Amiodarone HCl

Names

[ CAS No. ]:
19774-82-4

[ Name ]:
Amiodarone HCl

[Synonym ]:
(2-Butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone hydrochloride
(2-Butyl-3-benzofuranyl)[4-[2-(diethylamino)e
MFCD08064189
(2-Butyl-1-benzofur-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodphenyl}methanonhydrochlorid
(2-Butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone hydrochloride (1:1)
Ancaron
(2-butylbenzo[b]furan-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone hydrochloride
Cordarone
(2-Butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)methanone hydrochloride
(2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone,hydrochloride
EINECS 243-293-2
methanone, (2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]-, hydrochloride
Amiodarone HCl
Methanone, (2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]-, hydrochloride (1:1)
UNII-976728SY6Z
(2-butyl-1-benzofur-3-yl){4-[2-(diéthylamino)éthoxy]-3,5-diiodophényl}méthanone chlorhydrate
Ketone, 2-butyl-3-benzofuranyl 4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl, hydrochloride
PACERONE
Amiodarone hydrochloride
Amiodarone (hydrochloride)

Biological Activity

[Description]:

Amiodarone is an antiarrhythmic drug for inhibition of ATP-sensitive potassium channel with IC50 of 19.1 μM. IC50 Value: 1.5 uM ( inhibit TBARS, LOOH and FPL formation)[1]in vitro: It was found that 10 uM amiodarone induces accumulation of ethidium bromide (5 ug/ml) in Saccharomyces cerevisiae cells. At the same time, in yeast cells with inactivated MDR genes, accumulation of ethidium bromide was 6-fold higher even without amiodarone. Addition of non-lethal concentrations of amiodarone to MDR-deficient cells caused an increase of intracellular ethidium bromide to the level, which was even lower than the level in amiodarone-treated wild-type cells [2]. Cells treated with amiodarone were seen to have detached from the dish, with cell rounding, cytoplasmic blebbing and irregularity in shape. An increase in the sub-G1 phase fraction, from 15.43 to 21.34% and 79.83% and a reduction in the G1 phase fraction, from 48.83 to 41.63% and 11.52%, were observed in cells treated with amiodarone at concentrations of 0.1 and 1 mM, respectively [3].in vivo: Chronic treatment with oral amiodarone for 4 weeks reduced i.p. when myocytes were dialyzed with patch-pipettes containing either 10 mM Na+ or 80 mM Na+. In myocytes from untreated rabbits, acute exposure to amiodarone in vitro reduced i.p. when patch pipettes contained 10 mM Na+ but had no effect on i.p. at 80 mM Na+. Amiodarone had no effect on the voltage dependence of the pump or the affinity of the pump for extracellular K+ either after chronic treatment or during acute exposure [4].Clinical trial: Continuous Versus Episodic Amiodarone Treatment for the Prevention of Permanent Atrial Fibrillation . Phase not specified

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

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

Research Areas >> Cardiovascular Disease

[References]

[1]. Lapenna D, Ciofani G, Bruno C, Antioxidant activity of amiodarone on human lipoprotein oxidation. Br J Pharmacol. 2001 Jul;133(5):739-45.

[2]. Knorre DA, Krivonosova TN, Markova OV, Amiodarone inhibits multiple drug resistance in yeast Saccharomyces cerevisiae. Arch Microbiol. 2009 Aug;191(8):675-9.

[3]. Choi IS, Kim BS, Cho KS, Amiodarone induces apoptosis in L-132 human lung epithelial cell line. Toxicol Lett. 2002 Jun 7;132(1):47-55.

[4]. Gray DF, Mihailidou AS, Hansen PS, Amiodarone inhibits the Na(+)-K+ pump in rabbit cardiac myocytes after acute and chronic treatment. J Pharmacol Exp Ther. 1998 Jan;284(1):75-82.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.58 g/cm3

[ Boiling Point ]:
635.1ºC at 760 mmHg

[ Melting Point ]:
154-158°C

[ Molecular Formula ]:
C₂₅H₃₀ClI₂NO₃

[ Molecular Weight ]:
681.773

[ Flash Point ]:
337.9ºC

[ Exact Mass ]:
681.000366

[ PSA ]:
42.68000

[ LogP ]:
7.73820

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OB1361000

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

CAS REGISTRY NUMBER :: 19774-82-4

LAST UPDATED :: 199706

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C25-H29-I2-N-O3.Cl-H

MOLECULAR WEIGHT :: 681.81

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 3129 mg/kg/3Y-I

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

REFERENCE :: SMJOAV Southern Medical Journal. (Southern Medical Assoc., POB 2446, Birmingham, AL 35205) V.1- 1908- Volume(issue)/page/year: 89,85,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 240 mg/kg/6W-I

TOXIC EFFECTS :: Skin and Appendages - hair

REFERENCE :: AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 155,1106,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1128 mg/kg/56W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 86,134,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 2480 mg/kg/43W-I

TOXIC EFFECTS :: Endocrine - thyroid weight (goiter)

REFERENCE :: AMSVAZ Acta Medica Scandinavica. (Almqvist & Wiksell, POB 45150, S-10430 Stockholm, Sweden) V.52-224, 1919-88. Volume(issue)/page/year: 221,219,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 171 mg/kg/30D-I

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

REFERENCE :: AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 100,412,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 120 mg/kg/10D-I

TOXIC EFFECTS :: Cardiac - arrhythmias (including changes in conduction)

REFERENCE :: HUTODJ Human Toxicology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants., RG 21 2XS, UK) V.1- 1981- Volume(issue)/page/year: 4,169,1985

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 610 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 170 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 450 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 5 gm/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 23,682,1992 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 210 mg/kg/21D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Biochemical - Metabolism (Intermediary) - amino acids (including renal excretion)

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 13,154,1993 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 245 mg/kg

SEX/DURATION :: female 16-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 65,259,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 26,3871,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 26,3871,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 26,3871,1992

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
1230.0

[ WGK Germany ]:
3

[ RTECS ]:
OB1361000

[ Hazard Class ]:
3、6.1

[ HS Code ]:
2932999099

Customs

[ 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%

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