Molecular Formula	C8H16O2
Molecular Weight	144.21
Structure
State	solid
Clearance	0.56 L/hr/m<sup>2</sup>[label] Pediatric patients between 3 months and 10 years of age have 50% higher clearances by weight. Pediatric patients 10 years of age or older approximate adult values.[FDA Label]
Volume of distribution	11 L/1.73m<sup>2</sup>.[label]
Route of elimination	Most drug is eliminated through hepatic metabolism, about 30-50%.[label] The other major contributing pathway is mitochondrial beta-oxidation, about 40%. Other oxidative pathways make up an additional 15-20%. Less than 3% is excreted unchanged in the urine.
Protein binding	Protein binding is linear at low concentrations, 10% bound at 4 mcg/mL, but becomes non-linear at higher concentrations, increasing up to 18.5% bound at 135 mcg/mL.[label] This may be due to binding at separate high and low affinity sites on albumin proteins.[A178066] Binding is expected to decrease in the elderly and patients with hepatic dysfunction.
Half life	13-19 hours.[label] The half-life in neonates ranges from 10-67 hours while the half-life in pediatric patients under 2 months of age ranges from 7-13 hours.
Absorption	The intravenous and oral forms of valproic acid are expected to produce the same AUC, Cmax, and Cmin at steady-state.[label] The oral delayed-release tablet formulation has a Tmax of 4 hours. Differences in absorption rate are expected from other formulations but are not considered to be clinically important in the context of chronic therapy beyond impacting frequency of dosing. Differences in absorption may create earlier Tmax or higher Cmax values on initiation of therapy and may be affected differently by meals.[L6196] The extended release tablet formulation had Tmax increase from 4 hours to 8 hours when taken with food. In comparison, the sprinkle capsule formulation had Tmax increase from 3.3 hours to 4.8 hours. Bioavailability is reported to be approximately 90% with all oral formulations with enteric-coated forms possibly reaching 100%.[A178066]
Trade names	Depakote, Epilim, Convulex
Description	Antiepileptics; fatty acid derivative; branched short-chain fatty acid (SCFA) made from valeric acid; broad spectrum of anticonvulsant activity

Toxicity	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
MEMBRANE POTENTIAL	267.2 µM	30 mins	mouse	liver mitochondria	Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss)	decrease	EC20	36
RESPIRATION	> 400 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition.	decrease	EC20	36
RESPIRATION	44.9 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition.	decrease	EC20	36
MITOCHONDRIAL FATTY ACID BETA OXIDATION						affect		227
TRANSPORT OF PYRUVATE	0.5–2 mM	3min	rat	inverted submitochondrial vesicles (ISMV) from rat liver isolated mitochondria	The rate of the radiolabeled substrate [1-14C]-pyruvate uptake by ISMV was measured in the presence or absence of an inwardly directed proton gradient.	inhibitor		279
SWELLING	> 800 µM	30 mins	mouse	liver mitochondria	swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling )	increase	EC20	36
ROS PRODUCTION						increase		197

Target	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
NADH:ubiquinone reductase	> 400 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition.	inhibit	EC20	36
Succinate dehydrogenase	44.9 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition.	inhibit	EC20	36
carnitine palmitoyltransferases I						inhibit		227
Mitochondrial pyruvate carrier 1	0.5–2 mM	3min	rat	inverted submitochondrial vesicles (ISMV) from rat liver isolated mitochondria	The rate of the radiolabeled substrate [1-14C]-pyruvate uptake by ISMV was measured in the presence or absence of an inwardly directed proton gradient.	inhibit		279
Cytochrome c	> 800 µM	30 mins	mouse	liver mitochondria	Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline)	release	EC20	36

Pictogram	Signal	Statements	Precautionary Statement Codes
	Danger	Aggregated GHS information provided by 280 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (96.43%): Causes skin irritation [Warning Skin corrosion/irritation] H318 (60.71%): Causes serious eye damage [Danger Serious eye damage/eye irritation] H319 (35.71%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (14.29%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure Respiratory tract irritation] H360 (84.64%): May damage fertility or the unborn child [Danger Reproductive toxicity] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.	P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
	Danger	H302: Harmful if swallowed [Warning Acute toxicity, oral] H336: May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure Narcotic effects] H360: May damage fertility or the unborn child [Danger Reproductive toxicity] H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation] H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure] H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]	P201, P202, P260, P261, P263, P264, P270, P271, P281, P301+P312, P304+P340, P307+P311, P308+P313, P312, P314, P321, P330, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Acquired immunodeficiency syndrome

