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{{CF/Current peer reviews|Peer review/So It's Come to This: A Simpsons Clip Show/archive1|4|2008-10-13T21:58:48Z|extra={{{extra|}}}}}
{{drugbox |
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| IUPAC_name = 2-propylpentanoic acid
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| image = Valproic-acid-2D-skeletal.png
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| width=180
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| CAS_number = 99-66-1
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| ATC_prefix = N03
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| ATC_suffix = AG01
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| PubChem = 3121
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| DrugBank = APRD00256
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| C=8 | H=16 | O=2
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| smiles = CCCC(CCC)C(=O)O
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| molecular_weight = 144.211 g/mol
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| bioavailability = Rapid absorption
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| protein_bound = Concentration-dependent, from 90% at 40 µg/mL to 81.5% at 130 µg/mL
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| metabolism = [[Liver|Hepatic]]—[[glucuronidation|glucuronide conjugation]] 30–50%, mitochondrial β-oxidation over 40%
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| elimination_half-life = 9–16 hours
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| excretion = Less than 3% excreted unchanged in urine.
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| licence_US = Valproic+acid
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| pregnancy_category = D—[[teratogenic]]
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| legal_US = Rx-only
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| legal_UK = POM
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| routes_of_administration = Oral, [[intravenous therapy|intravenous]]
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}}
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'''Valproic acid''' ('''VPA''') is a [[chemical compound]] that has found clinical use as an [[anticonvulsant]] and [[mood stabilizer|mood-stabilizing]] [[medication|drug]], primarily in the treatment of [[epilepsy]], [[bipolar disorder]], and less commonly [[major depressive disorder|major depression]]. It is also used to treat [[migraine headache|migraine]] [[headache]]s and [[schizophrenia]].
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Related drugs include the sodium salts [[sodium valproate]], used as an anticonvulsant, and a combined formulation, [[valproate semisodium]], used as a mood stabilizer and additionally in the U.S. also as an anticonvulsant.
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==History==
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Valproic acid (by its official name ''2-propylvaleric acid'') was first synthesized in 1882 by Burton as an [[analog (chemistry)|analogue]] of [[valeric acid]], found naturally in [[Valerian (herb)|valerian]].<ref>Burton BS (1882). On the propyl derivatives and decomposition products of ethylacetoacetate. ''Am Chem J.'' 3:385-395.</ref> A clear liquid fatty acid at room temperature, for many decades its only use was in laboratories as a "metabolically inert" solvent for organic compounds. In 1962, the French researcher Pierre Eymard serendipitously discovered the anticonvulsant properties of valproic acid while using it as a vehicle for a number of other compounds that were being screened for anti-seizure activity. He found that it prevented [[pentylenetetrazol]]-induced convulsions in rodents.<ref>Meunier H, Carraz G, Meunier Y, Eymard P, Aimard M. (1963). Propriétés pharmacodynamiques de l’acide n-dipropylacetique. ''Therapie'' 18:435-438.</ref> Since then it has also been used for migraine and bipolar disorder.<ref>Henry T.R. (2003). The History of Valproate in Clinical Neuroscience. ''Psychopharmacology bulletin'' 37 (Suppl 2):5-16</ref>
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==Indications==
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As an anticonvulsant, valproic acid is used to control [[absence seizure]]s, [[tonic-clonic seizure]]s ([[grand mal]]), [[complex partial seizure]]s, [[juvenile myoclonic epilepsy]] and the [[seizure]]s associated with [[Lennox-Gastaut syndrome]]. It is also used in treatment of [[myoclonus]]. In some countries, [[parenteral]] (administered [[intravenous]]ly) preparations of valproate are used also as second-line treatment of [[status epilepticus]], as an alternative to [[phenytoin]]. Valproate is one of the most common drugs used to treat [[post-traumatic epilepsy]].<ref name=PosnerLorenzo>Posner E, Lorenzo N (October 11, 2006). "[http://www.emedicine.com/NEURO/topic318.htm Posttraumatic epilepsy]". Emedicine.com. Retrieved on [[2008-07-30]].</ref>
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According to [[Medical News Today]], valproic acid can be used for the treatment of [[manic episodes]] associated with [[bipolar disorder]], adjunctive therapy in multiple seizure types (including epilepsy), and prophylaxis of migraine headaches<ref> {{cite news
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| last =
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| first =
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| coauthors =
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| title = FDA Issues Approvable Letter For Stavzor Delayed Release Valproic Acid Capsules
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| publisher = 2007 MediLexicon International Ltd
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| date = 2007-10-25
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| url = http://www.medicalnewstoday.com/articles/86674.php
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| accessdate = 2007-10-29 }} </ref>.
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It is more recently being used to treat neuropathic pain, as a second line agent, particularly lancinating pain from A* fibres.
