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基本情報
- CAS
53902-12-8- 標準SMILES
COc1ccc(/C=C/C(=O)Nc2ccccc2C(=O)O)cc1OC- InChIKey
NZHGWWWHIYHZNX-CSKARUKUSA-N- 分子式
- C18H17NO5
- 平均分子量
- 327.3 g/mol
概要
Tranilast is an amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group. It has a role as an antineoplastic agent, a calcium channel blocker, an anti-asthmatic drug, an anti-allergic agent, a hepatoprotective agent, an aryl hydrocarbon receptor agonist and a nephroprotective agent. It is a secondary carboxamide, a member of cinnamamides, an amidobenzoic acid and a dimethoxybenzene. It is functionally related to an anthranilic acid.
名称と識別子
- 優先名称
- Tranilast
- IUPAC
- 2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid
- 現地名
- トラニラスト
- 英語名
- Tranilast
- 分子式
- C18H17NO5
- 分子量
- 327.33
名称と別名
tranilast53902-12-8RizabenTranilastumMK-341HVF50SMY6EN-(3,4-Dimethoxycinnamoyl)anthranilic acidNSC-758970CHEBI:775722-((3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic AcidBENZOIC ACID, 2-((3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)AMINO)-
名称をさらに表示
トラニラスト2-[[3-(3,4-ジメトキシフェニル)-1-オキソ-2-プロペニル]アミノ]安息香酸N-(3,4-ジメトキシシンナモイル)アントラニル酸トラニラスト (JP17)2-[[3-(3,4-ジメトキシフェニル)プロペノイル]アミノ]安息香酸トラメラス-PF2-[3-(3,4-ジメトキシフェニル)-1-オキソ-2-プロペニルアミノ]安息香酸バリアックテイブロックリザベントラメラスリチゲーンセシリノール2-[3-(3,4-ジメトキシフェニル)プロパ-2-エンアミド]安息香酸リザモントマゴチラストフスチゲンリザラストブレクルストピアスn-5’MK 341TraniLQunist
物性
構造計算による物性補完中
- XLogP
- 3.2
- 極性表面積
- 84.9 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 6
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 464
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
物理化学的性質
- 融点
- 166.2 · 166.2-168.2 °C (lit.)
- 沸点
- 465.23 °C · 465.23°C (rough estimate)
- 比重(密度)
- 1.3185 · 1.3185 (rough estimate)
- 屈折率
- 1.51 · 1.5100 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 18 mg/mL · DMSO: 18 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 3.47 · 3.47±0.36(Predicted)
- 色
- 白からベージュ
- Merck
- 14 · 14,9570
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 3 か月間保存できます。
- InChI
- 1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+
- InChIKey
- NZHGWWWHIYHZNX-CSKARUKUSA-N
- SMILES
- COc1ccc(\C=C\C(=O)Nc2ccccc2C(O)=O)cc1OC
- CAS データベース
- 53902 · 53902-12-8(CAS DataBase Reference)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tranilast
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 3
- rtecs
- DG8731000
- 毒性
- LD50 in male, female mice, male, female rats (mg/kg): 780, 680, 1600, 1100 orally; 410, 385, 405, 395 i.p.; 2630, 2820, 3630, 3060 s.c. (Nakazawa, p 385)
- hs_code
- 2924.29.6250
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 26-36
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
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.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
応用分野
用途ケミカルメディエーター遊離 抑制作用を有します。
用途ケミカルメディエーター遊離 抑制作用を有します。
使用Tranilast is a compound that exhibits anti-inflammatory and immunomodulatory effects by inhibiting lipid mediator and cytokine release from inflammatory cells and interfering with PDGF- and TGF-β1-induced proliferation and migration of vascular medial smooth muscle cells. Tranilast suppresses production of prostaglandin D2 (IC50 = 0.1 mM), prostaglandin E2 (IC50 = ~1-20 μM), thromboxane B2 (IC50 = ~10-50 μM), TGF-β1 (IC50 = ~100-200 μM), and interleukin-8 (IC50 = ~100 μM) in in vitro models as well as attenuates of the proinflammatory activity of human monocytes. While originally marketed as an antiallergenic drug, the efficacy of tranilast in preventing restenosis after percutaneous coronary intervention has been tested in a large-scale clinical trial. Additionally, tranilast inhibits VEGF-induced angiogenetic activities (i.e., proliferation, migration and tube formation of vascular endothelial cells) with IC50 values of 22, 18 and 193 μM, which may prove therapeutic for various retinal diseases.[Cayman Chemical]
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