TADALAFIL

Search structure
Trade Names:
Synonyms:
Status: Approved (2003)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G04BE08
UNII: 742SXX0ICT

Structure
InChI Key WOXKDUGGOYFFRN-IIBYNOLFSA-N
Smile CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c2ccc3c(c2)OCO3)C1=O
InChI
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H19N3O4
Molecular Weight 389.41
AlogP 2.21
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 74.87
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Phosphodiesterase 5A inhibitor DailyMed
Primary Target
phosphodiesterase 5A
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 26159 - - -
Enzyme Phosphodiesterase Phosphodiesterase 11 Phosphodiesterase 11A
- 10-60000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
78 1-9 - 5-10 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6A
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6B
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6C
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6D
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6G
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6H
- 980-5200 - - -
Enzyme
78 1-9 - 5-10 0
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 79433-100000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Erectile Dysfunction 4 D007172 ClinicalTrials
Muscular Dystrophy, Duchenne 3 D020388 ClinicalTrials
Raynaud Disease 3 D011928 ClinicalTrials
Glucose Intolerance 3 D018149 ClinicalTrials
Insulin Resistance 3 D007333 ClinicalTrials
Lung Diseases, Interstitial 3 D017563 ClinicalTrials
Heart Defects, Congenital 3 D006330 ClinicalTrials
Transposition of Great Vessels 3 D014188 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Scleroderma, Systemic 2 D012595 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Diabetes Mellitus, Type 2 2 D003924 ClinicalTrials
Obesity 2 D009765 ClinicalTrials
Gastroparesis 2 D018589 ClinicalTrials
Stroke 2 D020521 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Cushing Syndrome 2 D003480 ClinicalTrials
Dementia, Vascular 2 D015140 ClinicalTrials
Essential Hypertension 2 D000075222 ClinicalTrials
Eisenmenger Complex 2 D004541 ClinicalTrials
Priapism 2 D011317 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Heart Failure 1 D006333 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Head and Neck Neoplasms 0 D006258 ClinicalTrials
Muscular Dystrophies 0 D009136 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 42.0
Nervous system disorders Headache 32.0
Nervous system disorders Headache
Nervous system disorders Headache 15.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 14.0
Musculoskeletal and connective tissue disorders Myalgia 14.0
Gastrointestinal disorders Dyspepsia 13.0
General disorders and administration site conditions Flushing 13.0
Infections and infestations Nasopharyngitis 13.0
Infections and infestations Respiratory tract infection 13.0
Musculoskeletal and connective tissue disorders Back pain 12.0
Gastrointestinal disorders Diarrhoea 11.0
Nervous system disorders Headache 11.0
Gastrointestinal disorders Nausea 11.0
Musculoskeletal and connective tissue disorders Pain in extremity 11.0
Musculoskeletal and connective tissue disorders Back pain 10.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Dyspepsia 10.0
Gastrointestinal disorders Nausea 10.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 9.0
Cardiac disorders Dizziness
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 9.0
Musculoskeletal and connective tissue disorders Myalgia 9.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 9.0
Cardiac disorders Oedema peripheral
Respiratory, thoracic and mediastinal disorders Pulmonary hypertension
Respiratory, thoracic and mediastinal disorders Sinus congestion 9.0
Cardiac disorders Dizziness 8.0
Gastrointestinal disorders Dyspepsia 8.0
Respiratory, thoracic and mediastinal disorders Pulmonary hypertension 8.0
Infections and infestations Nasopharyngitis
Infections and infestations Respiratory tract infection 7.0
General disorders and administration site conditions Asthenia 6.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 6.0
Cardiac disorders Chest pain 6.0
Cardiac disorders Dyspnoea 6.0
General disorders and administration site conditions Fatigue 6.0
General disorders and administration site conditions Flushing 6.0
Nervous system disorders Headache 6.0
Infections and infestations Nasopharyngitis 6.0
Gastrointestinal disorders Nausea
Cardiac disorders Oedema peripheral 6.0
Infections and infestations Respiratory tract infection
Infections and infestations Upper respiratory tract infection 6.0
Gastrointestinal disorders Vomiting 6.0
Musculoskeletal and connective tissue disorders Back pain 5.0
Infections and infestations Bronchitis 5.0
Skin and subcutaneous tissue disorders Dermatitis 5.0
Gastrointestinal disorders Dyspepsia 5.0
Gastrointestinal disorders Gastroenteritis 5.0
Gastrointestinal disorders Gastrooesophageal reflux disease 5.0
Nervous system disorders Headache
Infections and infestations Influenza 5.0
Infections and infestations Nasopharyngitis
General disorders and administration site conditions Oedema 5.0
Musculoskeletal and connective tissue disorders Pain in extremity 5.0
Skin and subcutaneous tissue disorders Rash 5.0
Infections and infestations Respiratory tract infection 5.0
Gastrointestinal disorders Viral diarrhoea 5.0
Nervous system disorders Headache 4.1
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Constipation 4.0
Respiratory, thoracic and mediastinal disorders Cough 4.0
Gastrointestinal disorders Dyspepsia 4.0
Cardiac disorders Dyspnoea
Respiratory, thoracic and mediastinal disorders Epistaxis
Respiratory, thoracic and mediastinal disorders Epistaxis 4.0
