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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H10Cl2N4.ClH
Molecular Weight 281.569
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRACLONIDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=OTQYGBJVDRBCHC-UHFFFAOYSA-N
InChI=1S/C9H10Cl2N4.ClH/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);1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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.

CNS Activity

Originator

Approval Year

1987
121
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

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:
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

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:
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
303
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
303
 yes
Sourcing

Sourcing

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

PubMed

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

Patents

04596818
3
US4517199 A
3

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 17:57:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:52 GMT 2025
Record UNII
D2VW67N38H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IOPIDINE
Preferred Name English
APRACLONIDINE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
APRACLONIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
1,4-BENZENEDIAMINE, 2,6-DICHLORO-N(SUP 1)-2-IMIDAZOLIDINYLIDENE-, MONOHYDROCHLORIDE
Common Name English
AL02145
Code English
APRACLONIDINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
APRACLONIDINE HYDROCHLORIDE [MART.]
Common Name English
APRACLONIDINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
APRACLONIDINE HYDROCHLORIDE [MI]
Common Name English
Apraclonidine hydrochloride [WHO-DD]
Common Name English
APRACLONIDINE HCL
Common Name English
AL-02145
Code English
APRACLONIDINE HYDROCHLORIDE [USAN]
Common Name English
APRACLONIDINE HYDROCHLORIDE [JAN]
Common Name English
APRACLONIDINE HYDROCHLORIDE [USP-RS]
Common Name English
2-((4-AMINO-2,6-DICHLOROPHENYL)IMINO) IMIDAZOLIDINE MONOHYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
Code System Code Type Description
EVMPD
SUB12926MIG
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
PUBCHEM
51763
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
MERCK INDEX
m2008
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY Merck Index
RXCUI
91350
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL647
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
DRUG BANK
DBSALT000819
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
RS_ITEM_NUM
1041609
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
DAILYMED
D2VW67N38H
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
SMS_ID
100000077408
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID6045749
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
FDA UNII
D2VW67N38H
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
USAN
Z-50
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
CHEBI
2789
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
NCI_THESAURUS
C47401
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
CAS
73218-79-8
Created by admin on Mon Mar 31 17:57:52 GMT 2025 , Edited by admin on Mon Mar 31 17:57:52 GMT 2025
PRIMARY
Related Record Type Details
Structure of APRACLONIDINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of APRACLONIDINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966