基本情報
- CAS
26652-09-5- 標準SMILES
C[C@@H](NCCc1ccc(O)cc1)[C@@H](O)c1ccc(O)cc1- InChIKey
IOVGROKTTNBUGK-SJKOYZFVSA-N- 分子式
- C17H21NO3
- 平均分子量
- 287.35 g/mol
- 単同位体質量
- 287.15214353
概要
(1S,2R)-ritodrine is a 4-[2-[[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol that has (1S,2R)-configuration. It is an enantiomer of a (1R,2S)-ritodrine.
名称と識別子
- 優先名称
- 4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol
- IUPAC
- 4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol
- 現地名
- リトドリン
- 英語名
- RITODRINE
- 分子式
- C17H21NO3
- 分子量
- 287.35
名称と別名
4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenolrel-RITODRINERitodrina [INN-Spanish]Ritodrinium [INN-Latin]RitodriniumRitodrine [USAN:INN:BAN]UNII-I0Q6O6740J(+)-ritodrineEINECS 247-879-9BRN 2388728(1S,2R)-ritodrineRITODRINE [INN]
名称をさらに表示
(1R,2S)-2-(4-ヒドロキシフェネチルアミノ)-1-(4-ヒドロキシフェニル)-1-プロパノール(αR)-p-ヒドロキシ-α-[(S)-1-[(p-ヒドロキシフェネチル)アミノ]エチル]ベンジルアルコール(αR)-4-ヒドロキシ-α-[(1S)-1-[[2-(4-ヒドロキシフェニル)エチル]アミノ]エチル]ベンゼンメタノールプレマルラボパrel-(R*)-4-ヒドロキシ-α-[(S*)-1-[[2-(4-ヒドロキシフェニル)エチル]アミノ]エチル]ベンゼンメタノール(-)-リトドリン(1R,2S)-1-(4-ヒドロキシフェニル)-2-[(4-ヒドロキシフェネチル)アミノ]-1-プロパノール(-)-リトドリン塩酸塩(1R,2S)-2-[(4-ヒドロキシフェネチル)アミノ]-1-(4-ヒドロキシフェニル)-1-プロパノールrel-(αR*)-4-ヒドロキシ-α-[(1S*)-1-[[2-(4-ヒドロキシフェニル)エチル]アミノ]エチル]ベンゼンメタノールリトドリンrel-(αR*)-4-ヒドロキシ-α-[(S*)-1-[[2-(4-ヒドロキシフェニル)エチル]アミノ]エチル]ベンゼンメタノール(αR)-4-ヒドロキシ-α-[(S)-1-[[2-(4-ヒドロキシフェニル)エチル]アミノ]エチル]ベンゼンメタノール
物性
構造計算による物性
- XLogP
- 2.3
- 極性表面積
- 72.7 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 4
- 回転可能結合数
- 6
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 284
実験および物理化学的性質
SolubilityComplete
Melting Point88-90 °C
物理化学的性質
- 融点
- 88 · 88-90 °C
- 沸点
- 512.3 · 512.3±45.0 °C(Predicted)
- 比重(密度)
- 1.213 · 1.213±0.06 g/cm3(Predicted)
- 酸解離定数(Pka)
- 9 · pKa 9.0 (Uncertain)
化学と産業
薬理情報
Protein Binding~56%
Pharmacodynamics
Beta-2 adrenergic receptors are located at sympathetic neuroeffector junctions of many organs, including uterus. Ritodrine is beta-2 adrenergic agonist. It stimulates beta-2 adrenergic receptor, increases cAMP level and decreases intracellular calcium concentration. The decrease of calcium concentration leads to a relaxation of uterine smooth muscle and, therefore, a decrease in premature uterine contractions.
Mechanism of Action
Ritodrine is beta-2 adrenergic agonist. It binds to beta-2 adrenergic receptors on outer membrane of myometrial cell, activates adenyl cyclase to increase the level of cAMP which decreases intracellular calcium and leads to a decrease of uterine contractions.
Biological Half-Life1.7-2.6 hours
Metabolism/MetabolitesHepatic, by both the mother and fetus
応用分野
用途β受容体刺激剂主要用于治疗早产
説明Ritodrine, 4-hydroxy-α-[1-[(4′-hydroxyphenethyl)amino]ethyl]benzylic alcohol (11.1.19), differs slightly from epinephrine, and in the given example only one hydroxyl group has been added to the aromatic ring of the phenylethylamino region of classic sympathomimetics. The second major difference between the examined series is the replacement of the traditionally terminal iso-propyl or tert-butylamine region with a p-hydroxyphenylethylamine. Finally, the third difference is the presence of a methyl group at the α-atom of the phenylethylamine region of sympathomimetics, which makes it similar to isoetharine.
使用Ritodrine is a selective β2-adrenoreceptor stimulant, predominantly of the urino-genital system. It is used as a tocolytic agent for problems associated with premature miscarriages, and only in specialized medical facilities.
一般的な説明Ritodrine is a selective β2-agonist that wasdeveloped specifically for use as a uterine relaxant. Its uterineinhibitory effects are more sustained than its effects onthe cardiovascular system, which are minimal comparedwith those caused by nonselective β-agonists. The cardiovasculareffects usually associated with its administrationare mild tachycardia and slight diastolic pressure decrease.Usually, it is administered initially by intravenous infusionto stop premature labor and subsequently it may be givenorally.
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