Dipivefrine

Last updated
Dipivefrine
Dipivefrine.svg
Clinical data
Trade names Propine, Pivalephrine
Other namesDipivefrin
AHFS/Drugs.com International Drug Names
MedlinePlus a686005
Routes of
administration
Eye drops
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • [2-(2,2-Dimethylpropanoyloxy)-4-(1-hydroxy-2-methylamino-ethyl)-phenyl] 2,2-dimethylpropanoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H29NO5
Molar mass 351.443 g·mol−1
3D model (JSmol)
  • O=C(Oc1cc(ccc1OC(=O)C(C)(C)C)C(O)CNC)C(C)(C)C
  • InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3 Yes check.svgY
  • Key:OCUJLLGVOUDECM-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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[ citation needed ] as a 0.1% ophthalmic solution. It is no longer available in the United States. [3]

Contents

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]

Related Research Articles

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Glaucoma is a group of eye diseases that result in damage to the optic nerve and cause vision loss. The most common type is open-angle glaucoma, in which the drainage angle for fluid within the eye remains open, with less common types including closed-angle glaucoma and normal-tension glaucoma. Open-angle glaucoma develops slowly over time and there is no pain. Peripheral vision may begin to decrease, followed by central vision, resulting in blindness if not treated. Closed-angle glaucoma can present gradually or suddenly. The sudden presentation may involve severe eye pain, blurred vision, mid-dilated pupil, redness of the eye, and nausea. Vision loss from glaucoma, once it has occurred, is permanent. Eyes affected by glaucoma are referred to as being glaucomatous.

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Latanoprost

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References

  1. 1 2 KD Tripari. Essentials of Medical Pharmacology (5 ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN   81-8061-187-6.
  2. 1 2 3 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.