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Your Location：Home>Product Center >> Pharmaceutical API >> Amiodarone
  • Amiodarone
Name:Amiodarone
CAS No:1951-25-3

PRODUCT DESCRIPTION

【Name】
Methanone,(2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]-
【CAS Registry number】
1951-25-3
【Synonyms】
Ketone,2-butyl-3-benzofuranyl 4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl (7CI,8CI)
2-Butyl-3-[3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl]benzofuran
2-Butyl-3-benzofuranyl p-[(2-diethylamino)ethoxy]-m,m-diiodophenyl ketone
2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran
Amidorone
Ancaron
Sedacoron
Sedacorone
【EINECS(EC#)】
217-772-1
【Molecular Formula】
C25H29I2NO3 (Products with the same molecular formula)
【Molecular Weight】
645.3116
【Inchi】
InChI=1S/C25H29I2NO3/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
【InChIKey】
IYIKLHRQXLHMJQ-UHFFFAOYSA-N
【Canonical SMILES】
CCCCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)I)OCCN(CC)CC)I
【MOL File】
1951-25-3.mol

Chemical and Physical Properties

【Density】
1.58 g/cm3
【Melting Point】
156 deg C
【Boiling Point】
635.1°C at 760 mmHg
【Vapour】
4.95E-16mmHg at 25°C
【Flash Point】
337.9°C
【Water】
Stability Stable. Incompatible with strong oxidizing agents.Toxicology Harmful by ingestion. May be harmful by inhalation or throughskin contact. Typical Lowest published toxic doses
【Solubilities】

【Color/Form】
Crystalline powder; crystals from acetone
【Stability】
Stable. Incompatible with strong oxidizing agents.
【Storage temp】
2-8°C
【Spectral properties】
UV max (methanol): 208, 242 nm (E 10%/1 cm 662, 62)
【Computed Properties】
Molecular Weight:645.3116 [g/mol]
Molecular Formula:C25H29I2NO3
XLogP3:7.6
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:11
Exact Mass:645.02368
MonoIsotopic Mass:645.02368
Topological Polar Surface Area:42.7
Heavy Atom Count:31
Formal Charge:0
Complexity:547
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:3
Feature 3D Ring Count:3
Effective Rotor Count:11
Conformer Sampling RMSD:1.4
CID Conformer Count:35

Safety and Handling

【Hazard Codes】
Xn:Harmful;
【Risk Statements】
R20/21/22
【Safety Statements 】
S36
【Safety】

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 I− and NOx. A coronary vasodilator.
Hazard Codes: HarmfulXn 
Risk Statements: 20/21/22 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
Safety Statements: 36 
S36:Wear suitable protective clothing. 
WGK Germany: 3
RTECS: OB1361000

【Formulations/Preparations】
Amiodar, Ancaron, Cordarex, Cordarone, Ortacrone, Pacerone, Tachydaron, Trangorex
Oral tablets 200 mg Cordarone (with povidone; scored); Wyeth-Ayerst; Pacerone (with providone; scored), Upsher-Smith; 400 mg Pacerone (with povidone, scored), Upsher-Smith.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl amiodarone hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392). [
【Specification】

 The chemical synonymous of Amiodarone (CAS NO.1951-25-3) are (2-butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)-3,5-diidophenyl)methanone ; 2-butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran ; 2-butyl-3-(3,5-diiodo-4-(beta-diethylaminoethoxy)benzoyl)benzofuran ; 2-butyl-3-(3,5-diiodo-4-(beta-diethylaminoethoxy)-benzoyl)benzofuran ; 2-butyl-3-(4'-beta-n-diethylaminoethoxy-3',5'-diiodobenzoyl)benzofuran ; 2-butyl-3-benzofuranylp-((2-diethylamino)ethoxy)-m,m-diiodophenylketone ; 2-n-butyl-3',5'-diiodo-4'-n-diethylaminoethoxy-3-benzoylbenzofuran ; amiodarona .

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Usage】
Medication.

