VALPROIC ACID

Search structure
Trade Names:
Synonyms:
Status: Approved (1978)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N03AG01
UNII: 614OI1Z5WI

Structure
InChI Key NIJJYAXOARWZEE-UHFFFAOYSA-N
Smile CCCC(CCC)C(=O)O
InChI
InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H16O2
Molecular Weight 144.21
AlogP 2.29
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 10.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Succinate semialdehyde dehydrogenase inhibitor PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase GSK family
- - - - 65
Enzyme Oxidoreductase
- 56100-56100 - - -
Enzyme Transferase
- - - - 41
Epigenetic regulator Eraser Histone deacetylase HDAC class I
- 39000-40000 - - 7
Epigenetic regulator Eraser Histone deacetylase HDAC class IIa
- - - - 7
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - 7
Epigenetic regulator Eraser Histone deacetylase HDAC class IV
- - - - 7
Membrane receptor
- - - - 81-93
Surface antigen
- - - - 81-93
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 10
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 20

Metabolites

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Indications

Mesh Heading Maximum Phase Mesh ID Reference
Bipolar Disorder 4 D001714 ClinicalTrials
Epilepsy, Absence 4 D004832 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Status Epilepticus 3 D013226 ClinicalTrials
Paraparesis, Tropical Spastic 3 D015493 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
Muscular Atrophy, Spinal 2 D009134 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Muscular Atrophy, Spinal 2 D009134 ClinicalTrials
Alopecia 2 D000505 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Supranuclear Palsy, Progressive 2 D013494 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Retinitis Pigmentosa 2 D012174 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials
Sarcoma 1 D012509 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 1 D002289 ClinicalTrials
Wounds and Injuries 1 D014947 ClinicalTrials
Burkitt Lymphoma 1 D002051 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 1 D016403 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Ovarian Neoplasms 1 D010051 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Medulloblastoma 1 D008527 ClinicalTrials
Nasopharyngeal Neoplasms 1 D009303 ClinicalTrials
Lymphoma, Mantle-Cell 1 D020522 ClinicalTrials
Colorectal Neoplasms 1 D015179 ClinicalTrials
Sarcoma 1 D012509 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials
Shock 1 D012769 ClinicalTrials
Urinary Bladder Neoplasms 0 D001749 ClinicalTrials
Alzheimer Disease 0 D000544 ClinicalTrials

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
18.82
Psychiatric disorders
13.42
Injury, poisoning and procedural complications
8.69
General disorders and administration site conditions
8.26
Musculoskeletal and connective tissue disorders
5.59
Congenital, familial and genetic disorders
4.82
Pregnancy, puerperium and perinatal conditions
4.69
Gastrointestinal disorders
4.29
Investigations
4.25
Respiratory, thoracic and mediastinal disorders
3.46
Metabolism and nutrition disorders
3.12
Skin and subcutaneous tissue disorders
2.54
Vascular disorders
2.27
Cardiac disorders
2.16

Cross References

Resources Reference
CAS NUMBER 99-66-1
ChEBI 39867
ChEMBL CHEMBL109
DrugBank DB00313
DrugCentral 2803
EPA CompTox DTXSID6023733
FDA SRS 614OI1Z5WI
Human Metabolome Database HMDB0001877
Guide to Pharmacology 7009
KEGG C07185
PDB 2PP
PharmGKB PA451846
PubChem 3121
SureChEMBL SCHEMBL2275
ZINC ZINC000003008621
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