基本情報
- CAS
22664-55-7- 標準SMILES
CC(=O)Oc1c(C)cc(OCC(O)CNC(C)C)c(C)c1C- InChIKey
BQIPXWYNLPYNHW-UHFFFAOYSA-N- 分子式
- C17H27NO4
- 平均分子量
- 309.4 g/mol
- 単同位体質量
- 309.19400834
概要
Metipranolol is 3-(Propan-2-ylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is substituted by a 4-acetoxy-2,3,5-trimethylphenoxy group. A non-cardioselective beta-blocker, it is used to lower intra-ocular pressure in the management of open-angle glaucoma. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an anti-arrhythmia drug and an antiglaucoma drug. It is a propanolamine, an aromatic ether, an acetate ester and a secondary amino compound.
名称と識別子
- 優先名称
- Metipranolol
- IUPAC
- [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
- 現地名
- メチプラノロール
- 英語名
- metipranolol
- 分子式
- C17H27NO4
- 分子量
- 309.4
名称と別名
Metipranolol22664-55-7TrimepranolMetipranololumDTXSID4046078VUAB-6453VUAB6453X39AL81KEB(+-)-metipranololBM-01004BM01.004Phenol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2,3,6-trimethyl-, 1-acetate
名称をさらに表示
1-[(4-アセトキシ-2,3,5-トリメチルフェニル)オキシ]-3-(イソプロピルアミノ)プロパン-2-オール4-[2-ヒドロキシ-3-[(1-メチルエチル)アミノ]プロポキシ]-2,3,6-トリメチルフェノール1-アセタートメチプラノールメチプラノロールトリメプラノール1-(4-アセチルオキシ-2,3,5-トリメチルフェノキシ)-3-(イソプロピルアミノ)-2-プロパノールジソラト4-{2-ヒドロキシ-3-[(プロパン-2-イル)アミノ]プロポキシ}-2,3,6-トリメチルフェニル アセタート4-[2-ヒドロキシ-3-(イソプロピルアミノ)プロポキシ]-2,3,6-トリメチルフェノール1-アセタートDisoratGlausynGlaulineVUFB-64534-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)-2,3,6-TRIMETHYLPHENYL ACETATE4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethylphenol 1-acetate
Methypranol4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetateBM-01.004CHEBI:6897DTXCID2026078Acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl esterPhenol, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethyl-, 1-acetatemetipranololo
物性
構造計算による物性
- XLogP
- 2.7
- 極性表面積
- 67.8 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
- 8
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 348
実験および物理化学的性質
LogP
2.2
1.95
Solubility1.73e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiglaucoma Agents; Antiarrhythmics
Melting Point
105-107 °C
105 - 107 °C
Physical DescriptionSolid
Dissociation Constants9.54
物理化学的性質
- 融点
- 105 · 105-107℃
- 沸点
- 458.7 · 458.7±45.0 °C(Predicted)
- 比重(密度)
- 1.068 · 1.068
- 貯蔵温度
- 4 °C, · 4°C, protect from light
- 溶解性
- 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:6): 0.14 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml
- 外見
- A crystalline solid
- 酸解離定数(Pka)
- 13.91 · 13.91±0.20(Predicted)
- 色
- White to off-white
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]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- 毒性
- LD50 in mice (mg/kg): 31 i.v. (Bartsch)
化学と産業
薬理情報
ATC Code
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Metipranolol is a beta1 and beta2 (non-selective) adrenergic receptor-blocking agent that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Metipranolol is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Metipranolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. Metipranolol reduces intraocular pressure with little or no effect on pupil size or accommodation in contrast to the miosis which cholinergic agents are known to produce.
Mechanism of Action
Although it is known that metipranolol binds the beta1 and beta2 adrenergic receptors, the mechanism of metipranolol's action is not known. It has no significant intrinsic sympathomimetic activity, and has only weak local anesthetic (membrane-stabilizing) and myocardial depressant activity. It appears that the ophthalmic beta-adrenergic blocking agents reduce aqueous humor production, as demonstrated by tonography and fluorophotometry. A slight increase in aqueous humor outflow may be an additional mechanism.
FDA Pharmacological Classification
X39AL81KEB
METIPRANOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Metipranolol is a beta-Adrenergic Blocker. The mechanism of action of metipranolol is as an Adrenergic beta-Antagonist.
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
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