KEGG   DRUG: Amiodarone hydrochlorideHelp
Entry
D00636                      Drug                                   

Name
Amiodarone hydrochloride (JP17/USAN);
Ancaron (TN);
Cordarone (TN)
Product
  Generic
AMIODARONE HYDROCHLORIDE (A-S Medication Solutions), AMIODARONE HYDROCHLORIDE (A-S Medication Solutions), AMIODARONE HYDROCHLORIDE (A-S Medication Solutions), AMIODARONE HYDROCHLORIDE (APOTEX Corp), AMIODARONE HYDROCHLORIDE (APP Pharmaceuticals), AMIODARONE HYDROCHLORIDE (American Health Packaging), PACERONE (Aphena Pharma Solutions - Tennessee), AMIODARONE HYDROCHLORIDE (Aurobindo Pharma Limited), AMIODARONE HYDROCHLORIDE (AvKARE), PACERONE (Avera McKennan Hospital), AMIODARONE HYDROCHLORIDE (Cadila Healthcare Limited), AMIODARONE HYDROCHLORIDE (Cardinal Health), PACERONE (Cardinal Health), AMIODARONE HYDROCHLORIDE (Cardinal Health), AMIODARONE HYDROCHLORIDE (Eon Labs), AMIODARONE HYDROCHLORIDE (General Injectables & Vaccines), AMIODARONE HYDROCHLORIDE (General Injectables & Vaccines), AMIODARONE HYDROCHLORIDE (General Injectables and Vaccines), AMIODARONE HYDROCHLORIDE (Golden State Medical Supply), AMIODARONE HYDROCHLORIDE (Hospira), AMIODARONE HYDROCHLORIDE (Hospira), AMIODARONE HYDROCHLORIDE (Lake Erie Medical DBA Quality Care Products LLC), AMIODARONE HYDROCHLORIDE (Major Pharmaceuticals), AMIODARONE HCL (Mayne Pharma), AMIODARONE HYDROCHLORIDE (McKesson Contract Packaging), AMIODARONE HYDROCHLORIDE (McKesson Packaging a business unit of McKesson Corporation), AMIODARONE HYDROCHLORIDE (Mylan Institutional), AMIODARONE HYDROCHLORIDE (Mylan Institutional LLC), AMIODARONE HYDROCHLORIDE (NCS HealthCare of KY), AMIODARONE HYDROCHLORIDE (Physicians Total Care), AMIODARONE HYDROCHLORIDE (Physicians Total Care), PACERONE (Physicians Total Care), AMIODARONE HYDROCHLORIDE (REMEDYREPACK), AMIODARONE HYDROCHLORIDE (REMEDYREPACK), AMIODARONE HYDROCHLORIDE (REMEDYREPACK), AMIODARONE HYDROCHLORIDE (REMEDYREPACK), AMIODARONE HYDROCHLORIDE (Rebel Distributors Corp), PACERONE (RxPak Division of McKesson Corporation), AMIODARONE HYDROCHLORIDE (Sagent Pharmaceuticals), AMIODARONE HYDROCHLORIDE (State of Florida DOH Central Pharmacy), AMIODARONE HYDROCHLORIDE (Taro Pharmaceuticals U.S.A.), AMIODARONE HYDROCHLORIDE (Teva Pharmaceuticals USA), PACERONE (Upsher-Smith Laboratories), PACERONE (Upsher-Smith Laboratories), AMIODARONE HYDROCHLORIDE (West-Ward Pharmaceuticals Corp), AMIODARONE HYDROCHLORIDE (Wockhardt Limited), AMIODARONE HYDROCHLORIDE (Zydus Pharmaceuticals (USA))
  Other
Formula
C25H29I2NO3. HCl
Exact mass
681.0004
Mol weight
681.7725
Structure
Mol fileKCF fileDB searchJmolKegDraw
Class
Cardiovascular agent
 DG01456  Adrenergic receptor agonist
  DG01455  beta-Adrenergic receptor agonist
   DG01451  beta1-Adrenergic receptor agonist
 DG01653  Antiarrhythmics
  DG01648  Class III antiarrhythmic agent
Cyp substrate
 DG01892  CYP1A2 substrate
 DG01642  CYP2C9 substrate
 DG01644  CYP2D6 substrate
 DG01633  CYP3A substrate
Cyp inhibitor
 DG01634  CYP1A2 inhibitor
 DG01643  CYP2C9 inhibitor
 DG01645  CYP2D6 inhibitor
 DG01522  CYP3A4 inhibitor
Transporter inhibitor
 DG01622  P-glycoprotein inhibitor
Remark
Therapeutic category: 
ATC code: 
Chemical group: 
Activity
Antiarrhythmic, Potassium channel blocker
Comment
Class III anti arrhythmic agent
Amiodarone works by blocking potassium, sodium, and calcium channels.
