Basic information
- Standard SMILES
OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1- InChIKey
IZEKFCXSFNUWAM-UHFFFAOYSA-N- Molecular formula
- C24H40N8O4
- Average molar mass
- 504.6 g/mol
- Monoisotopic mass
- 504.31725176
Overview
Dipyridamole is a pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots. It has a role as a vasodilator agent, a platelet aggregation inhibitor, an adenosine phosphodiesterase inhibitor and an EC 3.5.4.4 (adenosine deaminase) inhibitor. It is a member of piperidines, a tetrol, a pyrimidopyrimidine and a tertiary amino compound.
Names & identifiers
- Preferred name
- Dipyridamole
- IUPAC
- 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
- English name
- Dipyridamole
- Molecular formula
- C24H40N8O4
- Molecular weight
- 504.63
Names & synonyms
dipyridamole58-32-2PersantinDipyridaminePersantineCurantylDipyudamineDipiridamolCleridium 150DypyridamolIv PersantineDipyridamolum
Show more names
DIPYRIDAMOLdypyridamoleAnginalDipyrdamoleDipyridamole (200 mg)ra8RA 8
NSC-515776DTXSID604066864ALC7F90CB01AC07NSC5157762-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)pyrimido[5,4-d][1,3]diazin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanolCHEBI:4653
Database identifiers
- CAS
58-32-2- PubChem CID
- 3108
- DTXSID
DTXSID6040668- ChEMBL
CHEMBL932- ChEBI
CHEBI:4653- UNII
- 64ALC7F90C
- EC Number
- 200-374-7
- Nikkaji
- J8.585E
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 12
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 561
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals
LogP1.5
Solubility
Slightly
9.22e-01 g/L
10.7 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
Breastfeeding; Lactation; Milk, Human; Phosphodiesterase Inhibitors; Vasodilator Agents; Platelet Aggregation Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point163 °C
Physical DescriptionSolid
Collision Cross Section
223.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
227.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
222.83 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 165 · 165-166 °C (lit.)
- Boiling point
- 593.96 °C · 593.96°C (rough estimate)
- Density
- 1.2046 · 1.2046 (rough estimate)
- refractive index
- 1.691 · 1.6910 (estimate)
- storage temp.
- room temp
- solubility
- DMSO: soluble
- form
- powder
- pka
- 6.4 · pKa 6.4 (Uncertain)
- color
- yellow
- Water Solubility
- Soluble in chloroform, methanol, dilute acids, ethanol. Slightly soluble in water.
- Merck
- 14 · 14,3346
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
- InChI
- 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
- InChIKey
- IZEKFCXSFNUWAM-UHFFFAOYSA-N
- SMILES
- C1(N(CCO)CCO)=NC(N2CCCCC2)=C2N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=N1
- NCI Dictionary of Cancer Terms
- dipyridamole
- FDA UNII
- 64 ALC7F90C · 64ALC7F90C
- NCI Drug Dictionary
- dipyridamole
- ATC code
- 1 AC07 · B01AC07
- NIST Chemistry Reference
- 2 · Pyrimidine, 2,6-bis(diethanolamino)-4,8-dipiperidino-pyrimido-(5,4-d)-(58-32-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Protein binding
- 97 · 97-99%
- Excreted unchanged in urine
- 1 · 1-5%
- Volume of distribution
- 1.33 · 1.33-3.53(L/kg)
- Biological half-life
- 9 · 9-12 / Unch
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 7450000 · KK7450000
- HS Code
- 29335990 · 29335990
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 in · LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (98.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 75 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (98.7%)
Toxicology
Hepatotoxicity
Dipyridamole has been associated with a low rate of serum enzyme elevations during therapy, but in large clinical trials the frequency of liver enzyme abnormalities was similar with dipyridamole therapy as with placebo. Cases of clinically apparent acute liver injury from dipyridamole have not been published although hepatitis is listed as a potential side effect in the product label. The clinical features of the liver injury linked to dipyridamole have not been described.
