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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
[Glaucoma as primary optic neuropathy].
2001
[Iopidine in the control of intraocular pressure after glaucoma laser treatment].
2001
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
Preventing intraocular pressure increase after phacoemulsification and the role of perioperative apraclonidine.
2002 Dec
Dorzolamide X apraclonidine in the prevention of the intraocular pressure spike after Nd : YAG laser posterior capsulotomy.
2002 Oct
The utility of 0.5% apraclonidine in the diagnosis of horner syndrome.
2003 Aug
New topical drugs for open-angle glaucoma.
2003 Feb
Ocular perfusion pressure and visual field indice modifications induced by alpha-agonist compound (clonidine 0.125%, apraclonidine 1.0% and brimonidine 0.2%) topical administration. An acute study on primary open-angle glaucoma patients.
2003 Jan-Feb
Medical therapy cost considerations for glaucoma.
2003 Jul
The effect of topical glaucoma medications evaluated by perimetry.
2003 Jun
Vitreal pathogenic role in optic pit foveolar retinoschisis and central serous retinopathy.
2003 Nov
The effects of antiglaucoma and systemic medications on ocular blood flow.
2003 Nov
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
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
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
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
Reduction of anterior-segment vascularity with preoperative topical apraclonidine 1%.
2006 Apr
Corneal thickness- and age-related biomechanical properties of the cornea measured with the ocular response analyzer.
2006 Dec
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
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
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
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
Effects of central corneal thickness on the efficacy of topical ocular hypotensive medications.
2008 Mar
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
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
[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
[Unilateral allergic contact dermatitis of the eyelid caused by Iopimax].
2009 Dec
[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 Fri Dec 16 18:09:09 UTC 2022
Edited
by admin
on Fri Dec 16 18:09:09 UTC 2022
Record UNII
843CEN85DI
Record Status Validated (UNII)
Record Version
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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 Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
NDF-RT N0000175552
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
NDF-RT N0000000209
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
NCI_THESAURUS C29709
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
WHO-VATC QS01EA03
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
Code System Code Type Description
WIKIPEDIA
APRACLONIDINE
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
NCI_THESAURUS
C61640
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
IUPHAR
7117
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
LACTMED
Apraclonidine
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
EPA CompTox
DTXSID1048415
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
DRUG CENTRAL
229
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PRIMARY
DRUG BANK
DB00964
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
DAILYMED
843CEN85DI
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
MERCK INDEX
M2008
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY Merck Index
CHEBI
134252
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
FDA UNII
843CEN85DI
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
EVMPD
SUB05539MIG
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
CHEBI
2789
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
ChEMBL
CHEMBL647
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
RXCUI
14845
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY RxNorm
MESH
C016986
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
CHEBI
2788
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
PUBCHEM
2216
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
CAS
66711-21-5
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
INN
6263
Created by admin on Fri Dec 16 18:09:09 UTC 2022 , Edited by admin on Fri Dec 16 18:09:09 UTC 2022
PRIMARY
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