KEGG   DRUG: D02910Help
Entry
D02910                      Drug                                   

Name
Amiodarone (USAN/INN)
Formula
C25H29I2NO3
Exact mass
645.0237
Mol weight
645.3116
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Cardiac depressant [anti-arrhythmic, ventricular] [DS:H00293]
Remark
Same as: 
ATC code: 
Drug group: 
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
hsa04261  Adrenergic signaling in cardiomyocytes
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
Structure map
Antiarrhythmic drugs
Sodium channel blocking drugs
Potassium channel blocking and opening drugs
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
      D02910  Amiodarone (USAN/INN)
USP drug classification [BR:br08302]
 Cardiovascular Agents
  Antiarrhythmics
   Amiodarone
    D02910  Amiodarone (USAN/INN)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel
     Amiodarone
      D02910  Amiodarone (USAN/INN)
   K+ channel, KCND, Kv4.x (Shal)
    voltage-gated potassium channel (KCND3)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
   K+ channel, KCNQ, Kv7.x (KQT-like)
    voltage-gated potassium channel (KCNQ1)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
   K+ channel, KCNH, Kv10-12.x (Ether-a-go-go)
    voltage-gated potassium channel (KCNH2)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
  Related to voltage-gated cation channels
   Inward rectifier channel (Kir)
    potassium inwardly-rectifying channel (KCNJ3)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
    potassium inwardly-rectifying channel (KCNJ5)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
    potassium inwardly-rectifying channel (KCNJ11)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
    potassium inwardly-rectifying channel (KCNJ12)
     Amiodarone
      D02910  Amiodarone (USAN/INN)
 Enzymes
  Hydrolases
   P-glycoprotein
    Amiodarone
     D02910  Amiodarone (USAN/INN)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP1A2
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP2C9
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP2D6
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP3A4
   Amiodarone
    D02910  Amiodarone (USAN/INN)
 Inhbitors
  CYP1A2
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP2C9
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP2D6
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP3A4
   Amiodarone
    D02910  Amiodarone (USAN/INN)
  CYP3A
   Amiodarone
    D02910  Amiodarone (USAN/INN)
BRITE hierarchy
Other DBs
CAS: 
1951-25-3
PubChem: 
DrugBank: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        31
            1   C8x C    17.7800  -21.6300
            2   C8x C    17.7800  -23.0300
            3   C8x C    18.9700  -23.7300
            4   C8y C    20.2300  -23.0300
            5   C8y C    20.2300  -21.6300
            6   C8x C    18.9700  -20.8600
            7   O2x O    21.5600  -23.4500
            8   C8y C    22.4000  -22.3300
            9   C8y C    21.5600  -21.1400
            10  C5a C    21.5600  -19.7400
            11  C8y C    22.7500  -19.0400
            12  O5a O    20.3700  -19.0400
            13  C8x C    24.0100  -19.7400
            14  C8y C    25.2000  -19.0400
            15  C8y C    25.2000  -17.6400
            16  C8y C    24.0100  -16.9400
            17  C8x C    22.7500  -17.6400
            18  O2a O    26.4600  -16.9400
            19  X   I    26.4600  -19.7400
            20  X   I    24.0100  -15.5400
            21  C1b C    27.6500  -17.6400
            22  C1b C    28.8400  -16.9400
            23  N1c N    30.0300  -17.6400
            24  C1b C    31.2200  -16.9400
            25  C1b C    30.0300  -19.0400
            26  C1a C    31.2200  -19.7400
            27  C1a C    32.4100  -17.6400
            28  C1b C    23.7300  -22.3300
            29  C1b C    24.4300  -23.5200
            30  C1b C    25.8300  -23.5200
            31  C1a C    26.5300  -24.7100
BOND        33
            1     1   2 2
            2     2   3 1
            3     3   4 2
            4     4   5 1
            5     5   6 2
            6     1   6 1
            7     4   7 1
            8     7   8 1
            9     8   9 2
            10    5   9 1
            11    9  10 1
            12   10  11 1
            13   10  12 2
            14   11  13 2
            15   13  14 1
            16   14  15 2
            17   15  16 1
            18   16  17 2
            19   11  17 1
            20   15  18 1
            21   14  19 1
            22   16  20 1
            23   18  21 1
            24   21  22 1
            25   22  23 1
            26   23  24 1
            27   23  25 1
            28   25  26 1
            29   24  27 1
            30    8  28 1
            31   28  29 1
            32   29  30 1
            33   30  31 1

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