Amiodarone

Modify Date: 2024-01-02 12:12:55

Amiodarone structure	Common Name	Amiodarone
	CAS Number	1951-25-3	Molecular Weight	645.31200
	Density	1.58 g/cm3	Boiling Point	635.1ºC at 760 mmHg
	Molecular Formula	C₂₅H₂₉I₂NO₃	Melting Point	156ºC
	MSDS	N/A	Flash Point	337.9ºC

Use of Amiodarone

Amiodarone is an antiarrhythmic drug for inhibition of ATP-sensitive potassium channel with IC50 of 19.1 μM. Target: Potassium ChannelAmiodarone shows beta blocker-like and potassium channel blocker-like actions on the SA and AV nodes, increases the refractory period via sodium- and potassium-channel effects, and slows intra-cardiac conduction of the cardiac action potential, via sodium-channel effects. Amiodarone (2-butyl, 3-(4-diethylaminoethoxy, 3,5-diiodo, benzoyl) benzofuran hydrochloride), an anti-anginal drug which causes coronary dilatation and depresses myocardial oxygen consumption, was found to protect anaesthetized guinea-pigs against ouabain-induced ventricular fibrillation.2. A 5% (73.4 mM) solution of amiodarone had no local anaesthetic action on guinea-pig skin [1]. Amiodarone proved safe in patients with severe congestive heart failure and severe myocardial damage. Its clinical efficacy was related to its electrophysiologic properties and to two unique properties: its wide safety margin and its cumulative effect [2].

Name	amiodarone
Synonym	More Synonyms

Description	Amiodarone is an antiarrhythmic drug for inhibition of ATP-sensitive potassium channel with IC50 of 19.1 μM. Target: Potassium ChannelAmiodarone shows beta blocker-like and potassium channel blocker-like actions on the SA and AV nodes, increases the refractory period via sodium- and potassium-channel effects, and slows intra-cardiac conduction of the cardiac action potential, via sodium-channel effects. Amiodarone (2-butyl, 3-(4-diethylaminoethoxy, 3,5-diiodo, benzoyl) benzofuran hydrochloride), an anti-anginal drug which causes coronary dilatation and depresses myocardial oxygen consumption, was found to protect anaesthetized guinea-pigs against ouabain-induced ventricular fibrillation.2. A 5% (73.4 mM) solution of amiodarone had no local anaesthetic action on guinea-pig skin [1]. Amiodarone proved safe in patients with severe congestive heart failure and severe myocardial damage. Its clinical efficacy was related to its electrophysiologic properties and to two unique properties: its wide safety margin and its cumulative effect [2].
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel Research Areas >> Cardiovascular Disease
References	[1]. Singh, B.N. and E.M. Vaughan Williams, The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br J Pharmacol, 1970. 39(4): p. 657-67. [2]. Rosenbaum, M.B., et al., Clinical efficacy of amiodarone as an antiarrhythmic agent. Am J Cardiol, 1976. 38(7): p. 934-44.

Description

Related Catalog

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

Research Areas >> Cardiovascular Disease

References

[1]. Singh, B.N. and E.M. Vaughan Williams, The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br J Pharmacol, 1970. 39(4): p. 657-67.

[2]. Rosenbaum, M.B., et al., Clinical efficacy of amiodarone as an antiarrhythmic agent. Am J Cardiol, 1976. 38(7): p. 934-44.

Density	1.58 g/cm3
Boiling Point	635.1ºC at 760 mmHg
Melting Point	156ºC
Molecular Formula	C₂₅H₂₉I₂NO₃
Molecular Weight	645.31200
Flash Point	337.9ºC
Exact Mass	645.02400
PSA	42.68000
LogP	6.93620
Vapour Pressure	4.95E-16mmHg at 25°C
Stability	Stable. Incompatible with strong oxidizing agents.

