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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10Cl2N4.ClH
Molecular Weight 281.5696
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRACLONIDINE HYDROCHLORIDE

SMILES

C1CN=C(N1)Nc2c(cc(cc2Cl)N)Cl.Cl

InChI

InChIKey=OTQYGBJVDRBCHC-UHFFFAOYSA-N
InChI=1S/C9H10Cl2N4.ClH/c10-6-3-5(12)4-7(11)8(6)15-9-13-1-2-14-9;/h3-4H,1-2,12H2,(H2,13,14,15);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H10Cl2N4
Molecular Weight 245.1087
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: https://www.drugs.com/ppa/apraclonidine.html | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=dc7d3a9f-c0b9-411c-9c62-0a14f1718b00

Apraclonidine (IOPIDINE) is an α2-adrenergic receptor agonist and a weak α1-adrenergic receptor agonist. It is used for the prevention and treatment of postsurgical intraocular pressure elevation. The following adverse events, occurring in less than 2% of patients, were reported in association with the use of IOPIDINE Ophthalmic Solution in laser surgery: ocular injection, upper lid elevation, irregular heart rate, nasal decongestion, ocular inflammation, conjunctival blanching, and mydriasis. Interactions with other agents have not been investigated.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
IOPIDINE

Approved Use

Apraclonidine hydrochloride ophthalmic solution) is indicated to control or prevent postsurgical elevations in intraocular pressure that occur in patients after argon laser trabeculplasty, argon laser iridotomy or Nd:YAG posterior capsulotomy.

Launch Date

5.6782081E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.9 ng/mL
1 drop 3 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
APRACLONIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8 h
1 drop 3 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
APRACLONIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
74.5%
unknown, topical
APRACLONIDINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.5 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.5 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.5 %, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: intraocular pressure
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Allergic reaction...
AEs leading to
discontinuation/dose reduction:
Allergic reaction (12.9%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Allergic reaction 12.9%
Disc. AE
0.5 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.5 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.5 %, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: intraocular pressure
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Reformulation and drop size of apraclonidine hydrochloride.
1992 Feb 15
[Iopidine in the control of intraocular pressure after glaucoma laser treatment].
2001
Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries.
2001 Aug
Contact dermatitis to topical drugs for glaucoma.
2001 Dec
Differential effects of alpha-adrenoceptor agonists on human retinal microvessel diameter.
2001 Jun
Brimonidine 0.2% versus apraclonidine 0.5% for prevention of intraocular pressure elevations after anterior segment laser surgery.
2001 Jun
Topically applied clonidine protects the rat retina from ischaemia/reperfusion by stimulating alpha(2)-adrenoceptors and not by an action on imidazoline receptors.
2001 Jun 15
Clonidine-induced nitric oxide-dependent vasorelaxation mediated by endothelial alpha(2)-adrenoceptor activation.
2001 Nov
The one-month effects of topical betaxolol, dorzolamide and apraclonidine on ocular blood flow velocities in patients with newly diagnosed primary open-angle glaucoma.
2001 Sep-Oct
Effects of topical antiglaucoma eye drops on prostaglandin E(2)-induced aqueous flare elevation in pigmented rabbits.
2002 Apr
A comparison of the short-term hypotensive effects and side effects of unilateral brimonidine and apraclonidine in patients with elevated intraocular pressure.
2002 Jan-Feb
Advances in topical glaucoma therapy.
2002 Mar
Apraclonidine attenuates the increases in spinal excitatory amino acid release in rats with adjuvant-induced inflammation.
2002 Mar
Dorzolamide X apraclonidine in the prevention of the intraocular pressure spike after Nd : YAG laser posterior capsulotomy.
2002 Oct
The effects of antiglaucoma and systemic medications on ocular blood flow.
2003 Nov
The effect of alpha2-agonist on IOP rise following Nd-YAG laser iridotomy.
2004 Apr
Intraocular pressure spike after YAG iridotomy in patients with pigment dispersion.
2004 Apr
The use of apraclonidine in the diagnosis of horner syndrome in pediatric patients.
2004 Feb
Neodymium:yttrium-aluminum-garnet capsulotomy and intraocular pressure in pseudophakic patients with glaucoma.
2004 Jul
The utility of 0.5% apraclonidine in the diagnosis of horner syndrome.
2005 Apr
The use of apraclonidine eyedrops to treat ptosis after the administration of botulinum toxin to the upper face.
2005 Mar 1
Treatment of ptosis as a complication of botulinum toxin injection.
2005 Mar-Apr
Comparative efficacy of acetazolamide and apraclonidine in the control of intraocular pressure following phacoemulsification.
2006
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum.
2006 Jul
Comparing efficacies of 0.5% apraclonidine with 4% cocaine in the diagnosis of horner syndrome in pediatric patients.
2006 Jun
Topical apraclonidine testing discloses pupillary sympathetic denervation in diabetic patients.
2006 Mar
Brinzolamide 1% versus apraclonidine 0.5% to prevent intraocular pressure elevation after neodymium:YAG laser posterior capsulotomy.
2006 Sep
Congenital Horner's syndrome and the usefulness of the apraclonidine test in its diagnosis.
2006 Sep
Apraclonidine in the diagnosis of Horner's syndrome.
2007 Jul
The acute morphologic changes that occur at the optic nerve head induced by medical reduction of intraocular pressure.
2007 Sep
Horner's syndrome, Pseudo-Horner's syndrome, and simple anisocoria.
2007 Sep
Medical management of primary open-angle glaucoma: Best practices associated with enhanced patient compliance and persistency.
2008 Feb 2
Use of 0.5% apraclonidine solution in evaluation of blepharoptosis.
2008 Jul-Aug
The role of cyclosporine and mycophenolate in an orthotopic porcine-to-rat corneal xenotransplantation.
2008 Jun
Differences in the histopathology and matrix metalloproteinase expression in Tenon's tissue of primary open-angle glaucoma and primary angle-closure glaucoma.
2008 Mar
Acupuncture treatment for idiopathic Horner's syndrome in a dog.
2008 Mar
False negative apraclonidine test in two patients with Horner syndrome.
2008 May
Fixed combination of topical brimonidine 0.2% and timolol 0.5% for glaucoma and uncontrolled intraocular pressure.
2008 Sep
Pupillary autonomic neuropathy simulating partial Horner syndrome in diabetes mellitus and its reversal with control of blood glucose.
2008 Sep
Positive apraclonidine test within two weeks of onset of Horner syndrome caused by carotid artery dissection.
2008 Sep
[Efficacy of topic ocular hipotensive agents after posterior capsulotomy].
2008 Sep-Oct
Topical apraclonidine to diagnose Bernard-Horner syndrome.
2009
Clinical efficacy and neuroprotective effects of brimonidine in the management of glaucoma and ocular hypertension.
2009
[Unilateral allergic contact dermatitis of the eyelid caused by Iopimax].
2009 Dec
Current pharmacologic testing for Horner syndrome.
2009 Sep
Patents

