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

• ChemBase ID: 332
• Molecular Formular: C19H29NO5
• Molecular Mass: 351.43726
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
• IUPAC Traditional name: dipivefrin
• Brand Name: AKPro; DPE; Dipivefrin HCL; Dipivefrin [USAN]; Dipivefrina [INN-Spanish]; Dipivefrine; Dipivefrinum [INN-Latin]; Ophtho-Dipivefrin; Propine; Propine C Cap B.I.D.
• Synonyms: Dipivefrin

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.00017
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5729072
• LogD (pH = 7.4): 1.8021725
• Log P: 3.7148545
• Molar Refractivity: 94.9381 cm^3
• Polarizability: 37.906097 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.17
• LOG S: -3.78
• Solubility (Water): 5.82e-02 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble as HCl salt
• Hydrophobicity(logP): 1.7

DETAILS

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