Aggression

Agitation

Amino acid metabolism disorder

Autoimmune disorder

Bipolar disorder

Complex partial seizures

Decreased interest

Dehydration

Delusion of grandeur

Depressed mood

Drug interaction

Epilepsy

Fasting

Flight of ideas

Headache

Hepatic enzyme increased

Hepatic function abnormal

Hostility

Hyperammonaemia

Hyperammonaemic encephalopathy

Hyperglycaemia

Hyperkinesia

Irritability

Lennox-Gastaut syndrome

Loss of consciousness

Major depression

Migraine

Myoclonic epilepsy

Nonketotic hyperglycinaemia

Partial seizures

Petit mal epilepsy

Pregnancy

Pressure of speech

Psychotic disorder

Somnolence

Status epilepticus

Systemic lupus erythematosus

Thrombocytopenia

Urinary tract infection

Coagulopathy (0.07)

Sleep disorder (0.04)

Abdominal pain

Affect lability

Alopecia

Amblyopia

Amnesia

Asthenia

Ataxia

Back pain

Body temperature increased

Bronchitis

Constipation

Decreased appetite

Depression

Dermatitis

Diarrhoea

Diplopia

Dizziness

Dyspepsia

Dyspnoea

Ecchymosis

Fatigue

Gastrointestinal pain

Headache

Increased appetite

Infection

Influenza

Injury

Insomnia

Mental disability

Mood swings

Muscle twitching

Nausea

Nervousness

Nystagmus

Oedema peripheral

Pain

Paraesthesia

Pharyngitis

Rash

Rhinitis

Somnolence

Tension

Thinking abnormal

Thrombocytopenia

Tinnitus

Tremor

Vision blurred

Vomiting

Weight decreased

Weight increased

(S)-2-propyl-4-pentanoate	(n-C3H7)2CHCOOH	2 -propylpentanoic acid
2 PP (base)	2,2-di-n-propylacetic acid	2-PROPYL-PENTANOIC ACID
2-Propylpentanoic acid	2-Propylpentanoic acid sodium salt	2-Propylpentanoic acid, 99%
2-PropylpentanoicAcid	2-Propylvaleric acid	2-n-Propyl-n-valeric acid
2-propyl-Pentanoate	33433-82-8	4-Heptanecarboxylic acid
614OI1Z5WI	6400-EP1441224A2	6400-EP2272537A2
6400-EP2272827A1	6400-EP2275420A1	6400-EP2280008A2
6400-EP2298764A1	6400-EP2298765A1	6400-EP2308867A2
6400-EP2308870A2	6400-EP2311494A1	6400-EP2311840A1
6400-EP2314585A1	6400-EP2374790A1	791-EP2306789A1
99-66-1	A-44090	A19450
AB0009719	AB00698315-06	ACMC-209sdq
ACT05281	AI3-10500	AK128830
AKOS009156895	ANW-41052	APO-divalproex
AS-11354	Abbott 44090	Acetic acid, dipropyl-
Acide valproique	Acide valproique [INN-French]	Acido valproico
Acido valproico [INN-Spanish]	Acidum valproicum	Acidum valproicum [INN-Latin]
Alti-Valproic	Apo-valproic	Apo-valproic syrup
Avugane	BDBM50003616	BIDD:GT0858
BRN 1750447	Baceca	C07185
CAS-99-66-1	CCG-221127	CHEBI:39867
CHEMBL109	CPD000499581	CS-1765
CTK3J3389	Certified Reference Material	Convulex
Convulex (Salt/Mix)	Convulsofin	D00399
DB00313	DOM-divalproex	DOM-valproic acid E.C.
DSSTox_CID_3733	DSSTox_GSID_23733	DSSTox_RID_77171
DTXSID6023733	Depacon (Salt/Mix)	Depakene
Depakene (TN)	Depakin	Depakin chrono
Depakine	Depakine chrono	Depakote (TM)
Depakote CP	Deproic	Di-n-propylacetic acid
Di-n-propylessigsaeure	Di-n-propylessigsaure	Di-n-propylessigsaure [German]
Dipropyl Acetate	Dipropylacetate	Dipropylacetic acid
