Compound Detail

CHEMBL932

DIPYRIDAMOLE

💊 Approved Drug

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

💊 Approved Drug

OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL932
Name	DIPYRIDAMOLE
Phase	Approved
Structure Type	MOL
InChI Key	IZEKFCXSFNUWAM-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Attia B01AC07 Cerebrovase 100 Cerebrovase 25 Dipiridamol Dipyridamole Dipyridamole component of aggrenox Iv persantine Modaplate NSC-515776 Ofcram pr Persantin +5 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

504.6

MW (Da)

-0.02

ALogP

HBA

HBD

145.4

PSA (Å²)

0.31

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1961
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Year

1963

Extended Properties

Molecular Formula	C24H40N8O4
MW	504.64
Aromatic Rings	2
Heavy Atoms	36
NP-Likeness	-0.52

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Equilibrative nucleoside transporter 1 inhibitor	INHIBITOR	Equilibrative nucleoside transporter 1	✓	✓
3',5'-cyclic phosphodiesterase inhibitor	INHIBITOR	3',5'-cyclic phosphodiesterase	✓	✓

Indications

Coronary Artery Disease Stroke Thrombosis Angina, Stable Cardiovascular Diseases Heart Diseases Myocardial Ischemia Severe Acute Respiratory Syndrome Anemia, Sickle Cell Arthritis, Rheumatoid Carotid Stenosis Ovarian Neoplasms Pancreatic Neoplasms HIV Infections Hypertension IgA Vasculitis

