dipivefrin

Trade name: propine

Small moleculeapproved

Approved

May 2, 1980

Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating α -and/or β2-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy. Dipivefrin is used as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma. — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 5 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Timeline

1980s

May 2, 1980
Allergan — Earliest FDA Approval
May 2, 1980
Allergan — NDA Secondary Org
May 2, 1980
Allergan — NDA Organization

1990s

Jun 30, 1994
Falcon Pharmaceuticals — Marketing Organization
May 19, 1995
Bausch & Lomb — Marketing Organization
Sep 29, 1995
Akorn, Inc. — Marketing Organization
Sep 29, 1995
Epic Pharma Llc — Marketing Organization

Indications

Approved for

Mechanism of action

Adrenergic receptorAGONIST
Adrenergic receptor agonist

Approval history

approvedPriority reviewMay 2, 1980

Chemistry & pharmacology

Loading structure…

SMILES

CNCC(O)c1ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c1

Mol. weight: 351.44 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Racemic Mixture
Inorganic: No
Polymer: No
Delivery: Topical
Availability: Discontinued

Oral

Parenteral

Topical

Yes

Prodrug

Sources

Also known as

1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol
1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol
(+-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate
(+-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate
4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate
4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate
adrenaline dipivalate
akpro
akpro
alcon brand of dipivefrin hydrochloride
allergan brand of dipivefrin hydrochloride
apo-dipivefrin
apotex brand of dipivefrin hydrochloride
d epifrin
diopine
dipivaloylepinephrine
dipivalyl epinephrine
dipivalyl epinephrine
dipivalyl epinephrine
dipivalyl epinephrine
dipivefrin
dipivefrin
dipivefrin
dipivefrin
dipivefrin
dipivefrin
dipivefrin
dipivefrina
dipivefrina
dipivefrin acetate, (+-)-isomer
dipivefrin citrate (1:1), (+-)-isomer
dipivefrine
dipivefrine
dipivefrine
dipivefrine
dipivéfrine
dipivéfrine
dipivefrine hydrochloride
dipivefrine hydrochloride
dipivefrin hcl
dipivefrin hcl
dipivefrin hcl
dipivefrin hydrochloride
dipivefrin hydrochloride
dipivefrin hydrochloride
dipivefrin hydrochloride
dipivefrin hydrochloride
dipivefrin hydrochloride
dipivefrin hydrochloride
dipivefrin hydrochloride, (+-)-isomer
dipivefrin monophosphate, (+-)-isomer
dipivefrin monosulfate, (+-)-isomer
dipivefrin nitrate, (+-)-isomer
dipivefrin perchlorate
dipivefrin propanoate, (+-)-isomer
dipivefrin, (r)-isomer
dipivefrin tartrate (1:1), (+-)-(r-(r*,r*))-isomer
dipivefrin tartrate (1:1), (r)-(r-(r*,r*))-isomer
dipivefrinum
dipivefrinum
dipoquin
dpe
dpe
glaucothil
glaudrops
ioquin brand of dipivefrin hydrochloride
pharm-allergan brand of dipivefrin hydrochloride
pharmascience brand of dipivefrin hydrochloride
pms-dipivefrin
pro-epinephrine
pro-epinephrine
propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (+-)-
propine
propine
propine
propine
ratio-dipivefrin
ratiopharm brand of dipivefrin hydrochloride

Organizations

Marketing (6)

Organization	Org type	Relationship	Date
Akorn, Inc.	For profit	MKTG	Sep 29, 1995
Allergan	For profit	NDA2	May 2, 1980
Allergan	For profit	NDA	May 2, 1980
Bausch & Lomb	For profit	MKTG	May 19, 1995
Epic Pharma Llc	For profit	MKTG	Sep 29, 1995
Falcon Pharmaceuticals	For profit	MKTG	Jun 30, 1994