Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H40N8O4 |
Molecular Weight | 504.6256 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCN(CCO)C1=NC2=C(N=C(N=C2C(=N1)N3CCCCC3)N(CCO)CCO)N4CCCCC4
InChI
InChIKey=IZEKFCXSFNUWAM-UHFFFAOYSA-N
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
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 |
---|---|---|---|---|
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 |
|
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 |
|
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 |
---|---|---|---|---|
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 |
|
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 |
|
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 |
---|---|---|---|---|
10.74 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 |
|
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 |
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 Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Disc. AE: Loss of consciousness, Respiratory distress... AEs leading to discontinuation/dose reduction: Loss of consciousness Sources: Page: p.75Respiratory distress Apnea Coma |
8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Disc. AE: Tachycardia, Hypotension... AEs leading to discontinuation/dose reduction: Tachycardia Sources: Page: e15Hypotension 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: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Disc. AE: Headache, Diarrhoea... AEs leading to discontinuation/dose reduction: Headache (9.1%) Sources: Page: p.1786Diarrhoea (3.5%) Nausea (1.5%) Vomiting (2%) Dyspepsia (1.5%) |
5 g single, oral Overdose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: Page: p.62 |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Angina pectoris Age Group: 62 Sex: F Population Size: 1 Sources: Page: p.62 |
Disc. AE: Myocardial infarction... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: Page: p.62 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Apnea | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Coma | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Loss of consciousness | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Respiratory distress | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Anuria | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Delirium | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Hypotension | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Multi-organ failure | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Renal failure | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Tachycardia | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
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: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
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: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
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: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
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: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
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: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Myocardial infarction | Disc. AE | 5 g single, oral Overdose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: Page: p.62 |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Angina pectoris Age Group: 62 Sex: F Population Size: 1 Sources: Page: p.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 |
---|---|---|
[Severe bradyarrhythmia during myocardial perfusion scintigraphy with injection of dipyridamole (Persantine)]. | 1999 Feb |
|
Reduced vasodilator capacity in syndrome X related to structure and function of resistance arteries. | 1999 Jan 15 |
|
Nucleoside transport in human colonic epithelial cell lines: evidence for two Na+-independent transport systems in T84 and Caco-2 cells. | 1999 Jun 9 |
|
Inhibition of Alzheimer's beta-amyloid induced vasoactivity and proinflammatory response in microglia by a cGMP-dependent mechanism. | 1999 May |
|
A1 adenosine receptor activation increases adipocyte leptin secretion. | 2000 Apr |
|
[Myocardial perfusion at rest and during stress. MR signal characteristics of persistent and reversible myocardial ischemia]. | 2000 Feb |
|
Cloning and characterization of PDE7B, a cAMP-specific phosphodiesterase. | 2000 Jan 4 |
|
Persistent myocardial ischemia after termination of dipyridamole-induced ventricular tachycardia by intravenous aminophylline: scintigraphic demonstration. | 2000 Mar |
|
Identification of human PDE7B, a cAMP-specific phosphodiesterase. | 2000 May 19 |
|
Heterogeneity of resting and hyperemic myocardial blood flow in healthy humans. | 2001 Apr |
|
Safety, feasibility, and prognostic implications of pharmacologic stress echocardiography in 1482 patients evaluated in an ambulatory setting. | 2001 Apr |
|
Characterization of TbPDE2A, a novel cyclic nucleotide-specific phosphodiesterase from the protozoan parasite Trypanosoma brucei. | 2001 Apr 13 |
|
Antiplatelet agents in tissue factor-induced blood coagulation. | 2001 Apr 15 |
|
The use of L-arginine [correction of F-arginine] and phosphodiesterase inhibitor (dipyridamole) to wean from inhaled nitric oxide. | 2001 Feb |
|
Extracellular adenosine-induced apoptosis in mouse neuroblastoma cells: studies on involvement of adenosine receptors and adenosine uptake. | 2001 Feb 15 |
|
Effect of dipyridamole on ischemia and reperfusion injury of canine liver. | 2001 Feb-Mar |
|
Functional testing for the detection of restenosis after percutaneous transluminal coronary angioplasty: a meta-analysis. | 2001 Jan |
|
The transport of a reversible proton pump antagonist, 5, 6-dimethyl-2-(4-Fluorophenylamino)-4-(1-methyl-1,2,3, 4-tetrahydroisoquinoline-2-yl) pyrimidine hydrochloride (YH1885), across caco-2 cell monolayers. | 2001 Jan |
|
Cloning of a novel isoform of the mouse NBMPR-sensitive equilibrative nucleoside transporter (ENT1) lacking a putative phosphorylation site. | 2001 Jan 10 |
|
High prevalence of myocardial perfusion abnormalities on positron emission tomography in asymptomatic persons with a parent or sibling with coronary artery disease. | 2001 Jan 30 |
|
Nucleoside transport inhibition in ischemic myocardium results in enhanced taurine efflux. | 2001 Jan 5 |
|
Abnormal renal vascular responses to dipyridamole-induced vasodilation in spontaneously hypertensive rats. | 2001 Mar |
|
Antiarrhythmic effects of adenosine on ischemia-induced ventricular fibrillation. | 2001 Mar |
|
Preliminary clinical results of photon energy recovery in simultaneous rest Tl-201/stress Tc-99m sestamibi myocardial SPECT. | 2001 Mar-Apr |
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C744
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NDF-RT |
N0000008832
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NDF-RT |
N0000175578
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NDF-RT |
N0000008832
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WHO-ATC |
B01AC07
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WHO-VATC |
QB01AC07
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CHEMBL932
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C445
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DB00975
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4807
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200-374-7
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4653
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64ALC7F90C
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1220506
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64ALC7F90C
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D004176
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924
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SUB07229MIG
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m4658
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3521
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515776
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1545
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3108
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58-32-2
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DIPYRIDAMOLE
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100000091735
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Dipyridamole
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DTXSID6040668
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ACTIVE MOIETY