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2-Propylpentanoic acid

Description Generic formulation Indications Dose titration Plasma levels monitoring Cautions Adverse effects Interactions Special populations Behavioural and cognitive effects in patients with epilepsy Psychiatric use
2-Propylpentanoic acid
2-Propylpentanoic acid structure
CAS No.
99-66-1
Chemical Name:
2-Propylpentanoic acid
Synonyms
VPA;44089;Epilim;Ergenyl;depakote;Mylproin;Valproic;Convulex;Depakene;Depakine
CBNumber:
CB7149528
Molecular Formula:
C8H16O2
Formula Weight:
144.21
MOL File:
99-66-1.mol

2-Propylpentanoic acid Properties

Melting point:
-21.25°C (estimate)
Boiling point:
220 °C (lit.)
Density 
0.9 g/mL at 25 °C (lit.)
vapor pressure 
0.01 hPa (20 °C)
refractive index 
n20/D 1.425(lit.)
Flash point:
232 °F
storage temp. 
Store below +30°C.
solubility 
H2O: slightly soluble
form 
Liquid
pka
4.6(at 25℃)
color 
Clear colorless to pale yellow
explosive limit
1%(V)
Odor Threshold
0.0033ppm
Water Solubility 
slightly soluble
Merck 
14,9913
BRN 
1750447
CAS DataBase Reference
99-66-1(CAS DataBase Reference)
EWG's Food Scores
2
FDA UNII
614OI1Z5WI
NCI Dictionary of Cancer Terms
Depakene; valproic acid
NCI Drug Dictionary
Depakote
Proposition 65 List
Valproate (Valproic acid)
NIST Chemistry Reference
Valproic Acid(99-66-1)
EPA Substance Registry System
Valproic acid (99-66-1)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS06,GHS08,GHS07,GHS05
Signal word  Danger
Hazard statements  H314-H318-H225-H301+H311+H331-H370-H302-H315-H319-H335-H360
Precautionary statements  P309-P310-P210-P260-P280-P301+P310-P311-P201-P301+P312+P330-P305+P351+P338-P308+P313
Hazard Codes  Xn,T,F
Risk Statements  22-36/37/38-39/23/24/25-23/24/25-11-34-61
Safety Statements  26-45-36/37-16-7-36/37/39-53
RIDADR  UN 1230 3/PG 2
WGK Germany  3
RTECS  YV7875000
HazardClass  8
PackingGroup  III
HS Code  29159080
Toxicity LD50 orally in rats: 670 mg/kg (Jenner)
NFPA 704
1
2 0

2-Propylpentanoic acid price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.14439 2-Propylvaleric acid for synthesis 99-66-1 25 mL $61.97 2021-03-22 Buy
Sigma-Aldrich V-006 Valproic acid solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 99-66-1 1 mL $86.6 2021-03-22 Buy
Sigma-Aldrich V0033000 Valproic acid European Pharmacopoeia (EP) Reference Standard 99-66-1 $190 2021-03-22 Buy
Sigma-Aldrich Y0001422 Valproic acid for system suitability European Pharmacopoeia (EP) Reference Standard 99-66-1 $190 2021-03-22 Buy
Sigma-Aldrich P6273 2-Propylpentanoic acid 99-66-1 100ml $168 2021-03-22 Buy

2-Propylpentanoic acid Chemical Properties,Uses,Production

Description

Valproate is a first- generation antiepileptic drug (AED) known with the proprietary brand names of Epilim® (Sanofi, Paris) and Episenta® (Desitin, Hamburg) in the UK and Depakote® (Sanofi, Paris) in the USA.

Generic formulation

MHRA/ CHM advice to minimize risk when switching patients with epilepsy between different manufacturers’ products (including generic products):

Indications

Epilepsy
Monotherapy and adjunctive therapy of focal and generalized seizures.

Recommendations summarized from NICE (2012)
Psychiatry
Treatment of acute mania associated with bipolar disorder.

Neurology
Migraine prophylaxis (unlicensed).

Dose titration

Epilepsy
600 mg daily divided into 1 or 2 doses, then increased by 150– 300 mg every 3 days; usual maintenance 1000– 2000 mg (or 20–30 mg/ kg) daily divided into 1 or 2 doses (max 2500 mg daily).

Mania
750 mg daily divided into 1 or 2 doses, adjusted according to response; usual maintenance 000– 2000 mg daily divided into 1 or 2 doses (doses greater than 45 mg/ kg daily require careful monitoring).

Plasma levels monitoring

Although plasma levels can be measured, and a therapeutic range has been postulated (40– 100 mg/ L), plasma valproate concentrations are not a useful index of efficacy. Therefore, routine monitoring is unhelpful.

Cautions

Adverse effects

Valproate can be associated with adverse effects at the level the nervous system and other systems.

Interactions

With AEDs With other drugs With alcohol/food
There are no specific foods that must be excluded from diet when taking valproate. Alcohol intake is not recommended during treatment with valproate.

Special populations

Hepatic impairment
Avoid if possible: hepatotoxicity and hepatic failure may occasionally occur (usually in first 6 months). Avoid in active liver disease.

