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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10Cl2N4
Molecular Weight 245.1087
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRACLONIDINE

SMILES

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

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

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
The effect of alpha2-agonist on IOP rise following Nd-YAG laser iridotomy.
2004 Apr
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
Are we ready to replace cocaine with apraclonidine in the pharmacologic diagnosis of Horner syndrome?
2005 Jun
The use of apraclonidine eyedrops to treat ptosis after the administration of botulinum toxin to the upper face.
2005 Mar 1
Comparing brimonidine 0.2% to apraclonidine 1.0% in the prevention of intraocular pressure elevation and their pupillary effects following laser peripheral iridotomy.
2005 Mar-Apr
Treatment of ptosis as a complication of botulinum toxin injection.
2005 Mar-Apr
The sensitivity and specificity of 0.5% apraclonidine in the diagnosis of oculosympathetic paresis.
2005 Nov
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
Postoperative IOP prophylaxis practice following uncomplicated cataract surgery: a UK-wide consultant survey.
2005 Oct 7
Brimonidine 0.15% versus apraclonidine 0.5% for prevention of intraocular pressure elevation after anterior segment laser surgery.
2005 Sep
[The effect of brimonidine on the pupillary reflex. A pupillographic study in healthy volunteers].
2005 Sep
Comparative efficacy of acetazolamide and apraclonidine in the control of intraocular pressure following phacoemulsification.
2006
Reduction of anterior-segment vascularity with preoperative topical apraclonidine 1%.
2006 Apr
Topical apraclonidine testing of pupillary sympathetic denervation in diabetic patients.
2006 Dec
Corneal thickness- and age-related biomechanical properties of the cornea measured with the ocular response analyzer.
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
The effect of topical apraclonidine on subconjunctival hemorrhage and flap adherence in LASIK patients.
2006 Jun
Topical apraclonidine testing discloses pupillary sympathetic denervation in diabetic patients.
2006 Mar
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.
2007 Apr
Apraclonidine in the diagnosis of Horner's syndrome.
2007 Jul
Adverse effects of apraclonidine used in the diagnosis of Horner syndrome in infants.
2007 Jun
Pharmacologic reversal of Horner's syndrome-related ptosis with apraclonidine.
2007 May
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
Congenital or acquired Horner's?
2007 Sep-Oct
The pupil.
2008 Feb
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
Post-penetrating keratoplasty glaucoma.
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
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
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
[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
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.
Name Type Language
APRACLONIDINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
APRACLONIDINE [VANDF]
Common Name English
APRACLONIDINE [INN]
Common Name English
APRACLONIDINE [WHO-DD]
Common Name English
APRACLONIDINE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EA03
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
NDF-RT N0000175552
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
NDF-RT N0000000209
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
NCI_THESAURUS C29709
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
WHO-VATC QS01EA03
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
Code System Code Type Description
WIKIPEDIA
APRACLONIDINE
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
NCI_THESAURUS
C61640
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
IUPHAR
7117
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
LACTMED
Apraclonidine
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
EPA CompTox
66711-21-5
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
DRUG CENTRAL
229
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
DRUG BANK
DB00964
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
MERCK INDEX
M2008
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY Merck Index
FDA UNII
843CEN85DI
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PRIMARY
EVMPD
SUB05539MIG
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
ChEMBL
CHEMBL647
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
RXCUI
14845
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY RxNorm
MESH
C016986
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
PUBCHEM
2216
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
CAS
66711-21-5
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY
INN
6263
Created by admin on Sat Jun 26 11:17:05 UTC 2021 , Edited by admin on Sat Jun 26 11:17:05 UTC 2021
PRIMARY