U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H10Cl2N4
Molecular Weight 245.109
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRACLONIDINE

SMILES

NC1=CC(Cl)=C(NC2=NCCN2)C(Cl)=C1

InChI

InChIKey=IEJXVRYNEISIKR-UHFFFAOYSA-N
InChI=1S/C9H10Cl2N4/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)

HIDE SMILES / InChI

Molecular Formula C9H10Cl2N4
Molecular Weight 245.109
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
Reversal of intraocular pressure increases with 0.5% apraclonidine after dilated fundus examination in patients with chronic open-angle glaucoma.
1999 Apr
Incidence of brimonidine allergy in patients previously allergic to apraclonidine.
2000 Jun
Contact dermatitis to topical drugs for glaucoma.
2001 Dec
Effectiveness of apraclonidine 1% in preventing intraocular pressure rise following macular hole surgery.
2001 Feb
Galanin/alpha2-adrenoceptor interactions in telencephalic and diencephalic regions of the rat.
2001 Jan 22
Differential effects of alpha-adrenoceptor agonists on human retinal microvessel diameter.
2001 Jun
Effects of acute topical administration of clonidine 0.125%, apraclonidine 1.0% and brimonidine 0.2% on visual field parameters and ocular perfusion pressure in patients with primary open-angle glaucoma.
2002
Cutaneous drug reaction case reports: from the world literature.
2002
Effects of topical antiglaucoma eye drops on prostaglandin E(2)-induced aqueous flare elevation in pigmented rabbits.
2002 Apr
Preventing intraocular pressure increase after phacoemulsification and the role of perioperative apraclonidine.
2002 Dec
The utility of 0.5% apraclonidine in the diagnosis of horner syndrome.
2003 Aug
Neodymium:yttrium-aluminum-garnet capsulotomy and intraocular pressure in pseudophakic patients with glaucoma.
2004 Jul
Managing adverse events associated with botulinum toxin type A: a focus on cosmetic procedures.
2005
The utility of 0.5% apraclonidine in the diagnosis of horner syndrome.
2005 Apr
Apraclonidine and LASIK.
2005 Dec
Topical apraclonidine in the diagnosis of suspected Horner syndrome.
2005 Jun
Effect of apraclonidine versus dorzolamide on intraocular pressure after phacoemulsification.
2005 Nov-Dec
Pharmacological testing of anisocoria.
2005 Oct
More than just an ocular solution.
2005 Oct
Comparative efficacy of acetazolamide and apraclonidine in the control of intraocular pressure following phacoemulsification.
2006
Topical apraclonidine testing of pupillary sympathetic denervation in diabetic patients.
2006 Dec
Effect of 0.5% apraclonidine on ptosis in Horner syndrome.
2006 Jan-Feb
The management of glaucoma and intraocular hypertension: current approaches and recent advances.
2006 Jun
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
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
Central alpha-2 adrenergic eye drops: case series of 3 pediatric systemic poisonings.
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
Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery.
2009
Clinical efficacy and neuroprotective effects of brimonidine in the management of glaucoma and ocular hypertension.
2009
Possible effect of systemic sympathicolytic drugs on apraclonidine test.
2009 Aug
[Unilateral allergic contact dermatitis of the eyelid caused by Iopimax].
2009 Dec
Nd: YAG capsulotomy for posterior capsule opacification after combined clear corneal phacoemulsification and vitrectomy.
2009 Feb
[Usefulness of apraclonidine in the diagnosis of Horner syndrome].
2009 Feb
False-negative apraclonidine testing in acute Horner syndrome.
2009 Feb
Ocular decompression retinopathy after trabeculectomy with mitomycin-C for angle recession glaucoma.
2009 Mar-Apr
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 Wed Jul 05 23:15:20 UTC 2023
Edited
by admin
on Wed Jul 05 23:15:20 UTC 2023
Record UNII
843CEN85DI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APRACLONIDINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
APRACLONIDINE [VANDF]
Common Name English
apraclonidine [INN]
Common Name English
APRACLONIDINE [MI]
Common Name English
Apraclonidine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EA03
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
NDF-RT N0000175552
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
NDF-RT N0000000209
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
NCI_THESAURUS C29709
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
WHO-VATC QS01EA03
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
Code System Code Type Description
WIKIPEDIA
APRACLONIDINE
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
NCI_THESAURUS
C61640
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
IUPHAR
7117
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
LACTMED
Apraclonidine
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID1048415
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
DRUG CENTRAL
229
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
DRUG BANK
DB00964
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
DAILYMED
843CEN85DI
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
MERCK INDEX
M2008
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY Merck Index
CHEBI
134252
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
FDA UNII
843CEN85DI
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
EVMPD
SUB05539MIG
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
CHEBI
2789
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL647
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
SMS_ID
100000087180
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
RXCUI
14845
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY RxNorm
MESH
C016986
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
CHEBI
2788
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
PUBCHEM
2216
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
CAS
66711-21-5
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
INN
6263
Created by admin on Wed Jul 05 23:15:20 UTC 2023 , Edited by admin on Wed Jul 05 23:15:20 UTC 2023
PRIMARY
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