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| Trade names | AKPro, D Epifrin, Diopine, Glaucothil, Pro-Epinephrine, Propine, Pivalephrine, Thilodrin, Vistapine, others |
| Other names | Dipivefrin; Dipivephrine; Dipivephrin; Dipivalyl epinephrine; Dipivalylepinephrine; DPE; Epinephrine dipivalate; Epinephrine dipivalate ester; Adrenaline dipivalate; Dipivalyl adrenaline; Dipivalyladrenaline; K-30081; 3,4-Dipivalyloxy-β-hydroxy-N-methylphenethylamine; 3,4-Dipivalyloxy-β-hydroxy-N-methyl-β-phenylethylamine |
| AHFS/Drugs.com | International Drug Names |
| MedlinePlus | a686005 |
| Routes of administration | Eye drops[1] |
| Drug class | Adrenergic receptor agonist;Sympathomimetic |
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| Formula | C19H29NO5 |
| Molar mass | 351.443 g·mol−1 |
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Dipivefrine, ordipivefrin, also known asepinephrine pivalate and sold under the brand namePropine among others, is asympathomimeticmedication which is used in the treatment ofopen-angle glaucoma.[2][3] It is available as a 0.1%ophthalmicsolution (eye drop).[1][4]
Side effects of dipivefrine include local eye reactions among others. Dipivefrine is aprodrug ofepinephrine (adrenaline) and hence acts as anon-selectiveadrenergic receptoragonist.[5] It is asubstituted phenethylamine andcatecholamine and is anester of epinephrine with much greaterfat solubility.[6][7][8]
Dipivefrine was first described by 1975.[9] It is widely marketed throughout the world.[10] However, it is no longer available in theUnited States.[11]
Dipivefrine is used in the treatment ofopen-angle glaucoma.[2]
Use innarrow-angle glaucoma may be dangerous because it could make the eye susceptible to an attack of angle closure,[3] causing an increase in pressure and pain and possibly loss of vision.
The most commonside 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 includetachycardia (fast heartbeat),hypertension (high blood pressure) andarrhythmias (irregular heartbeat).[3]
Dipivefrine penetrates thecornea and is thenhydrolysed to epinephrine byesteraseenzymes.[8] It increases outflow of theaqueous humour and also reduces its formation (mediated by its action onα1- andα2-adrenergic receptors), thus reducingpressure inside the eye. It also increases the conductivity oftrabecular filtering cells (aβ2-adrenergic-receptor-mediated action). It is preferred to epinephrine because it is longer-acting, more consistent in its action, and better-tolerated.[2]
Dipivefrine, also known as epinephrine dipivalate or as 3,4-dipivalyloxy-β-hydroxy-N-methylphenethylamine, is asubstituted phenethylamine andcatecholamine.[6] It is the 3,4-dipivalateester ofepinephrine (adrenaline).[6]
The experimentallog P of dipivefrine is 1.7 and its predicted log P ranges from 1.49 to 3.71.[6][1][12] It is dramatically morelipophilic (600-fold) than epinephrine,[7][8][4] which is highlyhydrophilic and has a log P of -1.37.[13] The lipophilicity of dipivefrine allows it to penetrate thecornea much more readily (17-fold) than epinephrine.[7][8][4] Eye drops containing 0.1% dipivefrine have similar effectiveness to conventional eye drops containing 2% epinephrine in loweringintraocular pressure.[4]
Dipivefrine is usedpharmaceutically mainly as thehydrochloridesalt.[14][10]
A similarcompound that was never marketed ispivenfrine, which is the 3-pivalate ester ofphenylephrine.[14]
Dipivefrine was first described in thescientific literature by 1975.[9]
Dipivefrine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name,BANTooltip British Approved Name, andDCFTooltip Dénomination Commune Française, whiledipivefrin is itsUSANTooltip United States Adopted Name anddipivefrina is itsDCITTooltip Denominazione Comune Italiana.[14][10][15] In the case of thehydrochloridesalt,dipivefrine hydrochloride is itsBANMTooltip British Approved Name whiledipivefrin hydrochloride is itsUSANTooltip United States Adopted Name andJANTooltip Japanese Accepted Name.[14][10][15]
Synonyms of dipivefrine includeepinephrine pivalate,adrenaline pivalate, anddipivalyl epinephrine, among others.[14][10]
Dipivefrine has been sold under brand names includingDiopine,Glaucothil,Pro-Epinephrine,Propine,Thilodrin, andVistapine, among many others.[14][10]
