Dipivefrine

Summary

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]

Dipivefrine
Clinical data
Trade namesPropine, Pivalephrine
Other namesDipivefrin
AHFS/Drugs.comInternational Drug Names
MedlinePlusa686005
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
  • 52365-63-6 checkY
PubChem CID
  • 3105
IUPHAR/BPS
  • 7166
DrugBank
  • DB00449 checkY
ChemSpider
  • 2994 checkY
UNII
  • 8Q1PVL543G
KEGG
  • D02349 checkY
ChEBI
  • CHEBI:4646 checkY
ChEMBL
  • ChEMBL1201262 ☒N
CompTox Dashboard (EPA)
  • DTXSID1048544 Edit this at Wikidata
Chemical and physical data
FormulaC19H29NO5
Molar mass351.443 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 checkY
  • Key:OCUJLLGVOUDECM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Contraindications edit

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 edit

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 edit

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 edit

  1. ^ a b KD Tripari (2004). Essentials of Medical Pharmacology (5 ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN 81-8061-187-6.
  2. ^ a b c 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. 2017 (2): CD010746. doi:10.1002/14651858.CD010746.pub2. PMC 5477062. PMID 28231380.