Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C24H40N8O4.2C7H8O3S |
| Molecular Weight | 849.029 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O.CC2=CC=C(C=C2)S(O)(=O)=O.OCCN(CCO)C3=NC4=C(N=C(N=C4C(=N3)N5CCCCC5)N(CCO)CCO)N6CCCCC6
InChI
InChIKey=YFHSNCOUDBQMCI-UHFFFAOYSA-N
InChI=1S/C24H40N8O4.2C7H8O3S/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;2*1-6-2-4-7(5-3-6)11(8,9)10/h33-36H,1-18H2;2*2-5H,1H3,(H,8,9,10)
| Molecular Formula | C24H40N8O4 |
| Molecular Weight | 504.6256 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C7H8O3S |
| Molecular Weight | 172.202 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00975Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/012836s057lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00975
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/012836s057lbl.pdf
Dipyridamole, a non-nitrate coronary vasodilator that also inhibits platelet aggregation, is combined with other anticoagulant drugs, such as warfarin, to prevent thrombosis in patients with valvular or vascular disorders. Dipyridamole is also used in myocardial perfusion imaging, as an antiplatelet agent, and in combination with aspirin for stroke prophylaxis. Dipyridamole likely inhibits both adenosine deaminase and phosphodiesterase, preventing the degradation of cAMP, an inhibitor of platelet function. This elevation in cAMP blocks the release of arachidonic acid from membrane phospholipids and reduces thromboxane A2 activity. Dipyridamole also directly stimulates the release of prostacyclin, which induces adenylate cyclase activity, thereby raising the intraplatelet concentration of cAMP and further inhibiting platelet aggregation. Used for as an adjunct to coumarin anticoagulants in the prevention of postoperative thromboembolic complications of cardiac valve replacement and also used in prevention of angina.
CNS Activity
Sources: https://web.archive.org/web/20170215181448/http://files.boehringer.com.au/files/PI/Persantin%20100%20PI.pdf
Curator's Comment: Dipyridamole does not cross the blood brain barrier.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17636949 |
144.8 nM [IC50] | ||
Target ID: CHEMBL4409 Sources: http://www.drugbank.ca/drugs/DB00975 |
1.2 µM [IC50] | ||
Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8254606 |
0.52 µM [IC50] | ||
Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873613 |
0.5 µM [IC50] | ||
Target ID: CHEMBL1910 Sources: http://www.drugbank.ca/drugs/DB00975 |
45.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Persantine Approved UsePersantine (dipyridamole USP) tablets are indicated as an adjunct to coumarin anticoagulants in the prevention
of postoperative thromboembolic complications of cardiac valve replacement. Launch Date1961 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
475 ng/mL |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1881 ng/mL |
200 mg 2 times / 2 weeks multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2781 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2825745 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2492 ng × h/mL |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15030 ng × h/mL |
200 mg 2 times / 2 weeks multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15779 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2825745 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10.3 h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.74 h |
200 mg 2 times / 2 weeks multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
DIPYRIDAMOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1750 mg single, oral Overdose |
healthy, 23 |
Disc. AE: Loss of consciousness, Respiratory distress... AEs leading to discontinuation/dose reduction: Loss of consciousness Sources: Respiratory distress Apnea Coma |
8 g single, oral Overdose |
healthy, 58 |
Disc. AE: Tachycardia, Hypotension... AEs leading to discontinuation/dose reduction: Tachycardia Sources: Hypotension Multi-organ failure Delirium Anuria Renal failure |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 61 |
Disc. AE: Headache, Diarrhoea... AEs leading to discontinuation/dose reduction: Headache (9.1%) Sources: Diarrhoea (3.5%) Nausea (1.5%) Vomiting (2%) Dyspepsia (1.5%) |
5 g single, oral Overdose |
unhealthy, 62 |
