Compound: dipivefrin
SMILES: O=C(Oc1c(OC(=O)C(C)(C)C)ccc(c1)C(O)CNC)C(C)(C)C
InChIKey: OCUJLLGVOUDECM-UHFFFAOYSA-N
Synonyms: dipivefrin, Dipivefrine, 52365-63-6, Dipivefrinum, Dipivefrina, dipivalyl epinephrine, 8Q1PVL543G, 1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol, CHEBI:4646, DTXSID1048544, 4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate, 2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate, Propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (+-)-, (+-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate, 4-(1-hydroxy-2-(methylamino)ethyl)-o-phenylene divavalate, Diopine, Glaudrops, (+-)-4-(1-hydroxy-2-(methylamino)ethyl)-o-phenylene divavalate, 2-((2,2-dimethylpropanoyl)oxy)-4-(1-hydroxy-2-(methylamino)ethyl)phenyl 2,2-dimethylpropanoate, 2-((2,2-dimethylpropanoyl)oxy)-5-(1-hydroxy-2-(methylamino)ethyl)phenyl 2,2-dimethylpropanoate, 2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate, dipivaloylepinephrine, adrenaline dipivalate, RefChem:589010, DTXCID1028100, S01EA02, Dipivefrin [USAN], Dipivefrine (INN), Dipivefrine [INN], Dipivefrin (USAN), [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate, Dipivefrinum [INN-Latin], Dipivefrina [INN-Spanish], 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene bis(2,2-dimethylpropanoate), 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-phenylene bis(2,2-dimethylpropanoate), K 30081, UNII-8Q1PVL543G, 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-phenylen dipivalat, (+-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol 3,4-dipivalate, DIPIVEFRIN [MI], (RS)-4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-phenylen dipivalat, Prestwick0_000632, Prestwick1_000632, Prestwick2_000632, Prestwick3_000632, DIPIVEFRIN [VANDF], DIPIVEFRINE [MART.], SCHEMBL24713, BSPBio_000624, DIPIVEFRINE [WHO-DD], SPBio_002843, BPBio1_000688, GTPL7166, orb1710755, CHEMBL1201262, SCHEMBL29710905, (+-)-4-(1-Hydroxy-2-methylaminoethyl)-o-phenylendipivalat, EX-A8161, EBC-26693, MFCD00673243, T0103L, AKOS003662293, DB00449, (+-)-2,2-Dimethylpropansaeure-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylenester, 2,2-Dimethylpropanoic acid 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diyl bis(2,2-dimethylpropanoate), NCGC00179499-01, NCGC00179499-05, DA-52576, HY-121398, AB00514686, CS-0081941, NS00003866, C06963, D02349, EN300-17997011, L000915, Q905952, BRD-A47494775-003-03-0, BRD-A47494775-003-11-3, (+/-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate, PROPANOIC ACID, 2,2-DIMETHYL-, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-1,2-PHENYLENE ESTER, (+/-)-
Theoretical properties:
molecular_formula: C19H29NO5
molecular_weight: 351.4 g/mol
exact_mass: 351.20457303 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 9
heavy_atom_count: 25
topological_polar_surface_area: 84.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 146-147
solubility: Freely soluble as HCl salt
Descriptions:
pubchem: 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+).
chebi: 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.
chembl: DIPIVEFRIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Dipivefrine, or dipivefrin, also known as epinephrine pivalate and sold under the brand name Propine among others, is a sympathomimetic medication which is used in the treatment of open-angle glaucoma. It is available as a 0.1% ophthalmic solution (eye drop).
Side effects of dipivefrine include local eye reactions among others. Dipivefrine is a prodrug of epinephrine (adrenaline) and hence acts as a non-selective adrenergic receptor agonist. It is a substituted phenethylamine and catecholamine and is an ester of epinephrine with much greater fat solubility.
Dipivefrine was first described by 1975. It is widely marketed throughout the world. However, it is no longer available in the United States.