Basic information
- CAS
73218-79-8- Standard SMILES
Cl.Nc1cc(Cl)c(NC2=NCCN2)c(Cl)c1- InChIKey
OTQYGBJVDRBCHC-UHFFFAOYSA-N- Molecular formula
- C9H11Cl3N4
- Average molar mass
- 281.6 g/mol
- Monoisotopic mass
- 280.004929
Overview
Apraclonidine hydrochloride is the hydrochloride salt of apraclonidine. It has a role as an alpha-adrenergic agonist and an antiglaucoma drug. It contains an apraclonidine.
Names & identifiers
- Preferred name
- Apraclonidine Hydrochloride
- IUPAC
- 2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine;hydrochloride
- English name
- Apraclonidine hydrochloride
- Molecular formula
- C9H11Cl3N4
- Molecular weight
- 281.57
Names & synonyms
APRACLONIDINE HYDROCHLORIDE73218-79-8Apraclonidine HClDTXSID6045749AL02145D2VW67N38H2-(4-Amino-2,6-dichlorophenylimino)imidazolidine hydrochloride3,5-Dichloro-4-(2-imidazolidinylidenimino)aniline hydrochlorideAL-02145CHEBI:2789DTXCID40257492,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine;hydrochloride
Show more names
AL 02145alo-2145Iopidine UDnc14hydrochlorideiopidineophthalmicsolutionpraclonidine hydrochlorideApracloniding Hydrochloride
Apraclonidine OphthalmicRefChem:57694IOPIDINE 1%apraclonidine hydrochloride ophthalmic solution1,4-Benzenediamine, 2,6-Dichloro-N(sup 1)-(4,5-dihydro-1H-imidazol-2-yl), Monohydrochloridep-Aminoclonidine hydrochloride2,6-dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine hydrochlorideIopidine
Database identifiers
- CAS
Properties
Computed structural properties
- Topological polar surface area
- 62.4 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 246
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 2300 C · >2300C
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL Solutions may be stored for several days at 4°C
- form
- solid
- color
- white
- Stability
- Moisture Sensitive
- Major Application
- pharmaceutical (small molecule)
- 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
- InChIKey
- OTQYGBJVDRBCHC-UHFFFAOYSA-N
- SMILES
- Clc1c(c(cc(c1)N)Cl)N=C2NCCN2.Cl
- CAS DataBase Reference
- 73218 · 73218-79-8(CAS DataBase Reference)
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (66.7%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P308+P316, P316, P319, P321, P330, P337+P317, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 1 (66.7%)
Safety data
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 1
- hs_code
- 2933290000
- risk_code
- 23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T
- safety_code
- 22-36/37/39-45
- hazard_class
- 6.1(b)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- III
- target organs
- Cardio-vascular system
- Hazard statements
- H300-H370
- Hazard Classifications
- Acute Tox. 1 OralSTOT SE 1
- Precautionary statements
- P301+P330+P331+P310-P308+P311
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
APRACLONIDINE HYDROCHLORIDE OPHTHALMIC SOLUTION
Adrenergic alpha-Agonists [MoA]; alpha-Adrenergic Agonist [EPC]
MeSH Pharmacological ClassificationCompounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS.
Applications
UsesApraclonidine hydrochloride can be used as α-Adrenergic agonist; structural analog of clonidine and be used for treatment of post-surgical elevated intraocular pressure.
Usesa-Adrenergic agonist; structural analog of clonidine. Used for treatment of post-surgical elevated intraocular pressure
Preparation methods
PreparationUsing 2,6-dichloro-4-nitroaniline, formic acid, and acetic anhydride as starting materials, a formylation reaction was carried out to obtain N-(2,6-dichloro-4-nitrophenyl)formamide; then, through chlorination and cyclization, 2-(2',6'-dichloro-4'-nitroanilino)-2-imidazoline was obtained. Finally, the nitro group in 2-(2',6'-dichloro-4'-nitroanilino)-2-imidazoline was reduced with hydrazine hydrate to prepare Apraclonidine hydrochloride (1), with an overall yield of 45%. The reduction of the nitro group in 2-(2',6'-dichloro-4'-nitroanilino)-2-imidazoline with hydrazine hydrate as a reducing agent was reported for the first time. No effect was observed on the imine bond, and the yield of this step was over 80%.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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