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Chemistry

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Also known as: 19774-82-4, Amiodarone hcl, Nexterone, Amiodar, Pacerone, Ritmocardyl
Molecular Formula
C25H30ClI2NO3
Molecular Weight
681.8  g/mol
InChI Key
ITPDYQOUSLNIHG-UHFFFAOYSA-N
FDA UNII
976728SY6Z

Amiodarone Hydrochloride
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.
1 2D Structure

Amiodarone Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone;hydrochloride
2.1.2 InChI
InChI=1S/C25H29I2NO3.ClH/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;1H
2.1.3 InChI Key
ITPDYQOUSLNIHG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)I)OCCN(CC)CC)I.Cl
2.2 Other Identifiers
2.2.1 UNII
976728SY6Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amiobeta

2. Amiodarex

3. Amiodarona

4. Amiodarone

5. Amiohexal

6. Aratac

7. Braxan

8. Corbionax

9. Cordarex

10. Cordarone

11. Hydrochloride, Amiodarone

12. Kordaron

13. L 3428

14. L-3428

15. L3428

16. Ortacrone

17. Rytmarone

18. Skf 33134 A

19. Skf 33134-a

20. Skf 33134a

21. Tachydaron

22. Trangorex

2.3.2 Depositor-Supplied Synonyms

1. 19774-82-4

2. Amiodarone Hcl

3. Nexterone

4. Amiodar

5. Pacerone

6. Ritmocardyl

7. Trangorex

8. Amiodarone (hydrochloride)

9. Uro-septra

10. Miodaron

11. Ortacrone

12. (2-butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)methanone Hydrochloride

13. Skf 33134-a

14. 51087 N Hcl

15. Nsc-85442

16. Mls000028520

17. Amiodarone Hydrochloride [jan]

18. Skf-33134-a

19. Methanone,(2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]-,hydrochloride

20. 976728sy6z

21. Smr000058296

22. L-3428

23. 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl Ketone Hydrochloride

24. 2-butyl-3-benzofuryl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl Ketone Hydrochloride

