Dipivefrine

This article is about the drug. It is not to be confused with Propyne.

Dipivefrine

Clinical data
Trade names	Propine
AHFS/Drugs.com	International Drug Names
MedlinePlus	a686005
Pregnancy category	US: B (No risk in non-human studies)
ATC code	S01EA02 (WHO)
Identifiers
IUPAC name [2-(2,2-dimethylpropanoyloxy)-4- (1-hydroxy-2-methylamino-ethyl)- phenyl] 2,2-dimethylpropanoate
CAS Number	52365-63-6 Y
PubChem (CID)	3105
IUPHAR/BPS	7166
DrugBank	DB00449 Y
ChemSpider	2994 Y
UNII	8Q1PVL543G Y
KEGG	D02349 Y
ChEBI	CHEBI:4646 Y
ChEMBL	CHEMBL1201262 N
Chemical and physical data
Formula	C19H29NO5
Molar mass	351.437 g/mol
3D model (Jmol)	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 Y Key:OCUJLLGVOUDECM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Dipivefrin (trade name Propine) is a prodrug of epinephrine, and is used to treat open-angle glaucoma. It is available as a 0.1% ophthalmic solution.

Mechanism of action

The drug when applied over the cornea, penetrates it and is then hydrolysed to epinephrine by the esterases. It increases uveo-scleral outflow and also reduces aqueous formation (an α₁ and α₂ mediated action), thus reducing the intraocular pressure. It also increases the hydraulic conductivity of trabecular filtering cells (a β₂ mediated action). It is preferred to epinephrine because it is longer acting, more consistent in its action and has better ocular tolerance.