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
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)
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 |
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL2094251 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | IOPIDINE Approved UseApraclonidine 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 Date5.6782081E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
74.5% |
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: |
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
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: |
unhealthy, adult Health Status: unhealthy Condition: intraocular pressure Age Group: adult Sex: unknown Sources: |
PubMed
Title | Date | PubMed |
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Reformulation and drop size of apraclonidine hydrochloride. | 1992 Feb 15 |
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Reversal of intraocular pressure increases with 0.5% apraclonidine after dilated fundus examination in patients with chronic open-angle glaucoma. | 1999 Apr |
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Incidence of brimonidine allergy in patients previously allergic to apraclonidine. | 2000 Jun |
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Contact dermatitis to topical drugs for glaucoma. | 2001 Dec |
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Effectiveness of apraclonidine 1% in preventing intraocular pressure rise following macular hole surgery. | 2001 Feb |
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Galanin/alpha2-adrenoceptor interactions in telencephalic and diencephalic regions of the rat. | 2001 Jan 22 |
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Differential effects of alpha-adrenoceptor agonists on human retinal microvessel diameter. | 2001 Jun |
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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 |
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Cutaneous drug reaction case reports: from the world literature. | 2002 |
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Effects of topical antiglaucoma eye drops on prostaglandin E(2)-induced aqueous flare elevation in pigmented rabbits. | 2002 Apr |
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Preventing intraocular pressure increase after phacoemulsification and the role of perioperative apraclonidine. | 2002 Dec |
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The utility of 0.5% apraclonidine in the diagnosis of horner syndrome. | 2003 Aug |
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Neodymium:yttrium-aluminum-garnet capsulotomy and intraocular pressure in pseudophakic patients with glaucoma. | 2004 Jul |
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Managing adverse events associated with botulinum toxin type A: a focus on cosmetic procedures. | 2005 |
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The utility of 0.5% apraclonidine in the diagnosis of horner syndrome. | 2005 Apr |
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Apraclonidine and LASIK. | 2005 Dec |
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Topical apraclonidine in the diagnosis of suspected Horner syndrome. | 2005 Jun |
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Effect of apraclonidine versus dorzolamide on intraocular pressure after phacoemulsification. | 2005 Nov-Dec |
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Pharmacological testing of anisocoria. | 2005 Oct |
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More than just an ocular solution. | 2005 Oct |
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Comparative efficacy of acetazolamide and apraclonidine in the control of intraocular pressure following phacoemulsification. | 2006 |
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Topical apraclonidine testing of pupillary sympathetic denervation in diabetic patients. | 2006 Dec |
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Effect of 0.5% apraclonidine on ptosis in Horner syndrome. | 2006 Jan-Feb |
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The management of glaucoma and intraocular hypertension: current approaches and recent advances. | 2006 Jun |
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Comparing efficacies of 0.5% apraclonidine with 4% cocaine in the diagnosis of horner syndrome in pediatric patients. | 2006 Jun |
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Topical apraclonidine testing discloses pupillary sympathetic denervation in diabetic patients. | 2006 Mar |
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Medical management of primary open-angle glaucoma: Best practices associated with enhanced patient compliance and persistency. | 2008 Feb 2 |
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Use of 0.5% apraclonidine solution in evaluation of blepharoptosis. | 2008 Jul-Aug |
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The role of cyclosporine and mycophenolate in an orthotopic porcine-to-rat corneal xenotransplantation. | 2008 Jun |
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Central alpha-2 adrenergic eye drops: case series of 3 pediatric systemic poisonings. | 2008 Mar |
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False negative apraclonidine test in two patients with Horner syndrome. | 2008 May |
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Fixed combination of topical brimonidine 0.2% and timolol 0.5% for glaucoma and uncontrolled intraocular pressure. | 2008 Sep |
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Pupillary autonomic neuropathy simulating partial Horner syndrome in diabetes mellitus and its reversal with control of blood glucose. | 2008 Sep |
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Positive apraclonidine test within two weeks of onset of Horner syndrome caused by carotid artery dissection. | 2008 Sep |
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[Efficacy of topic ocular hipotensive agents after posterior capsulotomy]. | 2008 Sep-Oct |
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Topical apraclonidine to diagnose Bernard-Horner syndrome. | 2009 |
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Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery. | 2009 |
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Clinical efficacy and neuroprotective effects of brimonidine in the management of glaucoma and ocular hypertension. | 2009 |
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Possible effect of systemic sympathicolytic drugs on apraclonidine test. | 2009 Aug |
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[Unilateral allergic contact dermatitis of the eyelid caused by Iopimax]. | 2009 Dec |
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Nd: YAG capsulotomy for posterior capsule opacification after combined clear corneal phacoemulsification and vitrectomy. | 2009 Feb |
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[Usefulness of apraclonidine in the diagnosis of Horner syndrome]. | 2009 Feb |
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False-negative apraclonidine testing in acute Horner syndrome. | 2009 Feb |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11481271
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
Edited
Wed Jul 05 23:15:20 UTC 2023
by
admin
on
Wed Jul 05 23:15:20 UTC 2023
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Record UNII |
843CEN85DI
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Record Status |
Validated (UNII)
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Record Version |
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S01EA03
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N0000175552
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N0000000209
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C29709
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WHO-VATC |
QS01EA03
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APRACLONIDINE
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C61640
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7117
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Apraclonidine
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DTXSID1048415
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
SHORT-ACTING
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TARGET -> AGONIST | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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