基本情報
- CAS
52365-63-6- 標準SMILES
CNCC(O)c1ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c1- InChIKey
OCUJLLGVOUDECM-UHFFFAOYSA-N- 分子式
- C19H29NO5
- 平均分子量
- 351.4 g/mol
- 単同位体質量
- 351.20457303
概要
Dipivefrin is the dipivalate ester of (+-)-epinephrine (racepinephrine). A pro-drug of epinephrine, the hydrochloride is used topically as eye drops to reduce intra-ocular pressure in the treatment of open-angle glaucoma or ocular hypertension. It has a role as a sympathomimetic agent, an adrenergic agonist, an antiglaucoma drug, a prodrug and an ophthalmology drug. It is a member of ethanolamines and a pivalate ester. It is functionally related to an adrenaline. It is a conjugate base of a dipivefrin(1+).
名称と識別子
- 優先名称
- Dipivefrin
- IUPAC
- [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate
- 現地名
- ジピベフリン
- 英語名
- Dipivefrine
- 分子式
- C19H29NO5
- 分子量
- 351.44
名称と別名
dipivefrinDipivefrine52365-63-6DipivefrinumDipivefrinadipivalyl epinephrine8Q1PVL543G1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanolCHEBI:4646DTXSID10485444-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
名称をさらに表示
ジピベフリンrac-4-[(R*)-1-ヒドロキシ-2-(メチルアミノ)エチル]-1,2-フェニレンビス(2,2-ジメチルプロパノアート)(±)-ジピベフリンビスピバル酸4-[1-ヒドロキシ-2-(メチルアミノ)エチル]-1,2-フェニレン2-[(2,2-ジメチルプロパノイル)オキシ]-4-[1-ヒドロキシ-2-(メチルアミノ)エチル]フェニル 2,2-ジメチルプロパノアートK30081K 30081K-30081dipiverfrinDipivefrine-d3Dipivefrine USP/EP/BP
Propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (+-)-(+-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate4-(1-hydroxy-2-(methylamino)ethyl)-o-phenylene divavalateDiopineGlaudrops(+-)-4-(1-hydroxy-2-(methylamino)ethyl)-o-phenylene divavalate2-((2,2-dimethylpropanoyl)oxy)-4-(1-hydroxy-2-(methylamino)ethyl)phenyl 2,2-dimethylpropanoate2-((2,2-dimethylpropanoyl)oxy)-5-(1-hydroxy-2-(methylamino)ethyl)phenyl 2,2-dimethylpropanoate
物性
構造計算による物性
- XLogP
- 2.9
- 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
- 6
- 回転可能結合数
- 9
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 463
実験および物理化学的性質
LogP1.7
Solubility
Freely soluble as HCl salt
5.82e-02 g/L
Melting Point146-147
Physical DescriptionSolid
物理化学的性質
- 融点
- 146 · 146-147°
- 酸解離定数(Pka)
- 8.4 · pKa 8.40(RT) (Uncertain)
化学と産業
薬理情報
ATC Code
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Dipivefrin is a member of a class of drugs known as prodrugs. Prodrugs are usually not active in themselves and require biotransformation to the parent compound before therapeutic activity is seen. These modifications are undertaken to enhance absorption, decrease side effects and enhance stability and comfort, thus making the parent compound a more useful drug. Enhanced absorption makes the prodrug a more efficient delivery system for the parent drug because less drug will be needed to produce the desired therapeutic response. Dipivefrin is a prodrug of epinephrine formed by the diesterification of epinephrine and pivalic acid. The addition of pivaloyl groups to the epinephrine molecule enhances its lipophilic character and, as a consequence, its penetration into the anterior chamber.
Mechanism of Action
Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating α -and/or β<sub>2</sub>-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy.
Metabolism/MetabolitesDipivefrin is converted to epinephrine inside the human eye by enzyme hydrolysis.
FDA Pharmacological Classification
8Q1PVL543G
DIPIVEFRIN
Mechanisms of Action [MoA] - Adrenergic Agonists
Established Pharmacologic Class [EPC] - Adrenergic Receptor Agonist
Dipivefrin is an Adrenergic Receptor Agonist. The mechanism of action of dipivefrin is as an Adrenergic Agonist.
MeSH Pharmacological ClassificationDrugs that bind to and activate adrenergic receptors.
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