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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 561
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals
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
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]
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
- 外見
- 粉
- 酸解離定数(Pka)
- 6.4 · pKa 6.4 (Uncertain)
- 色
- 黄色
- 水溶解度
- クロロホルム、メタノール、希酸、エタノールに可溶。水にわずかに溶ける。
- Merck
- 14 · 14,3346
- 安定性
- -20 °Cで最大3か月保存できます。 · DMSO溶液またはエタノール溶液で-20°Cで最大3か月保存できます。
- 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
- NISTの化学物質情報
- 2 · Pyrimidine, 2,6-bis(diethanolamino)-4,8-dipiperidino-pyrimido-(5,4-d)-(58-32-2)
化学的性質
化学的特性Yellow Powder
安全と法規制
GHS分類
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.
危険有害性情報
毒性情報
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.
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
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
- safety_code
- 26-36
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
B - Blood and blood forming organs
QB - Blood and blood forming organs
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.
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
用途と製造
応用分野
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.
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
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
関連ノート
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