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===Investigational===
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HDAC1 is needed for [[HIV]] to remain in infected cells. A study published in August 2005 found that three of four patients treated with valproic acid in addition to [[highly active antiretroviral therapy]] (HAART) showed a mean 75% reduction in latent HIV infection.<ref>{{cite journal | author = Lehrman G, Hogue I, Palmer S, Jennings C, Spina C, Wiegand A, Landay A, Coombs R, Richman D, Mellors J, Coffin J, Bosch R, Margolis D | title = Depletion of latent HIV-1 infection in vivo: a proof-of-concept study | journal = [[The Lancet|Lancet]] | volume = 366 | issue = 9485 | pages = 549–55 | year = 2005| pmid = 16099290 | doi = 10.1016/S0140-6736(05)67098-5}}</ref> Subsequent trials, however, have found no long term benefits of valproic acid in HIV infection.<ref>{{cite journal | author = Sagot-Lerolle N, Lamine A, Chaix ML, Boufassa F, Aboulker JP, Costagliola D, Goujard C, Paller C, Delfraissy JF, Lambotte O; ANRS EP39 study | title = Prolonged valproic acid treatment does not reduce the size of latent HIV reservoir | journal = [[AIDS (journal)|AIDS]] | volume = 22 | issue = 10 | pages = 1125-29 | year = 2008| pmid = 18525257}}</ref>
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According to the U.S. National Institutes of Health and others, valproic acid appears to have wide implications in the treatment of various [[cancer]]s,<ref>{{cite journal | author = Isenberg JS, Jia Y, Field L, Ridnour LA, Sparatore A, Del Soldato P, Sowers AL, Yeh GC, Moody TW, Wink DA, Ramchandran R, Roberts DD | title = Modulation of angiogenesis by dithiolethione-modified NSAIDs and valproic acid. | journal = [[Br J Pharmacol.|British Journal of Pharmacology]] | volume = Mar 12 | issue = | pages = | year = 2007 | pmid = 17273758}}</ref> including [[multiple myeloma]] (bone marrow cancer),<ref>{{cite journal | author = Schwartz C, Palissot V, Aouali N, Wack S, Brons NH, Leners B, Bosseler M, Berchem G | title = Valproic acid induces non-apoptotic cell death mechanisms in multiple myeloma cell lines. | journal = [[Int J Oncol.|International Journal of Oncology]] | volume = Mar | issue = 30 | pages = 573–82 | year = 2007 | pmid = 17273758}}</ref> [[glioma]] (an aggressive type of [[brain tumor]]),<ref>{{cite journal | author = A.M. Admirant, J. A. Hendricks, P.C. De Witt Hamer, S. Leenstra, W.P. Vandertop, C.J.F. van Noorden, and J.P. Medema | title = Valproic Acid is toxic to malignant glioma cells and increases sensitivity to irradiation and chemotherapy | journal = [[Abstracts for the Seventh Congress of the European Association for Neuro-Oncology (EANO)]] | volume = Sept 14-17 | issue = | pages = 334 | year = 2006 | id = | doi = 10.1186/1476-4598-5-71, | doi_brokendate = 2008-06-25 }}</ref> and melanoma.<ref>{{cite journal | author = Valentini A, Gravina P, Federici G, Bernardini S. | title = Valproic Acid Induces Apoptosis, p(16INK4A) Upregulation and Sensitization to Chemotherapy in Human Melanoma Cells | journal = [[Cancer Biol Ther.| Cancer Biology & Therapy]] | volume = Feb 5 | issue = 6 | pages = | year = 2007 | pmid = 17218782}}</ref> Valproic acid is cytotoxic to many different cancer types through its action as a histone-deacetylase inhibitor.
