KEGG   DRUG: D00399Help
Entry
D00399                      Drug                                   

Name
Valproic acid (USP);
Depakene (TN)
Product
  Generic
VALPROIC ACID (Aphena Pharma Solutions - Tennessee), VALPROIC ACID (Atlantic Biologicals Corps), VALPROIC ACID (Caraco Pharmaceutical Laboratories), VALPROIC ACID (Cardinal Health), VALPROIC ACID (Cardinal Health), VALPROIC ACID (Cardinal Health), VALPROIC (Clinical Solutions Wholesale), VALPROIC (Contract Pharmacy Services-PA), VALPROIC (Contract Pharmacy Services-PA), VALPROIC ACID (Hi-Tech Pharmacal), VALPROIC ACID (McKesson Packaging Services Business Unit of McKesson Corporation), VALPROIC ACID (Morton Grove Pharmaceuticals), VALPROIC ACID (Mylan Institutional), VALPROIC ACID (NCS HealthCare of KY), VALPROIC ACID (Pharmaceutical Associates), VALPROIC (Physicians Total Care), VALPROIC ACID (Pliva), VALPROIC ACID (Precision Dose), VALPROIC ACID (Qualitest Pharmaceuticals), VALPROIC ACID (REMEDYREPACK), VALPROIC ACID (Rebel Distributors Corp), VALPROIC ACID (Sun Pharmaceutical Industries Limited), VALPROIC ACID (Upsher-Smith Laboratories), VALPROIC ACID (Upsher-Smith Laboratories), VALPROIC ACID (Watson Laboratories), VALPROIC (Watson Laboratories)
Formula
C8H16O2
Exact mass
144.115
Mol weight
144.2114
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Anticonvulsant
Remark
Same as: 
ATC code: 
Drug group: 
Comment
Valproic acid is contraindicated in patients with known urea cycle disorders [DS:H00164 H00185 H00186 H00187 H01028 H01032]
Target
GABA transaminase inhibitor [HSA:18] [KO:K13524];
calcium channel T type blocker [HSA:8911 8912 8913] [KO:K04856 K04855 K04854];
histone acetyltransferase inhibitor [HSA:203611 253175 9085 9426] [KO:K00653];
histone deacetylases (HDACs) inhibitor [HSA:3065 3066 8841 9759 10014 10013 51564 55869 9734 83933] [KO:K06067 K11404 K11406 K11407 K11408 K11405 K11409]
  Pathway
hsa00250  Alanine, aspartate and glutamate metabolism
hsa00280  Valine, leucine and isoleucine degradation
hsa00410  beta-Alanine metabolism
hsa00640  Propanoate metabolism
hsa00650  Butanoate metabolism
hsa04010  MAPK signaling pathway
hsa04020  Calcium signaling pathway
hsa04727  GABAergic synapse  
 
Metabolism
Enzyme: CYP2C9 [HSA:1559], CYP3A4 [HSA:1576]
Interaction
Genomic biomarker: (1) NAGS [HSA:162417], CPS [HSA:1373], ASS [HSA:445], OTC [HSA:5009], ASL [HSA:435], ARG [HSA:383 384], (2) POLG [HSA:5428]
Drug interaction
Structure map
Anticonvulsants
Calcium channel blocking drugs
Antimigraines
Other map
Drug metabolism - cytochrome P450
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N03 ANTIEPILEPTICS
   N03A ANTIEPILEPTICS
    N03AG Fatty acid derivatives
     N03AG01 Valproic acid
      D00399  Valproic acid (USP)
USP drug classification [BR:br08302]
 Anticonvulsants
  Gamma-aminobutyric Acid (GABA) Augmenting Agents
   Valproate
    D00399  Valproic acid (USP)
 Antimigraine Agents
  Prophylactic
   Valproic acid
    D00399  Valproic acid (USP)
 Bipolar Agents
  Mood Stabilizers
   Valproic acid
    D00399  Valproic acid (USP)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Ca2+ channel, CACN alpha-1, CaVx.x
    calcium channel T type
     Valproic acid
      D00399  Valproic acid (USP)
 Enzymes
  Transferases
   histone acetyltransferase
    Valproic acid
     D00399  Valproic acid (USP)
   GABA transaminase
    Valproic acid
     D00399  Valproic acid (USP)
  Hydrolases
   histone deacetylase
    Valproic acid
     D00399  Valproic acid (USP)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP2C9
   Valproic acid
    D00399  Valproic acid (USP)
  CYP3A4
   Valproic acid
    D00399  Valproic acid (USP)
BRITE hierarchy
Other DBs
CAS: 
99-66-1
PubChem: 
DrugBank: 
PDB-CCD: 
LigandBox: 
NIKKAJI: 
LinkDB All DBs
KCF data Show

ATOM        10
            1   C1c C    25.4573  -18.6784
            2   C1b C    25.4573  -17.3002
            3   C1b C    24.2485  -19.3967
            4   C6a C    26.6604  -19.3967
            5   C1b C    24.2427  -16.5935
            6   C1b C    23.0396  -18.6784
            7   O6a O    26.6604  -20.7925
            8   O6a O    27.8692  -18.6784
            9   C1a C    23.0339  -17.3002
            10  C1a C    21.8367  -19.3967
BOND        9
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     2   5 1
            5     3   6 1
            6     4   7 1
            7     4   8 2
            8     5   9 1
            9     6  10 1

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