KEGG   DRUG: D08459Help
Entry
D08459                      Drug                                   

Name
Quinidine phenylethylbarbiturate;
Quinidine 5-ethyl 5-phenyl barbiturate;
Natisedine (TN)
Formula
C20H24N2O2. C12H12N2O3
Exact mass
556.2686
Mol weight
556.652
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Antiarrhythmic;
Antiprotozoal, antimalarial
Remark
ATC code: 
Comment
Target of Quinidine is voltage-gated sodium channel
Target
voltage-gated sodium channel (SCN1A) blocker [HSA:6323] [KO:K04833];
voltage-gated sodium channel (SCN2A) blocker [HSA:6326] [KO:K04834];
voltage-gated sodium channel (SCN3A) blocker [HSA:6328] [KO:K04836];
voltage-gated sodium channel (SCN4A) blocker [HSA:6329] [KO:K04837];
voltage-gated sodium channel (SCN5A) blocker [HSA:6331] [KO:K04838];
voltage-gated sodium channel (SCN8A) blocker [HSA:6334] [KO:K04840];
voltage-gated sodium channel (SCN9A) blocker [HSA:6335] [KO:K04841]
Metabolism
Enzyme: CYP3A4 [HSA:1576]
Transporter: SLC22A1 [HSA:6580], SLC22A3 [HSA:6581]
Interaction
Genomic biomarker: CYP2D6 [HSA:1565]
CYP inhibition: CYP2D6 [HSA:1565]
Transporter inhibition: SLC22A2 [HSA:6582], SLC22A1 [HSA:6580], SLC47A1 [HSA:55244], SCL47A2 [HSA:146802], ABCB1 [HSA:5243]
Drug interaction
Structure map
Quinolines
Antiarrhythmic drugs
Sodium channel blocking drugs
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 C CARDIOVASCULAR SYSTEM
  C01 CARDIAC THERAPY
   C01B ANTIARRHYTHMICS, CLASS I AND III
    C01BA Antiarrhythmics, class Ia
     C01BA01 Quinidine
      D08459  Quinidine phenylethylbarbiturate
USP drug classification [BR:br08302]
 Cardiovascular Agents
  Antiarrhythmics
   Quinidine
    D08459  Quinidine phenylethylbarbiturate
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel (SCN1A) [HSA:6323] [KO:K04833]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
    voltage-gated sodium channel (SCN2A) [HSA:6326] [KO:K04834]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
    voltage-gated sodium channel (SCN3A) [HSA:6328] [KO:K04836]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
    voltage-gated sodium channel (SCN4A) [HSA:6329] [KO:K04837]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
    voltage-gated sodium channel (SCN5A) [HSA:6331] [KO:K04838]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
    voltage-gated sodium channel (SCN8A) [HSA:6334] [KO:K04840]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
    voltage-gated sodium channel (SCN9A) [HSA:6335] [KO:K04841]
     Quinidine [ATC:C01BA01]
      D08459  Quinidine phenylethylbarbiturate
BRITE hierarchy
Other DBs
CAS: 
1400-48-2
PubChem: 
LigandBox: 
KCF data Show

ATOM        41
            1   C1z C    27.8054  -23.3458
            2   C8y C    28.9932  -22.6471
            3   C5x C    26.5478  -22.6471
            4   C5x C    27.8054  -24.7432
            5   C1b C    28.9932  -24.0445
            6   C8x C    30.1810  -23.2759
            7   C8x C    28.9932  -21.2497
            8   N1x N    25.3600  -23.3458
            9   O5x O    26.5478  -21.2497
            10  N1x N    26.5478  -25.4419
            11  O5x O    28.9932  -25.4419
            12  C1a C    30.3906  -24.0445
            13  C8x C    31.4386  -22.5772
            14  C8x C    30.1810  -20.4811
            15  C5x C    25.3600  -24.7432
            16  C8x C    31.4386  -21.1798
            17  O5x O    24.1722  -25.4419
            18  C8y C    17.6045  -25.9310
            19  C8y C    18.8621  -25.2323
            20  C8y C    17.6045  -27.3283
            21  C8x C    16.4167  -25.2323
            22  C1c C    18.8621  -23.8349
            23  C8x C    20.0499  -25.9310
            24  C8x C    16.4167  -28.0270
            25  N5x N    18.7923  -28.0270
            26  C8y C    15.1590  -25.9310
            27  C1y C    20.0499  -23.1362
            28  O1a O    17.6045  -23.1362
            29  C8x C    20.0499  -27.3283
            30  C8x C    15.1590  -27.3283
            31  O2a O    13.9713  -25.2323
            32  N1y N    21.5172  -22.2279
            33  C1x C    19.3512  -22.0881
            34  C1a C    13.9713  -23.8349
            35  C1x C    21.5172  -20.9702
            36  C1x C    22.9844  -23.0663
            37  C1y C    20.7486  -21.2497
            38  C1y C    20.7486  -20.2715
            39  C1x C    22.2857  -21.9484
            40  C2b C    20.1896  -18.9440
            41  C2a C    21.0979  -17.8261
BOND        45
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     1   5 1
            5     2   6 2
            6     2   7 1
            7     3   8 1
            8     3   9 2
            9     4  10 1
            10    4  11 2
            11    5  12 1
            12    6  13 1
            13    7  14 2
            14    8  15 1
            15   13  16 2
            16   15  17 2
            17   10  15 1
            18   14  16 1
            19   18  19 1
            20   18  20 1
            21   18  21 2
            22   19  22 1
            23   19  23 2
            24   20  24 2
            25   20  25 1
            26   21  26 1
            27   22  27 1
            28   22  28 1 #Down
            29   23  29 1
            30   24  30 1
            31   26  31 1
            32   27  32 1
            33   27  33 1
            34   31  34 1
            35   32  35 1
            36   32  36 1
            37   33  37 1
            38   35  38 1
            39   36  39 1
            40   38  40 1 #Up
            41   40  41 2
            42   25  29 2
            43   26  30 2
            44   37  38 1
            45   37  39 1

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