基本情報
- 標準SMILES
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1- InChIKey
PVHUJELLJLJGLN-UHFFFAOYSA-N- 分子式
- C18H20N2O6
- 平均分子量
- 360.4 g/mol
- 単同位体質量
- 360.13213636
名称と識別子
- 優先名称
- Nitrendipine
- IUPAC
- 5-O-ethyl 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- 現地名
- ニトレンジピン
- 英語名
- Nitrendipine
- 分子式
- C18H20N2O6
- 分子量
- 360.36
名称と別名
名称をさらに表示
データベース識別子
- CAS
39562-70-4- PubChem CID
- 4507
- DTXSID
DTXSID0023373- ChEMBL
CHEMBL3195219、CHEMBL475534- ChEBI
CHEBI:7582- UNII
- 9B627AW319
- EC Number
- 254-513-1
- Nikkaji
- J16.451H
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 110 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 7
- 回転可能結合数
- 6
- 重原子数
- 26
- 形式電荷
- 0
- 複雑度
- 661
実験および物理化学的性質
LogP
2.88
2.4
Solubility
Insoluble
1.42e-02 g/L
Melting Point
156-160 °C
156 - 160 °C
Collision Cross Section
181.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
182.2 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
191.32 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];180.38 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];189.51 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 1580 C · 1580C
- 沸点
- 492.4 °C · 492.4°C (rough estimate)
- 比重(密度)
- 1.3595 · 1.3595 (rough estimate)
- 屈折率
- 1.57 · 1.5700 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 15 mg/mL · メタノール: 15 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 2.79 · 2.79±0.70(Predicted)
- 色
- 黄色から緑色
- 水溶解度
- DMSO (17.5 mg/ml)、メタノール (15 mg/ml)、酢酸エチル、エタノール (25 mM) に溶解。水に溶けません。
- 安定性
- -20 °Cで最大1週間保存できます。 · 光を避けてください。 DMSOまたはエタノール溶液で-20°Cで最大1週間保存できます。
- InChI
- InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3
- InChIKey
- PVHUJELLJLJGLN-UHFFFAOYSA-N
- SMILES
- C1(C)NC(C)=C(C(OC)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OCC)=O
- CAS データベース
- 39562 · 39562-70-4(CAS DataBase Reference)
- NISTの化学物質情報
- Nitrendipine(39562-70-4)
化学的性質
化学的特性Crystalline Solid
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 1.1% (1 of 95) of reports.
Warning
H302+H312 (29.5%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal];H302 (29.5%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (73.7%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (44.2%): Harmful if inhaled [Warning Acute toxicity, inhalation];H361 (25.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 95 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 95 reports by companies.;There are 4 notifications provided by 94 of 95 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Nitrendipine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Based on limited data, it is unlikely that nitrendipine will reach the infant in clinically important amounts. However, it may be preferable to use another agent drug for which more safety information is available.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
安全データ
- wgk
- 1
- rtecs
- US5653000
- 毒性
- LD50 in mice, rats (mg/kg): 39, 12.6 i.v.; 2540, >10000 orally (Hoffmann)
- risk_code
- 20/21/22
- hazard_code
- Xn
- safety_code
- 36
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
C - Cardiovascular system;C08 - Calcium channel blockers;C08C - Selective calcium channel blockers with mainly vascular effects;C08CA - Dihydropyridine derivatives;C08CA08 - Nitrendipine
QC - Cardiovascular system;QC08 - Calcium channel blockers;QC08C - Selective calcium channel blockers with mainly vascular effects;QC08CA - Dihydropyridine derivatives;QC08CA08 - Nitrendipine
Pharmacodynamics
Nitrendipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nitrendipine is similar to other peripheral vasodilators. Nitrendipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
Mechanism of Action
By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, Nitrendipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs used to cause dilation of the blood vessels.
用途と製造
応用分野
用途カルシウム拮抗剤です。L 型 電位依存性カルシウムチャネルのN 部位に結 合し、細胞内へのカルシウムイオン流入を抑 制する作用を示します。
用途カルシウム拮抗剤です。L型 電位依存性カルシウムチャネルのN部位に結 合し、細胞内へのカルシウムイオン流入を抑 制する作用を示します。
用途薬理研究用。
説明Nitrendipine is a vasodilating, dihydropyridine calcium antagonist. Its prolonged therapeutic effect in comparison to nifedipine makes it useful in the once to twice daily treatment of hypertension.
使用Nitrendipine is a dihydropyridine calcium channel blocker. Nitrendipine is used in the treatment of primary (essential) hypertension to decrease blood pressure. Antihypertensive.
一般的な説明Nitrendipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic acid methyl ethylester (Baypress), is a second-generation dihydropyridinechannel blocker of the nifedipine type. It is more selectivefor vascular smooth muscle than for myocardial tissue andserves as an effective vasodilator. The drug is used in thetreatment of mild-to-moderate essential hypertension.
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in t e treatment of hypertension.
関連反応
関連ノート
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