KEGG   DRUG: D00636Help
Entry
D00636                      Drug                                   
Name
Amiodarone hydrochloride (JP16/USAN);
Ancaron (TN);
Cordarone (TN)
Product
  Generic
AMIODARONE HYDROCHLORIDE (APP Pharmaceuticals), AMIODARONE HYDROCHLORIDE (American Health Packaging), PACERONE (Aphena Pharma Solutions - Tennessee), AMIODARONE HYDROCHLORIDE (Bedford Laboratories), AMIODARONE HYDROCHLORIDE (Bedford Laboratories), AMIODARONE HYDROCHLORIDE (Cadila Healthcare Limited), AMIODARONE HYDROCHLORIDE (Cardinal Health), AMIODARONE HYDROCHLORIDE (Cardinal Health), PACERONE (Cardinal Health), AMIODARONE HYDROCHLORIDE (Eon Labs), AMIODARONE HYDROCHLORIDE (General Injectables & Vaccines), AMIODARONE HYDROCHLORIDE (General Injectables & Vaccines), AMIODARONE HYDROCHLORIDE (Golden State Medical Supply), AMIODARONE HYDROCHLORIDE (Hospira), AMIODARONE HCL (Libertas Pharma), AMIODARONE HYDROCHLORIDE (McKesson Contract Packaging), AMIODARONE HYDROCHLORIDE (McKesson Packaging Services 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 (Rebel Distributors Corp), AMIODARONE HYDROCHLORIDE (Sagent Pharmaceuticals), AMIODARONE HYDROCHLORIDE (Taro Pharmaceuticals U.S.A.), AMIODARONE HYDROCHLORIDE (Teva Pharmaceuticals USA), PACERONE (Upsher-Smith Laboratories), PACERONE (Upsher-Smith Laboratories), AMIODARONE HYDROCHLORIDE (West-ward Pharmaceutical 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
Activity
Antiarrhythmic [DS:H00293]
Remark
Therapeutic category: 
ATC code: 
Comment
Class III antiarrhythmic agent
Target
voltage-gated potassium channel (KCND3) blocker [HSA:3752] [KO:K04893];
voltage-gated potassium channel (KCNH2) blocker [HSA:3757] [KO:K04905];
voltage-gated potassium channel (KCNQ1) blocker [HSA:3784] [KO:K04926];
potassium inwardly-rectifying channel (KCNJ3) [HSA:3760] [KO:K04997];
potassium inwardly-rectifying channel (KCNJ5) [HSA:3762] [KO:K04999];
potassium inwardly-rectifying channel (KCNJ8) [HSA:3764] [KO:K05001];
potassium inwardly-rectifying channel (KCNJ11) [HSA:3767] [KO:K05004];
potassium inwardly-rectifying channel (KCNJ12) [HSA:3768] [KO:K05005];
voltage-gated sodium channel blocker;
P-glycoprotein inhibitor [HSA:5243] [KO:K05658];
alpha1-adrenergic receptor agonist [HSA:146 147 148] [KO:K04137 K04136 K04135];
beta1-adrenergic receptor agonist [HSA:153] [KO:K04141]
  Pathway
hsa04020  Calcium signaling pathway
hsa04080  Neuroactive ligand-receptor interaction
hsa04270  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
Pathway map
Autoimmune thyroid disease
Structure map
Antiarrhythmic drugs
Sodium channel blocking drugs
Potassium channel blocking and opening drugs
Brite
Therapeutic category of drugs in Japan [BR:br08301]
 2  Agents affecting individual organs
  21  Cardiovascular agents
   212  Antiarrhythmic agents
    2129  Others
     D00636  Amiodarone hydrochloride (JP16/USAN)
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 (JP16/USAN)
USP drug classification [BR:br08302]
 Cardiovascular Agents
  Antiarrhythmics
   Amiodarone
    D00636  Amiodarone hydrochloride (JP16/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 [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
   K+ channel, KCND, Kv4.x (Shal)
    voltage-gated potassium channel (KCND3) [HSA:3752] [KO:K04893]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
   K+ channel, KCNQ, Kv7.x (KQT-like)
    voltage-gated potassium channel (KCNQ1) [HSA:3784] [KO:K04926]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
   K+ channel, KCNH, Kv10-12.x (Ether-a-go-go)
    voltage-gated potassium channel (KCNH2) [HSA:3757] [KO:K04905]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
  Related to voltage-gated cation channels
   Inward rectifier channel (Kir)
    potassium inwardly-rectifying channel (KCNJ3) [HSA:3760] [KO:K04997]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
    potassium inwardly-rectifying channel (KCNJ5) [HSA:3762] [KO:K04999]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
    potassium inwardly-rectifying channel (KCNJ11) [HSA:3767] [KO:K05004]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
    potassium inwardly-rectifying channel (KCNJ12) [HSA:3768] [KO:K05005]
     Amiodarone [ATC:C01BD01]
      D00636  Amiodarone hydrochloride (JP16)
 Enzymes
  Hydrolases
   P-glycoprotein [HSA:5243] [KO:K05658]
    Amiodarone [ATC:C01BD01]
     D00636  Amiodarone hydrochloride (JP16)
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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