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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
Structure of DIPYRIDAMOLE DITOSYLATE

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)

HIDE SMILES / InChI

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

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
144.8 nM [IC50]
1.2 µM [IC50]
0.52 µM [IC50]
0.5 µM [IC50]
45.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Persantine

Approved Use

Persantine (dipyridamole USP) tablets are indicated as an adjunct to coumarin anticoagulants in the prevention of postoperative thromboembolic complications of cardiac valve replacement.

Launch Date

1961
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
DIPYRIDAMOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1750 mg single, oral
Overdose
Dose: 1750 mg
Route: oral
Route: single
Dose: 1750 mg
Sources:
healthy, 23
Health Status: healthy
Age Group: 23
Sex: F
Sources:
Disc. AE: Loss of consciousness, Respiratory distress...
AEs leading to
discontinuation/dose reduction:
Loss of consciousness
Respiratory distress
Apnea
Coma
Sources:
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
Disc. AE: Tachycardia, Hypotension...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Hypotension
Multi-organ failure
Delirium
Anuria
Renal failure
Sources:
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
Health Status: unhealthy
Age Group: 61
Sex: M+F
Sources:
Disc. AE: Headache, Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Headache (9.1%)
Diarrhoea (3.5%)
Nausea (1.5%)
Vomiting (2%)
Dyspepsia (1.5%)
Sources:
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: F
Sources:
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Sources:
AEs

AEs

AESignificanceDosePopulation
Apnea Disc. AE
1750 mg single, oral
Overdose
Dose: 1750 mg
Route: oral
Route: single
Dose: 1750 mg
Sources:
healthy, 23
Health Status: healthy
Age Group: 23
Sex: F
Sources:
Coma Disc. AE
1750 mg single, oral
Overdose
Dose: 1750 mg
Route: oral
Route: single
Dose: 1750 mg
Sources:
healthy, 23
Health Status: healthy
Age Group: 23
Sex: F
Sources:
Loss of consciousness Disc. AE
1750 mg single, oral
Overdose
Dose: 1750 mg
Route: oral
Route: single
Dose: 1750 mg
Sources:
healthy, 23
Health Status: healthy
Age Group: 23
Sex: F
Sources:
Respiratory distress Disc. AE
1750 mg single, oral
Overdose
Dose: 1750 mg
Route: oral
Route: single
Dose: 1750 mg
Sources:
healthy, 23
Health Status: healthy
Age Group: 23
Sex: F
Sources:
Anuria Disc. AE
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
Delirium Disc. AE
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
Hypotension Disc. AE
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
Multi-organ failure Disc. AE
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
Renal failure Disc. AE
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
Tachycardia Disc. AE
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 58
Health Status: healthy
Age Group: 58
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 61
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 61
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 61
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 61
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 61
Sex: M+F
Sources:
Myocardial infarction Disc. AE
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: F
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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 victimTox targets
PubMed

PubMed

TitleDatePubMed
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
Patents

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
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 Tue Apr 01 19:25:32 GMT 2025
Edited
by admin
on Tue Apr 01 19:25:32 GMT 2025
Record UNII
832L5C4A2V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,2',2'',2'''-((4,8-DIPIPERIDINOPYRIMIDO(5,4-D)PYRIMIDINE-2,6-DIYL)DINITRILO)TETRAETHANOL BIS(TOLUENE-P-SULFONATE)
Preferred Name English
DIPYRIDAMOLE DITOSYLATE
Common Name English
Ethanol, 2,2?,2??,2???-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-, bis(4-methylbenzenesulfonate) (salt)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID80198116
Created by admin on Tue Apr 01 19:25:32 GMT 2025 , Edited by admin on Tue Apr 01 19:25:32 GMT 2025
PRIMARY
PUBCHEM
6452173
Created by admin on Tue Apr 01 19:25:32 GMT 2025 , Edited by admin on Tue Apr 01 19:25:32 GMT 2025
PRIMARY
CAS
49845-74-1
Created by admin on Tue Apr 01 19:25:32 GMT 2025 , Edited by admin on Tue Apr 01 19:25:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
256-501-1
Created by admin on Tue Apr 01 19:25:32 GMT 2025 , Edited by admin on Tue Apr 01 19:25:32 GMT 2025
PRIMARY
FDA UNII
832L5C4A2V
Created by admin on Tue Apr 01 19:25:32 GMT 2025 , Edited by admin on Tue Apr 01 19:25:32 GMT 2025
PRIMARY
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