ATC Class: S01EA02
VA Class: OP103
Chemical Name: (±)-3,4-Dihydroxy-α-[(methylamino)methyl]benzyl alcohol 3,4-dipivalate
Molecular Formula: C19H29NO5
CAS Number: 64019-93-8
Synthetic sympathomimetic amine.78
Uses for Dipivefrin Hydrochloride
Ocular Hypertension and Glaucoma
Reduction of elevated IOP in patients with open-angle glaucoma.1 4 5 10 13 25 26 27 28 34 36 37 52 Used alone or in conjunction with other IOP-lowering drugs.1 4 5 7 10 13 25 26 27 28 31 34 36 37 38 51 52 53 56 57 59 60 62 87 88 May be used as initial therapy 1 7 10 13 25 26 27 28 34 52 or for control of IOP in those patients who have not responded adequately to other antiglaucoma agents.1 5 7 10 13 25 26 31 34 36 38 51 52 53 56 57 59 60 62 87 88
May be preferred as an alternative to topical epinephrine in some patients (e.g., those with cardiovascular disease)31 because of increased intraocular penetration (lower doses are needed) and resultant decreased adverse systemic effects (e.g., cardiovascular effects) compared with epinephrine.7 11 26 28 31 34 57 69
Does not produce miosis, accommodative spasm, blurred vision, or night blindness.1 Less likely than epinephrine to cause adenochrome staining of contact lenses.1 4 7 12 58 61 70 71 72
Has been used to reduce IOP in the treatment of other ocular conditions, including ocular hypertension† and pseudoexfoliative†, low-tension†, and secondary† (e.g., post-angle closure, pigmentary, traumatic, herpes zoster) glaucomas.34 52
Dipivefrin Hydrochloride Dosage and Administration
Adjust dosage according to individual requirements and response of patient as determined by tonometric readings before and during therapy.7
Because of diurnal variations in IOP, measure IOP at different times during the day to determine if an adequate hypotensive effect is maintained.7 Since IOP may not stabilize for a few weeks after initiating therapy, determine IOP after several weeks of therapy; thereafter, IOP should be determined as necessary.7 89 94
Apply topically to the eye as an ophthalmic solution.1 4 Not for injection.1
Avoid contamination of the solution container.6
Available as dipivefrin hydrochloride; dosage expressed in terms of the salt.1
Ocular Hypertension and Glaucoma
1 drop of a 0.1% solution in affected eye(s) every 12 hours.1 4 5 10
In patients receiving several drugs for the treatment of glaucoma, adjustments to the regimen should involve one drug at a time and should usually occur at intervals of at least 1 week.89
Initially, 1 drop of a 0.1% solution every 12 hours while therapy with other drugs is continued.1 Beginning on the following day1 and continuing at intervals of at least 1 week until optimum response is achieved, reduce dosage of one of the other drugs or discontinue one of the other drugs.89 Adjust remaining regimen according to the IOP response of the patient.89
Conversion to Dipivefrin TherapyOphthalmic
Conversion from monotherapy with epinephrine: Discontinue epinephrine and initiate dipivefrin at 1 drop of a 0.1% solution into affected eye(s) every 12 hours1 5 at the time of the next scheduled dose of epinephrine.89 94
Conversion from monotherapy with antiglaucoma agents other than epinephrine: On day 1, continue other antiglaucoma agent and add 1 drop of a 0.1% dipivefrin solution every 12 hours.1 On day 2, discontinue the other drug and continue dipivefrin.1
Cautions for Dipivefrin Hydrochloride
Angle-closure glaucoma, or patients predisposed to angle-closure.1 7
Known hypersensitivity to dipivefrin or any ingredient in the formulation.1 7
Blepharoconjunctivitis, requiring discontinuance of dipivefrin, reported after ≥5 months of therapy.4 36 37 54 55 59 63 Karyomegaly of conjunctival epithelial cells, 63 chemosis of the conjunctiva, 59 dry eczematoid dermatitis of the eyelids, 59 pruritus, 55 and blepharitis 25 53 55 reported.
