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

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

1987
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
Contact dermatitis to topical drugs for glaucoma.
2001 Dec
[Reduction of ocular pulse amplitude by apraclonidine--prospective double-blind, randomized clinical trial with 10 subjects].
2001 Mar
Effects of alpha(2)-adrenergic agonists on lipopolysaccharide-induced aqueous flare elevation in pigmented rabbits.
2001 May-Jun
Allergic contact dermatitis from apraclonidine in eyedrops.
2001 Oct
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
Cutaneous drug reaction case reports: from the world literature.
2002
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
Intraocular pressure spike after YAG iridotomy in patients with pigment dispersion.
2004 Apr
Neodymium:yttrium-aluminum-garnet capsulotomy and intraocular pressure in pseudophakic patients with glaucoma.
2004 Jul
Double-blind parallel comparison of multiple doses of apraclonidine, clonidine, and placebo administered intra-articularly to patients undergoing arthroscopic knee surgery.
2004 Jul-Aug
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
Pharmacological testing of anisocoria.
2005 Oct
More than just an ocular solution.
2005 Oct
[The effect of brimonidine on the pupillary reflex. A pupillographic study in healthy volunteers].
2005 Sep
Topical apraclonidine testing of pupillary sympathetic denervation in diabetic patients.
2006 Dec
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
Medical management of primary open-angle glaucoma: Best practices associated with enhanced patient compliance and persistency.
2008 Feb 2
Post-penetrating keratoplasty glaucoma.
2008 Jul-Aug
Central alpha-2 adrenergic eye drops: case series of 3 pediatric systemic poisonings.
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
Recurrent serous macular detachment after topical ocular hypotensive medication.
2008 Nov
Fixed combination of topical brimonidine 0.2% and timolol 0.5% for glaucoma and uncontrolled intraocular pressure.
2008 Sep
[Efficacy of topic ocular hipotensive agents after posterior capsulotomy].
2008 Sep-Oct
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 [MI]
Common Name English
Apraclonidine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EA03
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NDF-RT N0000175552
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NDF-RT N0000000209
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NCI_THESAURUS C29709
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WHO-VATC QS01EA03
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Code System Code Type Description
WIKIPEDIA
APRACLONIDINE
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PRIMARY
NCI_THESAURUS
C61640
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IUPHAR
7117
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LACTMED
Apraclonidine
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EPA CompTox
DTXSID1048415
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DRUG CENTRAL
229
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DRUG BANK
DB00964
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DAILYMED
843CEN85DI
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MERCK INDEX
m2008
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PRIMARY Merck Index
CHEBI
134252
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FDA UNII
843CEN85DI
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EVMPD
SUB05539MIG
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CHEBI
2789
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ChEMBL
CHEMBL647
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SMS_ID
100000087180
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RXCUI
14845
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PRIMARY RxNorm
MESH
C016986
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PRIMARY
CHEBI
2788
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PRIMARY
PUBCHEM
2216
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PRIMARY
CAS
66711-21-5
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PRIMARY
INN
6263
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