Renal impairment
In patients with renal insufficiency, it may be necessary to decrease dosage of valproate. As monitoring of plasma concentrations may be misleading, dosage should be adjusted according to clinical monitoring.

Pregnancy

Behavioural and cognitive effects in patients with epilepsy

The incidence of adverse psychiatric effects associated with valproate in patients with epilepsy is overall negligible (apart from reports of depression, irritability, and other behavioural symptoms in the context of encephalopathy). Cognitive difficulties have occasionally been reported in patients with epilepsy treated with valproate, especially affecting attention and memory functions.

Psychiatric use

Valproate is an effective mood stabilizer, licensed for the treatment of acute mania in patients with bipolar disorder. Although it has no formal indication, it is also considered a first- line agent for maintenance treatment in bipolar disorder. There is evidence suggesting efficacy of valproate in the treatment of hostility among patients with acute alcohol- associated hallucinosis or schizophrenia, and in impulsive/ aggressive behaviours, either in isolation or in the context of comorbid bipolar disorder or personality disorder. Available data show a limited efficacy of valproate in depressive disorders, schizophrenia, pathological gambling, as well as benzodiazepine/ cannabis/ cocaine dependence and acute alcohol withdrawal.

Description

Valproic acid and its salts are a new group of antiepileptic drugs that differs from the known drugs both structurally and in terms of its mechanism of action. It is believed that it acts on the metabolism of the GABA system. Valproic acid has been shown to elevate the level of GABA in the brain by means of competitive inhibition of GABA transaminase and the dehydrogenase of succinic semialdehyde.
This drug not only exhibits anticonvulsant action, but also betters the mental condition of the patient.

Chemical Properties

Colorless Liquid

Originator

Depakote,Abbott

Uses

Antiepileptic; increases levels of -aminobutyric acid(GABA) in the brain. Anticonvulsant that also has efficacy as a mood stabilizer in bipolar disorder

Uses

Antiepileptic; Anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.

Uses

For treatment and management of seizure disorders, mania, and prophylactic treatment of migraine headache. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures asso

Definition

ChEBI: A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.

Manufacturing Process

Dipropyl acetic acid or valproic acid may be prepared the next way. Propylbromide is mixed with cyanacetic acid in the presence of sodium ethylate, made from absolute ethanol and sodium. By that prepared α,α- dipropylcyanacetic acid ethyl ester is saponified with equimolecular amounts of NaOH to give dipropylacetonitril. The desired dipropylacetic acid is produced by saponification of dipropylacetonitryl with aquatic NaOH. It is colorless liquid. BP 219°-220°C.
Sodium salt of this acid may be prepared by adding of equivalent of NaOH.

brand name

Depakene (Abbott);Valproine;Vederon.

Therapeutic Function

Anticonvulsant

Biological Functions

Although it is marketed as both valproic acid (Depakene) and as sodium valproate (Depakote), it is the valproate ion that is absorbed from the gastrointestinal tract and is the active form.
As with several other AEDs, it is difficult to ascribe a single mechanism of action to valproic acid.This compound has broad anticonvulsant activity, both in experimental studies and in the therapeutic management of human epilepsy.Valproic acid has been shown to block voltage-dependent sodium channels at therapeutically relevant concentrations. In several experimental studies, valproate caused an increase in brain GABA; the mechanism was unclear.There is evidence that valproate may also inhibit T-calcium channels and that this may be important in its mechanism of action in patients with absence epilepsy.

General Description

VPA is an established AED with a simple chemical structurebut an unusually broad spectrum of action. It is generallywell tolerated, but its use is limited by two rare but significanttoxic side effects (hepatotoxicity and teratogenicity) thatcan be dose-dependent or idiosyncratic in nature.Thesedrawbacks are apparently shared by its equipotent activemetabolite, (E)-2-propyl-2-pentenoic acid (2-ene-VPA).
VPA is also an important inhibitor of the cytochrome P450isozymes, mainly of CYP2C9 and also of uridine diphosphate(UDP)-glucuronyl transferase and epoxide hydrolase.

General Description

Clear colorless liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Propylpentanoic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 2-Propylpentanoic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. 2-Propylpentanoic acid is incompatible with bases, oxidizing agents and reducing agents. 2-Propylpentanoic acid is corrosive. .

Fire Hazard

2-Propylpentanoic acid is combustible.