DivK1c_000273	Divalproex (Salt/Mix)	Dom-Valproic
Dom-valproate	Dom-valproic acid	Dom-valproic acid syrup
EC 202-777-3	EINECS 202-777-3	Epical (TM)
Epiject I.V.	Epilim	Epilim (Salt/Mix)
Epival er	Erganyl	Ergenyl
Eurekene (Salt/Mix)	F2191-0115	FT-0609289
G2M-777	GTPL7009	Gen-divalproex
HMS2089J06	HMS2231E06	HMS3259C18
HMS3370C21	HMS3715B15	HSDB 3582
HY-10585	Heptane-4-carboxylic acid	InChI=1/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
KBio1_000273	KBio2_001001	KBio2_002277
KBio2_003569	KBio2_004845	KBio2_006137
KBio2_007413	KBio3_002626	KBio3_002757
KBioGR_000871	KBioGR_002277	KBioSS_001001
KBioSS_002278	KS-00000CCR	KSC493G8T
Kyselina 2-propylvalerova	Kyselina 2-propylvalerova [Czech]	LMFA01020291
LS-161170	LS-2068	MCULE-7136317196
MFCD00002672	MLS001076682	MLS001335927
MLS001335928	MLS002415770	Med Valproic
Mylproin	Myproic Acid	NC00584
NCGC00091149-01	NCGC00091149-02	NCGC00091149-03
NCGC00091149-04	NCGC00091149-05	NCGC00091149-06
NCGC00091149-08	NCGC00091149-09	NCGC00162288-07
NCGC00254365-01	NCGC00259512-01	NIJJYAXOARWZEE-UHFFFAOYSA-
NIJJYAXOARWZEE-UHFFFAOYSA-N	NINDS_000273	NSC 93819
NSC-93819	NSC93819	Novo-Valproic
Novo-Valproic - ECC	Novo-divalproex	Novo-valproic soft gel cap
Nu-Valproic	P0823	PHL-valproate
PHL-valproic acid	PHL-valproic acid E.C.	PMS-Divalproex
PMS-Valproic Acid	PMS-valproate	PMS-valproic acid E.C.
Penta-Valproic	Pentanoic acid, 2-propyl-	Propylvaleric acid
Q-200321	Q240642	RTR-031980
Ratio-Valproic - ECC	S(-)-4-En-valproate	S-2-n-Propyl-4-pentenoate
SAM002564230	SBB065764	SBI-0050864.P003
SCHEMBL2275	SMR000499581	SPBio_000912
SR-01000075242-7	STL445581	Sandoz valproic
Savicol	Sodium valproate	Spectrum2_000946
Spectrum3_001733	Spectrum4_000376	Spectrum_000521
Stavzor	Stavzor	TR-031980
TRA0085608	Tox21_111091	Tox21_111091_1
Tox21_201963	Tox21_300603	UNII-614OI1Z5WI
VALPROIC ACID	VPA	Valdisoval (Salt/Mix)
Valeric acid, 2-propyl-	Valparin (Salt/Mix)	Valproate
Valproic Acid 1.0 mg/ml in Methanol	Valproic Acid, Sodium Salt (2:1)	Valproic acid (USP)
Valproic acid USP	Valproic acid [USAN:BAN:INN]	Valproic acid [USAN:INN:BAN]
Valproic acid [USAN:USP:INN:BAN]	Valproic acid for system suitability, European Pharmacopoeia (EP) Reference Standard	Valproic acid solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material
Valproic acid, European Pharmacopoeia (EP) Reference Standard	Valproic acid, Pharmaceutical Secondary Standard	Valproic acid, United States Pharmacopeia (USP) Reference Standard
Valproinsaeure	Valproinsaure	Vupral
WLN: QVY3 & 3	Z1511532065	ZINC3008621
di-n-propyl acetic acid	divalproex	n-DPA
n-Dipropylacetic acid

DrugBank Name	Valproic Acid
DrugBank	DB00313
CAS Number	1069-66-5, 362049-65-8, 76584-70-8, 99-66-1, 99-67-2
PubChem Compound	3121
KEGG Compound ID	C07185
KEGG Drug	D00399
PubChem.Substance	46505925
ChEBI	39867
PharmGKB	PA451846
ChemSpider	3009
BindingDB	50003616.0
TTD	DNC001659
Wikipedia	Valproic_Acid
HET	2PP
DPD	2115