DAPIPRAZOLE HYDROCHLORIDE

US Previously Marketed

First approved in 1990

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H27N5.ClH
Molecular Weight	361.912
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC1=C(C=CC=C1)N2CCN(CCC3=NN=C4CCCCN34)CC2

InChI

InChIKey=ZIODNPFQZIHCOE-UHFFFAOYSA-N

InChI=1S/C19H27N5.ClH/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;1H

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

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
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 The drug was marketed under the name Rev-Eyes, however it was withdrawn from market due to its slow effect.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
Effects of 2% ibopamine on pupil, refraction, anterior segment anatomy and intraocular pressure.	2001 Jun	11436942
Effect of asphyxia on the pupils of brain dead subjects.	2002 Oct	12297351
Mechanism of pupillary reflex dilation in awake volunteers and in organ donors.	2003 Dec	14639139
Effect of ibopamine on aqueous humor production in normotensive humans.	2003 Nov	14578408
Sympathetic and parasympathetic innervation of pupillary dilation during sustained processing.	2004 Mar	15003374
Dapiprazole for night halos caused by angle-supported phakic intraocular lenses.	2004 Sep-Oct	15523962
Brimonidine versus dapiprazole: Influence on pupil size at various illumination levels.	2005 Jul	16105609
Effects of peripheral sympathetic blockade with dapiprazole on the fear-inhibited light reflex.	2005 Mar	15728435
Pupil size and Perimetry--a pharmacological model using increment and decrement stimuli.	2005 Nov	15909157
Arousal and the pupil: why diazepam-induced sedation is not accompanied by miosis.	2007 Nov	17659380
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
Aceclidine, brimonidine tartrate, and dapiprazole: comparison of miotic effect and tolerability under different lighting conditions.	2009 Jan	19101423
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:15:32 GMT 2023` Edited by `admin` on `Fri Dec 15 15:15:32 GMT 2023`
Record UNII	DS9UJN1I0X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DAPIPRAZOLE HYDROCHLORIDE

Official Name

English

REV-EYES

Brand Name

English

Dapiprazole hydrochloride [WHO-DD]

Common Name

English

DAPIPRAZOLE MONOHYDROCHLORIDE

Common Name

English

DAPIPRAZOLE MONOHYDROCHLORIDE [MI]

Common Name

English

AF 2139

Code

English

DAPIPRAZOLE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

5,6,7,8-Tetrahydro-3-[2-(4-O-tolyl-1-piperazinyl)ethyl]-S-triazolo[4,3-a]pyridine monohydrochloride

Common Name

English

DAPIPRAZOLE HYDROCHLORIDE [MART.]

Common Name

English

AF-2139

Code

English

DAPIPRAZOLE HCL

Common Name

English

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

Common Name

English

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

Systematic Name

English

DAPIPRAZOLE HYDROCHLORIDE [USAN]

Common Name

English

DAPIPRAZOLE HYDROCHLORIDE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713