Dipivefrine

Dipivefrine (INN) or dipivefrin (USAN), trade name Propine among others, is a prodrug of epinephrine, and is used to treat open-angle glaucoma.[1][2] It is available as a 0.1% ophthalmic solution. It is no longer available in the United States.[3]

"Propine" redirects here. For the hydrocarbon compound, see propyne.
Dipivefrine
Clinical data
Trade namesPropine, Pivalephrine
Other namesDipivefrin
AHFS/Drugs.comInternational Drug Names
MedlinePlusa686005
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    administration    		Eye drops
    ATC code
    Legal status
    Legal status
    • In general: ℞ (Prescription only)
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC19H29NO5
    Molar mass351.443 g·mol−1
    3D model (JSmol)
     NY (what is this?)  (verify)

    Contraindications

    Use in narrow-angle glaucoma may be dangerous because it could make the eye susceptible to an attack of angle closure,[2] 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 those of epinephrine: tachycardia (fast heartbeat), hypertension (high blood pressure) and arrhythmias (irregular heartbeat).[2]

    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 receptors), thus reducing pressure inside the eye. It also increases the conductivity of trabecular filtering cells (a β2 receptor mediated action). It is preferred to epinephrine because it is longer acting, more consistent in its action and better tolerated.[1]

    References
    1. KD Tripari. Essentials of Medical Pharmacology (5 ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN 81-8061-187-6.
    2. Dipivefrin FDA Professional Drug Information.
    3. Zhang L, Weizer JS, Musch DC (2017). "Perioperative medications for preventing temporarily increased intraocular pressure after laser trabeculoplasty". Cochrane Database Syst Rev. 2: CD010746. doi:10.1002/14651858.CD010746.pub2. PMC 5477062. PMID 28231380.
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