2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate

• ChemBase编号: 332
• 分子式: C19H29NO5
• 平均质量: 351.43726
• 单一同位素质量: 351.20457303
• SMILES: O(C(=O)C(C)(C)C)c1c(OC(=O)C(C)(C)C)ccc(C(O)CNC)c1
• Canonical SMILES: CNCC(c1ccc(c(c1)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)O
• InChI: InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
• InChIKey: OCUJLLGVOUDECM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
• IUPAC传统名: dipivefrin
• 商标名: AKPro; DPE; Dipivefrin HCL; Dipivefrin [USAN]; Dipivefrina [INN-Spanish]; Dipivefrine; Dipivefrinum [INN-Latin]; Ophtho-Dipivefrin; Propine; Propine C Cap B.I.D.
• 别名: Dipivefrin

登记号

• CAS号: 52365-63-6
• PubChem SID: 160963795; 46504716
• PubChem CID: 3105

理论计算性质

JChem

• Acid pKa: 14.00017
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.5729072
• LogD (pH = 7.4): 1.8021725
• Log P: 3.7148545
• 摩尔折射率: 94.9381 cm^3
• 极化性: 37.906097 Å^3
• 极化表面积: 84.86 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.17
• LOG S: -3.78
• 溶解度: 5.82e-02 g/l

分子性质

理化性质

• 溶解度: Freely soluble as HCl salt
• 疏水性(logP): 1.7

详细说明

DrugBank - DB00449

• Drug Groups: approved
• Description: Dipivefrin is a prodrug of adrenaline, which is used to treat glaucoma. It is available as ophthalmic solution (eye drops).
• Indication: Dipivefrin is a prodrug which is used as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma.
• Pharmacology: 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.
• Toxicity: Oral LD₅₀ in rat is 183 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Dipivefrin is converted to epinephrine inside the human eye by enzyme hydrolysis.
• Absorption: Well absorbed following occular administration.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com