Dipivefrine

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

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
Molar 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.^[1] 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.^[1]

References

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

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Parasympathomimetics

muscarinic	Aceclidine Pilocarpine

muscarinic/nicotinic	Acetylcholine Carbachol

Acetylcholinesterase inhibitors	Demecarium Ecothiopate Stigmine (Fluostigmine Neostigmine Physostigmine) Paraoxon

Carbonic anhydrase inhibitors/
(sulfonamides)

Beta blocking agents

Prostaglandin analogues (F_2α)

Other agents

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