Additional Information
Valproate (VPA) and its valproic acid, sodium valproate, and valproate semisodium forms are medications primarily used to treat epilepsy and bipolar disorder and prevent migraine headaches. They are useful for the prevention of seizures in those with absence seizures, partial seizures, and generalized seizures. They can be given intravenously or by mouth, and the tablet forms exist in both long- and short-acting formulations.
Common side effects of valproate include nausea, vomiting, sleepiness, and dry mouth. Serious side effects can include liver failure, and regular monitoring of liver function tests is therefore recommended. Other serious risks include pancreatitis and an increased suicide risk. Valproate is known to cause serious abnormalities in babies if taken during pregnancy, and is contra-indicated for women of childbearing age unless the drug is essential to their medical condition. As of 2022 the drug was still prescribed in the UK to potentially pregnant women, but use declined by 51% from 2018\u201319 to 2020\u201321.
Valproate's precise mechanism of action is unclear. Proposed mechanisms include affecting GABA levels, blocking voltage-gated sodium channels, and inhibiting histone deacetylases. Valproic acid is a branched short-chain fatty acid (SCFA) made from valeric acid.
Valproate was first made in 1881 and came into medical use in 1962. It is on the World Health Organization's List of Essential Medicines and is available as a generic medication. In 2019, it was the 114th most commonly prescribed medication in the United States, with more than 5\u00a0million prescriptions.
| References |
: |
"Taggart, A,K,P,, et al,: J, Bio, Chem,, 280, 26649 (2005);" |
| Canonical SMILES |
: |
CCCCC(=O)O |
| Isomeric SMILES |
: |
CCCCC(=O)O |
| InChI |
: |
InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7) |
| InchIKey |
: |
NQPDZGIKBAWPEJ-UHFFFAOYSA-N |
| IUPAC Name |
: |
pentanoic acid |
| Exact Mass |
: |
102.068079557 |
| Color |
: |
Colorless liquid |
| Odor |
: |
UNPLEASANT ODOR, SIMILAR TO BUTYRIC ACID |
| Melting Point |
: |
-30.1 °F (NTP, 1992) |
| Boiling Point |
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365 °F at 760 mm Hg (NTP, 1992) |
| Solubility |
: |
10 to 50 mg/mL at 72° F (NTP, 1992) |
| Density |
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0.939 (USCG, 1999) |
| Chemical Classes |
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Other Classes -> Organic Acids |
| Use Classification |
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Food additives -> Flavoring Agents |
| Industry Uses |
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Intermediates |
| Consumer Uses |
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Lubricants and greases |
| Hazard Class |
: |
Skin Corr. 1B |
| Description |
: |
Valeric acid is a straight-chain saturated fatty acid containing five carbon atoms. It has a role as a plant metabolite. It is a short-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a valerate. |
| Disposal Methods |
: |
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations. |
| EC Number |
: |
203-677-2 |
| Vapor Pressure |
: |
1 mm Hg at 108 °F ; 40 mm Hg at 226.0° F; 760 mm Hg at 363.9° F (NTP, 1992) |
| Antidoteand Emergency Treatment |
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/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/ |
| Human Toxicity Excerpts |
: |
/ALTERNATIVE and IN VITRO TESTS/ An increase in the production of interferon was observed in Namalwa cells cultured for 24 hours or more in the presence of 5 mmol valeric acid and then induced with sendai virus. All substances which enhanced interferon production blocked thymidine incorporation into Namalwa cell DNA at concentrations equal to those effective in interferon stimulation. Apparently, these inducers of friend cell erythropoietic differentiation are also inducers of interferon production. |
