ソタロール

d-ソタロール · (+)-ソタロール · N-[4-[(S)-1-ヒドロキシ-2-[(1-メチルエチル)アミノ]エチル]フェニル]メタンスルホンアミド · N-[4-[1-ヒドロキシ-2-(イソプロピルアミノ)エチル]フェニル]メタンスルホンアミド · (R)-ソタロール · (αS)-4-[(メチルスルホニル)アミノ]-α-[(イソプロピルアミノ)メチル]ベンゼンメタノール · (-)-ソタロール · (S)-ソタロール

https://huagongshe.com/ja/chemical/5253

識別子と物理属性

CAS No.	3930-20-9
分子式	C12H20N2O3S
平均分子量	272.37 g/mol
単同位体質量	272.1194635 g/mol
SMILES	CC(C)NCC(O)c1ccc(NS(C)(=O)=O)cc1
InChIKey	ZBMZVLHSJCTVON-UHFFFAOYSA-N
PubChem CID	5253
ChEMBL	CHEMBL471
ChEBI	CHEBI:63622
EC No.	977-025-7
DTXSID	DTXSID0023589
現地名	ソタロール

化学・物理的性質

XLogP	0.2
極性表面積	86.8
水素結合供与体数	3
水素結合受容体数	5
回転可能結合数	6
重原子数	18
形式電荷	0
複雑度	330
医薬品	PharmaceuticalsPharmaceuticals -> Used in Switzerland
LogP（分配係数）	1.10.53
溶解度	7.82e-01 g/Lクロロホルム（わずかに、加熱）、メタノール（わずかに、超音波処理）
Human Drugs	Breast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsPharmaceuticals
融点	206.5 - 207 °C206.5-207 °C
Physical Description	Solid
Dissociation Constants	9.76
Collision Cross Section	167 Å² [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]
沸点	443.3±55.0 °C(Predicted)
密度	1.298 g/cm3
貯蔵条件	Hygroscopic, -20°C Freezer, Under inert atmosphere
外観・状態	個体
pKa（酸解離定数）	pK1 8.2, pK2 9.8(at 25℃)
色	淡黄色～淡黄色
BCS Class	1
安定性	Hygroscopic
InChI	InChI=1S/C12H20N2O3S/c1-9(2)13-8-12(15)10-4-6-11(7-5-10)14-18(3,16)17/h4-7,9,12-15H,8H2,1-3H3
InChIKey	ZBMZVLHSJCTVON-UHFFFAOYSA-N
SMILES	CS(NC1=CC=C(C(O)CNC(C)C)C=C1)(=O)=O
CAS データベース	3930-20-9(CAS DataBase Reference)
NISTの化学物質情報	Methanesulfonanilide, 4'-(1-hydroxy-2-(isopropylamino)ethyl)-(3930-20-9)
EPAの化学物質情報	Methanesulfonamide, N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]phenyl]- (3930-20-9)

安全性と法規制

GHS 分類	DangerH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P260, P263, P264, P264+P265, P270, P280, P302+P352, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard Classes and Categories	Skin Irrit. 2 (100%)
Hepatotoxicity	Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on sotalol and are usually transient and asymptomatic, resolving even with continuation of therapy. Sotalol has been linked to a single case of clinically apparent liver injury, with onset of an acute hepatitis-like syndrome with prolonged jaundice 12 weeks after sotalol was initiated. The injury improved but did not resolve with discontinuation of sotalol. In large case series of drug induced liver disease and acute liver failure, sotalol has not been listed as a cause. Other beta-blockers have been linked to rare instances of acute clinically apparent liver injury with a latency to onset ranging from 4 to 24 weeks, a hepatocellular pattern of serum enzyme elevations and a mild, self-limiting course without evidence of hypersensitivity or autoimmune reactions.
有害作用	Sotalol's adverse effect profile is inherent in the mechanisms of action as both a potassium channel blocker and a non-cardioselective β-blocker. The potassium channel blockade, primarily in phase 3 of the cardiac action potential, prolongs the QTc. Thus, the electrocardiogram (ECG) must be monitored upon initiating sotalol or adding other QTc-prolonging medications. Prolongation of the QT interval occurs in 1% to 2% of cases, which could lead to torsades de pointes or new ventricular tachycardia/ventricular fibrillation.
毒性の概要	Sotalol toxicity is inherent due to the mechanism of action as both a potassium channel blocker and a non-cardioselective β-blocker and mirrors the adverse effect profile. The most obvious and potentially problematic sign of toxicity is concentration-related QTc prolongation. If QTc is over 500 ms during initiation, the sotalol dose should be reduced or discontinued. If QTc exceeds 520 ms during the maintenance phase of dosing, the clinician should either reduce the dose or discontinue sotalol.
Drug Induced Liver Injury	Drug-Induced Liver Injury Severity and Toxicity (DILIst)sotalol

用途

一般的な説明

Sotalol, 4＇[1-hydroxy-2-(isopropylamino)ethyl]methylsulfonanilide (Betapace), is a relatively new antiarrhythmicdrug, characterized most often as a class IIIagent, and although it has effects that are related to the classII agents, it is not therapeutically considered a class II antiarrhythmic.It contains a chiral center and is marketed as theracemic mixture. Because of its enantiomers, its mechanismof action spans two of the antiarrhythmic drug classes. Thel(-) enantiomer has both β-blocking (class II) and potassiumchannel-blocking (class III) activities. The d(+) enantiomerhas class III properties similar to those of the (-) isomer,but its affinity for the -adrenergic receptor is 30 to 60 timeslower.