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Entry
D00512                      Drug                                   

Name
Phenytoin (JP16/USP/INN);
Dilantin (TN)
Product
  Generic
Formula
C15H12N2O2
Exact mass
252.0899
Mol weight
252.268
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Anticonvulsant [DS:H00808]
Remark
Same as: 
Therapeutic category: 
ATC code: 
Drug group: 
Comment
Hydantoins
There is a strong association between the risk of developing SJS/TEN with Phenytoin treatment and the presence of an inherited variant of the HLA-B gene, HLA-B*1502.
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: CYP2C9 [HSA:1559], CYP2C19 [HSA:1557], CYP3A [HSA:1576 1577 1551], CYP2B6 [HSA:1555]
Interaction
Genomic biomarker: HLA-B [HSA:3106]
CYP induction: CYP3A [HSA:1576 1577 1551], CYP1A2 [HSA:1544]
Transporter induction: ABCB1 [HSA:5243]
Drug interaction
Structure map
Anticonvulsants
Sodium channel blocking drugs
Other map
Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N03 ANTIEPILEPTICS
   N03A ANTIEPILEPTICS
    N03AB Hydantoin derivatives
     N03AB02 Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
USP drug classification [BR:br08302]
 Anticonvulsants
  Sodium Channel Agents
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 1  Agents affecting nervous system and sensory organs
  11  Agents affecting central nervous system
   113  Antiepileptics
    1132  Hydantoins
     D00512  Phenytoin (JP16/USP/INN)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel (SCN1A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
    voltage-gated sodium channel (SCN2A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
    voltage-gated sodium channel (SCN3A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
    voltage-gated sodium channel (SCN4A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
    voltage-gated sodium channel (SCN5A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
    voltage-gated sodium channel (SCN8A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
    voltage-gated sodium channel (SCN9A)
     Phenytoin
      D00512  Phenytoin (JP16/USP/INN)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP2B6
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
  CYP2C9
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
  CYP2C19
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
  CYP3A
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
 Inducers
  CYP1A2
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
  CYP3A
   Phenytoin
    D00512  Phenytoin (JP16/USP/INN)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00512  Phenytoin
  D00512  Phenytoin powder
  D00512  Phenytoin tablets
BRITE hierarchy
Other DBs
CAS: 
57-41-0
PubChem: 
DrugBank: 
LigandBox: 
NIKKAJI: 
LinkDB All DBs
KCF data Show

ATOM        19
            1   C1z C    21.1928  -17.0796
            2   N1x N    21.6897  -15.8145
            3   C2y C    20.5391  -14.9868
            4   N2x N    19.3790  -15.7706
            5   C5x C    19.8336  -17.0686
            6   O1a O    20.5108  -13.5697
            7   O5x O    19.0059  -18.2260
            8   C8y C    22.5928  -17.0796
            9   C8x C    23.2971  -18.2998
            10  C8x C    24.6971  -18.2999
            11  C8x C    25.3972  -17.0875
            12  C8x C    24.6928  -15.8673
            13  C8x C    23.2928  -15.8672
            14  C8y C    21.1928  -18.4796
            15  C8x C    19.9931  -19.1723
            16  C8x C    19.9932  -20.5723
            17  C8x C    21.2057  -21.2722
            18  C8x C    22.4053  -20.5795
            19  C8x C    22.4052  -19.1795
BOND        21
            1     1   2 1
            2     2   3 1
            3     3   4 2
            4     4   5 1
            5     1   5 1
            6     3   6 1
            7     5   7 2
            8     1   8 1
            9     8   9 2
            10    9  10 1
            11   10  11 2
            12   11  12 1
            13   12  13 2
            14    8  13 1
            15    1  14 1
            16   14  15 2
            17   15  16 1
            18   16  17 2
            19   17  18 1
            20   18  19 2
            21   14  19 1

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