Identification
- Summary
Apraclonidine is an alpha adrenergic agonist used to treat raised intraocular pressure.
- Brand Names
- Iopidine
- Generic Name
- Apraclonidine
- DrugBank Accession Number
- DB00964
- Background
Apraclonidine, also known as iopidine, is a sympathomimetic used in glaucoma therapy. It is an alpha2-adrenergic agonist.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Apraclonidine (DB00964)
- Weight
- Average: 245.109
Monoisotopic: 244.028251754 - Chemical Formula
- C9H10Cl2N4
- Synonyms
- 4-Aminoclonidine
- Apraclonidina
- Apraclonidine
- Apraclonidinum
Pharmacology
- Indication
For prevention or reduction of intraoperative and postoperative increases in intraocular pressure (IOP) before and after ocular laser surgery when used prophylactically. Also used as a short-term adjunctive therapy in patients with open-angle glaucoma who are on maximally tolerated medical therapy requiring additional IOP reduction.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Ocular hypertension •••••••••••• •••••••••• Prophylaxis of Postsurgical ocular hypertension •••••••••••• •••••••••• Treatment of Postsurgical ocular hypertension •••••••••••• •••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Apraclonidine significantly lowers intraocular pressure with minimal effects on cardiovascular and pulmonary parameters. It lowers intraocular pressure by reducing aqueous humor production and increasing uveoscleral outflow.
- Mechanism of action
Apraclonidine is a relatively selective alpha2 adrenergic receptor agonist that stimulates alpha1 receptors to a lesser extent. It has a peak ocular hypotensive effect occurring at two hours post-dosing. The exact mechanism of action is unknown, but fluorophotometric studies in animals and humans suggest that Apraclonidine has a dual mechanism of action by reducing aqueous humor production through the constriction of afferent ciliary process vessels, and increasing uveoscleral outflow.
Target Actions Organism AAlpha-1A adrenergic receptor agonistHumans AAlpha-2A adrenergic receptor agonistHumans UAlpha-2B adrenergic receptor agonistHumans - Absorption
Topical use of apraclonidine ophthalmic solution leads to systemic absorption. Studies of apraclonidine (0.5% ophthalmic solution) dosed one drop three times a day in both eyes for 10 days in normal volunteers yielded mean peak and trough concentrations of 0.9 ng/mL and 0.5 ng/mL, respectively.
- Volume of distribution
Not Available
- Protein binding
98.7%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
8 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Accidental or intentional ingestion of oral apraclonidine has been reported to cause apnea, arrhythmias, asthenia, bradycardia, conduction defects, diminished or absent reflexes, dryness of the mouth, hypotension, hypothermia, hypoventilation, irritability, lethargy, miosis, pallor, respiratory depression, sedation or coma, seizure, somnolence, transient hypertension, and vomiting.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAvanafil The risk or severity of hypotension can be increased when Avanafil is combined with Apraclonidine. Dipyridamole The risk or severity of hypotension can be increased when Dipyridamole is combined with Apraclonidine. Formoterol Apraclonidine may increase the sympathomimetic activities of Formoterol. Fostamatinib The risk or severity of hypotension can be increased when Fostamatinib is combined with Apraclonidine. Isocarboxazid Isocarboxazid may increase the alpha-adrenergic activities of Apraclonidine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Apraclonidine hydrochloride D2VW67N38H 73218-79-8 OTQYGBJVDRBCHC-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Iopidine Solution / drops 10 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1988-05-15 Not applicable US 
Iopidine Solution 0.5 % Ophthalmic Essential Pharma Switzerland Gmbh 1995-12-31 Not applicable Canada 
