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1951-25-3

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1951-25-3 Usage

Description

From the chemical point of view, amiodarone is completely different from other antiarrhythmics. It has two iodide atoms and a diethylaminoethanol group as substituents in the benzoyl part, and overall it is very similar to the structure of thyroxin-like molecules.

Originator

Cordarone,Labaz,France,1971

Uses

Different sources of media describe the Uses of 1951-25-3 differently. You can refer to the following data:
1. antibacterial
2. Amiodarone is a non-selective ion channel blocker. Antiarrhythmic (class III).

Definition

ChEBI: A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.

Indications

Clinical use of amiodarone is limited because of its high toxicity, which consists of cardiac block, bradycardia, cardiac insufficiency, damaged thyroid gland function, neuropathology, and increased sensitivity to light, all of which significantly limit use of amiodarona, and it is only used in therapy for extremely serious tachyarrhythmias such as reoccurring ventricular fibrillation and hemodynamic unstable ventricular tachycardia, and only under supervision of a physician in a clinical situation.

Manufacturing Process

135 grams of 2-n-butyl-3-(3,5-diiodo-4-hydroxybenzoyl)benzofuran dissolved in 600 cc of ethyl carbonate were treated with 5.7 grams of sodium in the form of sodium methoxide in methanol. Then, β-diethylaminoethyl chloride which had been obtained from 51.6 grams of the hydrochloride in ethyl carbonate was introduced into a suspension of the sodium salt. The mixture was heated to a temperature of approximately 90°C which was maintained for approximately 2 hours. The mixture was cooled and allowed to stand overnight during which time the sodium chloride settled down. The toluene solution containing diethylaminoethyl ether was extracted with increasingly diluted aqueous hydrochloric acid solutions while stirring. Extraction was continued until the alkalized solution produced no further precipitate. The combined aqueous solutions were washed with ether and then made strongly alkaline with aqueous sodium hydroxide. Extraction with ether was carried out three times. The organic layers were washed with water and then dried over anhydrous potassium carbonate. In order to produce the hydrochloride, the carbonate was filtered off and then the hydrochloride was precipitated from the ether solution with an ethereal hydrochloric acid solution. After the solution had been allowed to stand for a few hours, decantation was carried out and the syrupy hydrochloride residue was taken up in 500 cc of boiling acetone. The salt crystallized out by cooling. The substance was allowed to stand overnight at 0°C, and centrifuged, washed with ethyl acetate and then with ether and dried. 130 grams of 2-n-butyl-3- (3,5-diiodo-4-β-N-diethylaminoethoxybenzoyl)benzofuran hydrochloride in the form of a crystalline powder which melts at 156°C were obtained.

Brand name

Cordarone (Wyeth-Ayerst).

Therapeutic Function

Coronary vasodilator

Biological Functions

Amiodarone (Cordarone) is an iodine-containing benzofuran derivative identified as a class III agent because it predominantly prolongs action potentials. Amiodarone also blocks sodium and calcium channels and is a noncompetitive β-receptor blocker.Amiodarone is effective for the treatment of most arrhythmias. Toxicity associated with amiodarone has led the U. S. Food and Drug Administration (FDA) to recommend that it be reserved for use in patients with life-threatening arrhythmias.

General Description

Amiodarone, 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone (Cordarone),was introduced as an antianginal agent. It has very pronouncedclass III action and is especially effective in maintainingsinus rhythm in patients who have been treated bydirect current shock for atrial fibrillation. Like class IIIantiarrhythmic drugs, amiodarone lengthens the effective refractoryperiod by prolonging the action potential duration inall myocardial tissues. Amiodarone is eliminated very slowlyfrom the body, with a half-life of about 25 to 30 days after oraldoses. Although the drug has a broad spectrum of antiarrhythmicactivity, its main limitation is a slow onset of action.Drug action may not be initiated for several days, and thepeak effect may not be obtained for several weeks.

Mechanism of action

Amiodarone’s antiarrhythmic action is connected to its ability to block K, Na, and Ca2 channels while noncompetitively blocking α- and β-adrenergic receptors of the heart, thus prolonging the action potential and effective refractive period of atrial cells, atrioventricular junctions, and ventricles of the heart, which is accompanied by decreased automatism of sinus node and slowing of atrioventricular conductivity.

Clinical Use

Amiodarone has adverse effects involving many differentorgan systems. It also inhibits metabolism of drugscleared by oxidative microsomal enzymes. It contains iodinein its molecular structure and, as a result, has an effecton thyroid hormones. Hypothyroidism occurs in up to 11%of patients receiving amiodarone. The principal effect isthe inhibition of peripheral conversion of T4 to T3. Serumreverse T3 (rT3) is increased as a function of the dose as wellas the length of amiodarone therapy. As a result, rT3 levelshave been used as a guide for judging adequacy of amiodaronetherapy and predicting toxicity.

Side effects

Amiodarone’s most significant adverse effects include hepatitis, exacerbation of arrhythmias, worsening of congestive heart failure, thyroid dysfunction, and pulmonary fibrosis. Pulmonary fibrosis is frequently fatal and may not be reversed with discontinuation of the drug. Interestingly, despite significant prolongation of the QT interval, the risk of torsades de pointes is relatively low. Patients with underlying sinus node dysfunction tend to have significant worsening of nodal function, frequently requiring pacemaker implantation. Corneal microdeposits develop in most adults receiving amiodarone. As many as 10% of patients complain of halos or blurred vision. The corneal microdeposits are reversible with stoppage of the drug. Photosensitization occurs in 10% of patients. With continued treatment, the skin assumes a blue-gray coloration. The risk is increased in patients of fair complexion. The discoloration of the skin regresses slowly, if at all, after discontinuation of amiodarone. Amiodarone inhibits the peripheral and possibly intrapituitary conversion of thyroxine (T4) to triiodothyronine (T3) by inhibiting 5 -deiodination. The serum concentration of T4 is increased by a decrease in its clearance, and thyroid synthesis is increased by a reduced suppression of the pituitary thyrotropin T3. The concentration of T3 in the serum decreases, and reverse T3 appears in increased amounts.Despite these changes, most patients appear to be maintained in an euthyroid state. Manifestations of both hypothyroidism and hyperthyroidism have been reported. Tremors of the hands and sleep disturbances in the form of vivid dreams, nightmares, and insomnia have been reported in association with the use of amiodarone. Ataxia, staggering, and impaired walking have been noted. Peripheral sensory and motor neuropathy or severe proximal muscle weakness develops infrequently. Both neuropathic and myopathic changes are observed on biopsy. Neurological symptoms resolve or improve within several weeks of dosage reduction.

Safety Profile

Poison by intravenous and intraperitoneal routes. Human systemic effects by ingestion: photosensitivity of the skin. A flammable liquid. When heated to decomposition it emits very toxic fumes of Iand NO,. A coronary vasoddator

Synthesis

Amiodarone, 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone (18.1.21), is synthesized in the following manner. Benzofuran is acylated by butyric acid anhydride in the presence of phosphorous acid, forming 2-butyroylbenzfuran (18.1.16). Reduction of the carbonyl group in a Wolff–Kizhner reaction using hydrazine hydrate gives 2-butylbenzofurane (18.1.17). This is acylated with 4-methoxybenzoic acid chloride, giving 2-butyl-3-(4-methoxybenzoyl)benzofuran (18.1.18), which undergoes demethylation by pyridine hydrochloride, forming 2-butyl-3-(4-hydroxy-benzoyl)-benzofuran (18.1.19). The resulting product is iodized in the presence of potassium iodide, forming 2-butyl-3-benzofuranyl-4-(2-hydroxy-3,5-diiodophenyl) ketone (18.1.20), which is reacted further with 2-diethylaminoethylchoride, giving desired amiodarone (18.1.21) .

Drug interactions

Amiodarone increases the hypoprothrombinemic response to warfarin (an oral anticoagulant) by reducing its metabolism. Patients receiving digoxin may undergo an increase in serum digoxin concentrations when amiodarone is added to the treatment regimen. Amiodarone interferes with hepatic and renal elimination of flecainide, phenytoin, and quinidine.

Precautions

Amiodarone is contraindicated in patients with sick sinus syndrome and may cause severe bradycardia and secondand third-degree atrioventricular block. Amiodarone crosses the placenta and will affect the fetus, as evidenced by bradycardia and thyroid abnormalities. The drug is secreted in breast milk.

Check Digit Verification of cas no

The CAS Registry Mumber 1951-25-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,5 and 1 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1951-25:
(6*1)+(5*9)+(4*5)+(3*1)+(2*2)+(1*5)=83
83 % 10 = 3
So 1951-25-3 is a valid CAS Registry Number.
InChI:InChI=1/C25H29I2NO3.ClH/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3;/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3;1H

1951-25-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name amiodarone

1.2 Other means of identification

Product number -
Other names (2-Butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)methanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1951-25-3 SDS

1951-25-3Synthetic route

2-chloro-N,N-diethylethylamine hydrochloride
869-24-9

2-chloro-N,N-diethylethylamine hydrochloride

2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran
1951-26-4

2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran

Amiodarone
1951-25-3

Amiodarone

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 12h;91%
2-n-butyl 3-(4-methoxy benzoyl)-benzofuran
83790-87-8

2-n-butyl 3-(4-methoxy benzoyl)-benzofuran

Amiodarone
1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: boron tribromide / dichloromethane
2: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
3: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
1-(4-methoxyphenyl)-1,3-heptanedione
1137261-90-5

1-(4-methoxyphenyl)-1,3-heptanedione

Amiodarone
1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
2: boron tribromide / dichloromethane
3: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
4: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Amiodarone
1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydride / mineral oil; tetrahydrofuran / Reflux
2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
3: boron tribromide / dichloromethane
4: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
5: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
methyl valerate
624-24-8

methyl valerate

Amiodarone
1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydride / mineral oil; tetrahydrofuran / Reflux
2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
3: boron tribromide / dichloromethane
4: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
5: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
amiodarone decahydrochloride

amiodarone decahydrochloride

Amiodarone
1951-25-3

Amiodarone

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water for 5h;
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

Amiodarone
1951-25-3

Amiodarone

2,3,7,8-tetrafluorothianthrene-S-oxide

2,3,7,8-tetrafluorothianthrene-S-oxide

C37H32F4I2NO3S2(1+)*2BF4(1-)*H(1+)

C37H32F4I2NO3S2(1+)*2BF4(1-)*H(1+)

Conditions
ConditionsYield
With 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;92%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

Amiodarone
1951-25-3

Amiodarone

2,3,7,8-tetrafluorothianthrene-S-oxide

2,3,7,8-tetrafluorothianthrene-S-oxide

C37H32F4I2NO3S2(1+)*BF4(1-)

C37H32F4I2NO3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; Amiodarone; 2,3,7,8-tetrafluorothianthrene-S-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube;
Stage #2: sodium tetrafluoroborate In dichloromethane; water
92%
Amiodarone
1951-25-3

Amiodarone

di-tert-butyl chloromethyl phosphate
229625-50-7

di-tert-butyl chloromethyl phosphate

di-tert-butyl N-(phosphonooxymethyl)amiodaronium chloride

di-tert-butyl N-(phosphonooxymethyl)amiodaronium chloride

Conditions
ConditionsYield
With 1,2,2,6,6-pentamethylpiperidine; sodium iodide In acetonitrile at 40℃; for 24h;48%
Amiodarone
1951-25-3

Amiodarone

desethylamiodarone

desethylamiodarone

Conditions
ConditionsYield
in vivo metabolism (human);
With carbonochloridic acid 1-chloro-ethyl ester In toluene for 16h; Heating;
With human liver microsomes Kinetics; Concentration; Reagent/catalyst;
Amiodarone
1951-25-3

Amiodarone

A

desethylamiodarone

desethylamiodarone

B

Didesethyl-deiodo-amiodarone

Didesethyl-deiodo-amiodarone

C

Didesethylamiodarone

Didesethylamiodarone

D

Deiodoamiodarone

Deiodoamiodarone

Conditions
ConditionsYield
With ammonium hydroxide; ammonium formate In acetonitrile Reactivity; Electrochemical reaction;
Amiodarone
1951-25-3

Amiodarone

A

desethylamiodarone

desethylamiodarone

B

Didesethylamiodarone

Didesethylamiodarone

C

Deiodoamiodarone

Deiodoamiodarone

Conditions
ConditionsYield
With ammonium hydroxide; ammonium formate In acetonitrile Reactivity; Electrochemical reaction;
Amiodarone
1951-25-3

Amiodarone

A

desethylamiodarone

desethylamiodarone

B

Deiodoamiodarone

Deiodoamiodarone

Conditions
ConditionsYield
With ammonium hydroxide; ammonium formate In acetonitrile Reactivity; Electrochemical reaction;
Amiodarone
1951-25-3

Amiodarone

(+/-)-{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}[2-(3-hydroxybutyl)benzofuran-3-yl]methanone

(+/-)-{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}[2-(3-hydroxybutyl)benzofuran-3-yl]methanone

Conditions
ConditionsYield
With CYP2J2 recombinant enzyme; NADPH In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Enzymatic reaction;
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

Amiodarone
1951-25-3

Amiodarone

2,3,7,8-tetrafluorothianthrene
1225203-47-3

2,3,7,8-tetrafluorothianthrene

C37H32F4I2NO3S2(1+)*BF4(1-)

C37H32F4I2NO3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; Amiodarone; 2,3,7,8-tetrafluorothianthrene With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h;
Stage #2: sodium tetrafluoroborate With sodium hydrogencarbonate In dichloromethane; water
914 mg
Amiodarone
1951-25-3

Amiodarone

chloroamiodarone trifluoroacetic acid

chloroamiodarone trifluoroacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic anhydride / acetonitrile / 3 h / 0 - 25 °C / Sealed tube
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate; lithium chloride / acetonitrile / 8 h / 22 °C / Irradiation; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: trifluoroacetic anhydride / acetonitrile / 3 h / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate; lithium chloride / acetonitrile / 8 h / 22 °C / Irradiation; Inert atmosphere
View Scheme

1951-25-3Relevant articles and documents

REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION

-

Page/Page column 37; 38, (2020/06/01)

Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

Methods for predicting the response to statins

-

, (2011/10/13)

The invention provides methods for optimizing therapeutic efficacy for treating hypercholesterolemia in a subject having a cardiovascular disease (CVD), comprising (a) determining subject characteristics that affect the likelihood of reaching a goal level of low density lipoprotein (LDL); and (b) obtaining success probabilities of a variety of statin treatments for reaching said goal level of LDL using said subject characteristics and a multivariate model; and (c) administrating the optimal statin treatment with the highest success probability of step (b) to said subject thereby optimizing therapeutic efficacy for treating hypercholesterolemia in said subject.

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