기본 정보
- 표준 SMILES
OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1- InChIKey
IZEKFCXSFNUWAM-UHFFFAOYSA-N- 분자식
- C24H40N8O4
- 평균 분자량
- 504.6 g/mol
- 단동위원소 질량
- 504.31725176
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 현지명
- 디피리다몰
- 영어명
- Dipyridamole
- 분자식
- C24H40N8O4
- 분자량
- 504.63
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
58-32-2- PubChem CID
- 3108
- DTXSID
DTXSID6040668- ChEMBL
CHEMBL932- ChEBI
CHEBI:4653- UNII
- 64ALC7F90C
- EC Number
- 200-374-7
- Nikkaji
- J8.585E
물성
구조 계산 물성
- XLogP
- 0.7
- 극성 표면적
- 145 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 12
- 회전 가능 결합 수
- 12
- 무거운 원자 수
- 36
- 형식 전하
- 0
- 복잡도
- 561
실험 및 물리화학적 성질
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]
물리화학적 성질
- 녹는점
- 165 · 165-166 °C (lit.)
- 끓는 점
- 593.96 °C · 593.96°C (rough estimate)
- 밀도
- 1.2046 · 1.2046 (rough estimate)
- 굴절률
- 1.691 · 1.6910 (estimate)
- 저장 조건
- room temp
- 용해도
- DMSO: 용해될 수 있다
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 6.4 · pKa 6.4 (Uncertain)
- 색상
- 노란색
- 수용성
- 클로로포름, 메탄올, 묽은 산, 에탄올에 용해됩니다. 물에 약간 용해됩니다.
- Merck
- 14 · 14,3346
- 안정성
- 1 · 제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
- 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
- 2 · Pyrimidine, 2,6-bis(diethanolamino)-4,8-dipiperidino-pyrimido-(5,4-d)-(58-32-2)
화학적 성질
Yellow Powder
안전 및 규제
GHS 분류
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.
유해성 정보
독성 정보
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
안전 데이터
- wgk
- 2
- rtecs
- KK7450000
- 독성
- LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
- HS 번호
- 29335990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- 기존화학 물질
- KE-03014
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
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
용도 및 제조
응용 분야
용도Dipyridamole 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.
일반 설명Dipyridamole, 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.
상·하류 제품 정보
상류 원료
공급사50 곳
추가 설명
정의ChEBI: 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.
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