Sotalol

HCID 5253CAS 3930-20-9

기본 정보

표준 SMILES
CC(C)NCC(O)c1ccc(NS(C)(=O)=O)cc1
InChIKey
ZBMZVLHSJCTVON-UHFFFAOYSA-N
분자식
C12H20N2O3S
평균 분자량
272.37 g/mol
단동위원소 질량
272.1194635

개요

Sotalol is a sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias. It has a role as a beta-adrenergic antagonist, a xenobiotic, an anti-arrhythmia drug and an environmental contaminant. It is a member of ethanolamines, a sulfonamide, a secondary alcohol and a secondary amino compound. It is a conjugate base of a sotalol(1+).

이름 및 식별자

우선 이름
Sotalol
IUPAC
N-[4-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide
영어명
Sotalol
분자식
C12H20N2O3S
분자량
272.36

이름 및 동의어

sotalol3930-20-9beta-CardoneDL-SotalolSotalolumDarob miteDTXSID00235894'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulfonanilideMethanesulfonanilide, 4'-(1-hydroxy-2-(isopropylamino)ethyl)-C07AA07A6D97U294IN-(4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl)methanesulfonamide
이름 더 보기
SORBITOLSotalol (base and/or unspecified salts)SotololBetacotdoneAURORA KA-855Sotalol USP/EP/BPSotalol Intermediate
Methanesulfonamide, N-(4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)phenyl)-DTXCID303589CHEBI:63622Methanesulfonamide, N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]phenyl]-SotaloloN-(4-(1-hydroxy-2-((propan-2-yl)amino)ethyl)phenyl)methanesulfonamideRefChem:56607MJ1999

데이터베이스 식별자

CAS
3930-20-9
PubChem CID
5253
DTXSID
DTXSID0023589
ChEMBL
CHEMBL471
ChEBI
CHEBI:63622
UNII
A6D97U294I
EC Number
977-025-7
Nikkaji
J10.583J

물성

구조 계산 물성

XLogP
0.2
극성 표면적
86.8 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
5
회전 가능 결합 수
6
무거운 원자 수
18

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals

Pharmaceuticals -> Used in Switzerland

LogP · 2건

1.1

0.53

Solubility7.82e-01 g/L
Human Drugs · 2건

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics

Pharmaceuticals

Melting Point206.5 - 207 °C
Physical DescriptionSolid

물리화학적 성질

녹는점
206.5 · 206.5-207 °C
끓는 점
443.3 · 443.3±55.0 °C(Predicted)
밀도
1.298 g/cm3 · 1.298 g/cm3
저장 조건
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
용해도
클로로포름(약간 용해됨, 가열), 메탄올(약간 용해됨, 초음파 처리)
물리적 상태
고체

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H315 (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.

유해성 정보

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

독성 정보

Hepatotoxicity · 1건

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.

Adverse Effects · 1건

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.

Toxicity Summary · 1건

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 · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

sotalol

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

risk_code
36/37/38
hazard_code
Xi
safety_code
26-36

화학 및 산업

약리 정보

ATC Code · 3건

C07AA07

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding0%.
Pharmacodynamics · 1건

Sotalol is a competitive inhibitor of the rapid potassium channel. This inhibition lengthens the duration of action potentials and the refractory period in the atria and ventricles. The inhibition of rapid potassium channels is increases as heart rate decreases, which is why adverse effects like torsades de points is more likely to be seen at lower heart rates. L-sotalol also has beta adrenergic receptor blocking activity seen above plasma concentrations of 800ng/L. The beta blocking ability of sotalol further prolongs action potentials. D-sotalol does not have beta blocking activity but also reduces a patient's heart rate while standing or exercising. These actions combine to produce a negative inotropic effect that reduces the strength of contractility of muscle cells in the heart. Extension of the QT interval is also adversely associated with the induction of arrhythmia in patients. Hyperglycemia is a greater risk for non insulin dependant diabetics than insulin dependant diabetics. Beta blockers inhibit insulin secretion which may cause hyperglycemia in type II diabetes mellitus. The risk of hypoglycemia is higher in insulin dependant diabetes than non insulin dependant diabetics. Beta blockers decrease secretion of insulin, which may mask hypoglycemia in an insulin dependant patient. Beta blockers also increase glucose uptake into cells which may prolong or potentiate hypoglycemia. Further information regarding adverse reactions can be found here.

Mechanism of Action · 1건

Sotalol inhibits beta-1 adrenoceptors in the myocardium as well as rapid potassium channels to slow repolarization, lengthen the QT interval, and slow and shorten conduction of action potentials through the atria. The action of sotalol on beta adrenergic receptors lengthens the sinus node cycle, conduction time through the atrioventricular node, refractory period, and duration of action potentials.

Biological Half-Life · 1건

The terminal elimination half life is 10-20 hours in healthy patients. In patients with a creatinine clearance >80mL/min, the half life is 17.5±0.97h. In patients with a creatinine clearance 30-80mL/min, the half life is 22.7±6.4h. In patients with a creatinine clearance 10-30mL/min, the half life is 64±27.2h. In patients with a creatinine clearance <10mL/min, the half life is 97.9±57.3h.

Metabolism/MetabolitesSotalol is not metabolized.

용도 및 제조

UsesUse (kg) in Switzerland (2009): >250
Use ClassificationPharmaceuticals
응용 분야 · 1건

일반 설명Sotalol, 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.

상·하류 제품 정보

상류 원료

공급사24 곳

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
Anhui Zhongda Biotechnology Co., Ltd+86-15689548120 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Anhui Zhongda Biotechnology Co., Ltd+86-19956560829 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
추가 설명 · 1건

정의ChEBI: A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is sustituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and ardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.

관련 반응

5건

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