U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H29NO5.ClH
Molecular Weight 387.898
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPIVEFRIN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=VKFAUCPBMAGVRG-UHFFFAOYSA-N
InChI=1S/C19H29NO5.ClH/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;1H

HIDE SMILES / InChI
Molecular Formula C19H29NO5
Molecular Weight 351.4373
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

Approval Year

1980
62
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Agonist
2752
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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

1980
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
carboxylesterase
2
ACHE
10

carboxylesterase
4

non-specific esterase
2
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
carboxylesterase
2
 yes [IC50 3000 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
carboxylesterase
4
 yes [Km 1030 uM]
ACHE
10
 yes [Km 1410 uM]
non-specific esterase
2
 yes [Km 2160 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4646
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4646
ChemicalBook
CB6676807
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6676807
PubMed

PubMed

TitleDatePubMed
Comparison of chiral electrophoretic separation methods for phenethylamines and application on impurity analysis.
2010-12-15
Pupillary autonomic dysfunction in multiple system atrophy and Parkinson's disease: an assessment by eye-drop tests.
2010-06
Pupillary supersensitivity and visual disturbance in Parkinson's disease.
2008-02
Glaucoma alters the circadian timing system.
2008
Contact dermatitis by dipivefrine.
2005-03
[Effects of ocular hypotensive agents on the circadian rhythm in intraocular pressure in rabbits as measured by telemetry].
2003-09
Effects of latanoprost and dipivefrin, alone or combined, on intraocular pressure and on blood-aqueous barrier permeability.
1998-04
Corneal vascularization and opacification during long-term use of dipivefrin.
1995
Central vein thrombosis and topical dipivalyl epinephrine.
1990-08
Systemic hypertension in patients receiving dipivalyl adrenaline for glaucoma.
1988-09-17
Experience with dipivalyl epinephrine. Its effectiveness, alone or in combination, and its side effects.
1983-08
External ocular toxicity of dipivalyl epinephrine.
1979-12
Patents

Patents

018239-001
2
074382-001
2

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:47:24 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:24 GMT 2025
Record UNII
5QTH9UHV0K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPIVEFRIN HYDROCHLORIDE
JAN   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
DIPIVEFRINE HYDROCHLORIDE
EP   MART.   WHO-DD  
Preferred Name English
PROPINE
Brand Name English
DIPIVEFRIN HYDROCHLORIDE [MI]
Common Name English
DIPIVEFRIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DIPIVALYLEPINEPHRINE HYDROCHLORIDE
Common Name English
DIPIVEFRINE HYDROCHLORIDE [JAN]
Common Name English
(±)-3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)BENZYL ALCOHOL 3,4-DIPIVALATE HYDROCHLORIDE
Common Name English
DIPIVEFRIN HYDROCHLORIDE [VANDF]
Common Name English
DIPIVEFRIN HCL
Common Name English
AKPRO
Brand Name English
(RS)-4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-O-PHENYLENE DIPIVALATE HYDROCHLORIDE
Common Name English
DIPIVEFRINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
PROPANOIC ACID, 2,2-DIMETHYL-, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-1,2-PHENYLENE ESTER, (±)-, HYDROCHLORIDE
Common Name English
DIPIVEFRIN HYDROCHLORIDE [JAN]
Common Name English
DIPIVEFRIN HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
Dipivefrine hydrochloride [WHO-DD]
Common Name English
DIPIVEFRINE HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29705
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
Code System Code Type Description
PUBCHEM
71486
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
EVMPD
SUB01790MIG
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
NCI_THESAURUS
C47495
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
CAS
64019-93-8
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
DRUG BANK
DBSALT000626
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
CHEBI
48086
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID2045494
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
CHEBI
4647
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
MERCK INDEX
m4648
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY Merck Index
FDA UNII
5QTH9UHV0K
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
RXCUI
203156
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY RxNorm
SMS_ID
100000093057
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201262
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
264-609-5
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
DAILYMED
5QTH9UHV0K
Created by admin on Mon Mar 31 18:47:24 GMT 2025 , Edited by admin on Mon Mar 31 18:47:24 GMT 2025
PRIMARY
Related Record Type Details
Structure of DIPIVEFRIN HYDROCHLORIDE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of DIPIVEFRIN
PARENT -> SALT/SOLVATE
Structure of DIPIVEFRINE HYDROCHLORIDE, (R)-
ENANTIOMER -> RACEMATE
Structure of DIPIVEFRINE HYDROCHLORIDE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of N-ETHYL DIPIVEFRIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 4-PIVALOYL RACEPINEPHRINE
IMPURITY -> PARENT
Limit of 5-Pivaloyl racepinephrine and 4-Pivaloyl racepinephrine is not more than 0.3%
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 5-PIVALOYL RACEPINEPHRINE
IMPURITY -> PARENT
Limit of 5-Pivaloyl racepinephrine and 4-Pivaloyl racepinephrine not more than 0.3%
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-nitroso-dipivefrin
IMPURITY -> PARENT
Structure of 2-(2,2-DIMETHYL-PROPIONYLOXY)-5-(2-METHYLAMINO-ACETYL)-PHENYL 2,2-DIMETHYL-PROPIONATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of DIPIVEFRIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966