DIPYRIDAMOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (1961)
Entry Type: Small molecule
Molecule Category: Parent
ATC: B01AC07
UNII: 64ALC7F90C

Structure
InChI Key IZEKFCXSFNUWAM-UHFFFAOYSA-N
Smile OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1
InChI
InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H40N8O4
Molecular Weight 504.64
AlogP -0.02
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 12.0
Polar Surface Area 145.44
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 36.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 2.740 - EST
Atmospheric OH Rate Constant 3.11E-10 cm3/molecule-sec EST
Melting Point 163 deg C EXP

Pharmacology

Action Mechanism of Action Reference
INHIBITOR 3',5'-cyclic phosphodiesterase inhibitor DailyMed Wikipedia PubMed
Primary Target
Equilibrative nucleoside transporter 1
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1A
- 45000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1B
- 45000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1C
- 45000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 10 Phosphodiesterase 10A
- - - 1000 -
Enzyme Phosphodiesterase Phosphodiesterase 11 Phosphodiesterase 11A
- - - 400 16-92
Enzyme Phosphodiesterase Phosphodiesterase 2 Phosphodiesterase 2A
- 3240-4000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3A
- 43000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3B
- 43000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- 5270-6400 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- 500 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- 500 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- 500 - - -
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
- 520-574 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6A
- - - 125 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6B
- - - 125 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6C
- - - 125 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6D
- - - 125 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6G
- - - 125 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6H
- - - 125 -
Enzyme Phosphodiesterase Phosphodiesterase 7 Phosphodiesterase 7A
- - - 600 -
Enzyme Phosphodiesterase Phosphodiesterase 7 Phosphodiesterase 7B
- - - 600 3-92
Enzyme Phosphodiesterase Phosphodiesterase 8 Phosphodiesterase 8A
- - - - 13-88
Enzyme
- 3240-4000 - 1000 13-88
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 18
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- - - - 82
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 89-92
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 2600 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC28 and SLC29 families of nucleoside transporters SLC29 Facilitative nucleoside transporter family
- 145 - 8-9 87
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 26000 - - -
Transporter Electrochemical transporter
- 145 - 8-9 89-92
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 4000 - - 5
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 8300 - - 95

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Coronary Disease 4 D003327 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Angina, Stable 3 D060050 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Carotid Stenosis 2 D016893 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Heart Diseases 2 D006331 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Takotsubo Cardiomyopathy 2 D054549 ClinicalTrials
Purpura, Schoenlein-Henoch 1 D011695 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Hypertension 1 D006973 ClinicalTrials

