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Details

Stereochemistry ACHIRAL
Molecular Formula C8H16O2
Molecular Weight 144.2117
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALPROIC ACID

SMILES

CCCC(CCC)C(=O)O

InChI

InChIKey=NIJJYAXOARWZEE-UHFFFAOYSA-N
InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://psychopharmacologyinstitute.com/mood-stabilizers/valproate-in-psychiatry-approved-indications-and-off-label-uses/ | https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022152s002lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12847559 | https://www.ncbi.nlm.nih.gov/pubmed/11742974 | https://www.ncbi.nlm.nih.gov/pubmed/11473107

Valproic acid (VPA; valproate; di-n-propylacetic acid, DPA; 2-propylpentanoic acid, or 2-propylvaleric acid) was first synthesized in 1882, by Burton. FDA approved valproic acid for the treatment of manic episodes associated with bipolar disorder, for the monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures and adjunctive therapy in patients with multiple seizure types that include absence seizures and for the prophylaxis of migraine headaches. The mechanisms of VPA which seem to be of clinical importance in the treatment of epilepsy include increased gamma-aminobutyric acid (GABA)-ergic activity, reduction in excitatory neurotransmission, and modification of monoamines. Recently, it was discovered that the VPA is a class I selective histone deacetylase inhibitor. This activity can be distinguished from its therapeutically exploited antiepileptic activity.

Originator

Sources: Burton B.S. (1882) On the propyl derivatives and decomposition products of ethylacetoacetate. Am Chem J3: 385–395
Curator's Comment:: reference retrieved from https://link.springer.com/chapter/10.1007%2F978-3-0348-8759-5_1

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DEPAKENE

Approved Use

Depakene (valproic acid) is indicated as monotherapy and adjunctive therapy in the treatment of patients with complex partial seizures that occur either in isolation or in association with other types of seizures. Depakene (valproic acid) is indicated for use as sole and adjunctive therapy in the treatment of simple and complex absence seizures, and adjunctively in patients with multiple seizure types which include absence seizures. Simple absence is defined as very brief clouding of the sensorium or loss of consciousness accompanied by certain generalized epileptic discharges without other detectable clinical signs. Complex absence is the term used when other signs are also present.
Preventing
STAVZOR

Approved Use

Stavzor (valproic acid) delayed release capsules is indicated for: • Acute treatment of manic episodes associated with bipolar disorder • Monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures • Prophylaxis of migraine headaches

Launch Date

1.21720314E12
Primary
STAVZOR

Approved Use

Stavzor (valproic acid) delayed release capsules is indicated for: • Acute treatment of manic episodes associated with bipolar disorder • Monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures • Prophylaxis of migraine headaches

