dipyridamole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	924	58-32-2

Description:

Molecule

Description

Molfile Inchi Smiles Synonyms: dipyridamole cardoxil cardoxin cleridium dipyridamine dipyridamol dipyridan peridamol persantin stenocardil stimolcardio

A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752) Molecular weight: 504.64 Formula: C24H40N8O4 CLOGP: 1.49 LIPINSKI: 2 HAC: 12 HDO: 4 TPSA: 145.44 ALOGS: -2.74 ROTB: 12 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Drug dosage:

Dose	Unit	Route
0.40	g	O
0.20	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.01 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.10 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	13.21 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.82 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	2 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.01 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	13 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 6, 1961	FDA	BOEHRINGER INGELHEIM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Sedation complication	282.18	14.89	78	9926	3567	46672491
Cerebrovascular accident	226.27	14.89	181	9823	100858	46575200
Orthostatic hypotension	220.68	14.89	107	9897	24551	46651507
Creatinine renal clearance decreased	213.18	14.89	73	9931	6847	46669211
Sedation	209.80	14.89	101	9903	22809	46653249
Cognitive disorder	198.72	14.89	114	9890	36769	46639289
Blood calcium decreased	167.82	14.89	77	9927	15596	46660462
Balance disorder	128.28	14.89	108	9896	64413	46611645
Depressed level of consciousness	127.61	14.89	95	9909	47474	46628584
Transient ischaemic attack	114.97	14.89	79	9925	34824	46641234
Constipation	85.67	14.89	142	9862	173955	46502103
Fall	79.85	14.89	200	9804	328897	46347161
Mobility decreased	69.71	14.89	75	9929	60519	46615539
Hypotension	55.89	14.89	141	9863	232448	46443610
Drug ineffective	49.22	14.89	44	9960	677794	45998264
Cerebral infarction	42.06	14.89	37	9967	23329	46652729
Subdural haematoma	39.44	14.89	28	9976	12969	46663089
Extradural haematoma	28.75	14.89	11	9993	1412	46674646
Embolism	25.48	14.89	17	9987	7121	46668937
Rheumatoid arthritis	25.18	14.89	10	9994	240205	46435853
Neurological symptom	23.92	14.89	14	9990	4665	46671393
Subarachnoid haemorrhage	22.79	14.89	19	9985	11134	46664924
Fatigue	21.09	14.89	64	9940	608633	46067425
Acute myocardial infarction	19.75	14.89	29	9975	31895	46644163
Peripheral swelling	19.35	14.89	5	9999	158066	46517992
Oesophageal ulcer haemorrhage	19.30	14.89	6	9998	413	46675645
Gastrointestinal haemorrhage	18.60	14.89	47	9957	77326	46598732
Nail ridging	18.15	14.89	5	9999	225	46675833
Hyperlipidaemia	17.95	14.89	21	9983	18518	46657540
Cerebral haemorrhage	17.88	14.89	26	9978	28345	46647713
Headache	17.73	14.89	168	9836	478184	46197874
Stress cardiomyopathy	17.46	14.89	14	9990	7770	46668288
Mediastinal haemorrhage	16.97	14.89	3	10001	15	46676043
Off label use	16.96	14.89	35	9969	379806	46296252
Left ventricular end-diastolic pressure increased	16.55	14.89	5	9999	313	46675745
Carotid artery occlusion	16.41	14.89	9	9995	2650	46673408
Toxicity to various agents	15.75	14.89	88	9916	211678	46464380
Joint swelling	15.68	14.89	8	9996	166065	46509993