Disc. AE: Myocardial infarction... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Apnea | Disc. AE | 1750 mg single, oral Overdose |
healthy, 23 |
| Coma | Disc. AE | 1750 mg single, oral Overdose |
healthy, 23 |
| Loss of consciousness | Disc. AE | 1750 mg single, oral Overdose |
healthy, 23 |
| Respiratory distress | Disc. AE | 1750 mg single, oral Overdose |
healthy, 23 |
| Anuria | Disc. AE | 8 g single, oral Overdose |
healthy, 58 |
| Delirium | Disc. AE | 8 g single, oral Overdose |
healthy, 58 |
| Hypotension | Disc. AE | 8 g single, oral Overdose |
healthy, 58 |
| Multi-organ failure | Disc. AE | 8 g single, oral Overdose |
healthy, 58 |
| Renal failure | Disc. AE | 8 g single, oral Overdose |
healthy, 58 |
| Tachycardia | Disc. AE | 8 g single, oral Overdose |
healthy, 58 |
| Dyspepsia | 1.5% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 61 |
| Nausea | 1.5% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 61 |
| Vomiting | 2% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 61 |
| Diarrhoea | 3.5% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 61 |
| Headache | 9.1% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 61 |
| Myocardial infarction | Disc. AE | 5 g single, oral Overdose |
unhealthy, 62 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [Activation 27.71665 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
| yes [Activation 1.2589 uM] | ||||
| yes [Activation 10 uM] | ||||
| yes [Activation 10 uM] | ||||
| yes [Activation 5.0119 uM] | ||||
| yes [IC50 2.6 uM] | ||||
| yes [IC50 26 uM] | ||||
| yes [IC50 30 uM] | ||||
| yes [IC50 4 uM] | ||||
| yes [IC50 4.8 uM] | ||||
| yes [IC50 40 uM] | ||||
| yes [IC50 74 uM] | ||||
| yes [IC50 8.3 uM] | ||||
| yes [IC50 81 uM] | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
Page: 7.0 |
yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of power Doppler and digital subtraction techniques on the comparison of myocardial contrast echocardiography with SPECT. | 2001-05 |
|
| Saphenous vein endothelial cell viability: a comparative study of endoscopic and open saphenectomy for coronary artery bypass grafting. | 2001-04-17 |
|
| Antiplatelet agents in tissue factor-induced blood coagulation. | 2001-04-15 |
|
| Adenosine permeation of a dynamic in vitro blood-brain barrier inhibited by dipyridamole. | 2001-04-13 |
|
| Preliminary clinical results of photon energy recovery in simultaneous rest Tl-201/stress Tc-99m sestamibi myocardial SPECT. | 2001-04-11 |
|
| Prognostic value of dipyridamole SPECT imaging in low-risk patients after myocardial infarction. | 2001-04-11 |
|
| Dipyridamole myocardial SPECT with low heart rate response indicates cardiac autonomic dysfunction in patients with diabetes. | 2001-04-11 |
|
| Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block. | 2001-04-01 |
|
| Antithrombotic drugs for secondary stroke prophylaxis. | 2001-04 |
|
| Repeated thromboembolic and bleeding events after mechanical aortic valve replacement. | 2001-04 |
|
| Heterogeneity of resting and hyperemic myocardial blood flow in healthy humans. | 2001-04 |
|
| Safety, feasibility, and prognostic implications of pharmacologic stress echocardiography in 1482 patients evaluated in an ambulatory setting. | 2001-04 |
|
| Incremental prognostic value of stress echocardiography as an adjunct to exercise electrocardiography after uncomplicated myocardial infarction. | 2001-04 |
|
| Effect of dipyridamole on ischemia and reperfusion injury of canine liver. | 2001-03-27 |
|
| Activation of glutamate uptake by guanosine in primary astrocyte cultures. | 2001-03-26 |
|
| Usefulness of oral dipyridamole therapy for angiographic slow coronary artery flow. | 2001-03-15 |
|
| Echocardiographic assessment of viable myocardium. | 2001-03-10 |
|
| Stress echocardiography: technical considerations. | 2001-03-10 |
|
| Safety, feasibility, and diagnostic accuracy of accelerated high-dose dipyridamole stress echocardiography. | 2001-03-01 |
|
| Action of dipyridamole and warfarin on growth of human endothelial cells cultured in serum-free media. | 2001-03 |
|
| [Reporting echocardiography exams with the G8-Cardio ANMCO software]. | 2001-03 |
|
| Progressive intracranial vascular disease with strokes and seizures in a boy with progeria. | 2001-03 |
|
| Dipyridamole-atropine stress echocardiography versus exercise SPECT scintigraphy for detection of coronary artery disease in hypertensives with positive exercise test. | 2001-03 |