Launch Date

1.21720314E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
107.2 mg/L
500 mg 2 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
VALPROIC ACID plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1951 mg × h/L
500 mg 2 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
VALPROIC ACID plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16 h
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
VALPROIC ACID unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
150 mg/kg single, intravenous
Highest studied dose
Dose: 150 mg/kg
Route: intravenous
Route: single
Dose: 150 mg/kg
Sources: Page: p.6
healthy, 30.2 ± 11.7
n = 3
Health Status: healthy
Age Group: 30.2 ± 11.7
Sex: M+F
Population Size: 3
Sources: Page: p.6
DLT: Headache, Nausea...
Dose limiting toxicities:
Headache
Nausea
Sources: Page: p.6
140 mg/kg single, intravenous
MTD
Dose: 140 mg/kg
Route: intravenous
Route: single
Dose: 140 mg/kg
Sources: Page: p.6
healthy, 30.2 ± 11.7
n = 6
Health Status: healthy
Age Group: 30.2 ± 11.7
Sex: M+F
Population Size: 6
Sources: Page: p.6
25 g single, oral
Overdose
Dose: 25 g
Route: oral
Route: single
Dose: 25 g
Sources: Page: p.1
unhealthy, 37
n = 1
Health Status: unhealthy
Condition: Seizures |Bipolar disorder
Age Group: 37
Sex: M
Population Size: 1
Sources: Page: p.1
Disc. AE: Somnolence...
AEs leading to
discontinuation/dose reduction:
Somnolence
Sources: Page: p.1
100 g single, oral
Overdose
Dose: 100 g
Route: oral
Route: single
Dose: 100 g
Sources: Page: 110000
unhealthy, 41
n = 1
Health Status: unhealthy
Condition: Epilepsy
Age Group: 41
Sex: M
Population Size: 1
Sources: Page: 110000
Disc. AE: Coma...
AEs leading to
discontinuation/dose reduction:
Coma
Sources: Page: 110000
120 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 120 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 120 mg/kg, 1 times / day
Sources: Page: p.179
unhealthy, 62.5
n = 5
Health Status: unhealthy
Condition: Cancer
Age Group: 62.5
Sex: M+F
Population Size: 5
Sources: Page: p.179
DLT: Somnolence...
Dose limiting toxicities:
Somnolence (40%)
Sources: Page: p.179
60 mg/kg 1 times / day multiple, intravenous
MTD
Dose: 60 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg/kg, 1 times / day
Sources: Page: p.178
unhealthy, 62.5
n = 3
Health Status: unhealthy
Condition: Cancer
Age Group: 62.5
Sex: M+F
Population Size: 3
Sources: Page: p.178
60 mg/kg 1 times / day multiple, oral
Recommended
Dose: 60 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/kg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Seizures
Sources: Page: p.1
Disc. AE: Hepatotoxicity, Pancreatitis...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity
Pancreatitis
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Headache DLT
150 mg/kg single, intravenous
Highest studied dose
Dose: 150 mg/kg
Route: intravenous
Route: single
Dose: 150 mg/kg
Sources: Page: p.6
healthy, 30.2 ± 11.7
n = 3
Health Status: healthy
Age Group: 30.2 ± 11.7
Sex: M+F
Population Size: 3
Sources: Page: p.6
Nausea DLT
150 mg/kg single, intravenous
Highest studied dose
Dose: 150 mg/kg
Route: intravenous
Route: single
Dose: 150 mg/kg
Sources: Page: p.6
healthy, 30.2 ± 11.7
n = 3
Health Status: healthy
Age Group: 30.2 ± 11.7
Sex: M+F
Population Size: 3
Sources: Page: p.6
Somnolence Disc. AE
25 g single, oral
Overdose
Dose: 25 g
Route: oral
Route: single
Dose: 25 g
Sources: Page: p.1
unhealthy, 37
n = 1
Health Status: unhealthy
Condition: Seizures |Bipolar disorder
Age Group: 37
Sex: M
Population Size: 1
Sources: Page: p.1
Coma Disc. AE
100 g single, oral
Overdose
Dose: 100 g
Route: oral
Route: single
Dose: 100 g
Sources: Page: 110000
unhealthy, 41
n = 1
Health Status: unhealthy
Condition: Epilepsy
Age Group: 41
Sex: M
Population Size: 1
Sources: Page: 110000
Somnolence 40%
DLT
120 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 120 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 120 mg/kg, 1 times / day
Sources: Page: p.179
unhealthy, 62.5
n = 5
Health Status: unhealthy
Condition: Cancer
Age Group: 62.5
Sex: M+F
Population Size: 5
Sources: Page: p.179
Hepatotoxicity Disc. AE
60 mg/kg 1 times / day multiple, oral
Recommended
Dose: 60 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/kg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Seizures
Sources: Page: p.1
Pancreatitis Disc. AE
60 mg/kg 1 times / day multiple, oral
Recommended
Dose: 60 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/kg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Seizures
Sources: Page: p.1
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
minimal
minimal
minimal
no
weak [Ki 7975 uM]
weak [Ki 8553 uM]
weak [Ki 9150 uM]
yes [Ki 600 uM]
likely (co-administration study)
Comment: competitive inhibition; risk of pharmacokinetic drug–drug interactions should be taken into account during concomitant use of valproic acid and CYP2C9 substrates
Drug as victim
PubMed

