U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DIPYRIDAMOLE

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

HIDE SMILES / InChI

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
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
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
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
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
10.74 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

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: 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
Respiratory distress
Apnea
Coma
Sources: Page: p.75
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
Hypotension
Multi-organ failure
Delirium
Anuria
Renal failure
Sources: Page: e15
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%)
Diarrhoea (3.5%)
Nausea (1.5%)
Vomiting (2%)
Dyspepsia (1.5%)
Sources: Page: p.1786
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

AEs

AESignificanceDosePopulation
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

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
[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
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.
Name Type Language
DIPYRIDAMOLE
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
DIPYRIDAMOLE [ORANGE BOOK]
Common Name English
B01AC07
Code English
DIPYRIDAMOLE [MART.]
Common Name English
AGGRENOX COMPONENT DIPYRIDAMOLE
Common Name English
DIPYRIDAMOLE [VANDF]
Common Name English
Dipyridamole [WHO-DD]
Common Name English
DIPYRIDAMOLE [EP MONOGRAPH]
Common Name English
dipyridamole [INN]
Common Name English
RA-8
Code English
DIPYRIDAMOLE [USAN]
Common Name English
PERSANTINE
Brand Name English
DIPYRIDAMOLE COMPONENT OF AGGRENOX
Common Name English
DIPYRIDAMOLE [USP MONOGRAPH]
Common Name English
DIPYRIDAMOLE [MI]
Common Name English
DIPYRIDAMOLE [USP-RS]
Common Name English
DIPYRIDAMOLE [JAN]
Common Name English
NSC-515776
Code English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
NDF-RT N0000175578
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
WHO-ATC B01AC07
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
WHO-VATC QB01AC07
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL932
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
NCI_THESAURUS
C445
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
DRUG BANK
DB00975
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
IUPHAR
4807
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-374-7
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
CHEBI
4653
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
FDA UNII
64ALC7F90C
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
RS_ITEM_NUM
1220506
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PRIMARY
DAILYMED
64ALC7F90C
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
MESH
D004176
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PRIMARY
DRUG CENTRAL
924
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PRIMARY
EVMPD
SUB07229MIG
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
MERCK INDEX
m4658
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY Merck Index
RXCUI
3521
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY RxNorm
NSC
515776
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
INN
1545
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
PUBCHEM
3108
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
CAS
58-32-2
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
WIKIPEDIA
DIPYRIDAMOLE
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
SMS_ID
100000091735
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
LACTMED
Dipyridamole
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID6040668
Created by admin on Sat Dec 16 16:21:22 GMT 2023 , Edited by admin on Sat Dec 16 16:21:22 GMT 2023
PRIMARY