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19774-82-4

19774-82-4 structure
19774-82-4 structure
  • Name: Amiodarone HCl
  • Chemical Name: Amiodarone Hydrochloride
  • CAS Number: 19774-82-4
  • Molecular Formula: C25H30ClI2NO3
  • Molecular Weight: 681.773
  • Catalog: API Circulatory system medication Antiarrhythmic drug
  • Create Date: 2018-04-15 08:00:00
  • Modify Date: 2024-01-02 08:18:30
  • 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
Name Amiodarone Hydrochloride
Synonyms (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)
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
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.
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

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
Symbol GHS02 GHS06 GHS08
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
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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