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrooesophageal reflux disease
General disorders and administration site conditions Hot flush 4.0
Nervous system disorders Insomnia 4.0
Reproductive system and breast disorders Menopausal symptoms 4.0
Reproductive system and breast disorders Menorrhagia 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal stiffness 4.0
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 4.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 4.0
Infections and infestations Nasopharyngitis
Infections and infestations Nasopharyngitis 4.0
General disorders and administration site conditions Non-cardiac chest pain 4.0
General disorders and administration site conditions Therapeutic response unexpected 4.0
Infections and infestations Upper respiratory tract infection
Infections and infestations Upper respiratory tract infection 4.0
Infections and infestations Urinary tract infection 4.0
Reproductive system and breast disorders Uterine haemorrhage 4.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 3.0
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Dyspepsia 3.0
General disorders and administration site conditions Flushing 3.0
Gastrointestinal disorders Gastroenteritis 3.0
Gastrointestinal disorders Gastrooesophageal reflux disease 3.0
Nervous system disorders Headache 3.0
Vascular disorders Hypertension 3.0
Infections and infestations Influenza
Infections and infestations Influenza 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Myalgia 3.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 3.0
Infections and infestations Nasopharyngitis 3.0
Musculoskeletal and connective tissue disorders Pain in extremity 3.0
Skin and subcutaneous tissue disorders Rash
Infections and infestations Respiratory tract infection
Infections and infestations Upper respiratory tract infection 3.0
Gastrointestinal disorders Viral diarrhoea 3.0
Musculoskeletal and connective tissue disorders Back pain 2.4
Gastrointestinal disorders Dyspepsia 2.4
Nervous system disorders Headache
Infections and infestations Nasopharyngitis 2.1
Gastrointestinal disorders Abdominal pain 2.0
Musculoskeletal and connective tissue disorders Back pain 2.0
Infections and infestations Bronchitis 2.0
Respiratory, thoracic and mediastinal disorders Cough 2.0
Gastrointestinal disorders Diarrhoea 2.0
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Flushing
General disorders and administration site conditions Flushing 2.0
Gastrointestinal disorders Gastroenteritis
Gastrointestinal disorders Gastrointestinal pain 2.0
Gastrointestinal disorders Gastrooesophageal reflux disease 2.0
General disorders and administration site conditions Hot flush
Infections and infestations Influenza
Infections and infestations Influenza 2.0
Nervous system disorders Insomnia
Reproductive system and breast disorders Menopausal symptoms
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.0
Infections and infestations Nasopharyngitis 2.0
Musculoskeletal and connective tissue disorders Pain in extremity
Musculoskeletal and connective tissue disorders Pain in extremity 2.0
Infections and infestations Urinary tract infection 2.0
Gastrointestinal disorders Viral diarrhoea
Cardiac disorders Dizziness 1.7
Infections and infestations Nasopharyngitis
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Diarrhoea 1.4
Musculoskeletal and connective tissue disorders Pain in extremity 1.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.2
Musculoskeletal and connective tissue disorders Myalgia 1.2
Gastrointestinal disorders Abdominal pain 1.0
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Bronchitis
Cardiac disorders Chest pain
Gastrointestinal disorders Constipation
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 1.0
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 1.0
General disorders and administration site conditions Flushing
General disorders and administration site conditions Flushing 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Gastrointestinal disorders Gastrooesophageal reflux disease 1.0
Vascular disorders Hypertension 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
Respiratory, thoracic and mediastinal disorders Nasal congestion
General disorders and administration site conditions Oedema
Musculoskeletal and connective tissue disorders Pain in extremity
Musculoskeletal and connective tissue disorders Pain in extremity 1.0
Respiratory, thoracic and mediastinal disorders Sinus congestion
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Vomiting
Cardiac disorders Dizziness
Eye disorders Conjunctival hyperaemia 0.3
Eye disorders Eye pain 0.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Gastrointestinal disorders Dyspepsia

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
13.4
Nervous system disorders
10.96
Respiratory, thoracic and mediastinal disorders
9.27
Cardiac disorders
8.05
Vascular disorders
7.14
Gastrointestinal disorders
6.46
Injury, poisoning and procedural complications
5.79
Musculoskeletal and connective tissue disorders
5.41
Skin and subcutaneous tissue disorders
5.37
Eye disorders
4.75
Investigations
3.34
Psychiatric disorders
3.34
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.95
Infections and infestations
2.78
Metabolism and nutrition disorders
2.38
Reproductive system and breast disorders
2.34
Renal and urinary disorders
2.23

Cross References

Resources Reference
CAS NUMBER 171596-29-5
ChEBI 71940
ChEMBL CHEMBL779
DrugBank DB00820
DrugCentral 2553
EPA CompTox DTXSID9046786
FDA SRS 742SXX0ICT
Human Metabolome Database HMDB0014958
Guide to Pharmacology 7299
KEGG D02008
PDB CIA
PharmGKB PA10333
PubChem 110635
SureChEMBL SCHEMBL33333
ZINC ZINC000003993855
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