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アプラクロニジン

Apraclonidine

HCID 2216
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
66711-21-5
標準SMILES
Nc1cc(Cl)c(NC2=NCCN2)c(Cl)c1
InChIKey
IEJXVRYNEISIKR-UHFFFAOYSA-N
分子式
C9H10Cl2N4
平均分子量
245.11 g/mol
単同位体質量
244.02825168

概要

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is an imidazoline that is 2-amino 4,5-dihydro-1H-imidazoline in which one of the exocyclic amino hydrogens has been replaced by a 4-amino-2,6-dichlorophenyl group.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+).

名称と識別子

優先名称
Apraclonidine
IUPAC
2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
現地名
アプラクロニジン
英語名
Apraclonidine
分子式
C9H10Cl2N4
分子量
245.11

名称と別名

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
名称をさらに表示
p-アミノクロニジンアプロニジン2,6-ジクロロ-N-[(4,5-ジヒドロ-1H-イミダゾール)-2-イル]-1,4-ベンゼンジアミンアプラクロニジン2-[(4-アミノ-2,6-ジクロロフェニル)イミノ]イミダゾリジン2,6-ジクロロ-N1-(イミダゾリジン-2-イリデン)ベンゼン-1,4-ジアミン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]

物性

構造計算による物性補完中

XLogP
1.3
極性表面積
62.4 Ų
水素結合供与体数
3
水素結合受容体数
2
回転可能結合数
2
重原子数
15
形式電荷
0
複雑度
246

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LogP1.4
Solubility4.09e-01 g/L
Human DrugsBreast Feeding; Lactation; Adrenergic alpha-2 Receptor Agonists; Antiglaucoma Agents
Physical DescriptionSolid

物理化学的性質

融点
230 ° · >230°
沸点
395.5 · 395.5±52.0 °C(Predicted)
比重(密度)
1.63 · 1.63±0.1 g/cm3(Predicted)
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
45 % · 45% (w/v) 2-ヒドロキシプロピル-β-シクロデキストリン水溶液: 1.4mg/mL、溶液は 4°C で数日間保存可能
酸解離定数(Pka)
9.26 · 9.26±0.50(Predicted)
外見
個体
色
白い
CAS データベース
66711 · 66711-21-5(CAS DataBase Reference)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk
3
ridadr
UN 2811 6.1/PG 1
risk_code
23/24/25
hazard_code
T
safety_code
22-36/37/39-45

化学と産業

薬理情報

ATC Code · 3 件

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 · 1 件

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 · 6 件

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 · 1 件

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.

関連反応

1 件
反応記録を作成
HRID 637716 の反応式
HRID 637716生成物としてuspto-grants-1985_12

化合物ノート

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データベース識別子

CAS
66711-21-5
PubChem CID
2216
DTXSID
DTXSID1048415
ChEMBL
CHEMBL647
ChEBI
CHEBI:2788
UNII
843CEN85DI
EC Number
636-293-2
Nikkaji
J247.956G
Cellular Locations
Membrane
応用分野 · 1 件

一般的な説明In addition to its therapeutic use as an antihypertensiveagent, clonidine has been found to provide beneficialeffects in several other situations, including glaucoma,spasticity, migraine prophylaxis, opiate withdrawal syndrome,and anesthesia. This has prompted the developmentof analogs of clonidine for specific use in some of the mentionedareas. Two of such examples are apraclonidine andbrimonidine. Apraclonidine does not cross the BBB.However, brimonidine can cross the BBB and hence canproduce hypotension and sedation, although these CNSeffects are slight compared with those of clonidine. CNS effectsof these drugs are correlated well to their log P, pKa,and thus log D value. Both apraclonidine and brimonidineare selective α2-agonists with α1: α2 ratios of 30:1 and1,000:1, respectively. Brimonidine is a much more selectiveα2-agonist than clonidine or apraclonidine and is a firstlineagent for treating glaucoma. Apraclonidines’s primarymechanism of action may be related to a reduction of aqueousformation, whereas brimonidine lowers intraocularpressure by reducing aqueous humor production and increasinguveoscleral outflow. Apraclonidine is used specificallyto control elevations in intraocular pressure that canoccur during laser surgery on the eye. Another example istizanidine (Zanaflex), which finds use in treating spasticityassociated with multiple sclerosis or spinal cord injury. Bystimulating 2-adrenergic receptors, it is believed to decreasethe release of excitatory amino acid NTs from spinalcord interneurons.

上流・下流製品情報

上流原料

トルエンエチレンジアミン (無水)二塩化チオカルボニルアルミニウムニッケル触媒tert-ブチルメチルエーテルヘキサンイソプロピルアルコールメタノール

下流製品

アプラクロニジン塩酸塩

補足説明

定義ChEBI: An imidazoline compound having a 4-amino-2,6-dichloroanilino group at the 2-position.