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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 of DAPIPRAZOLE

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
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
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 The drug was marketed under the name Rev-Eyes, however it was withdrawn from market due to its slow effect.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

1990
108
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

6.626016E11
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Mechanism of pupillary reflex dilation in awake volunteers and in organ donors.
2003 Dec
Sympathetic and parasympathetic innervation of pupillary dilation during sustained processing.
2004 Mar
Dapiprazole for night halos caused by angle-supported phakic intraocular lenses.
2004 Sep-Oct
Brimonidine versus dapiprazole: Influence on pupil size at various illumination levels.
2005 Jul
Effects of peripheral sympathetic blockade with dapiprazole on the fear-inhibited light reflex.
2005 Mar
Pupil size and Perimetry--a pharmacological model using increment and decrement stimuli.
2005 Nov
Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion.
2008 Jul 9
Aerobic exercise and intraocular pressure in normotensive and glaucoma patients.
2009 Aug 13
Effectiveness of daily use of brimonidine as antimydriatic agent.
2009 Oct
Transdermal drug delivery of labetalol hydrochloride: Feasibility and effect of penetration enhancers.
2010 Oct
Patents

Patents

JP1052722A
2
JP2011528275A
455
JPH00232020A
2
JPH0232020A
2
JPH05194228A
2
JPS6452722A
2

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 15:44:18 UTC 2023
Edited
by admin
on Fri Dec 15 15:44:18 UTC 2023
Record UNII
5RNZ8GJO7K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAPIPRAZOLE
INN   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
WHO-VATC QS01EX02
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
NDF-RT N0000000099
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
NDF-RT N0000175553
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
Code System Code Type Description
IUPHAR
7155
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
CAS
72822-12-9
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID90223140
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
DRUG BANK
DB00298
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
EVMPD
SUB06906MIG
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
WIKIPEDIA
DAPIPRAZOLE
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
RXCUI
22298
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY RxNorm
CHEBI
51066
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
DAILYMED
5RNZ8GJO7K
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
FDA UNII
5RNZ8GJO7K
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201216
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
DRUG CENTRAL
781
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
MESH
C035289
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
PUBCHEM
3033538
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
MERCK INDEX
m4090
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY Merck Index
SMS_ID
100000083440
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
NCI_THESAURUS
C83648
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
INN
4983
Created by admin on Fri Dec 15 15:44:18 UTC 2023 , Edited by admin on Fri Dec 15 15:44:18 UTC 2023
PRIMARY
Related Record Type Details
ALPHA-1A ADRENERGIC RECEPTOR
TARGET -> INHIBITOR
Structure of DAPIPRAZOLE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
ALPHA-1D ADRENERGIC RECEPTOR
TARGET -> INHIBITOR
ALPHA-1B ADRENERGIC RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of DAPIPRAZOLE
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