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Cerebrovascular accident	266.28	13.49	208	8444	83269	29860557
Transient ischaemic attack	129.07	13.49	84	8568	25116	29918710
Cerebral haemorrhage	67.76	13.49	64	8588	32823	29911003
Headache	45.15	13.49	135	8517	182171	29761655
Splenic injury	32.16	13.49	6	8646	30	29943796
Peritoneal haematoma	28.18	13.49	6	8646	64	29943762
Carotid artery occlusion	24.85	13.49	12	8640	2013	29941813
Drug ineffective	24.41	13.49	38	8614	340349	29603477
Loss of consciousness	23.70	13.49	63	8589	79312	29864514
Cerebral infarction	23.03	13.49	33	8619	26340	29917486
Gastrointestinal haemorrhage	21.72	13.49	63	8589	83383	29860443
Vitreous haemorrhage	21.44	13.49	11	8641	2099	29941727
Labelled drug-drug interaction medication error	20.71	13.49	20	8632	10518	29933308
Aphasia	19.49	13.49	26	8626	19413	29924413
Fine motor delay	18.62	13.49	5	8647	150	29943676
Monocytosis	18.34	13.49	6	8646	360	29943466
Embolic stroke	18.33	13.49	12	8640	3610	29940216
Haemorrhage intracranial	18.06	13.49	22	8630	15010	29928816
Off label use	16.74	13.49	29	8623	249261	29694565
Tubulointerstitial nephritis	16.53	13.49	23	8629	17868	29925958
Ocular myasthenia	16.34	13.49	5	8647	241	29943585
Myalgia	16.34	13.49	54	8598	76613	29867213
Haematemesis	16.22	13.49	28	8624	26175	29917651
Intra-abdominal haemorrhage	15.88	13.49	9	8643	2093	29941733
Hypotension	15.50	13.49	105	8547	200460	29743366
Abdominal sepsis	15.23	13.49	7	8645	1050	29942776
Lacunar infarction	14.87	13.49	10	8642	3145	29940681
Diverticulitis intestinal haemorrhagic	14.35	13.49	5	8647	364	29943462
Lip swelling	14.26	13.49	18	8634	12726	29931100
Fatigue	13.86	13.49	47	8605	320626	29623200
Dizziness	13.86	13.49	100	8552	194809	29749017
Device related thrombosis	13.71	13.49	6	8646	803	29943023
Hemiparesis	13.63	13.49	19	8633	14783	29929043

Pharmacologic Action:

Source	Code	Description
ATC	B01AC07	BLOOD AND BLOOD FORMING ORGANS ANTITHROMBOTIC AGENTS ANTITHROMBOTIC AGENTS Platelet aggregation inhibitors excl. heparin
FDA PE	N0000008832	Decreased Platelet Aggregation
FDA EPC	N0000175578	Platelet Aggregation Inhibitor
CHEBI has role	CHEBI:35620	vasodilator
CHEBI has role	CHEBI:50427	platelet aggregation inhibitors
CHEBI has role	CHEBI:50445	adenosine deaminase inhibitors
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D006401	Hematologic Agents
MeSH PA	D010726	Phosphodiesterase Inhibitors
MeSH PA	D010975	Platelet Aggregation Inhibitors
MeSH PA	D014665	Vasodilator Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Chronic heart failure	indication	48447003
Atrial fibrillation	indication	49436004	DOID:0060224
Platelet Aggregation Inhibition	indication
Prevention of Cerebral Thrombosis	indication
Myocardial Perfusion Imaging Adjunct	indication
Cerebral embolism	off-label use	75543006	DOID:4372
Transient ischemic attack	off-label use	266257000	DOID:224
Thromboembolic disorder	off-label use	371039008
Myocardial Reinfarction Prevention	off-label use
Alcoholism	contraindication	7200002
Poisoning by digitalis glycoside	contraindication	12876009
Peptic ulcer	contraindication	13200003	DOID:750
Senile cardiac amyloidosis	contraindication	16573007
Myocardial infarction	contraindication	22298006	DOID:5844
Sick sinus syndrome	contraindication	36083008	DOID:13884
Gastrointestinal ulcer	contraindication	40845000
Myxedema	contraindication	43153006	DOID:11634
Hypokalemia	contraindication	43339004
Low blood pressure	contraindication	45007003
Sinus bradycardia	contraindication	49710005
Myocarditis	contraindication	50920009	DOID:820
Vitamin K deficiency	contraindication	52675005	DOID:11249
Nasal polyp	contraindication	52756005
Acute nephropathy	contraindication	58574008
Hypercalcemia	contraindication	66931009	DOID:12678
Ventricular fibrillation	contraindication	71908006
Factor II deficiency	contraindication	73975000
Reye's syndrome	contraindication	74351001	DOID:14525
Wolff-Parkinson-White pattern	contraindication	74390002	DOID:384
Gastrointestinal hemorrhage	contraindication	74474003
Thrombotic thrombocytopenic purpura	contraindication	78129009	DOID:10772
Cor pulmonale	contraindication	83291003	DOID:8515
Constrictive pericarditis	contraindication	85598007	DOID:11481
Gout	contraindication	90560007	DOID:13189
Kidney disease	contraindication	90708001	DOID:557
Hemophilia	contraindication	90935002
Anemia due to enzyme deficiency	contraindication	111577008
von Willebrand disorder	contraindication	128105004	DOID:12531
Hypomagnesemia	contraindication	190855004
Atrioventricular block	contraindication	233917008	DOID:0050820
Disease of liver	contraindication	235856003	DOID:409
Anemia	contraindication	271737000	DOID:2355
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Idiopathic hypertrophic subaortic stenosis	contraindication	360465008
Acute coronary syndrome	contraindication	394659003
Breastfeeding (mother)	contraindication	413712001
Restrictive cardiomyopathy	contraindication	415295002	DOID:397
Acute erosive gastritis	contraindication	444926003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.0	Basic
pKa2	8.52	Basic
pKa3	2.75	Basic
pKa4	2.12	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Phosphodiesterase 1	Enzyme	P54750 Q01064 Q14123	PDE1A_HUMAN PDE1B_HUMAN PDE1C_HUMAN	INHIBITOR	IC50	4.35		CHEMBL	CHEMBL
cGMP-dependent 3',5'-cyclic phosphodiesterase	Enzyme	O00408	PDE2A_HUMAN	INHIBITOR	IC50	5.49		CHEMBL	CHEMBL
Phosphodiesterase 3	Enzyme	Q13370 Q14432	PDE3A_HUMAN PDE3B_HUMAN	INHIBITOR	IC50	4.37		CHEMBL	CHEMBL
cGMP-specific 3',5'-cyclic phosphodiesterase	Enzyme	O76074	PDE5A_HUMAN	INHIBITOR	IC50	6.28		CHEMBL	CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4A	Enzyme	P27815	PDE4A_HUMAN	INHIBITOR	IC50	5.80		DRUG MATRIX	CHEMBL
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Enzyme	Q9Y233	PDE10_HUMAN	INHIBITOR	Ki	6		CHEMBL	CHEMBL
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A	Enzyme	O60658	PDE8A_HUMAN	INHIBITOR	IC50	5.10		CHEMBL	CHEMBL
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B	Enzyme	O95263	PDE8B_HUMAN	INHIBITOR	IC50	4.30		IUPHAR	CHEMBL
Equilibrative nucleoside transporter 1	Transporter	Q99808	S29A1_HUMAN	INHIBITOR	Ki	8.50		CHEMBL	CHEMBL
Phosphodiesterase 6	Enzyme	O43924 P16499 P18545 P35913 P51160 Q13956	CNCG_HUMAN CNRG_HUMAN PDE6A_HUMAN PDE6B_HUMAN PDE6C_HUMAN PDE6D_HUMAN	INHIBITOR	Ki	6.90		CHEMBL	CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 7B	Enzyme	Q9NP56	PDE7B_HUMAN	INHIBITOR	IC50	6		CHEMBL	CHEMBL
Phosphodiesterase 7	Enzyme	Q13946 Q9NP56	PDE7A_HUMAN PDE7B_HUMAN	INHIBITOR	Ki	6.22		CHEMBL	CHEMBL
Equilibrative nucleoside transporter 4	Transporter	Q7RTT9	S29A4_HUMAN	INHIBITOR	Ki	5.90		IUPHAR
Sodium/nucleoside cotransporter 1	Transporter	O00337	S28A1_HUMAN	INHIBITOR	Ki	7.54		DRUG MATRIX
Protein prune homolog	Enzyme	Q86TP1	PRUNE_HUMAN		IC50	6.11		CHEMBL
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A	Enzyme	Q9HCR9	PDE11_HUMAN		Ki	6.40		CHEMBL
Arachidonate 15-lipoxygenase	Enzyme		LOX15_RABIT		IC50	5.16		DRUG MATRIX
Cyclic AMP-specific phosphodiesterase SSPDE4A1A	Enzyme		O77823_PIG		IC50	5.28		CHEMBL
Cyclic nucleotide phosphodiesterase PDE3A	Enzyme		Q9XSW7_PIG		IC50	4.36		CHEMBL
ORF 73	Unclassified		O40947_HHV8		AC50	5.05		CHEMBL
Main protease (M-PRO)	Enzyme		R1AB_SARS2	INHIBITOR	IC50	6.26		SCIENTIFIC LITERATURE