Allergic reactions may be caused by excipients in the preparation.66
Cross-sensitivity reported in patients who have previously exhibited a sensitivity reaction to epinephrine.1 13 51 54 55 63
Reversible macular edema reported in aphakic patients with glaucoma treated with epinephrine; caution is advised.1 5 52 55 64 65 89
Ophthalmic use of epinephrine occasionally causes systemic sympathomimetic effects, such as tachycardia,1 7 arrhythmias,1 28 31 and hypertension;1 28 31 however, systemic sympathomimetic effects occur rarely with topical administration of dipivefrin.5
Use with caution in patients with vascular hypertension or cardiac disorders, including arrhythmias and cardiovascular disease; consider cardiovascular status before initiating therapy.15 89 94
Not known whether dipivefrin distributed into milk.1 Caution advised if topical dipivefrin is used.1
Safety and efficacy not established.1
No substantial differences in safety and efficacy relative to younger adults.1
Common Adverse Effects
Ocular congestion or hyperemia,1 25 34 36 37 52 59 63 burning,1 4 5 10 15 25 26 stinging.1 5 10 15 25 51
Interactions for Dipivefrin Hydrochloride
Ocular hypotensive agents
Additive IOP-lowering effects1 26 38 51 54 56 57 59 60
Used to therapeutic advantage1 7 26 38 54 56 57 59 60
Dipivefrin Hydrochloride Pharmacokinetics
Following topical application to the eye, about 7% of administered dose absorbed across the cornea into the aqueous humor mainly as epinephrine.8 Lipid solubility enhances ocular absorption of dipivefrin over that of epinephrine.7 8 13 16 38
Rarely, absorption following topical application to the eye may be sufficient to cause systemic sympathomimetic effects to occur.31
Reduction in IOP usually evident within 30 minutes after topical application and peaks within 1 hour.1 4 5 7
Reduction in IOP persists for ≥12 hours.89 94
Rapidly distributed throughout ocular tissues and fluids in rabbits.7 16 30 39 44 In humans, dipivefrin and its metabolites detected in the cornea,8 aqueous humor,8 and to a lesser extent, the tissues and fluids of the contralateral untreated eye;16 32 however, distribution in human ocular tissues and fluids not fully characterized.94
Systemic distribution following administration of topical dipivefrin not determined.94
Not known whether dipivefrin crosses the placenta or distributes into milk; 1 94 however, systemically absorbed epinephrine crosses the placenta and distributes into milk.4 42
Following topical application and ocular absorption, rapidly and extensively hydrolyzed to epinephrine via esterases (e.g., acetylcholinesterase, pseudocholinesterase, carbonic anhydrase) in the cornea, conjunctiva, and aqueous humor.1 4 5 8 11 14 16 30 33 39 40 46 47 50 74
Epinephrine released from the prodrug is metabolized by catechol-O-methyltransferase (COMT) and MAO in the eye, liver, and other tissues.11 16 39 45 46 48 49
Averages 1.8, 0.9, and 3.1 hours in the cornea, aqueous humor, and iris/ciliary body, respectively.44
Tight, light-resistant containers at 15–30°C.1 98
Prodrug with little or no pharmacologic activity until hydrolyzed into epinephrine.1 7 9 12 14 22 35 89
Lowers IOP1 4 5 10 13 25 26 27 28 34 36 37 52 in patients with glaucoma;1 4 5 10 13 25 26 27 28 34 36 37 52 lowers IOP to a lesser extent in the normal eye; causes mydriasis.27 77 Appears to lower IOP by stimulating α -and/or β2-adrenergic receptors, 7 11 23 24 67 90 93 95 96 resulting in an increase in pressure-independent (uveoscleral) and, to a lesser extent in pressure-dependent (trabecular) aqueous humor outflow.1 4
Advice to Patients
Importance of learning and adhering to proper administration techniques to avoid contamination of the product.1
Advise patients to consult a clinician immediately regarding continued use of ophthalmic preparations if an intercurrent ocular condition (e.g., trauma, infection, sensitivity, irritation) occurs.1 89 94
Importance of informing clinicians of existing or contemplated concomitant therapy, including prescription and OTC drugs and dietary or herbal supplements, as well as concomitant illnesses.1
Importance of women informing clinicians if they are or plan to become pregnant or plan to breast-feed.1
Importance of informing patients of other important precautionary information. (See Cautions.)
Excipients in commercially available drug preparations may have clinically important effects in some individuals; consult specific product labeling for details.
Please refer to the ASHP Drug Shortages Resource Center for information on shortages of one or more of these preparations.
* available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name
Dipivefrin Hydrochloride Ophthalmic Solution
Bausch & Lomb, Falcon
Propine (with benzalkonium chloride)
AHFS DI Essentials. © Copyright 2018, Selected Revisions May 1, 2007. American Society of Health-System Pharmacists, Inc., 4500 East-West Highway, Suite 900, Bethesda, Maryland 20814.
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Other brands: Propine