Dipivefrine

Dipivefrine
Clinical data
Trade names	Propine, Pivalephrine
Other names	Dipivefrin
AHFS/Drugs.com	International Drug Names
MedlinePlus	a686005
Pregnancy; category	US: B (No risk in non-human studies) ;
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 ;
PubChem CID	3105;
IUPHAR/BPS	7166;
DrugBank	DB00449 ;
ChemSpider	2994 ;
UNII	8Q1PVL543G;
KEGG	D02349 ;
ChEBI	CHEBI:4646 ;
ChEMBL	ChEMBL1201262 ;
CompTox Dashboard (EPA)	DTXSID1048544 ;
Chemical and physical data
Formula	C19H29NO5
Molar mass	351.443 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 ; Key:OCUJLLGVOUDECM-UHFFFAOYSA-N ;
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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 as a 0.1% ophthalmic solution. It is no longer available in the United States.[3]

Contraindications

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

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

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]

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References

KD Tripari. Essentials of Medical Pharmacology (5 ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN 81-8061-187-6.
Dipivefrin FDA Professional Drug Information.
Zhang L, Weizer JS, Musch DC (2017). "Perioperative medications for preventing temporarily increased intraocular pressure after laser trabeculoplasty". Cochrane Database Syst Rev. 2: CD010746. doi:10.1002/14651858.CD010746.pub2. PMC 5477062. PMID 28231380.

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

[Drugs.com-2] Dipivefrin FDA Professional Drug Information.

[Zhang-3] Zhang L, Weizer JS, Musch DC (2017). "Perioperative medications for preventing temporarily increased intraocular pressure after laser trabeculoplasty". Cochrane Database Syst Rev. 2: CD010746. doi:10.1002/14651858.CD010746.pub2. PMC 5477062. PMID 28231380.