DAPIPRAZOLE

US Previously Marketed

First approved in 1990

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H27N5
Molecular Weight	325.4512
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC=C1N2CCN(CCC3=NN=C4CCCCN34)CC2

InChI

InChIKey=RFWZESUMWJKKRN-UHFFFAOYSA-N

InChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3

HIDE SMILES / InChI

Molecular Formula	C19H27N5
Molecular Weight	325.4512
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.reviewofoptometry.com/article/reversal-of-fortune
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/019849_S011_REV-EYES.pdf

Dapiprazole is an alpha-1 adrenergic receptors antagonist which was developed for for the treatment of drug induced mydriasis produced by adrenergic or parasympatholytic agents. The drug was marketed under the name Rev-Eyes, however it was withdrawn from market due to its slow effect.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/019849_S011_REV-EYES.pdf	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pharmacologically induced mydriasis 2 Sources: http://www.aoa.org/documents/optometrists/CPG-5.pdf	Secondary		Approved 8583	REV-EYES Approved Use Dapiprazole hydrochloride 0.5% (Rev-Eyes) is an alpha-adrenergic blocking agent used to reverse pharmacologically induced mydriasis. Launch Date 1990

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51066	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51066
ChemicalBook	CB6297819	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6297819
ZINC	ZINC000000001246	http://zinc15.docking.org/substances/ZINC000000001246

PubMed

Title	Date	PubMed
Transdermal drug delivery of labetalol hydrochloride: Feasibility and effect of penetration enhancers.	2010-10	21180464
Preparation and in vivo evaluation of indomethacin loaded true nanoemulsions.	2009-11-07	21179369
Effectiveness of daily use of brimonidine as antimydriatic agent.	2009-10	19781497
Aerobic exercise and intraocular pressure in normotensive and glaucoma patients.	2009-08-13	19678955
Aceclidine, brimonidine tartrate, and dapiprazole: comparison of miotic effect and tolerability under different lighting conditions.	2009-01	19101423
Regression of urrets-zavalia syndrome after deep lamellar keratoplasty for keratoconus: a case study.	2008-08-08	19516912
Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion.	2008-07-09	18613981
Arousal and the pupil: why diazepam-induced sedation is not accompanied by miosis.	2007-11	17659380
Pupil size and Perimetry--a pharmacological model using increment and decrement stimuli.	2005-11	15909157
Brimonidine versus dapiprazole: Influence on pupil size at various illumination levels.	2005-07	16105609
Effects of peripheral sympathetic blockade with dapiprazole on the fear-inhibited light reflex.	2005-03	15728435
Dapiprazole for night halos caused by angle-supported phakic intraocular lenses.	2004-11-05	15523962
Sympathetic and parasympathetic innervation of pupillary dilation during sustained processing.	2004-03	15003374
Mechanism of pupillary reflex dilation in awake volunteers and in organ donors.	2003-12	14639139
Effect of ibopamine on aqueous humor production in normotensive humans.	2003-11	14578408
Effect of asphyxia on the pupils of brain dead subjects.	2002-10	12297351
Effects of 2% ibopamine on pupil, refraction, anterior segment anatomy and intraocular pressure.	2001-06	11436942

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is 2 drops (0.5% solution) followed 5 minutes later by 2 drops.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:10 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:10 GMT 2025`
Record UNII	5RNZ8GJO7K
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

5,6,7,8-TETRAHYDRO-3-(2-(4-O-TOLYL-1-PIPERAZINYL)ETHYL))-S-TRIAZOLO(4,3-A)PYRIDINE

Preferred Name

English

DAPIPRAZOLE

Official Name

English

1,2,4-TRIAZOLO(4,3-A)PYRIDINE, 5,6,7,8-TETRAHYDRO-3-(2-(4-(2-METHYLPHENYL)-1-PIPERAZINYL)ETHYL)-

Systematic Name

English

Dapiprazole [WHO-DD]

Common Name

English

5,6,7,8-TETRAHYDRO-3-(2-(4-(2-METHYLPHENYL)-1-PIPERAZINYL)ETHYL)-1,2,4-TRIAZOLO(4,3-A)PYRIDINE

Systematic Name

English

dapiprazole [INN]

Common Name

English

DAPIPRAZOLE [MI]

Common Name

English

DAPIPRAZOLE [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

S01EX02