KEGG   DRUG: AmiodaroneHelp
Entry
D02910                      Drug                                   

Name
Amiodarone (USAN/INN)
Formula
C25H29I2NO3
Exact mass
645.0237
Mol weight
645.3116
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  CYP3A4 substrate
Cyp inhibitor
 DG01634  CYP1A2 inhibitor
 DG01643  CYP2C9 inhibitor
 DG01645  CYP2D6 inhibitor
 DG01522  CYP3A4 inhibitor
Transporter inhibitor
 DG01622  P-glycoprotein inhibitor
Remark
Same as: 
ATC code: 
Chemical group: 
Activity
Antiarrhythmic, Potassium channel blocker
Comment
Class III antiarrhythmic agent
Treatment of ventricular arrhythmia
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];
voltage-gated sodium channel;
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
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]
 CYP 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)
 CYP 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)
 Transporter inhibitors
  ABCB1
   Amiodarone
    D02910  Amiodarone (USAN/INN)
BRITE hierarchy
Other DBs
CAS: 
1951-25-3
PubChem: 
DrugBank: 
PDB-CCD: 
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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