25. Dsstox_cid_17185

26. Dsstox_rid_79304

27. Dsstox_gsid_37185

28. (2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone;hydrochloride

29. Rythmarone

30. Angoron

31. Atlansil

32. Miodrone

33. Renodoron

34. Amiodaronum Hydrochloride

35. L 3428 Labaz

36. Sr-01000003087

37. Ncgc00015096-12

38. Cas-19774-82-4

39. Ancaron

40. Amio-aqueous

41. Unii-976728sy6z

42. Hsdb 6525

43. Cordarone (tn)

44. Nexterone (tn)

45. Prestwick_707

46. Amiodarone Hydrochloride [usp:jan]

47. Ancaron (tn)

48. Einecs 243-293-2

49. Skf 33134 A

50. Mfcd00069204

51. Nsc 85442

52. Amiodaronehydrochloride

53. Cpd000058296

54. Opera_id_568

55. Schembl41348

56. Mls001076313

57. Mls001424272

58. Mls002222247

59. Spectrum2300165

60. Chebi:2664

61. Amiodarone Hydrochloride Solution

62. Chembl1083993

63. Dtxsid7037185

64. Amiodarone Hydrochloride - Bio-x

65. Calcium Channel (l Type) Blocker

66. Hms1569a20

67. Pharmakon1600-02300165

68. Act02681

69. Amiodarone Hydrochloride, >/=98%

70. Bcp13645

71. Nsc85442

72. Ketone,5-diiodophenyl, Hydrochloride

73. Tox21_113478

74. Tox21_300395

75. Tox21_500122

76. Ac-078

77. Amiodarone Hydrochloride [mi]

78. Ccg-39607

79. Nsc759560

80. Pm-101

81. S1979

82. Sk&f-33134-a

83. Amiodarone Hydrochloride (jp17/usp)

84. Akos015844018

85. Amiodarone Hydrochloride [hsdb]

86. Cs-1371

87. Ks-5249

88. Lp00122

89. Nc00423

90. Nsc-759560

91. {2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine Hydrochloride

92. Amiodarone Hydrochloride [mart.]

93. Amiodarone Hydrochloride [vandf]

94. Amiodarone Hydrochloride [usp-rs]

95. Amiodarone Hydrochloride [who-dd]

96. Ncgc00093613-01

97. Ncgc00093613-02

98. Ncgc00093613-03

99. Ncgc00093613-04

100. Ncgc00254295-01

101. Ncgc00260807-01

102. Ba139263

103. Hy-14188

104. Methanone, (2-butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)-, Hydrochloride

105. Methanone,5-diiodophenyl]-, Hydrochloride

106. Eu-0100122

107. Ft-0622300

108. Sw196856-4

109. Amiodarone Hydrochloride [orange Book]

110. A 8423

111. Amiodarone Hydrochloride [ep Monograph]

112. Amiodarone Hydrochloride [usp Monograph]

113. D00636

114. D86460

115. 774a824

116. Q-200626

117. Sr-01000003087-2

118. Sr-01000003087-8

119. Wln: T56 Boj C4 Dvr Ci Ei Do2n2&2 &gh

120. Q27271976

121. Z2210825534

122. Amiodarone Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

123. (2-butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)methanonehydrochloride

124. 2-butyl-3-benzofuranyl 4-[(2-diethylamino)ethoxy] 3,5-diiodophenyl Ketone, Hydrochloride

125. Ketone, 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl, Hydrochloride

126. (2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone;hydron;chloride

127. (2-butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone Hydrochloride (1:1)

128. (2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone Hydrochloride

129. Amiodarone Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

130. Methanone, (2-butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)- Hydrochloride

131. Methanone, (2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]-, Hydrochloride (1:1)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 681.8 g/mol
Molecular Formula C25H30ClI2NO3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count11
Exact Mass681.00037 g/mol
Monoisotopic Mass681.00037 g/mol
Topological Polar Surface Area42.7 Ų
Heavy Atom Count32
Formal Charge0
Complexity547
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAmiodarone hydrochloride
Drug LabelAmiodarone hydrochloride is a member of a class of antiarrhythmic drugs with predominantly Class III (Vaughan Williams classification) effects, available for oral administration as pink, scored tablets containing 200 mg of amiodarone hydrochloride...
Active IngredientAmiodarone hydrochloride
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength300mg; 50mg/ml; 200mg; 100mg; 400mg
Market StatusPrescription
CompanyWockhardt; Teva Pharms; Fresenius Kabi Usa; Hospira; Gland Pharma; Mylan Institutional; Apotex; Hikma Farmaceutica; Taro; Zydus Pharms Usa; Sandoz; Mylan; Murty Pharms; Akorn; Barr

2 of 6  
Drug NameNexterone
PubMed HealthAmiodarone
Drug ClassesAntiarrhythmic, Group III
Drug LabelNEXTERONE contains amiodarone HCl (C25H29I2NO3HCl), a class III antiarrhythmic drug. Amiodarone HCl is (2-butyl-3-benzo-furanyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone hydrochloride.Amiodarone HCl has the following structural formul...
Active IngredientAmiodarone hydrochloride
Dosage FormInjectable
RouteInjection
Strength360mg/200ml (1.8mg/ml); 150mg/100ml (1.5mg/ml); 50mg/ml
Market StatusPrescription
CompanyBaxter Hlthcare

3 of 6  
Drug NamePacerone
Drug LabelPacerone (amiodarone hydrochloride) Tablets are a member of a class of antiarrhythmic drugs with predominantly Class III (Vaughan Williams classification) effects, available for oral administration as light yellow, scored tablets. Each tablet fo...
Active IngredientAmiodarone hydrochloride
Dosage FormTablet
RouteOral
Strength200mg; 100mg
Market StatusPrescription
CompanyUpsher Smith

4 of 6  
Drug NameAmiodarone hydrochloride
Drug LabelAmiodarone hydrochloride is a member of a class of antiarrhythmic drugs with predominantly Class III (Vaughan Williams classification) effects, available for oral administration as pink, scored tablets containing 200 mg of amiodarone hydrochloride...
Active IngredientAmiodarone hydrochloride
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength300mg; 50mg/ml; 200mg; 100mg; 400mg
Market StatusPrescription
CompanyWockhardt; Teva Pharms; Fresenius Kabi Usa; Hospira; Gland Pharma; Mylan Institutional; Apotex; Hikma Farmaceutica; Taro; Zydus Pharms Usa; Sandoz; Mylan; Murty Pharms; Akorn; Barr

