Dipivefrine

Medical uses

Dipivefrine is used in the treatment of open-angle glaucoma.

Contraindications

Use in narrow-angle glaucoma may be dangerous because it could make the eye susceptible to an attack of angle closure, causing an increase in pressure and pain and possibly loss of vision.

Side effects

The most common side effects of dipivefrine are burning, stinging, and other irritations of the eye. Possible but uncommon side effects are the same as those of epinephrine and include tachycardia (fast heartbeat), hypertension (high blood pressure) and arrhythmias (irregular heartbeat).

Pharmacology

Dipivefrine penetrates the cornea and is then hydrolysed to epinephrine by esterase enzymes. It increases outflow of the aqueous humour and also reduces its formation (mediated by its action on α1- and α2-adrenergic receptors), thus reducing pressure inside the eye. It also increases the conductivity of trabecular filtering cells (a β2-adrenergic-receptor-mediated action). It is preferred to epinephrine because it is longer-acting, more consistent in its action, and better-tolerated.

Chemistry

Dipivefrine, also known as epinephrine dipivalate or as 3,4-dipivalyloxy-β-hydroxy-N-methylphenethylamine, is a substituted phenethylamine and catecholamine. It is the 3,4-dipivalate ester of epinephrine (adrenaline).

The experimental log P of dipivefrine is 1.7 and its predicted log P ranges from 1.49 to 3.71. It is dramatically more lipophilic (600-fold) than epinephrine, which is highly hydrophilic and has a log P of -1.37. The lipophilicity of dipivefrine allows it to penetrate the cornea much more readily (17-fold) than epinephrine. Eye drops containing 0.1% dipivefrine have similar effectiveness to conventional eye drops containing 2% epinephrine in lowering intraocular pressure.

Dipivefrine is used pharmaceutically mainly as the hydrochloride salt.

A similar compound that was never marketed is pivenfrine, which is the 3-pivalate ester of phenylephrine.

History

Dipivefrine was first described in the scientific literature by 1975.

Society and culture

Names

Dipivefrine is the generic name of the drug and its , , and , while dipivefrin is its and dipivefrina is its . In the case of the hydrochloride salt, dipivefrine hydrochloride is its while dipivefrin hydrochloride is its and .

Synonyms of dipivefrine include epinephrine pivalate, adrenaline pivalate, and dipivalyl epinephrine, among others.

Dipivefrine has been sold under brand names including Diopine, Glaucothil, Pro-Epinephrine, Propine, Thilodrin, and Vistapine, among many others.

References

References

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