Iopidine Solution 5 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1993-10-01 Not applicable US Iopidine Solution 1 % Ophthalmic Essential Pharma Switzerland Gmbh 1992-12-31 Not applicable Canada Iopidine 1% Solution / drops 10 mg/1mL Ophthalmic Harrow Eye, LLC 2023-08-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apraclonidine Solution 5.75 mg/1mL Ophthalmic FALCON Pharmaceuticals, Ltd. 2009-07-19 2011-07-29 US Apraclonidine Solution 5.75 mg/1mL Ophthalmic Sandoz Inc 2009-07-19 Not applicable US Apraclonidine Ophthalmic Solution / drops 5 mg/1mL Ophthalmic Akorn 2009-08-12 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image IOPIDINE %0,5 5 ML OFTALMIK SOLUSYON Apraclonidine (0.5 %) Solution Ophthalmic ALCON LABORATUVARLARI TİC. A.Ş. 2018-10-03 2018-10-03 Turkey 
Categories
- ATC Codes
- S01EA03 — Apraclonidine
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-2 Receptor Agonists
- Adrenergic alpha-Agonists
- Antiglaucoma Preparations and Miotics
- EENT Drugs, Miscellaneous
- Hypotensive Agents
- Imidazoles
- Imidazolines
- Neurotransmitter Agents
- Ophthalmics
- Ophthalmologicals
- Sensory Organs
- Sympathomimetics in Glaucoma Therapy
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- Aniline and substituted anilines / Aryl chlorides / Imidazolines / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organochlorides show 1 more
- Substituents
- 1,3-dichlorobenzene / 2-imidazoline / Amine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carboximidamide / Guanidine show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- guanidines, dichlorobenzene, imidazolines (CHEBI:2788)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 843CEN85DI
- CAS number
- 66711-21-5
- InChI Key
- IEJXVRYNEISIKR-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 2,6-dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
- SMILES
- NC1=CC(Cl)=C(NC2=NCCN2)C(Cl)=C1
References
- General References
- Chen PL, Chen JT, Lu DW, Chen YC, Hsiao CH: Comparing efficacies of 0.5% apraclonidine with 4% cocaine in the diagnosis of horner syndrome in pediatric patients. J Ocul Pharmacol Ther. 2006 Jun;22(3):182-7. [Article]
- Aslanides lM, Tsiklis NS, Ozkilic E, Coskunseven E, Pallikaris lG, Jankov MR: The effect of topical apraclonidine on subconjunctival hemorrhage and flap adherence in LASIK patients. J Refract Surg. 2006 Jun;22(6):585-8. [Article]
- Koc F, Kansu T, Kavuncu S, Firat E: Topical apraclonidine testing discloses pupillary sympathetic denervation in diabetic patients. J Neuroophthalmol. 2006 Mar;26(1):25-9. [Article]
- Garibaldi DC, Hindman HB, Grant MP, Iliff NT, Merbs SL: Effect of 0.5% apraclonidine on ptosis in Horner syndrome. Ophthal Plast Reconstr Surg. 2006 Jan-Feb;22(1):53-5. [Article]
- Onal S, Gozum N, Gucukoglu A: Effect of apraclonidine versus dorzolamide on intraocular pressure after phacoemulsification. Ophthalmic Surg Lasers Imaging. 2005 Nov-Dec;36(6):457-62. [Article]
- Costa VP, Harris A, Stefansson E, Flammer J, Krieglstein GK, Orzalesi N, Heijl A, Renard JP, Serra LM: The effects of antiglaucoma and systemic medications on ocular blood flow. Prog Retin Eye Res. 2003 Nov;22(6):769-805. [Article]
- External Links
- Human Metabolome Database
- HMDB0015099
- KEGG Compound
- C07668
- PubChem Compound
- 2216
- PubChem Substance
- 46505614
- ChemSpider
- 2130
- BindingDB
- 81926
- 14845
- ChEBI
- 2788
- ChEMBL
- CHEMBL647
- ZINC
- ZINC000000020231
- Therapeutic Targets Database
- DAP000236
- PharmGKB
- PA164748866
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Apraclonidine
- FDA label
- Download (119 KB)
- MSDS
- Download (57.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Not Yet Recruiting Treatment Facial Nerve Palsy / Synkinesis 1 2 Completed Treatment Myasthenia Gravis / Ocular Myasthenia Gravis 1 Not Available Unknown Status Treatment Glaucoma / Ocular Hypertension 1
Pharmacoeconomics
- Manufacturers
- Akorn inc
- Alcon laboratories inc
- Packagers
- Akorn Inc.
