KEGG   DRUG: Fosphenytoin sodiumHelp
Entry
D02096                      Drug                                   

Name
Fosphenytoin sodium (USP);
Cerebyx (TN)
Product
  Generic
Formula
C16H13N2O6P. 2Na
Exact mass
406.0307
Mol weight
406.2375
Structure
Mol fileKCF fileDB searchJmolKegDraw
Simcomp SIMCOMP
Class
Neuropsychiatric agent
 DG02031  Hydantoin antiepileptics
Cyp substrate
 DG01639  CYP2C19 substrate
Remark
ATC code: 
Chemical group: 
Activity
Anticonvulsant
Comment
Hydantoin derivative
Active form of prodrug: Phenytoin [DR:D00512]
Target
SCN1A [HSA:6323] [KO:K04833];
SCN2A [HSA:6326] [KO:K04834];
SCN3A [HSA:6328] [KO:K04836];
SCN4A [HSA:6329] [KO:K04837];
SCN5A [HSA:6331] [KO:K04838];
SCN8A [HSA:6334] [KO:K04840];
SCN9A [HSA:6335] [KO:K04841];
SCN10A [HSA:6336] [KO:K04842]
Metabolism
Enzyme: CYP2C9 [HSA:1559], CYP2C19 [HSA:1557]
Interaction
CYP induction: CYP3A4 [HSA:1576], CYP2B6 [HSA:1555]
Drug interaction
Structure map
Anticonvulsants
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N03 ANTIEPILEPTICS
   N03A ANTIEPILEPTICS
    N03AB Hydantoin derivatives
     N03AB05 Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
USP drug classification [BR:br08302]
 Anticonvulsants
  Sodium Channel Agents
   Fosphenytoin
    D02096  Fosphenytoin sodium (USP)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel (SCN1A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
    voltage-gated sodium channel (SCN2A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
    voltage-gated sodium channel (SCN3A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
    voltage-gated sodium channel (SCN4A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
    voltage-gated sodium channel (SCN5A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
    voltage-gated sodium channel (SCN8A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
    voltage-gated sodium channel (SCN9A)
     Fosphenytoin
      D02096  Fosphenytoin sodium (USP)
Cytochrome P450 interactions [BR:br08309]
 CYP inducers
  CYP2B6
   Fosphenytoin
    D02096  Fosphenytoin sodium (USP)
  CYP3A4
   Fosphenytoin
    D02096  Fosphenytoin sodium (USP)
 CYP substrates
  CYP2C9
   Fosphenytoin
    D02096  Fosphenytoin sodium (USP)
  CYP2C19
   Fosphenytoin
    D02096  Fosphenytoin sodium (USP)
Neurological agents [br08367.html]
 Antiepileptic agents
  D02096
Orphan drugs in the USA [br08355.html]
 Orphan drugs in the USA
  D02096
BRITE hierarchy
Other DBs
CAS: 
92134-98-0
PubChem: 
ChEMBL: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        27
            1   Z   Na   13.2864  -17.8245 #+
            2   Z   Na    9.8618  -21.7310 #+
            3   C1z C    17.0800  -21.2800
            4   N1x N    17.5700  -20.0200
            5   C5x C    16.4500  -19.2500
            6   N1y N    15.2600  -20.0200
            7   C5x C    15.7500  -21.2800
            8   O5x O    16.4500  -17.7800
            9   O5x O    14.9800  -22.4700
            10  C8y C    18.4800  -21.2800
            11  C8x C    19.1800  -22.5400
            12  C8x C    20.6500  -22.5400
            13  C8x C    21.3500  -21.3500
            14  C8x C    20.5800  -20.0900
            15  C8x C    19.1800  -20.0900
            16  C8y C    17.0800  -22.7500
            17  C8x C    15.8900  -23.3800
            18  C8x C    15.8900  -24.7800
            19  C8x C    17.1500  -25.5500
            20  C8x C    18.3400  -24.8500
            21  C8x C    18.3400  -23.4500
            22  C1b C    14.1400  -19.3200
            23  O2b O    12.9500  -20.0200
            24  P1b P    11.7600  -19.3200
            25  O1c O    10.4300  -20.1600 #-
            26  O1c O    11.7600  -17.9200 #-
            27  O1c O    10.5700  -18.6200
BOND        27
            1     3   4 1
            2     4   5 1
            3     5   6 1
            4     6   7 1
            5     3   7 1
            6     5   8 2
            7     7   9 2
            8     3  10 1
            9    10  11 2
            10   11  12 1
            11   12  13 2
            12   13  14 1
            13   14  15 2
            14   10  15 1
            15    3  16 1
            16   16  17 2
            17   17  18 1
            18   18  19 2
            19   19  20 1
            20   20  21 2
            21   16  21 1
            22   22   6 1
            23   22  23 1
            24   23  24 1
            25   24  25 1
            26   24  26 1
            27   24  27 2

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