5 of 6  
Drug NameNexterone
PubMed HealthAmiodarone
Drug ClassesAntiarrhythmic, Group III
Drug LabelNEXTERONE contains amiodarone HCl (C25H29I2NO3HCl), a class III antiarrhythmic drug. Amiodarone HCl is (2-butyl-3-benzo-furanyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone hydrochloride.Amiodarone HCl has the following structural formul...
Active IngredientAmiodarone hydrochloride
Dosage FormInjectable
RouteInjection
Strength360mg/200ml (1.8mg/ml); 150mg/100ml (1.5mg/ml); 50mg/ml
Market StatusPrescription
CompanyBaxter Hlthcare

6 of 6  
Drug NamePacerone
Drug LabelPacerone (amiodarone hydrochloride) Tablets are a member of a class of antiarrhythmic drugs with predominantly Class III (Vaughan Williams classification) effects, available for oral administration as light yellow, scored tablets. Each tablet fo...
Active IngredientAmiodarone hydrochloride
Dosage FormTablet
RouteOral
Strength200mg; 100mg
Market StatusPrescription
CompanyUpsher Smith

4.2 Therapeutic Uses

Anti-Arrhythmia Agents; Enzyme Inhibitors; Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Anti-arrhythmic class III

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 85


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.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 95


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.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 95


Amiodarone has been used in a limited number of patients for the management of chronic stable angina pectoris.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1511


4.3 Drug Warning

Pulmonary toxicity, which is potentially fatal, is the most severe adverse effect associated with oral amiodarone therapy. Amiodarone induced pulmonary toxicity may result from pulmonary interstitial pneumonitis (or alveolitis) or from hypersensitivity pneumonitis. Clinically apparent interstitial pneumonitis (or alveolitis), hypersensitivity pneumonitis, and pulmonary fibrosis have occurred in up to 10-17% of patients with ventricular arrhythmias receiving amiodarone hydrochloride therapy at oral dosages of about 400 mg daily, and an abnormal diffusion capacity without symptoms occurs in a much higher percentage of patients. ... Amiodarone induced pulmonary toxicity has been fatal in about 10% of cases. Rarely, amiodarone has been associated with exacerbation of bronchial asthma, possibly because of its antiadrenergic effects in at least one patient receiving aminodarone. Hemoptysis was reported.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1513


Amiodarone induced peripheral neuropathy ... is usually symmetrical and involves all four limbs; the neurologic deficit is usually more marked in the lower limbs than in the upper limbs. Signs and symptoms may include distal sensory loss, sensory ataxia, loss of vibratory sensation, paresthesia, and/or decreased tendon reflexes. Proximal muscle weakness may also be present. Nerve biopsies in patients with amiodarone induced peripheral neuropathy have demonstrated complete loss of a large myelinated fibers, marked reduction of small myelinated and unmyelinated axons, and evidence of lysosomal inclusion bodies within Schwann cells. Nerve conduction studies have demonstrated normal or reduced nerve conduction velocities.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1514


Amiodarone induced hypothyroidism has been reported in about 2-4% of patients receiving oral drug therapy in most clinical studies, although this effect may occur more frequently. Limited data suggest that hypothyroidism may be more likely to occur in females and in patients with a prior history of thyroid dysfunction.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1514


Arrhythmogenic effects associated with amiodarone have occurred in approximately 2-5% of patients and have included progression of ventricular tachycardia to ventricular fibrillation, sustained ventricular tachycardia, increased resistance to cardioversion, atrial fibrillation, nodal arrhythmia, and atypical ventricular tachycardia (torsade de pointes). Transient exacerbation of preexisting cardiac arrhythmias with subsequent control during continued therapy has also been reported. ... Acceleration of ventricular rate was reported in a patient receiving IV amiodarone for the treatment of atrial fibrillation associated with Wolff-Parkinson-White syndrome.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1514


For more Drug Warnings (Complete) data for AMIODARONE HYDROCHLORIDE (28 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Cytochrome P-450 CYP1A2 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)


Cytochrome P-450 CYP3A Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)


Sodium Channel Blockers

A class of drugs that act by inhibition of sodium influx through cell membranes. Blockade of sodium channels slows the rate and amplitude of initial rapid depolarization, reduces cell excitability, and reduces conduction velocity. (See all compounds classified as Sodium Channel Blockers.)


