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Flecainide

Product Name
Flecainide
CAS No.
54143-55-4
Chemical Name
Flecainide
Synonyms
Flecaine;Flecanide;FLECAINIDE;Flecainide-d4;rac Flecainide;FLECAINTDE BASE;Flecainide USP/EP/BP;(±)-Flecainide solution;N-(Piperidin-2-ylmethyl);-2,5-bis(2,2,2-trifluoroethoxy)
CBNumber
CB0663265
Molecular Formula
C17H20F6N2O3
Formula Weight
414.34
MOL File
54143-55-4.mol
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Flecainide Property

Melting point:
105-1070C
Boiling point:
434.9±45.0 °C(Predicted)
Density 
1.286±0.06 g/cm3(Predicted)
Flash point:
9℃
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
pKa 9.3 (Uncertain)
color 
White to Off-White
BCS Class
1 or 2?
CAS DataBase Reference
54143-55-4(CAS DataBase Reference)
NIST Chemistry Reference
Benzamide, n-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-(54143-55-4)
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Safety

Hazard Codes 
F,T
Risk Statements 
11-23/24/25-39/23/24/25
Safety Statements 
7-16-36/37-45
RIDADR 
3249
WGK Germany 
1
HazardClass 
6.1(b)
PackingGroup 
III
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H370Causes damage to organs

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P311Call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F-017
Product name
(±)-Flecainide solution
Purity
1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$72
Updated
2024/03/01
TRC
Product number
F390000
Product name
Flecainide
Packaging
100mg
Price
$160
Updated
2021/12/16
Usbiological
Product number
450098
Product name
Flecainide-d4
Packaging
1mg
Price
$375
Updated
2021/12/16
TRC
Product number
F390000
Product name
Flecainide
Packaging
1g
Price
$1295
Updated
2021/12/16
Matrix Scientific
Product number
099655
Product name
N-(Piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
Purity
95+%
Packaging
1g
Price
$588
Updated
2021/12/16
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Flecainide Chemical Properties,Usage,Production

Description

From the chemical point, flecainide is an analog of procainamide, to which a 2.2.2-trifluoroethoxyl group was added at C2 and C3 of the benzene ring, and a diaminoethyl side chain is ended in the piperidine ring.

Chemical Properties

White Crystalline Powder

Originator

Tambocor,Kettelhack Riker,W. Germany,1982

Uses

Flecainide, as with other local anesthetics, is used for naturally occurring ventricular arrhythmia.

Uses

Flecainide is an antiarrhythmic (class IC).

Definition

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with the primary amino group of piperidin-2-ylmethylamine. An antiarrhythmic agent used (in the form of its acetate salt) to prev nt and treat tachyarrhythmia (abnormal fast rhythm of the heart).

Manufacturing Process

Under a nitrogen atmosphere 2-aminomethylpiperidine (0.249 mol, 28.4 g) is treated dropwise over 25 minutes with 2,2,2-trifluoroethyl 2,5-bis(2,2,2- trifluoroethoxy)benzoate (0.0249 mol, 10.0 g). After 3 hours 50 ml of benzene is added to the thick mixture and stirred for about 40 hours at 45°C. The mixture is then concentrated under vacuum with heating to remove the volatile components. The residue solidifies after cooling, is steam distilled for further purification and is separated by filtration and extracted into dichloromethane. The dichloromethane solution is washed with saturated sodium chloride solution, and the organic layer is dried over anhydrous magnesium sulfate. The magnesium sulfate is removed by filtration and 4 ml of 8.4 N hydrogen chloride in isopropanol is added to the dichloromethane solution with stirring.After 2 hours the mixture is cooled to about 0°C and the crude product is collected by filtration, washed with diethyl ether and dried in a vacuum oven. After treatment with decolorizing charcoal and recrystallization from an equivolume mixture of isopropanol and methanol, the product, 2,5-bis(2,2,2- trifluoroethoxy)-N-(2-piperidylmethyl)benzamide hydrochloride has a MP of 228°C to 229°C.

brand name

Tambocor (3M Pharmaceuticals).

Therapeutic Function

Antiarrhythmic

World Health Organization (WHO)

The membrane-stabilizing antiarrhythmic agent flecainide was introduced into medicine in 1982. The decision to delete the indications for patients with asymptomatic and less severe symptomatic ventricular arrhythmias was taken on the basis of the results of a trial (CAST study) that showed a two-fold increase in deaths in post-myocardiac patients taking flecainide compared with the placebo group.

Hazard

Human systemic effects.