Biomedical Effects and Toxicity

【Pharmacological Action】
- 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.
- Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
- Drugs used to cause dilation of the blood vessels.
【Therapeutic Uses】
Anti-Arrhythmia Agents; Enzyme Inhibitors; Vasodilator Agents
Anti-arrhythmic class III
Amiodarone in the oral dosage form is indicated only in the treatment of recurrent hemodynamically unstable ventricular tachycardia and recurrent ventricular fibrillation unresponsive to documented adequate doses of other available antiarrythmic medications or when alternative agents cannot be tolerated. In patients from whom the oral form of amiodarone is indicated, but who are unable to take oral medication, the intravenous form may be used.
Amiodarone is used to suppress and prevent recurrence of supraventricular arrythmias refractory to conventional treatment, especially when associated with Wolff-Parkinson-White (W-P-W) syndrome, including paroxysmal atrial fibrillation, atrial fibrillation, atrial flutter, ectopic atrial tachycardia, and paroxysmal supraventricular tachycardia from both atriovantricular (AV) nodal re-entrant and AV re-entrant tachycardia in patients with W-P-W syndrome.
Amiodarone has been used in a limited number of patients for the management of chronic stable angina pectoris.
【Biomedical Effects and Toxicity】
Plasma concentration of amiodarone appear to decline in at least a biphasic manner, although more complex, multicompartmental pharmacokinetics have been described. Following a single IV dose in healthy adults, the half-life of the drug in the terminal elimination phase has been reported to average 25 days (range 9-47 days). The elimination half-life of the major metabolite, N-desethylamiodarone, is equal to or longer than that of the parent drug. Following single dose admin of amiodarone in a limited number of healthy individuals, amiodarone exhibits multicompartmental pharmacokinetics; the mean apparent terminal plasma elimination half-life of amiodarone and N-desethylamiodarone were 58 (range: 15-142) and 36 (range: 14-75) days, respectively. The half-life of amiodarone appears to be substantially more prolonged following multiple rather than single doses. It has been suggested that differences in reported elimination half-lives may result in part from misinterpretation of slow distribution phases as elimination phases following IV administration of the drug. Following chronic oral administration of amiodarone hydrochloride in patients with cardiac arrhythmias (200-600 mg daily for 2-52 months), the drug appears to be eliminated in a biphasic manner with an initial elimination half-life of about 2.5-10 days, which is followed by a terminal elimination half-life averaging 53 days (range: 26-107 days), with most patients exhibiting a terminal elimination half-life in the range of 40-55 days. The elimination half-life of the major metabolite, N-desethylamiodarone, averages 57-61 days (range 20-118 days) following long-term oral administration of amiodarone. The elimination profile of amiodarone may reflect an initial elimination of the drug from well-perfused tissues followed by prolonged elimination from poorly perfused tissues such as adipose tissue.
Following iv administration of amiodarone in healthy individuals, total plasma clearance of the drug averages approximately 1.9 ml/min/kg (range: 1.4-2.5 ml/min/kg). Although not clearly established, total apparent plasma clearance of the drug appears to decrease with time. Clinical experience suggests that clearance of amiodarone may be more rapid in pediatric patients; however, further studies are needed to fully determine the effects of age on clearance of the drug. Factors of age, gender, or renal or hepatic disease appear to have no effect on the disposition of amiodarone or its major metabolite, N-desethylamiodarone.
Amiodarone hydrochloride is slowly and variably absorbed from the GI tract following oral administration. The absolute bioavailability of commercially available amiodarone hydrochloride tablets averages approximately 50%, but varies considerably, ranging from 22-86%.
