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Details

Stereochemistry RACEMIC
Molecular Formula C19H29NO5
Molecular Weight 351.4373
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPIVEFRIN

SMILES

CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1

InChI

InChIKey=OCUJLLGVOUDECM-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/18239s25lbl.pdf

Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating α -and/or β2-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy. Dipivefrin is used as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROPINE

Approved Use

PROPINE (dipivefrin HCI ophthalmic solution, USP) is indicated as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma.

Launch Date

3.25987205E11
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 3000 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Km 1030 uM]
yes [Km 1410 uM]
yes [Km 2160 uM]
PubMed

PubMed

TitleDatePubMed
External ocular toxicity of dipivalyl epinephrine.
1979 Dec
Systemic hypertension in patients receiving dipivalyl adrenaline for glaucoma.
1988 Sep 17
Corneal vascularization and opacification during long-term use of dipivefrin.
1995 Spring
Effects of latanoprost and dipivefrin, alone or combined, on intraocular pressure and on blood-aqueous barrier permeability.
1998 Apr
Pupillary supersensitivity and visual disturbance in Parkinson's disease.
2008 Feb
Comparison of chiral electrophoretic separation methods for phenethylamines and application on impurity analysis.
2010 Dec 15
Pupillary autonomic dysfunction in multiple system atrophy and Parkinson's disease: an assessment by eye-drop tests.
2010 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Initial Glaucoma Therapy The usual dosage of Dipivefrin Hydrochloride Ophthalmic Solution 0.1% is one drop in the eye(s) every 12 hours.
Route of Administration: Irrigation
In Vitro Use Guide
Dipivefrin caused a reduction in bovine trabecular cell density at concentration 103-260 uM
Name Type Language
DIPIVEFRIN
MI   USAN   VANDF  
USAN  
Official Name English
Dipivefrine [WHO-DD]
Common Name English
dipivefrine [INN]
Common Name English
DIPIVEFRINE
INN   MART.   WHO-DD  
INN  
Official Name English
DIPIVALYL EPINEPHRINE
Common Name English
PROPANOIC ACID, 2,2-DIMETHYL-, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-1,2-PHENYLENE ESTER, (±)-
Common Name English
DIPIVEFRIN [VANDF]
Common Name English
DIPIVEFRIN [MI]
Common Name English
DIPIVEFRINE [MART.]
Common Name English
DIPIVEFRIN [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EA02
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
NDF-RT N0000000122
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
NCI_THESAURUS C29705
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
WHO-VATC QS01EA02
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
NDF-RT N0000175883
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
Code System Code Type Description
DRUG BANK
DB00449
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
DRUG CENTRAL
922
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
INN
4429
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
WIKIPEDIA
DIPIVEFRINE
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
RXCUI
23410
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201262
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
FDA UNII
8Q1PVL543G
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
CAS
52365-63-6
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
PUBCHEM
3105
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
SMS_ID
100000093038
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
IUPHAR
7166
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID1048544
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
MERCK INDEX
m4648
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY Merck Index
EVMPD
SUB07217MIG
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
NCI_THESAURUS
C61729
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
CHEBI
4646
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY
MESH
C015173
Created by admin on Fri Dec 15 18:55:51 UTC 2023 , Edited by admin on Fri Dec 15 18:55:51 UTC 2023
PRIMARY