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OB1360000

CHEMICAL NAME :: Ketone, 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl

CAS REGISTRY NUMBER :: 1951-25-3

BEILSTEIN REFERENCE NO. :: 1271711

LAST UPDATED :: 199703

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C25-H29-I2-N-O3

MOLECULAR WEIGHT :: 645.35

WISWESSER LINE NOTATION :: T56 BOJ C4 DVR CI EI DO2N2&2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1714 mg/kg/21W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - cough Lungs, Thorax, or Respiration - cyanosis Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 308,779,1983

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 568 mg/kg/9W-I

TOXIC EFFECTS :: Cardiac - pulse rate Liver - fatty liver degeneration

REFERENCE :: JOPDAB Journal of Pediatrics. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) V.1- 1932- Volume(issue)/page/year: 107,967,1985

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1869 mg/kg/22W-I

TOXIC EFFECTS :: Behavioral - coma Vascular - BP lowering not characterized in autonomic section Endocrine - evidence of thyroid hypofunction

REFERENCE :: AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 77,751,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 416 mg/kg/30D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 147,50,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 133 mg/kg/23D-I

TOXIC EFFECTS :: Skin and Appendages - photosensitivity (after systemic exposure)

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,51,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 3651 mg/kg/2.3Y-I

TOXIC EFFECTS :: Liver - hepatitis, fibrous (cirrhosis, post-necrotic scarring) Liver - liver function tests impaired Liver - multiple effects

REFERENCE :: AJGAAR American Journal of Gastroenterology. (American College of Gastroenterology, Inc., 428 E. Preston St., Baltimore, MD 21202) V.21- 1954- Volume(issue)/page/year: 83,161,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 36 mg/kg/1D-I

TOXIC EFFECTS :: Endocrine - evidence of thyroid hyperfunction

REFERENCE :: IJMDAI Israel Journal of Medical Sciences. (POB 1435, Jerusalem 91013, Israel) V.1- 1965- Volume(issue)/page/year: 21,165,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 26 mg/kg/1D-C

TOXIC EFFECTS :: Cardiac - arrhythmias (including changes in conduction) Cardiac - EKG changes not diagnostic of specified effects

REFERENCE :: AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 131,1214,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 57 mg/kg/5D-I

TOXIC EFFECTS :: Cardiac - pulse rate increase, without fall in BP

REFERENCE :: AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 97,561,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 48 mg/kg/3D-I

TOXIC EFFECTS :: Cardiac - pulse rate increase, without fall in BP

REFERENCE :: AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 130,399,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Multiple routes

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1475 mg/kg/7W-I

TOXIC EFFECTS :: Cardiac - other changes

REFERENCE :: AJCDAG American Journal of Cardiology. (Technical Pub. Co., 875 Third Ave., New York, NY 10022) V.1- 1958- Volume(issue)/page/year: 58,1110,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 885 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0076973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0076973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 254 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJTXAZ European Journal of Toxicology and Environmental Hygiene. (Paris, France) V.7-9, 1974-76. For publisher information, see TOERD9. Volume(issue)/page/year: 8,122,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 178 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJTXAZ European Journal of Toxicology and Environmental Hygiene. (Paris, France) V.7-9, 1974-76. For publisher information, see TOERD9. Volume(issue)/page/year: 8,188,1975

Hazard Codes	Xn:Harmful;
Risk Phrases	R20/21/22
Safety Phrases	S36
WGK Germany	3
RTECS	OB1361000
HS Code	2932999099

HS Code	2932999099
Summary	2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

(2-Butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)methanone

AMidorone

MFCD00242801

Atlansil

amiodarona

Amiodarone

Sedacorone

2-butyl-3-benzofuranyl 4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone

Tranquerone

(2-{4-[(2-butyl-1-benzofuran-3-yl)carbonyl]-2,6-diiodophenoxy}ethyl)diethylamine

Sedacoron

Amiodarons

EINECS 217-772-1

2-butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran

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Amiodarone

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