|
| Use of dobutamine stress echocardiography in determination of myocardial viability. | 2001-03 |
|
| An abnormal dipyridamole thallium/sestamibi fails to predict long-term cardiac events in vascular surgery patients. | 2001-03 |
|
| Abnormal renal vascular responses to dipyridamole-induced vasodilation in spontaneously hypertensive rats. | 2001-03 |
|
| Global myocardial blood flow and global flow reserve measurements by MRI and PET are comparable. | 2001-03 |
|
| Myocardial flow reserve parametric map, assessed by first-pass MRI compartmental analysis at the chronic stage of infarction. | 2001-03 |
|
| Coronary flow reserve in angiographically normal coronary arteries with one-vessel coronary artery disease without traditional risk factors. | 2001-03 |
|
| Antiarrhythmic effects of adenosine on ischemia-induced ventricular fibrillation. | 2001-03 |
|
| Aggrenox and stress testing. | 2001-02-27 |
|
| Peripheral flow response to transient arterial forearm occlusion does not reflect myocardial perfusion reserve. | 2001-02-27 |
|
| Hypoxanthine transport in human tumour cell lines: relationship to the inhibition of hypoxanthine rescue by dipyridamole. | 2001-02-15 |
|
| Extracellular adenosine-induced apoptosis in mouse neuroblastoma cells: studies on involvement of adenosine receptors and adenosine uptake. | 2001-02-15 |
|
| Assessment of the effect of revascularization early after CABG using ECG-gated perfusion single-photon emission tomography. | 2001-02 |
|
| Preoperative dipyridamole-thallium scanning, selective coronary revascularization and long-term survival in patients with critical lower limb ischemia. | 2001-02 |
|
| The use of L-arginine [correction of F-arginine] and phosphodiesterase inhibitor (dipyridamole) to wean from inhaled nitric oxide. | 2001-02 |
|
| Newer antiplatelet therapies in stroke prevention. | 2001-02 |
|
| Antiplatelet therapy in the elderly. Aspirin, ticlopidine-clopidogrel, and GPIIb/GPIIIa antagonists. | 2001-02 |
|
| Antithrombotic therapy in valvular heart disease. | 2001-02 |
|
| Risks and benefits of adding anti-platelet therapy to warfarin among patients with prosthetic heart valves: a meta-analysis. | 2001-02 |
|
| Enhanced detection of reversible perfusion defects by Tc-99m sestamibi compared to Tc-99m tetrofosmin during vasodilator stress SPECT imaging in mild-to-moderate coronary artery disease. | 2001-02 |
|
| Quantification of myocardial perfusion in human subjects using 82Rb and wavelet-based noise reduction. | 2001-02 |
|
| Use of wavelet transforms in analysis of time-activity data from cardiac PET. | 2001-02 |
|
| Automated assessment of dipyridamole 201Tl myocardial SPECT perfusion scintigraphy by case-based reasoning. | 2001-02 |
|
| Predictive value of cardiac autonomic neuropathy in diabetic patients with or without silent myocardial ischemia. | 2001-02 |
|
| Paravertebral venous plexus distention (Batson's): an inciting etiologic agent in lumbar radiculopathy as observed by venous angiography. | 2001-02 |
|
| Serial evaluation of coronary flow reserve by transesophageal doppler echocardiography after angioplasty of proximal left anterior descending coronary artery: a 6-month follow-up study. | 2001-02 |
|
| Inhibitors of the Cl-/HCO3- exchanger activate an apical anion conductance with similar features in the epithelial cells of rabbit gallbladder: analysis in intact epithelium. | 2001-01 |
|
| Myocardial contrast echocardiography: a new gold standard for perfusion imaging? | 2001-01 |
Sample Use Guides
Adjunctive Use in Prophylaxis of Thromboembolism after Cardiac Valve Replacement. The recommended dose is 75-100 mg four times daily as an adjunct to the usual warfarin therapy.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16103157
Mengovirus plaque formation in HeLa or L cells was inhibited nearly 100% by the presence of 80 uM dipyridamole.
| Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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on
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| Record UNII |
832L5C4A2V
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| Record Status |
Validated (UNII)
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| Record Version |
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