PubMed

TitleDatePubMed
Hepatic encephalopathy associated with combined clozapine and divalproex sodium treatment.
1997 Apr
Reversible cortical atrophy and cognitive decline induced by valproic acid.
1998
Influence of adenosine agonists and antiepileptic drugs on theophylline-induced seizures in rats.
1998 Oct
Cognitive dysfunction induced by phenytoin and valproate in rats: effect of nitric oxide.
1999 Jul
[A case report of valproate encephalopathy].
1999 Oct
Pathomorphological changes in mouse liver and kidney during prolonged valproate administration.
2000
Fatal deterioration of neurological disease after orthotopic liver transplantation for valproic acid-induced liver damage.
2000 Aug
Nonspecific stimulation of the maternal immune system. I. Effects On teratogen-induced fetal malformations.
2000 Dec
[Lyell syndrome associated with lamotrigine].
2000 Dec 16-31
Inappropriate liver transplantation in a child with Alpers-Huttenlocher syndrome misdiagnosed as valproate-induced acute liver failure.
2000 Feb
Effects of anticonvulsants on local anaesthetic-induced neurotoxicity in rats.
2000 Feb
A multicenter randomized controlled trial on the clinical impact of therapeutic drug monitoring in patients with newly diagnosed epilepsy. The Italian TDM Study Group in Epilepsy.
2000 Feb
Phenytoin poisoning after using Chinese proprietary medicines.
2000 Jul
Valproic acid-induced hyperammonemic encephalopathy with triphasic waves.
2000 Jul
Incidence of intravenous site reactions in neurotrauma patients receiving valproate or phenytoin.
2000 Jun
Visual and auditory hallucinations with the association of bupropion and valproate.
2000 Mar
[Valproic acid in prophylaxis of bipolar disorder. A case of valproate-induced encephalopathy].
2000 May
Prenatal exposure of rats to valproic acid reproduces the cerebellar anomalies associated with autism.
2000 May-Jun
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy.
2000 Nov
Renal tubular function in patients receiving anticonvulsant therapy: a long-term study.
2000 Nov
Vitamin E decreases valproic acid induced neural tube defects in mice.
2000 Oct 13
Influence of chronic barbiturate administration on sleep apnea after hypersomnia presentation: case study.
2000 Sep
Effects of combined administration of zonisamide and valproic acid or phenytoin to nitric oxide production, monoamines and zonisamide concentrations in the brain of seizure-susceptible EL mice.
2000 Sep 15
[Dementia and extrapyramidal problems caused by long-term valproic acid].
2000 Sep-Oct
Action of valproic acid on Xenopus laevis development: teratogenic effects on eyes.
2001
Benzodiazepines and anticonvulsants for social phobia (social anxiety disorder).
2001
Valproate, but not lamotrigine, induces ovarian morphological changes in Wistar rats.
2001 Feb
Treatment and management of cluster headache.
2001 Feb
The use of baclofen in cluster headache.
2001 Feb
Recommendations for the management of behavioral and psychological symptoms of dementia.
2001 Feb
[Treatment of cluster headache].
2001 Feb
Glutamate receptor antagonists differentially affect the protective activity of conventional antiepileptics against amygdala-kindled seizures in rats.
2001 Feb
Effect of coadministered drugs and ethanol on the binding of therapeutic drugs to human serum in vitro.
2001 Feb
Divalproex sodium augmentation of haloperidol in hospitalized patients with schizophrenia: clinical and economic implications.
2001 Feb
Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy.
2001 Feb
Different control of GH secretion by gamma-amino- and gamma-hydroxy-butyric acid in 4-year abstinent alcoholics.
2001 Feb 1
Independent short-term variability of spike-like (600 Hz) and postsynaptic (N20) cerebral SEP components.
2001 Feb 12
The impact of pharmacogenetics for migraine.
2001 Feb 9
Valproic acid has temporal variability in urinary clearance of metabolites.
2001 Jan
Pharmacologic treatment of patients hospitalized with the diagnosis of schizoaffective disorder.
2001 Jan
Evaluating the tolerability of the newer mood stabilizers.
2001 Jan
Contribution of sodium valproate to the syndrome of inappropriate secretion of antidiuretic hormone.
2001 Jan
[Febrile pleuropericarditis during valproic acid treatment].
2001 Jan 20
Weight change associated with valproate and lamotrigine monotherapy in patients with epilepsy.
2001 Jan 23
Hypothermia and thermoregulatory derangements induced by valproic acid.
2001 Jan 9
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy.
2001 Jan 9
Mood stabilizers and ion regulation.
2001 Jan-Feb
Mood-stabilisers reduce the risk of developing antidepressant-induced maniform states in acute treatment of bipolar I depressed patients.
2001 Mar
Synthesis and intramitochondrial levels of valproyl-coenzyme A metabolites.
2001 Mar 1
Placebo-controlled study of divalproex sodium for agitation in dementia.
2001 Winter
Patents

