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Substance Name: Amiodarone [USAN:INN:BAN]
RN: 1951-25-3
UNII: N3RQ532IUT
InChIKey: IYIKLHRQXLHMJQ-UHFFFAOYSA-N

Notes

  • An antianginal and antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting Na,K-activated myocardial adenosine triphosphatase. There is a resulting decrease in heart rate and in vascular resistance.
  • An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.

Molecular Formula

  • C25-H29-I2-N-O3

Molecular Weight

  • 645.3081
 

Classification Codes

  • Anti-Arrhythmia Agents
  • Cardiac Depressant (Anti-Arrhythmic, Ventricular)
  • Cardiovascular Agents
  • Cytochrome P-450 CYP1A2 Inhibitors
  • Cytochrome P-450 CYP2C9 Inhibitors
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Membrane Transport Modulators
  • Potassium Channel Blockers
  • Sodium Channel Blockers
  • Vasodilator Agents

Names and Synonyms

Name of Substance

  • Amiodarone
  • Amiodarone [USAN:INN:BAN]

MeSH Heading

  • Amiodarone

Synonyms

  • (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-(4'-beta-N-diethylaminoethoxy-3',5'-diiodobenzoyl)benzofuran
  • 2-Butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone
  • 2-Butyl-3-benzofuranyl p-((2-diethylamino)ethoxy)-m,m-diiodophenyl ketone
  • 2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran
  • 5-18-02-00353 (Beilstein Handbook Reference)
  • Amiodarona
  • Amiodarona [INN-Spanish]
  • Amiodarone
  • Amiodaronum
  • Amiodaronum [INN-Latin]
  • Amjodaronum
  • BRN 1271711
  • CCRIS 9360
  • Cordarone
  • EINECS 217-772-1
  • L 3428
  • L-3428
  • Methanone, (2-butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)-
  • SKF 33134-A
  • UNII-N3RQ532IUT

Systematic Names

  • Amiodarone
  • Ketone, 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl
  • Methanone, (2-butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)-

Registry Numbers

CAS Registry Number

  • 1951-25-3

FDA UNII

  • N3RQ532IUT

System Generated Number

  • 0001951253

Structure Descriptors

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

Smiles

CCCCc1oc2ccccc2c1C(=O)c3cc(I)c(OCCN(CC)CC)c(I)c3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 568mg/kg/9W-I (568mg/kg) CARDIAC: PULSE RATE

LIVER: FATTY LIVER DEGERATION
Journal of Pediatrics. Vol. 107, Pg. 967, 1985.
man LDLo oral 1869mg/kg/22W (1869mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

ENDOCRINE: EVIDENCE OF THYROID HYPOFUNCTION

BEHAVIORAL: COMA
American Journal of Medicine. Vol. 77, Pg. 751, 1984.
man LDLo oral 2086mg/kg/2Y- (2086mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Netherlands Journal of Medicine. Vol. 29, Pg. 303, 1986.
man LDLo unreported 3650mg/kg/3.5 (3650mg/kg) LIVER: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

ENDOCRINE: OTHER CHANGES
Clinical Endocrinology Vol. 45, Pg. 365, 1996.
man TDLo intravenous 4286ug/kg (4.286mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE Critical Care Medicine. Vol. 13, Pg. 688, 1985.
man TDLo intravenous 26mg/kg/1D-C (26mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
American Heart Journal. Vol. 131, Pg. 1214, 1996.
man TDLo oral 60mg/kg/2W-I (60mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: CHANGES IN OTHER CELL COUNT (UNSPECIFIED)
Chest. Vol. 88, Pg. 630, 1985.
man TDLo oral 133mg/kg/23D- (133mg/kg) SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE Lancet. Vol. 1, Pg. 51, 1984.
man TDLo oral 390mg/kg/39W- (390mg/kg) ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
Netherlands Journal of Medicine. Vol. 42, Pg. 21, 1993.
man TDLo oral 1714mg/kg/21W (1714mg/kg) LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
New England Journal of Medicine. Vol. 308, Pg. 779, 1983.
man TDLo oral 3651mg/kg/2.3 (3651mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: MULTIPLE EFFECTS
American Journal of Gastroenterology. Vol. 83, Pg. 161, 1988.
man TDLo unreported 51mg/kg/6D-C (51mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 296, Pg. 1322, 1988.
man TDLo unreported 57mg/kg/5D-I (57mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Annals of Internal Medicine. Vol. 97, Pg. 561, 1982.
mouse LD50 intraperitoneal 254mg/kg (254mg/kg)   European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 122, 1975.
mouse LD50 intravenous 178mg/kg (178mg/kg)   European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 188, 1975.
mouse LD50 oral > 4gm/kg (4000mg/kg)   European Patent Application. Vol. #0076973,
rat LD50 intraperitoneal 885mg/kg (885mg/kg)   European Patent Application. Vol. #0076973,
women TDLo intravenous 3mg/kg (3mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE Critical Care Medicine. Vol. 13, Pg. 688, 1985.
women TDLo intravenous 36mg/kg/1D-I (36mg/kg) ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION Israel Journal of Medical Sciences. Vol. 21, Pg. 165, 1985.
women TDLo multiple routes 1475mg/kg/7W- (1475mg/kg) CARDIAC: OTHER CHANGES American Journal of Cardiology. Vol. 58, Pg. 1110, 1986.
women TDLo oral 64mg/kg/4D-I (64mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Lancet. Vol. 350, Pg. 1300, 1997.
women TDLo oral 416mg/kg/30D- (416mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Archives of Internal Medicine. Vol. 147, Pg. 50, 1987.
women TDLo oral 5200mg/kg/5Y- (5200mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ANOREXIA (HUMAN
Respiration. Vol. 49, Pg. 157, 1986.
women TDLo oral 5796mg/kg/69W (5796mg/kg) MUSCULOSKELETAL: OTHER CHANGES

ENDOCRINE: OTHER CHANGES
Italian Journal of Neurological Sciences. Vol. 8, Pg. 605, 1987.
women TDLo unreported 48mg/kg/3D-I (48mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP American Heart Journal. Vol. 130, Pg. 399, 1995.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 7.57 (none)   EXP
Water Solubility 2.83E-04 mg/L 25 EST
Vapor Pressure 3.41E-13 mm Hg 25 EST
Henry's Law Constant 1.80E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.66E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.