Sample Use Guides

One drop of Ophthalmic Solution should be instilled in the scheduled operative eye one hour before initiating anterior segment laser surgery and a second drop should be instilled to the same eye immediately upon completion of the laser surgical procedure. Use a separate container for each single-drop dose and discard each container after use.
Route of Administration: Topical
The alpha(2)-adrenoceptor agonists apraclonidine induced vasoconstriction in the porcine ciliary artery with the potency EC(50) equal to 13.0 nM.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:56:36 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:36 UTC 2021
Record UNII
D2VW67N38H
Record Status Validated (UNII)
Record Version
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Name Type Language
APRACLONIDINE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
APRACLONIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
1,4-BENZENEDIAMINE, 2,6-DICHLORO-N(SUP 1)-2-IMIDAZOLIDINYLIDENE-, MONOHYDROCHLORIDE
Common Name English
AL02145
Code English
IOPIDINE
Brand Name English
APRACLONIDINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
APRACLONIDINE HYDROCHLORIDE [MART.]
Common Name English
APRACLONIDINE HYDROCHLORIDE [MI]
Common Name English
APRACLONIDINE HCL
Common Name English
AL-02145
Code English
APRACLONIDINE HYDROCHLORIDE [USAN]
Common Name English
APRACLONIDINE HYDROCHLORIDE [JAN]
Common Name English
APRACLONIDINE HYDROCHLORIDE [WHO-DD]
Common Name English
APRACLONIDINE HYDROCHLORIDE [USP-RS]
Common Name English
APRACLONIDINE HYDROCHLORIDE [USP]
Common Name English
2-((4-AMINO-2,6-DICHLOROPHENYL)IMINO) IMIDAZOLIDINE MONOHYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
Code System Code Type Description
EVMPD
SUB12926MIG
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
PUBCHEM
51763
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
MERCK INDEX
M2008
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY Merck Index
RXCUI
91350
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL647
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
DRUG BANK
DBSALT000819
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
USP_CATALOG
1041609
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY USP-RS
EPA CompTox
73218-79-8
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
FDA UNII
D2VW67N38H
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
NCI_THESAURUS
C47401
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
CAS
73218-79-8
Created by admin on Fri Jun 25 20:56:37 UTC 2021 , Edited by admin on Fri Jun 25 20:56:37 UTC 2021
PRIMARY
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