External reference:

ID	Source
4017884	VUID
N0000146237	NUI
D00302	KEGG_DRUG
4017884	VANDF
C0308607	UMLSCUI
CHEBI:4653	CHEBI
CHEMBL932	ChEMBL_ID
DB00975	DRUGBANK_ID
D004176	MESH_DESCRIPTOR_UI
3108	PUBCHEM_CID
4807	IUPHAR_LIGAND_ID
1545	INN_ID
64ALC7F90C	UNII
203015	RXNORM
2493	MMSL
2527	MMSL
3353	MMSL
4619	MMSL
d00213	MMSL
000691	NDDF
387371005	SNOMEDCT_US
66859009	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Aspirin and Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	0093-3064	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	27 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1461	TABLET, FILM COATED	25 mg	ORAL	ANDA	21 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1462	TABLET, FILM COATED	50 mg	ORAL	ANDA	21 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1463	TABLET, FILM COATED	75 mg	ORAL	ANDA	21 sections
Aggrenox	HUMAN PRESCRIPTION DRUG LABEL	2	0597-0001	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	NDA	29 sections
Persantine	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0017	TABLET, COATED	25 mg	ORAL	NDA	21 sections
Persantine	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0018	TABLET, COATED	50 mg	ORAL	NDA	21 sections
Persantine	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0019	TABLET, COATED	75 mg	ORAL	NDA	21 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	0641-2569	INJECTION	5 mg	INTRAVENOUS	ANDA	19 sections
Aspirin and Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	16714-964	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	27 sections
Aggrenox	HUMAN PRESCRIPTION DRUG LABEL	2	21695-656	CAPSULE	200 mg	ORAL	NDA	17 sections
Aspirin and Extended-Release Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	42291-116	CAPSULE	200 mg	ORAL	ANDA	26 sections
Aspirin and Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	43598-339	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	26 sections
Aspirin and Dipyridamole Extended Release	Human Prescription Drug Label	2	47335-927	CAPSULE	200 mg	ORAL	ANDA	25 sections
Aspirin and Extended - Release Dipyridamole Capsules, 25 mg / 200 mg	HUMAN PRESCRIPTION DRUG LABEL	2	49884-007	CAPSULE	200 mg	ORAL	ANDA	25 sections
Aspirin and Extended-Release Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	51407-271	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	19 sections
DIPYRIDAMOLE	HUMAN PRESCRIPTION DRUG LABEL	1	51662-1447	INJECTION	5 mg	INTRAVENOUS	ANDA	11 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	51808-204	SOLUTION	5 mg	INTRAVENOUS	Unapproved drug other	7 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	52584-569	INJECTION	5 mg	INTRAVENOUS	ANDA	11 sections
Aggrenox	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5143	CAPSULE	200 mg	ORAL	NDA	19 sections
Aspirin and Extended-Release Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	62175-330	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	19 sections
Aspirin and Extended-Release Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	62559-850	CAPSULE	200 mg	ORAL	ANDA	26 sections
DIPYRIDAMOLE	HUMAN PRESCRIPTION DRUG LABEL	1	64980-133	TABLET, FILM COATED	25 mg	ORAL	ANDA	19 sections
DIPYRIDAMOLE	HUMAN PRESCRIPTION DRUG LABEL	1	64980-134	TABLET, FILM COATED	50 mg	ORAL	ANDA	19 sections
DIPYRIDAMOLE	HUMAN PRESCRIPTION DRUG LABEL	1	64980-135	TABLET, FILM COATED	75 mg	ORAL	ANDA	19 sections
Aspirin and Extended-Release Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	2	65162-596	CAPSULE	200 mg	ORAL	ANDA	27 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	65841-662	TABLET, FILM COATED	25 mg	ORAL	ANDA	1 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	65841-663	TABLET, FILM COATED	50 mg	ORAL	ANDA	1 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	65841-664	TABLET, FILM COATED	75 mg	ORAL	ANDA	1 sections
Dipyridamole	HUMAN PRESCRIPTION DRUG LABEL	1	68151-2996	TABLET	25 mg	ORAL	NDA authorized generic	17 sections