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=C(C=CC=C1)N2CCN(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

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 The drug was marketed under the name Rev-Eyes, however it was withdrawn from market due to its slow effect.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-1 169 Target ID: CHEMBL2094251 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/019849_S011_REV-EYES.pdf	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pharmacologically induced mydriasis 2 Sources: http://www.aoa.org/documents/optometrists/CPG-5.pdf	Secondary		Approved 8429	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
Dapiprazole for night halos caused by angle-supported phakic intraocular lenses.	2004 Sep-Oct	15523962
Effects of peripheral sympathetic blockade with dapiprazole on the fear-inhibited light reflex.	2005 Mar	15728435
Regression of urrets-zavalia syndrome after deep lamellar keratoplasty for keratoconus: a case study.	2008 Aug 8	19516912
Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion.	2008 Jul 9	18613981
Aerobic exercise and intraocular pressure in normotensive and glaucoma patients.	2009 Aug 13	19678955
Effectiveness of daily use of brimonidine as antimydriatic agent.	2009 Oct	19781497
Preparation and in vivo evaluation of indomethacin loaded true nanoemulsions.	2010 Jan-Mar	21179369
Transdermal drug delivery of labetalol hydrochloride: Feasibility and effect of penetration enhancers.	2010 Oct	21180464

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

Name

Type

Language

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

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

Common 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