Sample Use Guides

Usual Adult Dose for Epilepsy Complex partial seizures: Initial dose: 10 to 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased by 5 to 10 mg/kg per week if necessary according to clinical response Maintenance dose: 10 to 60 mg/kg per day in divided doses Maximum dose: 60 mg/kg per day Simple and complex absence seizures: Initial dose: 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased at one week intervals by 5 to 10 mg/kg/day according to seizure control and tolerability Maximum dose: 60 mg/kg per day Comments: -If the total daily dose exceeds 250 mg, it should be given in 2 to 3 divided doses. -Use of IV valproate sodium for periods longer than 14 days has not been studied; patients should be converted to oral valproate as soon as clinically feasible. -When switching from oral to IV valproate, the total daily dose of IV valproate should be equivalent to the total daily dose of oral valproate, and administered at the same frequency as the oral product. -Equivalence between IV and oral valproate products at steady state has only been evaluated in a 6-hourly dosing regimen. Trough plasma level monitoring may be required if IV valproate is administered 2 to 3 times a day. -Complex partial seizures: When converting patients to valproate monotherapy, concomitant antiepileptic drug dosage can generally be reduced by approximately 25% every 2 weeks, commencing either at the start of valproate therapy or delayed by 1 to 2 weeks. Patients should be monitored closely during this period for increased seizure frequency. Uses: Monotherapy and adjunctive therapy in the treatment of complex partial seizures; sole and adjunctive therapy for simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures. Usual Adult Dose for Mania Delayed-release capsules : Initial dose: 750 mg orally per day in divided doses Maximum dose: 60 mg/kg orally per day Duration: Safety and efficacy beyond 3 weeks has not been established Comments: -The dose should be increased as rapidly as possible to achieve the lowest therapeutic dose which produces the desired clinical effect or the desired range of plasma concentrations. -In placebo-controlled clinical trials of acute mania, patients were dosed to a clinical response with a trough plasma concentration of 50 to 125 mcg/mL. -Maximum concentrations were generally achieved within 14 days. -Safety and efficacy for longer term use in the maintenance of the initial response and prevention of new manic episodes has not been systematically evaluated in clinical trials. Use for extended periods should be accompanied by regular review for the long-term usefulness of the drug for the individual patient. Use: Treatment of manic episodes associated with bipolar disorder. Usual Adult Dose for Migraine Prophylaxis Delayed release oral capsules: Initial dose: 250 mg orally twice a day Comments: -Some patients may benefit from doses up to 1000 mg per day. -In clinical trials, there was no evidence that higher doses led to greater efficacy. Usual Pediatric Dose for Epilepsy 10 years of age or older: Complex partial seizures: Initial dose: 10 to 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased by 5 to 10 mg/kg per week if necessary according to clinical response Maintenance dose: 10 to 60 mg/kg per day in divided doses Maximum dose: 60 mg/kg per day Simple and complex absence seizures: Initial dose: 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased at one week intervals by 5 to 10 mg/kg/day according to seizure control and tolerability Maximum dose: 60 mg/kg per day Comments: -If the total daily dose exceeds 250 mg, it should be given in 2 to 3 divided doses. -Use of IV valproate sodium for periods longer than 14 days has not been studied; patients should be converted to oral valproate as soon as clinically feasible. -When switching from oral to IV valproate, the total daily dose of IV valproate should be equivalent to the total daily dose of oral valproate, and administered at the same frequency as the oral product. -Equivalence between IV and oral valproate products at steady state has only been evaluated in a 6-hourly dosing regimen. Trough plasma level monitoring may be required if IV valproate is administered 2 to 3 times a day. -Complex partial seizures: When converting patients to valproate monotherapy, concomitant antiepileptic drug dosage can generally be reduced by approximately 25% every 2 weeks, commencing either at the start of valproate therapy or delayed by 1 to 2 weeks. Patients should be monitored closely during this period for increased seizure frequency. Uses: Monotherapy and adjunctive therapy in the treatment of complex partial seizures; sole and adjunctive therapy for simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures.