Related Entries

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Cardiac disorders Angina pectoris 19.7
Cardiac disorders Chest pain 19.7
Immune system disorders Bronchospasm 15.0
Cardiac disorders Dizziness 13.6
Nervous system disorders Headache 12.2
Cardiac disorders Dizziness 11.8
Gastrointestinal disorders Diarrhoea 9.3
Nervous system disorders Transient ischaemic attack 9.0
Investigations Electrocardiogram abnormal 7.5
Cardiac disorders Ventricular fibrillation 7.0
Cardiac disorders Ventricular tachycardia 7.0
Gastrointestinal disorders Vomiting 6.6
Gastrointestinal disorders Abdominal discomfort 6.1
Investigations Electrocardiogram abnormal 5.2
Cardiac disorders Extrasystoles 5.2
Cardiac disorders Ventricular extrasystoles 5.2
Vascular disorders Hypotension 4.6
Gastrointestinal disorders Nausea 4.6
General disorders and administration site conditions Flushing 3.4
Investigations Electrocardiogram abnormal 3.2
Cardiac disorders Tachycardia 3.2
Cardiac disorders Dyspnoea 2.6
General disorders and administration site conditions Pain 2.6
Skin and subcutaneous tissue disorders Dermatitis 2.3
Nervous system disorders Headache 2.3
Skin and subcutaneous tissue disorders Rash 2.3
Vascular disorders Hypertension 1.5
Nervous system disorders Paraesthesia 1.3
General disorders and administration site conditions Asthenia 1.2
General disorders and administration site conditions Fatigue 1.2
Cardiac disorders Cardiac arrest 1.0
Gastrointestinal disorders Dyspepsia 1.0
Cardiac disorders Pulmonary oedema 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.9
Musculoskeletal and connective tissue disorders Myalgia 0.9
Gastrointestinal disorders Dry mouth 0.8
Gastrointestinal disorders Abdominal pain 0.7
Gastrointestinal disorders Gastrointestinal pain 0.7
Musculoskeletal and connective tissue disorders Back pain 0.6
Gastrointestinal disorders Flatulence 0.6
General disorders and administration site conditions Hyperhidrosis 0.4
Gastrointestinal disorders Vomiting 0.4
Musculoskeletal and connective tissue disorders Arthralgia 0.3
General disorders and administration site conditions Asthenia 0.3
General disorders and administration site conditions Discomfort 0.3
General disorders and administration site conditions Feeling abnormal 0.3
Musculoskeletal and connective tissue disorders Hypertonia 0.3
General disorders and administration site conditions Ill-defined disorder 0.3
General disorders and administration site conditions Malaise 0.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.3
Cardiac disorders Palpitations 0.3
Gastrointestinal disorders Pharyngitis 0.3
Psychiatric disorders Anxiety 0.2
Cardiac disorders Bradycardia 0.2
Cardiac disorders Atrial fibrillation 0.1
Cardiac disorders Atrioventricular block 0.1
General disorders and administration site conditions Chills 0.1
Cardiac disorders Dizziness 0.1
Gastrointestinal disorders Dysgeusia 0.1
Ear and labyrinth disorders Ear pain 0.1
Gastrointestinal disorders Eructation 0.1
Psychiatric disorders Hyperventilation 0.1
General disorders and administration site conditions Injection site pain 0.1
Nervous system disorders Loss of consciousness 0.1
Nervous system disorders Orthostatic hypotension 0.1
Infections and infestations Rhinitis 0.1
Vascular disorders Shock 0.1
Cardiac disorders Supraventricular tachycardia 0.1
Cardiac disorders Syncope 0.1
Ear and labyrinth disorders Tinnitus 0.1
Nervous system disorders Tremor 0.1
Gastrointestinal disorders Anorectal discomfort 0.03
Reproductive system and breast disorders Breast pain 0.03
Cardiac disorders Cardiomyopathy 0.03
Nervous system disorders Coordination abnormal 0.03
Respiratory, thoracic and mediastinal disorders Cough 0.03
Depersonalisation 0.03
Gastrointestinal disorders Dysphagia 0.03
Nervous system disorders Dysphonia 0.03
Eye disorders Eye pain 0.03
General disorders and administration site conditions Increased appetite 0.03
Vascular disorders Intermittent claudication 0.03
Nervous system disorders Migraine 0.03
Musculoskeletal and connective tissue disorders Muscle spasms 0.03
General disorders and administration site conditions Oedema 0.03
Reproductive system and breast disorders Perineal pain 0.03
Respiratory, thoracic and mediastinal disorders Pleuritic pain 0.03
Gastrointestinal disorders Proctalgia 0.03
Gastrointestinal disorders Rectal tenesmus 0.03
Renal and urinary disorders Renal pain 0.03
Nervous system disorders Somnolence 0.03
General disorders and administration site conditions Thirst 0.03
Ear and labyrinth disorders Vertigo 0.03

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
22.35
Nervous system disorders
16.79
Cardiac disorders
7.6
Gastrointestinal disorders
7.18
Respiratory, thoracic and mediastinal disorders
6.84
Injury, poisoning and procedural complications
6.3
General disorders and administration site conditions
5.93
Infections and infestations
3.94
Psychiatric disorders
3.18
Blood and lymphatic system disorders
2.47
Surgical and medical procedures
2.38
Musculoskeletal and connective tissue disorders
2.35
Skin and subcutaneous tissue disorders
2.21

Cross References

Resources Reference
CAS NUMBER 58-32-2
ChEBI 4653
ChEMBL CHEMBL932
DrugBank DB00975
DrugCentral 924
EPA CompTox DTXSID6040668
FDA SRS 64ALC7F90C
Human Metabolome Database HMDB0015110
Guide to Pharmacology 4807
PharmGKB PA449367
PubChem 3108
SureChEMBL SCHEMBL16119
ZINC ZINC000000643046
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