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Compound Detail

CHEMBL109

VALPROIC ACID
💊 Approved Drug
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💊 Approved Drug
CCCC(CCC)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL109
Name VALPROIC ACID
Phase Approved
Structure Type MOL
InChI Key NIJJYAXOARWZEE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

44089 Acide valproique Acido valproico Convulex Depakene Depakote NSC-93819 Pentanoic acid, 2-propyl Stavzor Valproate Valproic acid Valproic acid extended release
12
Targets
69
Activities
3
Assay Types
30
PK Parameters
20
Publications
12
Known Names
20
Indications
1
Mechanisms

Molecular Properties

144.2
MW (Da)
2.29
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.64
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1978
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1975

Extended Properties

Molecular Formula C8H16O2
MW 144.21
Aromatic Rings 0
Heavy Atoms 10
NP-Likeness 0.38

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Succinate semialdehyde dehydrogenase inhibitor INHIBITOR Succinate-semialdehyde dehydrogenase, mitochondrial ✓ ✓

Indications

Bipolar Disorder Bipolar Disorder Epilepsy Epilepsy, Absence Epilepsy, Absence Epilepsy, Complex Partial Mitochondrial Diseases Seizures Alcoholism Alzheimer Disease Anxiety Autistic Disorder Dementia Depressive Disorder Migraine Disorders Muscular Atrophy, Spinal Paraparesis, Tropical Spastic Psychomotor Agitation Schizophrenia Status Epilepticus

