3338. Dipivefrin

Nomenclature

CAS number: 52365-63-6
2,2-Dimethylpropanoic acid 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester; (±)-3,4-dihydroxy-α-[(methylamino)methyl]benzyl alcohol 3,4-dipivalate; 1-(3′,4′-dipivaloyloxyphenyl)-2-methylamino-1-ethanol; dipivalyl epinephrine; DPE.
C19H29NO5; mol wt 351.44.
C 64.93%, H 8.32%, N 3.99%, O 22.76%.

Description and 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).

Chemical structure

Properties

Crystals from ether, mp 146-147°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 64019-93-8
Diopine (Allergan); d Epifrin (Allergan); Diphemin (Alcon); Pivalephrine (Santen); Propine (Allergan).
C19H29NO5.HCl; mol wt 387.90.
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.

Therapeutic Category

Adrenergic (ophthalmic); antiglaucoma.

Keywords

α-Adrenergic Agonist; Antiglaucoma