KEGG   DRUG: D02356Help
Entry
D02356                      Drug                                   

Name
Verapamil (USAN/INN)
Formula
C27H38N2O4
Exact mass
454.2832
Mol weight
454.6016
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Vasodilator [coronary]
Remark
Same as: 
ATC code: 
Drug group: 
Comment
Class IV antiarrhythmic agent
Target
calcium channel L type blocker [HSA:775 776 778 779] [KO:K04850 K04851 K04853 K04857];
potassium inwardly-rectifying channel (KCNJ6) blocker [HSA:3763] [KO:K05000];
voltage-gated potassium channel (KCNA10) blocker [HSA:3744] [KO:K04881];
voltage-gated potassium channel (KCNA3) blocker [HSA:3738] [KO:K04876];
voltage-gated potassium channel (KCNA7) blocker [HSA:3743] [KO:K04880];
voltage-gated potassium channel (KCNC2) blocker [HSA:3747] [KO:K04888]
  Pathway
hsa04010  MAPK signaling pathway
hsa04020  Calcium signaling pathway
hsa04260  Cardiac muscle contraction
hsa04270  Vascular smooth muscle contraction  
 
Metabolism
Enzyme: CYP3A4 [HSA:1576], CYP1A2 [HSA:1544], CYP3A5 [HSA:1577], CYP3A7 [HSA:1551]
Interaction
CYP inhibition: CYP1A2 [HSA:1544], CYP2D6 [HSA:1565], CYP3A4 [HSA:1576], CYP3A5 [HSA:1577], CYP3A7 [HSA:1551]
Transporter inhibition: ABCB1 [HSA:5243], ABCB4 [HSA:5244], SLC22A3 [HSA:6581]
Drug interaction
Structure map
Calcium channel blocking drugs
Antiarrhythmic drugs
Antimigraines
Other map
Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 C CARDIOVASCULAR SYSTEM
  C08 CALCIUM CHANNEL BLOCKERS
   C08D SELECTIVE CALCIUM CHANNEL BLOCKERS WITH DIRECT CARDIAC EFFECTS
    C08DA Phenylalkylamine derivatives
     C08DA01 Verapamil
      D02356  Verapamil (USAN/INN)
USP drug classification [BR:br08302]
 Cardiovascular Agents
  Calcium Channel Blocking Agents
   Verapamil
    D02356  Verapamil (USAN/INN)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Ca2+ channel, CACN alpha-1, CaVx.x
    calcium channel L type
     Verapamil
      D02356  Verapamil (USAN/INN)
   K+ channel, KCNA, Kv1.x (Shaker)
    voltage-gated potassium channel (KCNA3)
     Verapamil
      D02356  Verapamil (USAN/INN)
    voltage-gated potassium channel (KCNA7)
     Verapamil
      D02356  Verapamil (USAN/INN)
    voltage-gated potassium channel (KCNA10)
     Verapamil
      D02356  Verapamil (USAN/INN)
   K+ channel, KCNC, Kv3.x (Shaw)
    voltage-gated potassium channel (KCNC2)
     Verapamil
      D02356  Verapamil (USAN/INN)
  Related to voltage-gated cation channels
   Inward rectifier channel (Kir)
    potassium inwardly-rectifying channel (KCNJ6)
     Verapamil
      D02356  Verapamil (USAN/INN)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP1A2
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A4
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A5
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A7
   Verapamil
    D02356  Verapamil (USAN/INN)
 Inhbitors
  CYP1A2
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP2D6
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A4
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A5
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A7
   Verapamil
    D02356  Verapamil (USAN/INN)
  CYP3A
   Verapamil
    D02356  Verapamil (USAN/INN)
BRITE hierarchy
Other DBs
CAS: 
52-53-9
PubChem: 
DrugBank: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        33
            1   C1d C    21.2293  -18.3108
            2   C8y C    20.0265  -19.0115
            3   C1b C    22.4436  -19.0056
            4   C1c C    21.2001  -16.9563
            5   C8x C    18.8122  -18.3108
            6   C8x C    20.0265  -20.4125
            7   C1b C    23.6580  -18.3049
            8   C1a C    22.4146  -16.2441
            9   C1a C    19.9916  -16.2557
            10  C8y C    17.5979  -19.0115
            11  C8x C    18.8122  -21.1190
            12  C1b C    24.8665  -18.9939
            13  C8y C    17.5979  -20.4125
            14  O2a O    16.3778  -18.3108
            15  N1c N    26.0808  -18.2991
            16  O2a O    16.3778  -21.1190
            17  C1a C    15.1634  -19.0115
            18  C1b C    27.2951  -18.9881
            19  C1a C    26.0808  -16.8455
            20  C1a C    15.1634  -20.4183
            21  C1b C    28.5094  -18.2932
            22  C8y C    29.7120  -18.9822
            23  C8x C    30.9265  -18.2815
            24  C8x C    29.6480  -20.3775
            25  C8y C    32.1351  -18.9764
            26  C8x C    30.9322  -21.0781
            27  C8y C    32.1409  -20.3716
            28  O2a O    33.3493  -18.2700
            29  O2a O    33.3610  -21.0722
            30  C1a C    34.5695  -18.9647
            31  C1a C    34.5752  -20.3658
            32  C3b C    21.2293  -19.7108
            33  N3a N    21.2293  -21.1108
BOND        34
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     2   5 2
            5     2   6 1
            6     3   7 1
            7     4   8 1
            8     4   9 1
            9     5  10 1
            10    6  11 2
            11    7  12 1
            12   10  13 2
            13   10  14 1
            14   12  15 1
            15   13  16 1
            16   14  17 1
            17   15  18 1
            18   15  19 1
            19   16  20 1
            20   18  21 1
            21   21  22 1
            22   22  23 1
            23   22  24 2
            24   23  25 2
            25   24  26 1
            26   25  27 1
            27   25  28 1
            28   27  29 1
            29   28  30 1
            30   29  31 1
            31   11  13 1
            32   26  27 2
            33    1  32 1
            34   32  33 3

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