Route of Administration: Other
H9C2 cells were cultured and allotted to the blank, vehicle, and valproic acid (VPA)-treated groups: the VPA treated group received VPA exposure at concentrations of 2.0, 4.0 and 8.0 mmol/L. VPA might result in acetylation/deacetylation imbalances by inhibiting HDAC1-3 protein expression and total HDAC activity, leading to the down-regulation of mRNA and protein expression of Vangl2 and Scrib.
Name Type Language
VALPROIC ACID
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
VALPROIC ACID [MI]
Common Name English
VALPROIC ACID [VANDF]
Common Name English
VALPROIC ACID [USP]
Common Name English
DEPAKENE
Brand Name English
PENTANOIC ACID, 2-PROPYL
Common Name English
VALPROIC ACID [INCI]
Common Name English
44089
Code English
VALPROIC ACID [USP-RS]
Common Name English
VALPROATE
Systematic Name English
VALPROIC ACID [ORANGE BOOK]
Common Name English
VALPROIC ACID [HSDB]
Common Name English
PROPYLVALERIC ACID
Systematic Name English
VALPROIC ACID [EP]
Common Name English
VALPROIC ACID EXTENDED RELEASE
Common Name English
VALPROIC ACID [USP MONOGRAPH]
Common Name English
VALPROIC ACID [INN]
Common Name English
VALPROIC ACID [EP MONOGRAPH]
Common Name English
VALPROIC ACID [MART.]
Common Name English
VALPROIC ACID [USAN]
Common Name English
Classification Tree Code System Code
LIVERTOX 1017
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
FDA ORPHAN DRUG 563116
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
FDA ORPHAN DRUG 256908
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WHO-ESSENTIAL MEDICINES LIST 05
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WHO-ATC N03AG01
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WHO-VATC QN03AG01
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WHO-ESSENTIAL MEDICINES LIST 24.2.2
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
NCI_THESAURUS C264
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EU-Orphan Drug EU/3/16/1792
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NDF-RT N0000175751
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NDF-RT N0000175753
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NDF-RT N0000008486
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Code System Code Type Description
EPA CompTox
99-66-1
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PRIMARY
HSDB
3582
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PRIMARY
NCI_THESAURUS
C29536
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PRIMARY
FDA UNII
614OI1Z5WI
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PRIMARY
USP_CATALOG
1708707
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PRIMARY USP-RS
EVMPD
SUB00015MIG
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PRIMARY
RXCUI
11118
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PRIMARY
IUPHAR
7009
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
PRIMARY
LACTMED
Valproic Acid
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
PRIMARY
DRUG CENTRAL
2803
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
PRIMARY
RXCUI
40254
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
ALTERNATIVE
PUBCHEM
3121
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PRIMARY
CAS
99-66-1
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
PRIMARY
ChEMBL
CHEMBL109
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PRIMARY
INN
3300
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PRIMARY
ECHA (EC/EINECS)
202-777-3
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PRIMARY
MERCK INDEX
M11369
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PRIMARY Merck Index
DRUG BANK
DB00313
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PRIMARY
MESH
D014635
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
PRIMARY
WIKIPEDIA
VALPROIC ACID
Created by admin on Fri Jun 25 20:56:04 UTC 2021 , Edited by admin on Fri Jun 25 20:56:04 UTC 2021
PRIMARY