ジピリダモール

Dipyridamole

HCID 3108CAS 58-32-2

基本情報

標準SMILES
OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1
InChIKey
IZEKFCXSFNUWAM-UHFFFAOYSA-N
分子式
C24H40N8O4
平均分子量
504.6 g/mol
単同位体質量
504.31725176

概要

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.

名称と識別子

優先名称
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
現地名
ジピリダモール
英語名
Dipyridamole
分子式
C24H40N8O4
分子量
504.63

名称と別名

dipyridamole58-32-2PersantinDipyridaminePersantineCurantylDipyudamineDipiridamolCleridium 150DypyridamolIv PersantineDipyridamolum
名称をさらに表示
ジピリダモールペルミルチン2,2',2'',2'''-[(4,8-ジ-1-ピペリジニルピリミド[5,4-d]ピリミジン-2,6-ジイル)ジニトリロ]テトラキスエタノールグリオスチンシフノスコロサンN,N,N',N'-テトラキス(2-ヒドロキシエチル)-4,8-ジピペリジノピリミド[5,4-d]ピリミジン-2,6-ジアミンジピリダミンコリボンピロアンヨウリダモールメトロポリンカルジオフルックスニチリダモールコロキシントーモルペルチスタンカルコラジピリダモールS2,2',2'',2'''-[[4,8-ビス(1-ピペリジニル)ピリミド[5,4-d]ピリミジン-2,6-ジイル]ビスニトリロ]テトラキスエタノール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

データベース識別子

CAS
58-32-2
PubChem CID
3108
DTXSID
DTXSID6040668
ChEMBL
CHEMBL932
ChEBI
CHEBI:4653
UNII
64ALC7F90C
EC Number
200-374-7
Nikkaji
J8.585E

物性

構造計算による物性

XLogP
0.7
極性表面積
145 Ų
水素結合供与体数
4
水素結合受容体数
12
回転可能結合数
12
重原子数
36

実験および物理化学的性質

Drugs · 3 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals

LogP1.5
Solubility · 3 件

Slightly

9.22e-01 g/L

10.7 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 4 件

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

物理化学的性質

融点
165 · 165-166 °C (lit.)
沸点
593.96 °C · 593.96°C (rough estimate)
比重(密度)
1.2046 · 1.2046 (rough estimate)
屈折率
1.691 · 1.6910 (estimate)
貯蔵温度
room temp
溶解性
DMSO:可溶

化学的性質

化学的特性Yellow Powder

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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%)

毒性情報

Hepatotoxicity · 1 件

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 · 6 件

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

安全データ

wgk
2
rtecs
KK7450000
毒性
LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
hs_code
29335990
risk_code
36/37/38
hazard_code
Xi

化学と産業

薬理情報

ATC Code · 2 件

B - Blood and blood forming organs

QB - Blood and blood forming organs

Protein Binding99%
Pharmacodynamics · 1 件

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 · 1 件

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

用途と製造

UsesUse (kg; approx.) in Germany (2009): >10000
Use ClassificationPharmaceuticals
応用分野 · 3 件

用途冠血管拡張作用を示します。

使用Dipyridamole 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.

一般的な説明Dipyridamole, 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.

サプライヤー50 社

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]
補足説明 · 1 件

定義ChEBI: 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.

関連反応

1 件

関連ノート

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