APRACLONIDINE

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 Search

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19779s018,019lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-2A adrenergic receptor 26 Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19779s018,019lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/6246501 \| https://www.ncbi.nlm.nih.gov/pubmed/11481271	Agonist 2752
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19779s018,019lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/6246501	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 52 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19779s018,019lbl.pdf	Preventing		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
0.9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
74.5% DRUG LABEL https://www.google.ru/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&ved=2ahUKEwiUl-C6ho7sAhWj_CoKHXPHBYkQFjAYegQIHBAB&url=http%3A%2F%2Fwww.ask.novartispharma.ca%2Fdownload.htm%3Fres%3Diopidine_scrip_e.pdf%26resTitleId%3D1430&usg=AOvVaw2NI2gLoHBJh4I8Nn1NkVE2	unknown, topical		APRACLONIDINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf	Disc. AE: Allergic reaction... AEs leading to discontinuation/dose reduction: Allergic reaction (12.9%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020258s026lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9305586/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2788	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2788
ZINC	ZINC000000020231	http://zinc15.docking.org/substances/ZINC000000020231

PubMed

Title	Date	PubMed
[Unilateral allergic contact dermatitis of the eyelid caused by Iopimax].	2009-12	20038377
Current pharmacologic testing for Horner syndrome.	2009-09	19664368
Possible effect of systemic sympathicolytic drugs on apraclonidine test.	2009-08	19606173
Exposure to topical apraclonidine in children with glaucoma.	2009-06-16	19525731
Brimonidine and apraclonidine as vasoconstrictors in adjustable strabismus surgery.	2009-04	19393510
Ocular decompression retinopathy after trabeculectomy with mitomycin-C for angle recession glaucoma.	2009-02-25	19237794
Nd: YAG capsulotomy for posterior capsule opacification after combined clear corneal phacoemulsification and vitrectomy.	2009-02	19436607
[Usefulness of apraclonidine in the diagnosis of Horner syndrome].	2009-02	19253181
False-negative apraclonidine testing in acute Horner syndrome.	2009-02	19169332
Topical apraclonidine to diagnose Bernard-Horner syndrome.	2009	19927485
Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery.	2009	19668590
Clinical efficacy and neuroprotective effects of brimonidine in the management of glaucoma and ocular hypertension.	2009	19668554
Recurrent serous macular detachment after topical ocular hypotensive medication.	2008-11	18537988
Fixed combination of topical brimonidine 0.2% and timolol 0.5% for glaucoma and uncontrolled intraocular pressure.	2008-09	19668752
Pupillary autonomic neuropathy simulating partial Horner syndrome in diabetes mellitus and its reversal with control of blood glucose.	2008-09	18769297
Positive apraclonidine test within two weeks of onset of Horner syndrome caused by carotid artery dissection.	2008-09	18769292
Use of 0.5% apraclonidine solution in evaluation of blepharoptosis.	2008-07-23	18645436
Post-penetrating keratoplasty glaucoma.	2008-06-27	18579984
The role of cyclosporine and mycophenolate in an orthotopic porcine-to-rat corneal xenotransplantation.	2008-06	18583888
False negative apraclonidine test in two patients with Horner syndrome.	2008-05	18454417
Central alpha-2 adrenergic eye drops: case series of 3 pediatric systemic poisonings.	2008-03	18347496
Effects of central corneal thickness on the efficacy of topical ocular hypotensive medications.	2008-03	18344753
Differences in the histopathology and matrix metalloproteinase expression in Tenon's tissue of primary open-angle glaucoma and primary angle-closure glaucoma.	2008-03	18323704
Acupuncture treatment for idiopathic Horner's syndrome in a dog.	2008-03	18296897
Medical management of primary open-angle glaucoma: Best practices associated with enhanced patient compliance and persistency.	2008-02-02	19920977
The pupil.	2008-02	18180650
[Efficacy of topic ocular hipotensive agents after posterior capsulotomy].	2008-01-13	19039468
The acute morphologic changes that occur at the optic nerve head induced by medical reduction of intraocular pressure.	2007-09	17873718
Horner's syndrome, Pseudo-Horner's syndrome, and simple anisocoria.	2007-09	17764630
Congenital or acquired Horner's?	2007-08-19	17699962
Apraclonidine in the diagnosis of Horner's syndrome.	2007-07	17824139
Adverse effects of apraclonidine used in the diagnosis of Horner syndrome in infants.	2007-06	17572343
Pharmacologic reversal of Horner's syndrome-related ptosis with apraclonidine.	2007-05	17580803
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.	2007-04	17496723
Topical apraclonidine testing of pupillary sympathetic denervation in diabetic patients.	2006-12	17204928
Corneal thickness- and age-related biomechanical properties of the cornea measured with the ocular response analyzer.	2006-12	17122122
Efficacy of apraclonidine 0.5% in the diagnosis of Horner syndrome in pediatric patients under low or high illumination.	2006-09	16935593
Brinzolamide 1% versus apraclonidine 0.5% to prevent intraocular pressure elevation after neodymium:YAG laser posterior capsulotomy.	2006-09	16931262
Congenital Horner's syndrome and the usefulness of the apraclonidine test in its diagnosis.	2006-09	16921219
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum.	2006-07	16879492
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006-06	18360593
Comparing efficacies of 0.5% apraclonidine with 4% cocaine in the diagnosis of horner syndrome in pediatric patients.	2006-06	16808679
The effect of topical apraclonidine on subconjunctival hemorrhage and flap adherence in LASIK patients.	2006-06	16805122
Reduction of anterior-segment vascularity with preoperative topical apraclonidine 1%.	2006-04	16698500
Topical apraclonidine testing discloses pupillary sympathetic denervation in diabetic patients.	2006-03	16518162
Effect of 0.5% apraclonidine on ptosis in Horner syndrome.	2006-01-19	16418668
Comparative efficacy of acetazolamide and apraclonidine in the control of intraocular pressure following phacoemulsification.	2006	17095879
Effect of apraclonidine versus dorzolamide on intraocular pressure after phacoemulsification.	2005-12-17	16355950
Apraclonidine and LASIK.	2005-12	16325717
Brimonidine 0.15% versus apraclonidine 0.5% for prevention of intraocular pressure elevation after anterior segment laser surgery.	2005-09	16246772

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 18:08:22 GMT 2025` Edited by `admin` on `Mon Mar 31 18:08:22 GMT 2025`
Record UNII	843CEN85DI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APRACLONIDINE

Official Name

English

APRACLONIDINE [MI]

Preferred Name

English

APRACLONIDINE [VANDF]

Common Name

English

apraclonidine [INN]

Common Name

English

Apraclonidine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

S01EA03