アクリバスチン
(E)-3-[6-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ium-1-ylprop-1-enyl]-2-pyridinyl]prop-2-enoate
基本情報
- CAS
87848-99-5- 標準SMILES
Cc1ccc(/C(=C\C[NH+]2CCCC2)c2cccc(/C=C/C(=O)[O-])n2)cc1- InChIKey
PWACSDKDOHSSQD-IUTFFREVSA-N- 分子式
- C22H24N2O2
- 平均分子量
- 348.4 g/mol
- 単同位体質量
- 348.18377801
概要
Acrivastine is a triprolidine analog antihistamine indicated for the treatment of allergies and hay fever. As an H1 receptor antagonist, it functions by blocking the action of histamine at this receptor thereby preventing the symptoms associated with histamine release such as pruritis, vasodilation, hypotension, edema, bronchoconstriction, and tachycardia. Acrivastine is currently available in combination with pseudoephedrine as the FDA-approved product Semprex-D.
名称と識別子
- 優先名称
- (E)-3-[6-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ium-1-ylprop-1-enyl]-2-pyridinyl]prop-2-enoate
- IUPAC
- (E)-3-[6-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ium-1-ylprop-1-enyl]-2-pyridinyl]prop-2-enoate
- 現地名
- アクリバスチン
- 英語名
- Acrivastine
- 分子式
- C22H24N2O2
- 分子量
- 348.44
名称と別名
(E)-3-[6-[(E)-1-(4-メチルフェニル)-3-(1-ピロリジニル)-1-プロペニル]-2-ピリジル]プロペン酸センプレックス(E)-6-[(E)-3-(ピロリジン-1-イル)-1-(4-メチルフェニル)-1-プロペニル]-2-ピリジンプロペン酸アクリバスチン(E)-3-[6-[(E)-1-(4-メチルフェニル)-3-(1-ピロリジニル)-1-プロペニル]-2-ピリジニル]プロペン酸(2E)-3-{6-[(1E)-1-(4-メチルフェニル)-3-(ピロリジン-1-イル)プロパ-1-エン-1-イル]ピリジン-2-イル}プロパ-2-エン酸(E)-3-(6-((E)-3-(Pyrrolidin-1-yl)-1-(p-tolyl)prop-1-en-1-yl)pyridin-2-yl)acrylic acidSemprexBW-825CBW-270CBW-A825CAcrivastin
名称をさらに表示
ACRIVASTINEAcrivastine>Acrivastine/BW825CAcrivastine USP/EP/BP
データベース識別子
- CAS
87848-99-5- PubChem CID
- 40466858
物性
構造計算による物性
- XLogP
- 2.3
- 極性表面積
- 57.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 5
- 重原子数
- 26
- 形式電荷
- 0
- 複雑度
- 509
物理化学的性質
- 融点
- 222 ° · 222° (dec)
- 沸点
- 555.1 · 555.1±50.0 °C(Predicted)
- 比重(密度)
- 1.17 · 1.170±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 2 mg/mL · DMSO: >2mg/mL (加温)
- 外見
- 粉
- 酸解離定数(Pka)
- 1.99 · 1.99±0.10(Predicted)
- 色
- 白からベージュ
- 安定性
- 光に敏感
- InChI
- InChI=1S/C22H24N2O2/c1-17-7-9-18(10-8-17)20(13-16-24-14-2-3-15-24)21-6-4-5-19(23-21)11-12-22(25)26/h4-13H,2-3,14-16H2,1H3,(H,25,26)/b12-11+,20-13+
- InChIKey
- PWACSDKDOHSSQD-IUTFFREVSA-N
- SMILES
- C(O)(=O)/C=C/C1=NC(/C(/C2=CC=C(C)C=C2)=C/CN2CCCC2)=CC=C1
- CAS データベース
- 87848 · 87848-99-5(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。
安全データ
- wgk
- 3
- rtecs
- UD3474000
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Protein BindingAcrivastine binding to human plasma proteins was 50 ± 2.0%.
Biological Half-LifeThe mean terminal half-life for acrivastine was 1.9 ± 0.3 hours following single oral doses and increased to 3.5 ± 1.9 hours at steady state. The terminal half-life for the propionic acid metabolite was 3.8 ± 1.4 hours.
Absorption, Distribution and Excretion
Acrivastine was absorbed rapidly from the combination capsule following oral administration and was as bioavailable as a solution of acrivastine. After administration of SEMPREX-D Capsules, maximum plasma acrivastine concentrations were achieved at 1.14 ± 0.23 hour.
A mass balance study in 7 healthy volunteers showed that acrivastine is primarily eliminated by the kidneys. Over a 72-hour collection period, about 84% of the administered total radioactivity was recovered in urine and about 13% in feces, for a combined recovery of about 97%.
0.46 ± 0.05 L/kg
2.9 ± 0.7 mL/min/kg
Metabolite PathwaysAcrivastine H1-Antihistamine Action
応用分野
説明Acrivastine is an orally-active HI .receptor antagonist reportedly useful in the treatment of allergic rhinitis. The main advantages of acrivastine in comparison to older antihistamines are its low sedative potential and the absence of anticholinergic side-effects.
使用Acrivastine has been used as an antihistamine to investigate the relation between the increased residence time of antihistamine at the histamine H1 receptor (H1R) and the duration of effective target-inhibition by this antagonist.
一般的な説明Acrivastine, (E, E)-3-[6-[1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl-2-pyridinyl]-2-propenoic acid(Semprex), is a fixed-combination product of the antihistamineacrivastine (8 mg) with the decongestant pseudoephedrine(60 mg). Acrivastine is an odorless, white to pale cream crystallinepowder that is soluble in chloroform and alcohol andslightly soluble in water.Acrivastine is an analog of triprolidine containing acarboxyethenyl moiety at the 6-position of the pyridylring. Acrivastine shows antihistaminic potency and durationof action comparable to those of triprolidine (Table23.2). Unlike triprolidine, acrivastine does not display significantanticholinergic activity at therapeutic concentrations.Also, the enhanced polarity of this compound resultingfrom carboxyethenyl substitution limits BBBaccumulation, and thus, this compound produces less sedationthan triprolidine.Limited pharmacokinetic data are available for this compound.Orally administered drug has a half-life of about 1.7hours and a total body clearance of 4.4 mL/min per kilogram.The mean peak plasma concentrations are reported tovary widely, and the drug appears to penetrate the CNSpoorly. The metabolic fate of acrivastine has not beenreported.
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