Following oral administration, peak plasma amiodarone concentrations usually occur within 3-7 hours (range: 2-12 hours). Following oral administration of a single 400 mg dose of amiodarone hydrochloride in fasting, healthy adults, peak plasma amiodarone concentration of approximately 0.15-0.7 ug/ml are attained. Within the oral dosage range of 100-600 mg daily, steady state plasma concentrations of the drug are approximately proportional to dosage, increasing by an average of 0.5 ug/ml per 100 mg increment in dosage; however, there is considerable interindividual variation in plasma concentrations attained with a given dosage. Following continuous oral administration of the drug in the absence of an initial loading dose regimen, steady state plasma amiodarone concentrations would not be attained for at least 1 month and generally not for up to 5 months or longer. Following chronic oral administration of amiodarone, plasma concentrations of N-desethylamiodarone, the major metabolite of the drug, are approximately 0.5-2 times those of unchanged drug.
Amiodarone and possibly N-desethylamiodarone cross the placenta to a limited extent. In pregnant women receiving amiodarone, ratios of umbilical venous to maternal venous plasma concentrations of amiodarone and N-desethylamiodarone were 0.1-0.28 and 0.25-0.55, respectively.
Following iv administration, amiodarone is rapidly and widely distributed. The apparent volume of distribution of the drug or its major metabolite, N-desethylamiodarone, in healthy adults reportedly averages 65.8 l/kg (range: 18.3-147.7 l/kg) or ranges from 68-168 l/kg, respectively, following a single IV dose.
In vitro, amiodarone is approximately 96% bound to plasma proteins, mainly to albumin and, to a lesser extent, a high density lipoprotein that is probably a beta-lipoprotein.
Distribution of amiodarone into human body tissues and fluids has not been fully characterized. Following iv administration in rats, amiodarone is distributed extensively into many tissues, including adipose tissue, liver, kidneys, heart, and, to a lesser extent, the CNS. Following chronic oral administration of the drug in humans, amiodarone and N-desethylamiodarone are distributed extensively into many body tissues and fluids, including adipose tissue, liver, lung, spleen, skeletal muscle, bone marrow, adrenal glands, kidneys, pancreas, testes, semen, saliva, lymph nodes, myocardium, thyroid gland, skin, and brain. Amiodarone is also distributed into bile. Limited data indicate that peak biliary concentrations of the drug may be approximately 50 times greater than peak plasma concentrations. Tissue concentrations of amiodarone generally exceed concurrent plasma concentrations of the drug. N-Desethylamiodarone appears to accumulate in the same body tissues as amiodarone; however, after long term therapy, concentrations of the metabolite are usually substantially higher than concentrations of unchanged drug in almost all tissues, except adipose tissue, which mainly contains amiodarone. N-Desethylamiodarone and, to a lesser extent, amiodarone also distribute into erythrocytes. Ratios of erythrocyte-to-plasma concentrations of amiodarone and N-desethylamiodarone were 0.33 and 0.67, respectively, after a single oral dose of amiodarone and 0.38-0.48 and 1.3-1.76, respectively, after long-term oral therapy with the drug. Following a single iv dose, the mean blood-to-plasma ratio for amiodarone is 0.73.
The excretory patterns of amiodarone and its metabolite have not been well characterized. Following oral or IV administration, amiodarone appears to be excreted almost completely in feces as unchanged drug and N-desethylamiodarone, presumably via biliary elimination. Although not clearly established, limited data suggest that amiodarone may undergo enterohepatic circulation. Renal excretion of amiodarone and N-desethylamiodarone appears to be negligible.
Amiodarone and its major metabolite are distributed into milk in concentrations substantially higher than concurrent maternal plasma concentrations. Limited data in a lactating woman indicate amiodarone and N-desethylamiodarone milk-to-plasma ratios ranging from 2.3-9.1 and 0.8-3.8, respectively.
Five cases are studied in which amiodarone was given during pregnancy, in two of them also during the breast feeding period, to estimate the risks for adverse effects. The concentrations of amiodarone and its major metabolite desethylamiodarone in maternal plasma, cord plasma, infant plasma, placental tissue and breast milk and the thyroid hormones were measured in maternal and neonatal serum. Also, the neonates were examined for amiodarone associated adverse effects over a period varying from 8 months up to 5 years. A limited maternal-fetal transfer of amiodarone and desethylamiodarone was observed, while the concentration of desethylamiodarone in placental tissue was relatively high. Considerable amounts of amiodarone and desethylamiodarone were present in breast milk. One infant appeared to be hypothyroid, detected by the neonatal thyroid screening. [Plomp TA et al; Eur J Obstet Gynecol Reprod Biol 43 (3): 201-7 (1992)] PubMed Abstract

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