardiac disorders Dizziness 1.9
Nervous system disorders Nervous system disorder 1.9
Cardiac disorders Dizziness 1.7
Vascular disorders Hypotension 1.5
Infections and infestations Urinary tract infection 1.5
Cardiac disorders Dizziness
Nervous system disorders Nervous system disorder
Infections and infestations Rhinitis 1.4
Skin and subcutaneous tissue disorders Dermatitis 1.2
Gastrointestinal disorders Gastrointestinal pain 1.2
Skin and subcutaneous tissue disorders Rash 1.2
Gastrointestinal disorders Gastrointestinal disorder 1.15
Gastrointestinal disorders Nausea 1.15
Gastrointestinal disorders Diarrhoea 1.1
General disorders and administration site conditions Discomfort 1.1
General disorders and administration site conditions Feeling abnormal 1.1
General disorders and administration site conditions Ill-defined disorder 1.1
General disorders and administration site conditions Malaise 1.1
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Cardiac disorders Palpitations 0.7
Vascular disorders Angiopathy
Vascular disorders Hypotension
General disorders and administration site conditions Discomfort 0.5
General disorders and administration site conditions Feeling abnormal 0.5
Nervous system disorders Headache
Vascular disorders Hypotension 0.5
General disorders and administration site conditions Ill-defined disorder 0.5
General disorders and administration site conditions Malaise 0.5
Gastrointestinal disorders Nausea 0.5
Nervous system disorders Nervous system disorder
Skin and subcutaneous tissue disorders Pruritus 0.5
Skin and subcutaneous tissue disorders Dermatitis 0.4
Skin and subcutaneous tissue disorders Rash 0.4
Infections and infestations Bronchitis 0.3
Gastrointestinal disorders Diarrhoea 0.2
Infections and infestations Upper respiratory tract infection 0.2
Gastrointestinal disorders Gastrointestinal pain 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
13.36
Cardiac disorders
10.76
Vascular disorders
9.75
Respiratory, thoracic and mediastinal disorders
8.99
General disorders and administration site conditions
8.49
Skin and subcutaneous tissue disorders
8.07
Gastrointestinal disorders
6.89
Psychiatric disorders
5.63
Immune system disorders
5.21
Investigations
5.21
Musculoskeletal and connective tissue disorders
4.37
Injury, poisoning and procedural complications
2.94

Cross References

Resources Reference
CAS NUMBER 87679-37-6
ChEBI 9649
ChEMBL CHEMBL1519
DrugBank DB00519
DrugCentral 2712
EPA CompTox DTXSID2023692
FDA SRS 1T0N3G9CRC
Human Metabolome Database HMDB0014660
Guide to Pharmacology 6453
KEGG D00383
PharmGKB PA451737
PubChem 5484727
SureChEMBL SCHEMBL16610
ZINC ZINC000001853205
CONTENTS