ATC Classification

N03AG01
valproic acid
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 63 meas. best 5.33
Ki 5 meas.
EC50 1 meas. best 4.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 5.33 5.33 4660.0 1
HCT-116
CHEMBL394
 IC50 5.33 5.33 4660.0 1
HepG2
CHEMBL395
 IC50 5.33 5.33 4660.0 1
HeLa
CHEMBL399
 IC50 5.33 5.33 4660.0 1
Unchecked
CHEMBL612545
 EC50 4.93 4.93 11730.0 1
Histone deacetylase 1
CHEMBL325
 IC50 4.41 4.34 39000.0 5
Aldo-keto reductase family 1 member A1
CHEMBL2246
 IC50 4.3 4.3 50100.0 1
Aldo-keto reductase family 1 member A1
CHEMBL3871
 IC50 4.3 4.275 50100.0 2
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 4.25 4.25 56100.0 4
Aldo-keto reductase family 1 member B7
CHEMBL3421523
 IC50 4.25 4.25 56100.0 1
Unchecked
CHEMBL612545
 IC50 4.25 4.2433 56100.0 3
Aldo-keto reductase family 1 member B1
CHEMBL3081
 IC50 4.24 4.24 57400.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 4.21 4.21 62000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 299.6 - Chlorocebus sabaeus
CL 0.16 mL.min-1.kg-1 Homo sapiens
CL 0.16 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.11 mL.min-1.kg-1 Homo sapiens
CL 0.16 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.kg-1 Canis lupus familiaris
CL 4.0 mL.min-1.kg-1 Macaca
CL 4.2 mL.min-1.kg-1 Rattus norvegicus
CL - - Homo sapiens
CL - - Homo sapiens
CL 0.56 L/hr/1.73 m2 Homo sapiens
CL 4.6 L/hr/1.73 m2 Homo sapiens
CL 4.7 L/hr/1.73 m2 Homo sapiens
CL 4.8 L/hr/1.73 m2 Homo sapiens
F 80.0 % Homo sapiens
F 90.0 % Homo sapiens
Fu 0.084 - Homo sapiens
Fu 0.084 - Homo sapiens
Fu 0.052 - Homo sapiens
Fu 0.88 - Rattus norvegicus
MRT 15.0 hr Homo sapiens
PPB 10.0 % Homo sapiens
PPB 18.5 % Homo sapiens
T1/2 12.0 hr Homo sapiens
t1/2 - - Bos taurus
T1/2 0.03333 hr Mus musculus
T1/2 9.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens
T1/2 7.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HepG2 IC50 = 4660.0 nM 5.33 Antiproliferative activity against human HepG2 cells measured after 24 hrs by MT... 37875056
HCT-116 IC50 = 4660.0 nM 5.33 Antiproliferative activity against human HCT-116 cells measured after 24 hrs by ... 37875056
MCF7 IC50 = 4660.0 nM 5.33 Antiproliferative activity against human MCF7 cells measured after 24 hrs by MTT... 37875056
HeLa IC50 = 4660.0 nM 5.33 Antiproliferative activity against human HeLa cells measured after 24 hrs by MTT... 37875056
Unchecked EC50 = 11730.0 nM 4.93 Reduction of propionyl-CoA in human hepatocytes derived from propionic acidemia ... 33848153
Histone deacetylase 1 IC50 = 39000.0 nM 4.41 Inhibition of human recombinant HDAC1 21874153
Histone deacetylase 1 IC50 = 39000.0 nM 4.41 Inhibition of HDAC1 (unknown origin) 39092855
Histone deacetylase 1 IC50 = 40000.0 nM 4.4 Inhibition of HADC1 (unknown origin) 31415174
Histone deacetylase 1 IC50 = 40000.0 nM 4.4 Inhibition of human recombinant HDAC1 using fluorogenic substrate 35148101
Aldo-keto reductase family 1 member A1 IC50 = 50100.0 nM 4.3 Inhibition of rat kidney aldehyde reductase at 0.1 mM after 20 mins by spectrome... 20189816
Aldo-keto reductase family 1 member A1 IC50 = 50100.0 nM 4.3 Inhibition of AK1A1 20936791
Aldo-keto reductase family 1 member A1 IC50 = 56100.0 nM 4.25 Inhibition of Fischer-344 rat kidney AK1A1 20936791
Aldo-keto reductase family 1 member B1 IC50 = 56100.0 nM 4.25 Inhibition of ALR1 in Wistar rat kidney assessed as reduction in NADPH consumpti... 29074349
Aldo-keto reductase family 1 member B1 IC50 = 56100.0 nM 4.25 Inhibition of Wistar rat kidney ALR1 assessed as reduction in NADPH oxidation us... 28259841
Aldo-keto reductase family 1 member B7 IC50 = 56100.0 nM 4.25 Inhibition of Wistar rat kidney aldehyde reductase using D-glucuronate as substr... 25695864
Aldo-keto reductase family 1 member B1 IC50 = 56100.0 nM 4.25 Inhibition of Fischer-344 rat kidney ALR1 using D-glucuronate as substrate by sp... 24630695
Aldo-keto reductase family 1 member B1 IC50 = 56100.0 nM 4.25 Inhibition of Fischer-344 rat kidney ALR1 using D,L-glyceraldehyde as substrate ... 23312612
Unchecked IC50 = 56100.0 nM 4.25 Inhibition of Wistar rat kidney aldose reductase 1 18395454
Unchecked IC50 = 57400.0 nM 4.24 Inhibition of purified calf kidney ALR1 preincubated for 10 mins by UV spectroph... -
Aldo-keto reductase family 1 member B1 IC50 = 57400.0 nM 4.24 Inhibition of ALR1 in calf kidney using sodium D-glucoronate as substrate treate... 26005026

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1422
- 10.6019/CHEMBL3885881 Rattus norvegicus 892
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5058577 HEK-293T 304
20420384 10.1021/jm100170w Mus musculus 37
19296679 10.1021/jm900017f Mus musculus 27
28934547 10.1021/acs.jmedchem.7b01114 Mus musculus 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
8691481 10.1021/jm950761q Mus musculus 16
27739690 10.1021/acs.jmedchem.6b01039 Unchecked 16
26970661 10.1016/j.bmc.2016.02.026 Mus musculus 15
1495012 10.1021/jm00093a012 Rattus norvegicus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2308142 10.1021/jm00165a007 Mus musculus 14
33329762 10.1021/acsmedchemlett.0c00375 Unchecked 13
26241874 10.1016/j.ejmech.2015.07.017 Mus musculus 13

Data from ChEMBL 36 via Core Engine