Apraclonidine
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Grundinformationen
- CAS
66711-21-5- Standard-SMILES
Nc1cc(Cl)c(NC2=NCCN2)c(Cl)c1- InChIKey
IEJXVRYNEISIKR-UHFFFAOYSA-N- Summenformel
- C9H10Cl2N4
- Durchschnittliche Molmasse
- 245,11 g/mol
- Monoisotopische Masse
- 244,02825168
Überblick
Apraclonidine is an imidazoline that is 2-amino 4,5-dihydro-1H-imidazoline in which one of the exocyclic amino hydrogens has been replaced by a 4-amino-2,6-dichlorophenyl group. It has a role as a diagnostic agent, a beta-adrenergic agonist, an alpha-adrenergic agonist, an antiglaucoma drug and an ophthalmology drug. It is a dichlorobenzene, a member of guanidines and a member of imidazolines. It is a conjugate base of an apraclonidine(1+).
Namen und Bezeichner
- Bevorzugter Name
- Apraclonidine
- IUPAC
- 2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
- Englischer Name
- Apraclonidine
- Summenformel
- C9H10Cl2N4
- Molmasse
- 245.11
Namen und Synonyme
apraclonidine66711-21-54-AminoclonidineApraclonidinaApraclonidinump-aminoclonidine2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine843CEN85DICHEBI:2788DTXSID10484151,4-Benzenediamine, 2,6-dichloro-N'-(4,5-dihydro-1H-imidazol-2-yl)-para-aminoclonidine
Weitere Namen anzeigen
NC-14ApraclonldineApraclondine HclApraclonidine USP/EP/BPApraclonidine - API Standards2-((4-Amino-2,6-dichlorophenyl)imino)imidazolidine2,6-Dichloro-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
Iopimax2-(4-amino-2,6-dichloro)phenyliminoimidazolidineRefChem:57693DTXCID9028388S01EA03AplonidineApraclonidinum [INN-Latin]Apraclonidina [INN-Spanish]
Datenbank-Bezeichner
- CAS
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,3
- Polarare Oberfläche (TPSA)
- 62,4 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 246
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.4
Solubility4.09e-01 g/L
Human DrugsBreast Feeding; Lactation; Adrenergic alpha-2 Receptor Agonists; Antiglaucoma Agents
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 230 ° · >230°
- Siedepunkt
- 395.5 · 395.5±52.0 °C(Predicted)
- Dichte
- 1.63 · 1.63±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL Solutions may be stored for several days at 4°C
- pka
- 9.26 · 9.26±0.50(Predicted)
- Aggregatzustand
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 1
- risk_code
- 23/24/25
- hazard_code
- T
- safety_code
- 22-36/37/39-45
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S01EA03
S - Sensory organs
QS - Sensory organs
Protein Binding98.7%
PharmacodynamicsApraclonidine 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.
Biological Half-Life8 hours
FDA Pharmacological Classification
843CEN85DI
APRACLONIDINE
Mechanisms of Action [MoA] - Adrenergic alpha-Agonists
Established Pharmacologic Class [EPC] - alpha-Adrenergic Agonist
Apraclonidine is an alpha-Adrenergic Agonist. The mechanism of action of apraclonidine is as an Adrenergic alpha-Agonist.
APRACLONIDINE
MeSH Pharmacological ClassificationCompounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS.
Absorption, Distribution and Excretion
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.
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