Apraclonidine (CED0009214)

Record Information
Version1.0
Creation Date2016-05-25 18:23:58 UTC
Update Date2026-08-25 06:56:17 UTC
Accession NumberCHEM022210
Identification
Common NameApraclonidine
ClassSmall Molecule
Description
Apraclonidine is an organic compound with the chemical formula C9H10Cl2N4 and an average molecular weight of 245.11 g/mol. Apraclonidine belongs to the halobenzenes, a subclass of benzene and substituted derivatives within the organic compounds. It is categorized under the superclass of benzenoids. The compound acts as an agonist for three recorded protein targets: the Alpha-2A adrenergic receptor (ADRA2A), the Alpha-1A adrenergic receptor (ADRA1A), and the Alpha-2B adrenergic receptor (ADRA2B). Regarding its recorded exposure routes, it is administered ophthalmically. Apraclonidine is found in or released from seven recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is used in miotics and antiglaucoma preparations. It is also associated with electrical and electronic equipment, specifically electrically stimulated smoking devices. Additionally, it is present in household cleaning and consumer products, including perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-AminoclonidineChEBI
ApraclonidinaChEBI
ApraclonidinumChEBI
IopidineKegg
2-(4-Amino-2,6-dichloro)phenyliminoimidazolidineHMDB
Apraclonidine hydrochlorideHMDB
p-AminoclonidineHMDB
Para-aminoclonidineHMDB
IopimaxHMDB
Chemical FormulaC9H10Cl2N4
Average Molecular Mass245.109 g/mol
Monoisotopic Mass244.028 g/mol
CAS Registry Number66711-21-5
IUPAC Name2,6-dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
Traditional Nameapraclonidine
SMILESNC1=CC(Cl)=C(NC2=NCCN2)C(Cl)=C1
InChI IdentifierInChI=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)
InChI KeyIEJXVRYNEISIKR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 1,3-dichlorobenzene
  • Aniline or substituted anilines
  • Aryl chloride
  • Aryl halide
  • 2-imidazoline
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP2.14ALOGPS
logP1.66ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)8.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area62.44 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity63.79 m³·mol⁻¹ChemAxon
Polarizability23.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00ou-5920000000-28f1d13ea709b508ad30Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-0090000000-cb6e75e3d9735efd5ed7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-1090000000-b91486dba62438f47496Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-015c-9110000000-bca8ec7c4ae6535e617dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0190000000-f27e13e6cfd2fa999857Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1290000000-1666f43d7842c6113374Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ba-7920000000-b2aa97677fc433d0b3d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6b457e59e044eeafe452Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6b457e59e044eeafe452Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2910000000-bc8c9593f9ee08dbbecaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-33d32226692485f879c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-9070000000-8e5823baacac144b77bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-c2fa753da65a4bac80a1Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
37.0Log mg/kg[20:65]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
398Antiglaucoma preparations and mioticsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Apraclonidine Drug Metabolism Action Pathway
Apraclonidine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)4.98235
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)7.94062
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)18.2167
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)8.32987
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)9.41976
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)18.5281
Nischarin structureClick to view 3D structureNischarinQ9Y2I1HumansPredicted (SEA)1.47914
Click to view 3D structureAlpha-2B adrenergic receptorP19328Rattus norvegicusPredicted (SEA)0.934191
Click to view 3D structureAlpha-1A adrenergic receptorP18130Bos taurusPredicted (SEA)14.9471
Click to view 3D structureNischarinQ4G017Rattus norvegicusPredicted (SEA)2.49118
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)126.894
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)166.831
Click to view 3D structureAlpha-2A adrenergic receptorQ28838Bos taurusPredicted (SEA)5.83869
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)79.4062
Click to view 3D structureAlpha-1B adrenergic receptorG3HDX1Cricetulus griseusPredicted (SEA)0.233548
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)341.525
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)343.393
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)446.855
Click to view 3D structureAlpha-1B adrenergic receptorP15823Rattus norvegicusPredicted (SEA)78.0828
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)305.091
Click to view 3D structureAlpha-2A adrenergic receptorP22909Rattus norvegicusPredicted (SEA)85.3227
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)1097.52
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)1264.5
Solute carrier family 22 member 1 structureClick to view 3D structureSolute carrier family 22 member 1O15245HumansPredicted (SEA)34.7208
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)5938.34
Concentrations
Not Available
External Links
DrugBank IDDB00964
HMDB IDHMDB0015099
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkApraclonidine
Chemspider ID2130
ChEBI ID2788
PubChem Compound ID2216
Kegg Compound IDC07668
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
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