Mechanism of action

Although its mechanism of action is not clearly established, valproate appears to increase the inhibitory effect of GABA, possibly by activation of glutamic acid decarboxylase or inhibition of GABA-transaminase). The high drug concentrations required, however, cast doubt on the clinical relevance of this effect. Furthermore, valproate recently has been shown to decrease the uptake of GABA into cultured astrocytes; this action may contribute to the AED efficacy. Valproate is known to produce a blockade of high-frequency repetitive firing by slowing the rate of Na+ recovery from inactivation, a mechanism consistent with the actions of phenytoin and CBZ. Valproate blocks the low-threshold T-type Ca2+ channel. Consequently, the overall therapeutic utility of valproate is likely caused by multiple effects.
Valproate is indicated for initial or adjunct treatment of absence seizures or as an adjunct when absence seizures occur in combination with either tonic-clonic seizures, myoclonic seizures, or both. For patients with unambiguous idiopathic generalized epilepsy, valproate often is the drug of choice, because it controls absence, myoclonic, and generalized tonic-clonic seizures well. It also is approved by U.S. FDA for use in complex partial seizures, occurring with or without other seizure types in adults or children 10 years of age or older. In new patients with typical absence seizures, ethosuximide is preferred to valproate because of the latter drug's risk of producing hepatotoxicity. In a comparative trial, sodium valproate and ethosuximide were equally effective when either drug was given alone or in combination with other AEDs in children with typical absence seizures. In atypical absence seizures (Lennox-Gastaut syndrome), sodium valproate is more effective, whereas in myoclonic seizures, it is less effective than clonazepam. Valproate is approved by the U.S. FDA for use in bipolar disorder and against migraine headaches.

Pharmacokinetics

Valproate undergoes rapid and complete absorption, which is only slightly slowed by food. It is 90% protein bound, and its clearance is dose-dependent because of an increase in the free fraction of the drug at higher doses. It is metabolized almost entirely by the liver, with 30 to 50% of an orally administered dose being eliminated in the urine as its acyl glucuronide conjugate, 40% from mitochondrial β-oxidation, approximately 15 to 20% by ω-oxidation, and less than 3% is excreted unchanged in urine. Its major active metabolite is (E)-2-ene valproate (trans 2-ene valproate). Its 4-ene metabolite has been proposed to be a reactive metabolite responsible for the hepatotoxicity of valproate. Other metabolites found in the urine include 3-oxo- and 4-hydroxyvalproate. The elimination half-life for valproate ranged from 9 to 16 hours following oral dosing regimens of 250 to 1,000 mg. Patients who are not taking enzyme-inducing AEDs (carbamazepine, phenytoin, and phenobarbital) will clear valproate more rapidly; therefore, monitoring of AED plasma concentrations should be intensified whenever concurrent AEDs are introduced or withdrawn.

Clinical Use

Valproic acid is well absorbed from the gastrointestinal tract and is highly bound (~90%) to plasma protein, and most of the compound is therefore retained within the vascular compartment.Valproate rapidly enters the brain from the circulation; the subsequent decline in brain concentration parallels that in plasma, indicating equilibration between brain and capillary blood. A large number of metabolites have been identified, but it is not known whether they play a role in the anticonvulsant effect of the parent drug. Valproic acid inhibits the metabolism of several drugs, including phenobarbital, primidone, carbamazepine, and phenytoin, leading to an increased blood level of these compounds. At high doses, valproic acid can inhibit its own metabolism. It can also displace phenytoin from binding sites on plasma proteins, with a resultant increase in unbound phenytoin and increased phenytoin toxicity. In this instance, the dosage of phenytoin should be adjusted as required. These examples reinforce the need to determine serum anticonvulsant levels in epileptic patients when polytherapy is employed.
Valproic acid has become a major AED against several seizure types. It is highly effective against absence seizures and myoclonic seizures. In addition, valproic acid can be used either alone or in combination with other drugs for the treatment of generalized tonic– clonic epilepsy and for partial seizures with complex symptoms.

Side effects

The most serious adverse effect associated with valproic acid is fatal hepatic failure. Fatal hepatotoxicity is most likely to occur in children under age 2 years, especially in those with severe seizures who are given multiple anticonvulsant drug therapy. The hepatotoxicity is not dose related and is considered an idiosyncratic reaction; it can occur in individuals in other age groups, and therefore, valproic acid should not be administered to patients with hepatic disease or significant hepatic dysfunction or to those who are hypersensitive to it. Valproic acid administration has been linked to an increased incidence of neural tube defects in the fetus of mothers who received valproate during the first trimester of pregnancy. Patients taking valproate may develop clotting abnormalities.
Valproic acid causes hair loss in about 5% of patients, but this effect is reversible. Transient gastrointestinal effects are common, and some mild behavioral effects have been reported. Metabolic effects, including hyperglycemia, hyperglycinuria, and hyperammonemia, have been reported. An increase in body weight also has been noted. Valproic acid is not a CNS depressant, but its administration may lead to increased depression if it is used in combination with phenobarbital, primidone, benzodiazepines, or other CNS depressant agents.

Chemical Synthesis

Valproic acid, 2-propylvaleric acid (9.4.3), is synthesized by the alkylation of cyanoacetic ester with two moles of propylbromide, to give dipropylcyanoacetic ester (9.4.1). Hydrolysis and decarboxylation of the carbethyoxy group gives dipropylacetonitrile (9.4.2), which is hydrolyzed into valproic acid (9.4.3) [12–15].

2-Propylpentanoic acid Preparation Products And Raw materials

Raw materials

Preparation Products


2-Propylpentanoic acid Suppliers

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View Lastest Price from 2-Propylpentanoic acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-07-23 2-Propylpentanoic acid USP/EP/BP
99-66-1
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
2021-07-13 Valproic acid
99-66-1
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
2021-07-10 Valproic acid
99-66-1
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

2-Propylpentanoic acid Spectrum


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