Dipivefrin

Title: Dipivefrin
CAS Registry Number: 52365-63-6
CAS Name: 2,2-Dimethylpropanoic acid 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester
Additional Names: (±)-3,4-dihydroxy-a-[(methylamino)methyl]benzyl alcohol 3,4-dipivalate; 1-(3¢,4¢-dipivaloyloxyphenyl)-2-methylamino-1-ethanol; dipivalyl epinephrine; DPE
Molecular Formula: C19H29NO5
Molecular Weight: 351.44
Percent Composition: C 64.93%, H 8.32%, N 3.99%, O 22.76%
Literature References: Dipivalyl ester of epinephrine, q.v. Prepn: D. Henschler et al., DE 2152058; eidem, US 4085270 (1973, 1978 both to Klinge); A. Hussain, J. E. Truelove, DE 2343657; eidem, US 3809714 and US 3839584 (all 1974 to Interx). In vitro study: A. H. Neufeld, E. D. Page, Invest. Ophthalmol. Visual Sci. 16, 1118 (1977). Pharmacology: B. C. Wang et al., J. Pharmacol. Exp. Ther. 203, 442 (1977). Effects on intraocular pressure in dogs: R. M. Gwin et al., Am. J. Vet. Res. 39, 83 (1978). Metabolism: I. Abramovsky, J. S. Mindel, Arch. Ophthalmol. 97, 1937 (1979). Clinical study: M. A. Kass et al., ibid. 1865. General pharmacology, toxicology and clinical experience in glaucoma: D. A. McClure, ACS Symp. Ser. 14, 224-235 (1975). Comprehensive description: G. M. Wall, T. Y. Fan, Anal. Profiles Drug Subs. Excip. 22, 229-262 (1993).
Properties: Crystals from ether, mp 146-147°.
Melting point: mp 146-147°
Derivative Type: Hydrochloride
CAS Registry Number: 64019-93-8
Trademarks: Diopine (Allergan); d Epifrin (Allergan); Diphemin (Alcon); Pivalephrine (Santen); Propine (Allergan)
Molecular Formula: C19H29NO5.HCl
Molecular Weight: 387.90
Percent Composition: C 58.83%, H 7.80%, N 3.61%, O 20.62%, Cl 9.14%
Properties: Crystals from ethyl acetate, mp 158-159°. Sol in water and ethanol. pKa 8.40.
Melting point: mp 158-159°
pKa: pKa 8.40
Therap-Cat: Adrenergic (ophthalmic); antiglaucoma.
Keywords: a-Adrenergic Agonist; Antiglaucoma.
Diploicin Diponium Bromide Diprenorphine Dipropalin Dipropetryn

Dipivefrine
Dipivefrine.svg
Systematic (IUPAC) name
[2-(2,2-dimethylpropanoyloxy)-4- (1-hydroxy-2-methylamino-ethyl)- phenyl] 2,2-dimethylpropanoate
Clinical data
Trade names Propine
AHFS/Drugs.com International Drug Names
MedlinePlus a686005
Pregnancy cat. B (US)
Legal status  ?
Identifiers
CAS number 52365-63-6 YesY
ATC code S01EA02
PubChem CID 3105
DrugBank DB00449
ChemSpider 2994 YesY
UNII 8Q1PVL543G YesY
KEGG D02349 YesY
ChEBI CHEBI:4646 YesY
ChEMBL CHEMBL1201262 N
Chemical data
Formula C19H29NO5 
Mol. mass 351.437 g/mol
 N (what is this?)  (verify)

Dipivefrine (trade name Propine) is a prodrug of epinephrine, and is used to treat open-angle glaucoma.[1] It is available as a 0.1% ophthalmic solution.