- Alcon Laboratories
- Dispensing Solutions
- Falcon Pharmaceuticals Ltd.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Solution Ophthalmic 5.75 mg/1mL Solution / drops Ophthalmic 5 mg/1mL Solution Ophthalmic 0.5 % Solution Ophthalmic 1 % Solution Ophthalmic 5 mg/1mL Solution / drops Ophthalmic 10 mg/1mL Solution / drops Ophthalmic 5 mg/ml Solution / drops Ophthalmic 0.5 % - Prices
Unit description Cost Unit Iopidine 0.5% Solution 10ml Bottle 196.37USD bottle Iopidine 0.5% Solution 5ml Bottle 98.84USD bottle Iopidine 1 Box = 24 Packets Plastic Container 16.44USD plastic Iopidine 1% eye drops 15.81USD each Iopidine 0.5 % Solution 4.79USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5212196 No 1993-05-18 2010-05-18 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.409 mg/mL ALOGPS logP 2.14 ALOGPS logP 1.66 Chemaxon logS -2.8 ALOGPS pKa (Strongest Basic) 8.48 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 62.44 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 63.79 m3·mol-1 Chemaxon Polarizability 23.27 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9685 Blood Brain Barrier + 0.9398 Caco-2 permeable + 0.8503 P-glycoprotein substrate Substrate 0.625 P-glycoprotein inhibitor I Non-inhibitor 0.9406 P-glycoprotein inhibitor II Non-inhibitor 0.9142 Renal organic cation transporter Inhibitor 0.7327 CYP450 2C9 substrate Non-substrate 0.8621 CYP450 2D6 substrate Non-substrate 0.7005 CYP450 3A4 substrate Non-substrate 0.6636 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.7046 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8713 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8947 Ames test Non AMES toxic 0.8937 Carcinogenicity Non-carcinogens 0.9263 Biodegradation Not ready biodegradable 0.9954 Rat acute toxicity 3.4656 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8192 hERG inhibition (predictor II) Non-inhibitor 0.891
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00ou-5920000000-28f1d13ea709b508ad30 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-89104b35d7f63c0c7d61 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-0b30f143f3a473c79379 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0190000000-5340b94b65db99c8d502 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1190000000-cf9386410e36b404c4d2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-4910000000-886c33a48b5233a9072d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-5bfb3ba555ae9b605065 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 147.4957706 predictedDarkChem Lite v0.1.0 [M-H]- 145.46834 predictedDeepCCS 1.0 (2019) [M+H]+ 148.3415706 predictedDarkChem Lite v0.1.0 [M+H]+ 147.82635 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.3011706 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.40474 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Moodley AA, Spooner RB: Apraclonidine in the diagnosis of Horner's syndrome. S Afr Med J. 2007 Jul;97(7):506-7. [Article]
- Mirzai H, Baser EF: Congenital Horner's syndrome and the usefulness of the apraclonidine test in its diagnosis. Indian J Ophthalmol. 2006 Sep;54(3):197-9. [Article]
- Sueke H, Chandna A: Using apraclonidine in diagnosing Horner syndrome in children. Am J Ophthalmol. 2010 May;149(5):869; author reply 870. doi: 10.1016/j.ajo.2010.01.023. [Article]
- Kawasaki A, Borruat FX: False negative apraclonidine test in two patients with Horner syndrome. Klin Monbl Augenheilkd. 2008 May;225(5):520-2. doi: 10.1055/s-2008-1027349. [Article]
- Watts P, Satterfield D, Lim MK: Adverse effects of apraclonidine used in the diagnosis of Horner syndrome in infants. J AAPOS. 2007 Jun;11(3):282-3. [Article]
- Chen PL, Hsiao CH, Chen JT, Lu DW, Chen WY: Efficacy of apraclonidine 0.5% in the diagnosis of Horner syndrome in pediatric patients under low or high illumination. Am J Ophthalmol. 2006 Sep;142(3):469-74. [Article]
- Freedman KA, Brown SM: Topical apraclonidine in the diagnosis of suspected Horner syndrome. J Neuroophthalmol. 2005 Jun;25(2):83-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Wikberg-Matsson A, Simonsen U: Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55. [Article]
- Moodley AA, Spooner RB: Apraclonidine in the diagnosis of Horner's syndrome. S Afr Med J. 2007 Jul;97(7):506-7. [Article]
- Mirzai H, Baser EF: Congenital Horner's syndrome and the usefulness of the apraclonidine test in its diagnosis. Indian J Ophthalmol. 2006 Sep;54(3):197-9. [Article]
- Authors unspecified: New topical drugs for open-angle glaucoma. Drug Ther Bull. 2003 Feb;41(2):12-4. [Article]
- Costa VP, Harris A, Stefansson E, Flammer J, Krieglstein GK, Orzalesi N, Heijl A, Renard JP, Serra LM: The effects of antiglaucoma and systemic medications on ocular blood flow. Prog Retin Eye Res. 2003 Nov;22(6):769-805. [Article]
- Scheinfeld N: The use of apraclonidine eyedrops to treat ptosis after the administration of botulinum toxin to the upper face. Dermatol Online J. 2005 Mar 1;11(1):9. [Article]
- Sueke H, Chandna A: Using apraclonidine in diagnosing Horner syndrome in children. Am J Ophthalmol. 2010 May;149(5):869; author reply 870. doi: 10.1016/j.ajo.2010.01.023. [Article]
- Watts P, Satterfield D, Lim MK: Adverse effects of apraclonidine used in the diagnosis of Horner syndrome in infants. J AAPOS. 2007 Jun;11(3):282-3. [Article]
- Chen PL, Hsiao CH, Chen JT, Lu DW, Chen WY: Efficacy of apraclonidine 0.5% in the diagnosis of Horner syndrome in pediatric patients under low or high illumination. Am J Ophthalmol. 2006 Sep;142(3):469-74. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Epinephrine binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49565.8 Da
References
- Liu JH, Dacus AC, Bartels SP: Adrenergic mechanism in circadian elevation of intraocular pressure in rabbits. Invest Ophthalmol Vis Sci. 1991 Jul;32(8):2178-83. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:46