Dipivefrine

Dipivefrine

Systematic (IUPAC) name
[2-(2,2-dimethylpropanoyloxy)-4- (1-hydroxy-2-methylamino-ethyl)- phenyl] 2,2-dimethylpropanoate
Clinical data
Trade names	Propine
AHFS/Drugs.com	International Drug Names
MedlinePlus	a686005
Pregnancy category	US: B (No risk in non-human studies)
Identifiers
CAS Number	52365-63-6 Y
ATC code	S01EA02 (WHO)
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 data
Formula	C19H29NO5
Molecular mass	351.437 g/mol
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 uveosacral 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.