Target
KCND3 [HSA:3752] [KO:K04893];
KCNH2 [HSA:3757] [KO:K04905];
KCNQ1 [HSA:3784] [KO:K04926];
KCNJ3 [HSA:3760] [KO:K04997];
KCNJ5 [HSA:3762] [KO:K04999];
KCNJ8 [HSA:3764] [KO:K05001];
KCNJ11 [HSA:3767] [KO:K05004];
KCNJ12 [HSA:3768] [KO:K05005];
ABCB1 (CD243) [HSA:5243] [KO:K05658];
ADRA1 [HSA:148 147 146] [KO:K04135 K04136 K04137];
ADRB1 [HSA:153] [KO:K04141]
  Pathway
Calcium signaling pathway
Neuroactive ligand-receptor interaction
Adrenergic signaling in cardiomyocytes
Vascular smooth muscle contraction
Metabolism
Enzyme: CYP3A4 [HSA:1576], CYP1A2 [HSA:1544], CYP2C9 [HSA:1559], CYP2D6 [HSA:1565]
Interaction
CYP inhibition: CYP2C9 [HSA:1559], CYP2D6 [HSA:1565], CYP3A4 [HSA:1576], CYP1A2 [HSA:1544]
Transporter inhibition: ABCB1 [HSA:5243]
Drug interaction
Structure map
Antiarrhythmic drugs
Sodium channel blocking drugs
Potassium channel blocking and opening drugs
Other map
Autoimmune thyroid disease
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 C CARDIOVASCULAR SYSTEM
  C01 CARDIAC THERAPY
   C01B ANTIARRHYTHMICS, CLASS I AND III
    C01BD Antiarrhythmics, class III
     C01BD01 Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
USP drug classification [BR:br08302]
 Cardiovascular Agents
  Antiarrhythmics
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
Therapeutic category of drugs in Japan [BR:br08301]
 2  Agents affecting individual organs
  21  Cardiovascular agents
   212  Antiarrhythmic agents
    2129  Others
     D00636  Amiodarone hydrochloride (JP17/USAN)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
   K+ channel, KCND, Kv4.x (Shal)
    voltage-gated potassium channel (KCND3)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
   K+ channel, KCNQ, Kv7.x (KQT-like)
    voltage-gated potassium channel (KCNQ1)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
   K+ channel, KCNH, Kv10-12.x (Ether-a-go-go)
    voltage-gated potassium channel (KCNH2)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
  Related to voltage-gated cation channels
   Inward rectifier channel (Kir)
    potassium inwardly-rectifying channel (KCNJ3)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
    potassium inwardly-rectifying channel (KCNJ5)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
    potassium inwardly-rectifying channel (KCNJ11)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
    potassium inwardly-rectifying channel (KCNJ12)
     Amiodarone
      D00636  Amiodarone hydrochloride (JP17/USAN)
 Enzymes
  Hydrolases
   P-glycoprotein
    Amiodarone
     D00636  Amiodarone hydrochloride (JP17/USAN)
Cytochrome P450 interactions [BR:br08309]
 CYP inhbitors
  CYP1A2
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP2C9
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP2D6
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP3A4
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP3A
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
 CYP substrates
  CYP1A2
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP2C9
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP2D6
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
  CYP3A4
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
 Transporter inhibitors
  ABCB1
   Amiodarone
    D00636  Amiodarone hydrochloride (JP17/USAN)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00636  Amiodarone hydrochloride
  D00636  Amiodarone hydrochloride tablets
Cardiovascular agents [br08364.html]
 Antiarrhythmics
  D00636
Orphan drugs in the USA [br08355.html]
 Orphan drugs in the USA
  D00636
BRITE hierarchy
Other DBs
CAS: 
19774-82-4
PubChem: 
DrugBank: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        32
            1   X   Cl   30.8700  -29.7500
            2   C8x C    16.7300  -27.2300
            3   C8x C    16.7300  -28.6300
            4   C8x C    17.9424  -29.3300
            5   C8y C    19.1549  -28.6300
            6   C8y C    19.1549  -27.2300
            7   C8x C    17.9424  -26.5300
            8   O2x O    20.4864  -29.0626
            9   C8y C    21.3093  -27.9300
            10  C8y C    20.4864  -26.7974
            11  C5a C    20.4864  -25.3974
            12  C8y C    21.7108  -24.6902
            13  O5a O    19.2971  -24.7108
            14  C8x C    22.9237  -25.3902
            15  C8y C    24.1360  -24.6900
            16  C8y C    24.1357  -23.2900
            17  C8y C    22.9229  -22.5900
            18  C8x C    21.7105  -23.2902
            19  O2a O    25.3499  -22.5887
            20  X   I    25.3678  -25.4007
            21  X   I    22.9222  -21.2104
            22  C1b C    26.5641  -23.2894
            23  C1b C    27.7419  -22.6091
            24  N1c N    28.9383  -23.2997
            25  C1b C    30.1249  -22.6143
            26  C1b C    28.9387  -24.7097
            27  C1a C    30.1297  -25.3972
            28  C1a C    31.3168  -23.3024
            29  C1b C    22.6800  -27.9300
            30  C1b C    23.3800  -29.1424
            31  C1b C    24.7798  -29.1424
            32  C1a C    25.4703  -30.3380
BOND        33
            1     2   3 2
            2     3   4 1
            3     4   5 2
            4     5   6 1
            5     6   7 2
            6     2   7 1
            7     5   8 1
            8     8   9 1
            9     9  10 2
            10    6  10 1
            11   10  11 1
            12   11  12 1
            13   11  13 2
            14   12  14 2
            15   14  15 1
            16   15  16 2
            17   16  17 1
            18   17  18 2
            19   12  18 1
            20   16  19 1
            21   15  20 1
            22   17  21 1
            23   19  22 1
            24   22  23 1
            25   23  24 1
            26   24  25 1
            27   24  26 1
            28   26  27 1
            29   25  28 1
            30    9  29 1
            31   29  30 1
            32   30  31 1
            33   31  32 1

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