Potassium Channel Blockers

A class of drugs that act by inhibition of potassium efflux through cell membranes. Blockade of potassium channels prolongs the duration of ACTION POTENTIALS. They are used as ANTI-ARRHYTHMIA AGENTS and VASODILATOR AGENTS. (See all compounds classified as Potassium Channel Blockers.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Cytochrome P-450 CYP2C9 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2C9. (See all compounds classified as Cytochrome P-450 CYP2C9 Inhibitors.)


Cytochrome P-450 CYP2D6 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2D6. (See all compounds classified as Cytochrome P-450 CYP2D6 Inhibitors.)


Anti-Arrhythmia Agents

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. (See all compounds classified as Anti-Arrhythmia Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cytochrome P450 1A2 Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Antiarrhythmic [EPC]
5.3 Absorption, Distribution and Excretion

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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1522


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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1522


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%.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1521


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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1521


For more Absorption, Distribution and Excretion (Complete) data for AMIODARONE HYDROCHLORIDE (11 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

The drug appears to be extensively metabolized, probably in the liver and possibly in the intestinal lumen and/or GI mucosa, to at least one major metabolite. The major metabolite, N-desethylamiodarone, is formed by N-deethylation. Although not clearly established, limited data in animals indicate that the desethyl metabolite may possess some antiarrhythmic activity. ... A minor metabolite of amiodarone, di-N-desethylamiodarone, has been identified in animals following chronic administration of the drug. Amiodarone and N-desethylamiodarone may undergo deiodination to form deiodoamiodarone and deiodo-N-desethylamiodarone, respectively; iodine (in the form of iodide); and possibly other iodine containing metabolites. It is not known whether deiodinated metabolites are pharmacologically active.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 835


Amiodarone undergoes hepatic metabolism by cytochrome P450 3A4 to desethyl-amiodarone.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 956


5.5 Biological Half-Life

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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1522


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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1522


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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1522


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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1522


5.6 Mechanism of Action

Amiodarone prolongs the action potential duration of myocardial cells without altering the resting membrane potential. Consequently the drug alters repolarization (QT prolongation) without affecting spontaneous (phase 4) depolarization. Since neither class I nor class II antiarrhythmic drugs possess both these properties, amiodarone is classified as a class III antiarrhythmic agent. The effect of amiodarone on thyroid metabolism remains unclear but probably involves an intracellular rather than a central or peripheral action.

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 529


Although several investigators have suggested that the myocardial effects observed during chronic amiodarone therapy are comparable to those associated with hypothyroidism and may be related to competitive inhibition of sodium-potassium-activated adenosine triphosphatase (Na+ -K+ -ATPase) activity, other data suggest that amiodarone's effects on thyroid function contribute minimally, if at all, to the overall electrophysiologic effects of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1520


The drug also appears to inhibit transmembrane influx of extracellular sodium ions via fast sodium channels, as indicated by a decrease in the maximal rate of depolarization of phase O of the action potential. Like class I antiarrhythmic agents, amiodarone is believed to combine with fast sodium channels in their inactive state and thereby inhibit recovery after repolarization in a time- and voltage-dependent manner which is associated with subsequent dissociation of the drug from the sodium channels. Amiodarone appears to have little affinity for activated fast sodium channels.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1520


Amiodarone has mild negative inotropic effect that is more prominent with intravenous than with oral administration but that usually does not depress left ventrical function. Amiodarone causes coronary and peripheral vasodialation and, therefore, decrease peripheral vascular resistance but only causes hypotension in large doses.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 89


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06-Jan-2021
20-Jul-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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