ATC Classification

B01AC07

dipyridamole

Level 1: BLOOD AND BLOOD FORMING ORGANS

Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 56 meas. best 8.09

Ki 10 meas. best 8.09

EC50 1 meas. best 7.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Equilibrative nucleoside transporter 1 CHEMBL1997	IC50	8.09	7.465	8.1	2
Equilibrative nucleoside transporter 1 CHEMBL1997	Ki	8.09	8.075	8.2	2
Unchecked CHEMBL612545	IC50	7.82	5.8788	15.0	8
Unchecked CHEMBL612545	Ki	7.54	6.3667	29.0	3
Replicase polyprotein 1ab CHEMBL4523582	Ki	7.4	7.4	40.0	1
SARS-CoV-2 CHEMBL4303835	EC50	7.0	7.0	100.0	1
Phosphodiesterase 6 CHEMBL2097163	Ki	6.9	6.9	125.0	1
L1210 CHEMBL386	IC50	6.47	6.47	340.0	1
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A CHEMBL2717	Ki	6.4	6.4	400.0	1
Phosphodiesterase 4 CHEMBL2093863	IC50	6.3	5.925	500.0	2
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	6.28	6.0233	520.0	3
Replicase polyprotein 1ab CHEMBL4523582	IC50	6.22	6.22	600.0	1
Phosphodiesterase 7 CHEMBL2111411	IC50	6.22	6.22	600.0	1
Phosphodiesterase 7 CHEMBL2111411	Ki	6.22	6.22	600.0	1
Exopolyphosphatase PRUNE1 CHEMBL2079850	IC50	6.11	6.11	780.0	1
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A CHEMBL4409	Ki	6.0	6.0	1000.0	1
Plasmodium falciparum CHEMBL364	IC50	5.89	5.3311	1300.0	9
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	5.7	5.39	2000.0	2
Solute carrier family 22 member 2 CHEMBL1743122	IC50	5.58	5.58	2600.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	5.55	5.55	2800.0	1
cGMP-dependent 3',5'-cyclic phosphodiesterase CHEMBL2652	IC50	5.49	5.4433	3240.0	3
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A CHEMBL4640	IC50	5.4	5.4	4000.0	1
Bile salt export pump CHEMBL6020	IC50	5.4	5.4	4000.0	1
Phosphodiesterase 4A CHEMBL3333	IC50	5.28	5.235	5270.0	2
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.19	5.19	6400.0	1
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358	IC50	5.16	5.16	6956.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	5.13	5.13	7450.0	1
Heat shock protein HSP90 CHEMBL2095165	IC50	4.68	4.68	21068.2	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.64	4.5733	22700.0	3
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	4.58	4.58	26000.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.53	4.53	29330.0	1
ATP-binding cassette sub-family C member 5 CHEMBL2046258	IC50	4.52	4.52	30000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.41	4.41	38640.0	1
Phosphodiesterase 3 CHEMBL2094125	IC50	4.37	4.37	43000.0	1
Phosphodiesterase 3A CHEMBL3061	IC50	4.36	4.36	44000.0	1
Phosphodiesterase 1 CHEMBL2095150	IC50	4.35	4.35	45000.0	1
Leishmania donovani CHEMBL367	IC50	4.21	4.21	62020.0	1
Multidrug and toxin extrusion protein 2 CHEMBL1743127	IC50	4.13	4.13	74000.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.09	4.09	81000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	3440.64	ng.hr.mL-1	Homo sapiens
Cmax	3960.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Equilibrative nucleoside transporter 1	Ki	=	8.18	nM	8.09	Inhibition of ENT1 in human K562 cells by flow cytometric assay	17636949
Equilibrative nucleoside transporter 1	IC50	=	8.1	nM	8.09	Inhibition of the equilibrative nucleoside transporter (ENT1, SLC29A1) as assess...	31551431
Equilibrative nucleoside transporter 1	Ki	=	8.79	nM	8.06	Displacement of 5-(SAENTA)-X8-fluorescein from K562 cell nucleoside transporter	15081020
Unchecked	IC50	=	15.0	nM	7.82	Inhibition of ENT-mediated [3H]thymidine incorporation in human COR-L23 cells by...	21366300
Unchecked	Ki	=	29.0	nM	7.54	DRUGMATRIX: Sodium/nucleoside co-transporter radioligand binding (ligand: nitrob...	-
Replicase polyprotein 1ab	Ki	=	40.0	nM	7.4	Binding affinity to C-terminal GST-tagged full-length recombinant SARS-CoV-2 3CL...	37659195
Unchecked	IC50	=	83.0	nM	7.08	DRUGMATRIX: Sodium/nucleoside co-transporter radioligand binding (ligand: nitrob...	-
SARS-CoV-2	EC50	=	100.0	nM	7.0	Antiviral activity against SARS-CoV-2 infected in African green monkey Vero E6 c...	37659195
Phosphodiesterase 6	Ki	=	125.0	nM	6.9	Inhibition of human phosphodiesterase 6	15887951
Equilibrative nucleoside transporter 1	IC50	=	144.8	nM	6.84	Inhibition of ENT1 in human K562 cells by flow cytometric assay	17636949
Unchecked	Ki	=	311.0	nM	6.51	DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun...	-
L1210	IC50	=	340.0	nM	6.47	Inhibition of [3H]thymidine uptake in L1210 cells	15369395
Unchecked	IC50	=	382.0	nM	6.42	DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun...	-
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A	Ki	=	400.0	nM	6.4	Inhibition of human phosphodiesterase 11	15887951
Phosphodiesterase 4	IC50	=	500.0	nM	6.3	Inhibition of Phosphodiesterase 4 (PDE4) from guinea pig macrophages	9873613
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	520.0	nM	6.28	Inhibitory activity against cyclic GMP-phosphodiesterase (PDE V) isolated from p...	8254606
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	574.0	nM	6.24	Inhibition of phosphodiesterase 5 (PDE5) from porcine platelets, range 0.244-1.3...	10891111
Replicase polyprotein 1ab	IC50	=	600.0	nM	6.22	Inhibition of SARS-CoV-2 3CL protease by FRET assay	37659195
Unchecked	IC50	=	600.0	nM	6.22	Inhibition of PDE7 (unknown origin)	35985255
Phosphodiesterase 7	IC50	=	600.0	nM	6.22	Inhibition of PDE7 (unknown origin)	39098133

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	227
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	65
21051535	10.1124/dmd.110.034629	ADMET	15
35985255	10.1016/j.ejmech.2022.114631	Mus musculus	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
18024584	10.1073/pnas.0709695104	H4	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
11602674	-	ATP-dependent translocase ABCB1	7
15369395	10.1021/jm040772w	L1210	7
21599003	10.1021/jm2001629	ADMET	5
21366300	10.1021/jm101493z	Unchecked	4
23591260	10.1016/j.bmc.2013.03.031	Unchecked	4
37584424	10.1021/acs.jmedchem.3c01044	Mus musculus	4
31035240	10.1016/j.ejmech.2019.04.020	Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
11716514	10.1006/bbrc.2001.6000	ATP-dependent translocase ABCB1	3
31035240	10.1016/j.ejmech.2019.04.020	High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A	3

Data from ChEMBL 36 via Core Engine