Adverse EffectsThe most frequently reported adverse effects include:
Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Dipyridamole
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- rtecs
- KK7450000
- hs_code
- 29335990
- Toxicity
- LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
B - Blood and blood forming organs
QB - Blood and blood forming organs
Protein Binding99%
Pharmacodynamics
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.
Mechanism of Action
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.
Biological Half-Life40 minutes
Metabolism/Metaboliteshepatic
FDA Pharmacological Classification
64ALC7F90C
DIPYRIDAMOLE
Physiologic Effects [PE] - Decreased Platelet Aggregation
Established Pharmacologic Class [EPC] - Platelet Aggregation Inhibitor
Dipyridamole is a Platelet Aggregation Inhibitor. The physiologic effect of dipyridamole is by means of Decreased Platelet Aggregation.
DIPYRIDAMOLE
MeSH Pharmacological Classification
Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Drugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion
70%
Dipyridamole is metabolized in the liver to the glucuronic acid conjugate and excreted with the bile.
1 to 2.5 L/kg
2.3-3.5 mL/min/kg
Cellular LocationsCytoplasm
Metabolite PathwaysDipyridamole (Antiplatelet) Action Pathway
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10000
Use ClassificationPharmaceuticals
Applications
DescriptionDipyridamole (58-32-2) is a phosphodiesterase inhibitor (IC50=0.37, 0.38, 0.45, 0.9 and 4.5 μM for PDE11, 6, 10, 5 and 8 respectively.1,2 Potent equilibrative nucleoside transporter 1 (ENT1) inhibitor Ki=8.2 nM vs. 144.8 nM for ENT1 and ENT2 respectively.3 Antiplatelet activity.4
UsesSelective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation
UsesA phosphodiester, cGMP, and non-specific nucleoside transport inhibitor
UsesDipiridamol is known as a coronary vasodilating agent, although it also possesses specific antiaggregant activity. It is used for preventing thrombo-formation after cardiac valve replacement in combination with warfarin.
UsesDipyridamole prevents platelets sticking to the replacement heart valve and causing a blood clot on the valve. It is used to dilate blood vessels in people with peripheral arterial disease and coronary artery disease. This compound has been shown to suppress high glucose-induced osteopontin mRNA expression and protein secretion, as well as inhibit cAMP and cGMP hydrolysis. Research indicates that Dipyridamole is a non-specific nucleoside transport inhibitor with the ability to increase the effects of adenosine in sinoatrial and atrioventricular nodes. Dipyridamole is an inhibitor of ENT1 and ENT2.
General DescriptionDipyridamole, 2,2',2',2'''-[(4,8-di-1piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]-tetrakisethanol (Persantine), may be used for coronary andmyocardial insufficiency. Its biggest use today, however, isas an antithrombotic in patients with prosthetic heart valves.It is a bitter, yellow, crystalline powder, soluble in diluteacids, methanol, or chloroform. A formulation containingdipyridamole and aspirin (Aggrenox) is currently beingmarketed as an antithromobotic.Dipyridamole is a long-acting vasodilator. Its vasodilatingaction is selective for the coronary system; it is indicatedfor long-term therapy of chronic angina pectoris. Thedrug also inhibits adenosine deaminase in erythrocytesand interferes with the uptake of the vasodilator adenosineby erythrocytes. These actions potentiate the effect ofprostacyclin (PGI2), which acts as an inhibitor to plateletaggregation.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Jai Radhe Sales+(91)-(79)-26431096/65255722 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
江西瑞威尔生物科技有限公司18502762009 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
山西新宝源制药有限公司0352-7606558
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
潍坊鲁泽新材料有限公司0536-7971999 13583611556 · [email protected]
上海乾劲化工科技有限公司021-20900665 17321230821 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
武汉励合化学新材料有限公司027-88395709
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试（上海）科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技（武汉）有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
Additional notes
DefinitionChEBI: A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.
Related reactions
1 records
Linked notes
Loading…