2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine

• ChemBase ID: 840
• Molecular Formular: C9H10Cl2N4
• Molecular Mass: 245.1085
• Monoisotopic Mass: 244.0282517
• SMILES: Clc1c(NC2=NCCN2)c(Cl)cc(N)c1
• Canonical SMILES: Nc1cc(Cl)c(c(c1)Cl)NC1=NCCN1
• 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)
• InChIKey: IEJXVRYNEISIKR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
• IUPAC Traditional name: apraclonidine
• Brand Name: Aplonidine; Iopidine; Iopidine Eye
• Synonyms: Apraclonidina [INN-Spanish]; Apraclonidinum [INN-Latin]; P-Aminoclonidine Hydrochloride; Apraclonidine Hydrochloride; Apraclonidine

Database IDs

• CAS Number: 66711-21-5
• PubChem SID: 46505614; 160964303
• PubChem CID: 2216

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.65617114
• LogD (pH = 7.4): 0.5622336
• Log P: 1.6561627
• Molar Refractivity: 63.7892 cm^3
• Polarizability: 23.09249 Å^3
• Polar Surface Area: 62.44 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.14
• LOG S: -2.78
• Solubility (Water): 4.09e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.4

DETAILS

DrugBank - DB00964

• Drug Groups: approved
• Description: Apraclonidine, also known as iopidine, is a sympathomimetic used in glaucoma therapy. It is an alpha2-adrenergic agonist.
• 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.
• Pharmacology: 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.
• 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.
• Affected Organisms: Humans and other mammals
• 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.
• Half Life: 8 hours
• Protein Binding: 98.7%
• 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. [Pubmed] ; Aslanides M, Tsiklis NS, Ozkilic E, Coskunseven E, Pallikaris G, 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. [Pubmed] ; 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. [Pubmed] ; 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. [Pubmed] ; 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. [Pubmed] ; 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. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

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. Pubmed
• Aslanides M, Tsiklis NS, Ozkilic E, Coskunseven E, Pallikaris G, 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. Pubmed
• 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. Pubmed
• 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. Pubmed
• 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. Pubmed
• 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. Pubmed