Mechanism of action

Flecainide is effective if administered intravenously and orally; its effect is long-lasting. The drug combines the modes of action of class I a and I b drugs with those of class III.

Clinical Use

Flecainide (Tambocor) is a fluorinated aromatic hydrocarbon examined initially for its local anesthetic action and subsequently found to have antiarrhythmic effects. Flecainide inhibits the sodium channel, leading to conduction slowing in all parts of the heart, but most notably in the His-Purkinje system and ventricular myocardium. It has relatively minor effects on repolarization. Flecainide also inhibits abnormal automaticity.
Flecainide is effective in treating most types of atrial arrhythmias. It is also used for life-threatening ventricular arrhythmias. However, flecainide should be used with extreme caution in any patient with structural heart disease. Flecainide crosses the placenta, with fetal levels reaching approximately 70% of maternal levels. In many centers, it is the second-line drug after digoxin for therapy of fetal arrhythmias. Because of the high incidence of proarrhythmia, initiation of therapy or significant increases in dosing should be performed only on inpatients.

Side effects

Most adverse effects occur within a few days of initial drug administration. The most frequently reported effects are dizziness, light-headedness, faintness, unsteadiness, visual disturbances, blurred vision (e.g., spots before the eyes, difficulty in focusing), nausea, headache, and dyspnea.
Worsening of heart failure and prolongation of the PR and QRS intervals are likely to occur with flecainide, and an increased risk of proarrhythmia has been reported.

Synthesis

Flecainide, N-(2-piperidylmethyl)-2,5-bis-(2,2,2-trifluoroethoxy)benzamide (18.1.14), is synthesized from 2,5-dihydroxybenzoic acid. Reacting this with trifluoroethylfluoromethylsulfonate gives 2.2.2-trifluoroethoxylation of all three hydroxyl groups, to produce 2,2,2-trifluoroethyl ester of 2,5-bis-(2,2,2-trifluoroethoxy)benzoic acid (18.1.12). Reacting this with 2-aminomethylpiridine gives the corresponding amide (18.1.13), which upon reduction of the pyridine ring with hydrogen gives flecainide (18.1.14).

Drug interactions

In patients whose condition has been stabilized by flecainide, the addition of cimetidine may reduce the rate of flecainide’s hepatic metabolism, increasing the potential for toxicity. Flecainide may increase digoxin concentrations on concurrent administration.

Precautions

Flecainide is contraindicated in patients with preexisting second- or third-degree heart block or with bundle branch block unless a pacemaker is present to maintain ventricular rhythm. It should not be used in patients with cardiogenic shock.

Flecainide Preparation Products And Raw materials

Raw materials

Preparation Products

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Flecainide Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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76
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Sphinx Scientific Laboratory (Tianjin) Co., Ltd.
Tel
022-66211289-843 13672102692
Fax
QQ:2377893365
Email
contact@sphinxpharm.com
Country
China
ProdList
361
Advantage
62
T&W GROUP
Tel
021-61551611 13296011611
Fax
+86 21-50676805
Email
contact@trustwe.com
Country
China
ProdList
9895
Advantage
58
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
0755-83725681-603
Fax
+86 755 28094224
Country
China
ProdList
4496
Advantage
50
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
Shanghai Meishui Chemical Technology Co., Ltd
Tel
021-60549325 18616193163
Fax
021-33250306
Country
China
ProdList
4526
Advantage
56
Finetech Industry Limited
Tel
027-87465837 19945049750
Fax
027-8777-2287
Email
sales@finetechnology-ind.com
Country
China
ProdList
9649
Advantage
58
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View Lastest Price from Flecainide manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Flecainide 54143-55-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11
Career Henan Chemical Co
Product
Flecainide 54143-55-4
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2020-02-17

54143-55-4, FlecainideRelated Search:


  • N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
  • FLECAINTDE BASE
  • Benzamide, N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-
  • Flecaine
  • rac Flecainide
  • Flecainide-d4
  • N-(Piperidin-2-ylMethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzaMide
  • -2,5-bis(2,2,2-trifluoroethoxy)
  • N-(Piperidin-2-ylmethyl)
  • n-(2-piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
  • (±)-Flecainide solution
  • FLECAINIDE
  • Flecanide
  • Flecainide USP/EP/BP
  • 1-Piperazinecarboxylicacid,4-(3-bromopropyl)-,1,5-dimethylethylester
  • 54143-55-4
  • 35480-31-5
  • C17H20F6N2O3
  • C17H2OF6N2O3
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals