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

Dipivefrine
Dipivefrine.svg
Clinical data
Trade namesPropine, Pivalephrine
Other namesDipivefrin
AHFS/Drugs.comInternational Drug Names
MedlinePlusa686005
Routes of
administration		Eye drops
ATC code
  • S01EA02 (WHO)
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • [2-(2,2-Dimethylpropanoyloxy)-4-(1-hydroxy-2-methylamino-ethyl)-phenyl] 2,2-dimethylpropanoate
CAS Number
  • 52365-63-6 check
PubChem CID
  • 3105
IUPHAR/BPS
  • 7166
DrugBank
  • DB00449 check
ChemSpider
  • 2994 check
UNII
  • 8Q1PVL543G
KEGG
  • D02349 check
ChEBI
  • CHEBI:4646 check
ChEMBL
  • ChEMBL1201262 ☒
CompTox Dashboard (EPA)
  • DTXSID1048544 Edit this at Wikidata
Chemical and physical data
FormulaC19H29NO5
Molar mass351.443 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(Oc1cc(ccc1OC(=O)C(C)(C)C)C(O)CNC)C(C)(C)C
InChI
  • 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 check
  • Key:OCUJLLGVOUDECM-UHFFFAOYSA-N check
 ☒check (what is this?)  (verify)

ContraindicationsEdit

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 effectsEdit

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]

PharmacologyEdit

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]

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.