基本情報
- CAS
17598-65-1- 標準SMILES
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3C[C@@H](O)[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)C[C@H](O)[C@@H]1O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](C)O2)[C@@H](C)O1- InChIKey
OBATZBGFDSVCJD-LALPQLPRSA-N- 分子式
- C47H74O19
- 平均分子量
- 943.1 g/mol
- 単同位体質量
- 942.48243013
概要
Deslanoside is a cardenolide glycoside that is lanatoside C with the acetoxy group replaced by a hydroxy group. It has a role as a metabolite, an anti-arrhythmia drug, a cardiotonic drug and an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is a 12beta-hydroxy steroid, a 14beta-hydroxy steroid, a cardenolide glycoside and a tetrasaccharide derivative.
名称と識別子
- 優先名称
- Deslanoside
- IUPAC
- 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- 現地名
- デスラノシド
- 英語名
- Deslanoside
- 分子式
- C47H74O19
- 分子量
- 943.08
名称と別名
deslanoside17598-65-1Deacetyllanatoside CDesacetyllanatoside CCedilanid-DDeslanosidoDeslanosidumglucodigoxinDeacetylanatoside CDTXSID1022897Desacetyl-Lanatoside CYGY317RK75
名称をさらに表示
デスラノシドデアセチルラナトシドCデスラノシド (JP17)デスラノシンデスラナトシドCデスラノシドCセジラニドD3β-[[4-O-[4-O-(4-O-β-D-グルコピラノシル-2,6-ジデオキシ-β-D-ribo-ヘキソピラノシル)-2,6-ジデオキシ-β-D-ribo-ヘキソピラノシル]-2,6-ジデオキシ-β-D-ribo-ヘキソピラノシル]オキシ]-12β,14-ジヒドロキシ-5β,14β-カルダ-20(22)-エノリドデスラノシト3β-[[4-O-[4-O-[4-O-(β-D-グルコピラノシル)-2,6-ジデオキシ-β-D-ribo-ヘキソピラノシル]-2,6-ジデオキシ-β-D-ribo-ヘキソピラノシル]-2,6-ジデオキシ-β-D-ribo-ヘキソピラノシル]オキシ]-12β,14-ジヒドロキシ-5β-カルダ-20(22)-エノリド4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aS)-3a,11-ジヒドロキシ-7-{[(2R,4S,5S,6R)-4-ヒドロキシ-5-{[(2S,4S,5S,6R)-4-ヒドロキシ-5-{[(2S,4S,5S,6R)-4-ヒドロキシ-6-メチル-5-{[(2S,3R,4S,5S,6R)-3,4,5-トリヒドロキシ-6-(ヒドロキシメチル)オキサン-2-イル]オキシ}オキサン-2-イル]オキシ}-6-メチルオキサン-2-イル]オキシ}-6-メチルオキサン-2-イル]オキシ}-9a,11a-ジメチル-ヘキサデカヒドロ-1H-シクロペンタ[a]フェナントレン-1-イル]-2,5-ジヒドロフラン-2-オン
物性
構造計算による物性
- XLogP
- -0.3
- 極性表面積
- 282 Ų
- 水素結合供与体数
- 9
- 水素結合受容体数
- 19
- 回転可能結合数
- 10
- 重原子数
- 66
- 形式電荷
- 0
- 複雑度
- 1,760
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.2
Solubility4.68e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
物理化学的性質
- 融点
- 220 · 220-235°C
- 比旋光度
- 20 · D20 +12° (c = 1.084 in 75% alc)
- 沸点
- 732.1 °C · 732.1°C (rough estimate)
- 比重(密度)
- 1.1255 · 1.1255 (rough estimate)
- 屈折率
- 1.65 · 1.6500 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 1 mg/ml; · DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml
- 外見
- Solid
- 酸解離定数(Pka)
- 12.89 · 12.89±0.70(Predicted)
- 色
- White to off-white
- 主な用途
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
Danger
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P270, P271, P284, P301+P316, P304+P340, P316, P319, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Other Safety Information
IMAP assessments - Card-20(22)-enolide, 3-[(O-.beta.-D-glucopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-, (3.beta.,5.beta.,12.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (50%)
安全データ
- wgk
- WGK 3
- ridadr
- 2811
- 毒性
- cat,LD50,intravenous,230ug/kg (0.23mg/kg),"Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 190, 1963.
- hs_code
- 2938900000
- risk_code
- 23/25-33
- safety_code
- 1-22-45
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 3 OralSTOT RE 2
- ストレージクラス
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding20%
PharmacodynamicsDeslanoside is a cardiac glycoside used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.
Mechanism of Action
Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Deslanoside also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
Biological Half-Life36 hours
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Absorption, Distribution and ExcretionLittle absorption from the gastrointestinal tract (40%).
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