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Another potential indication may be [[leukemia]] in juvenile patients. Studies conducted by several European centres are ongoing. Although it is too early to make a definitive statement, preliminary results are encouraging.{{Fact|date=March 2007}}
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==Contraindications==
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Valproate is relatively [[contraindication|contraindicated]] in pregnancy due to its [[teratogenesis|teratogenicity]]; women who become pregnant while taking valproate should be counselled as to its risks, take high dose [[folic acid]] and be offered [[antenatal screening]] ([[alpha-fetoprotein]] and second [[trimester]] [[ultrasound scan]]s).<ref name="BNF">[[British National Formulary]] (March 2003) '''45'''</ref> It is a known folate antagonist, which can cause [[neural tube defects]]. Thus, folic acid supplements may alleviate the teratogenic problems. A recent study showed that children of mothers taking valproate during pregnancy are at risk for significantly lower IQs.<ref>{{cite web | url = http://www.medscape.com/viewarticle/549073 | title = NEAD: In Utero Exposure To Valproate Linked to Poor Cognitive Outcomes in Kids | last = Cassels | first = Caroline | date = [[December 8]] [[2006]] | publisher = Medscape | accessdate = 2007-05-23}}</ref><ref>{{cite journal |author=Meador KJ, Baker GA, Finnell RH, ''et al'' |title=In utero antiepileptic drug exposure: fetal death and malformations |journal=Neurology |volume=67 |issue=3 |pages=407–12 |year=2006 |pmid=16894099 |doi=10.1212/01.wnl.0000227919.81208.b2}}</ref> Exposure of the human [[embryo]] to valproic acid is also associated with risk of [[autism]], and it is possible to duplicate features characteristic of autism by exposing rat embryos to valproic acid at the time of neural tube closure.<ref name=Arndt>{{cite journal|journal=Int J Dev Neurosci|date=2005|volume=23|issue=2–3|pages=189–99|title=The teratology of autism|author=Arndt TL, Stodgell CJ, Rodier PM|doi=10.1016/j.ijdevneu.2004.11.001|pmid=15749245}}</ref> One study found that valproate exposure on embryonic day 11.5 led to significant local recurrent connectivity in the juvenile rat [[neocortex]], consistent with the underconnectivity theory of autism.<ref>{{cite journal|journal=Cereb Cortex|date=2007|title=Hyperconnectivity of local neocortical microcircuitry induced by prenatal exposure to valproic acid|author=Rinaldi T, Silberberg G, Markram H|doi=10.1093/cercor/bhm117|pmid=17638926 | volume = 18 | pages = 763}}</ref>
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Valproate is contraindicated in overweight patients because it might cause weight gain.{{Fact|date=September 2007}}
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Preexisting hepatic (liver) and/or renal (kidney) damage or [[cancer]], [[hepatitis]], [[pancreatitis]], end-stage [[AIDS]] [[HIV]] infection, [[bone marrow]] depression, urea cycle disorders, and [[coagulation]] hematological disorders are absolute contraindications.
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==Adverse effects==
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Common [[adverse drug reaction|side effects]] are [[dyspepsia]] and/or weight gain. Less common are [[fatigue (medical)|fatigue]], [[peripheral edema]], [[dizziness]], drowsiness, [[hair loss]], headaches, [[nausea]], [[sedation]] and [[tremor]]s. Valproic acid also causes [[hyperammonemia]], which can lead to brain damage.<ref>[http://www.jabfm.org/cgi/content/abstract/20/5/499 Valproate-associated Hyperammonemic Encephalopathy - Wadzinski et al. 20 (5): 499 - The Journal of the American Board of Family Medicine<!-- Bot generated title -->]</ref> Valproate levels within the normal range are capable of causing hyperammonemia and ensuing [[encephalopathy]]. There have been reports of brain encephalopathy developing without hyperammonemia or elevated valproate levels.<ref>[http://www.thieme-connect.com/ejournals/abstract/neuropediatrics/doi/10.1055/s-2006-973995 Thieme-connect - Abstract<!-- Bot generated title -->]</ref>
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Rarely, valproic acid can cause [[dyscrasia|blood dyscrasia]], impaired [[liver]] function, [[jaundice]], [[thrombocytopenia]], and prolonged [[coagulation]] times. In about 5% of pregnant users, valproic acid will cross the [[placenta]] and cause [[congenital defect|congenital anomalies]]. Due to these side effects, most doctors will ask for blood tests, initially as often as once a week and then once every 2 months. Temporary liver enzyme increase has been reported in 20% of cases during the first few months of taking the drug. Inflammation of the liver ([[hepatitis]]), the first symptom of which is [[jaundice]], is found in rare cases.
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Valproic acid may also cause acute hematological toxicities, especially in children, including rare reports of myelodysplasia and acute leukemia-like syndrome.<ref>{{cite journal | author = Williams DC Jr, Massey GV, Russell EC, Riley RS, Ben-Ezra J. | title = Translocation positive acute myeloid leukemia associated with valproic acid therapy | journal = [[Pediatric Blood and Cancer]] | volume = Mar 29 | issue = | pages = 641| year = 2007 | pmid = 17262798 | doi = 10.1002/pbc.21149}}</ref><ref>{{cite journal | author = Coyle TE, Bair AK, Stein C, Vajpayee N, Mehdi S, Wright J. | title = Acute leukemia associated with valproic acid treatment: a novel mechanism for leukemogenesis? | journal = [[Pediatric Blood and Cancer]] | volume = Apr | issue = 78 | pages = 256–60 | year = 2005 | pmid = 15795916 | doi = 10.1002/ajh.20273}}</ref>
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There have also been reports of cognitive dysfunction, [[Parkinsonism]]<ref name="pmid15971646">{{cite journal |author=Ricard C, Martin K, Tournier M, Bégaud B, Verdoux H |title=[A case of Parkinsonian syndrome, cognitive impairment and hyperammonemia induced by divalproate sodium prescribed for bipolar disorder] |language=French |journal=L'Encéphale |volume=31 |issue=1 Pt 1 |pages=98–101 |year=2005 |pmid=15971646 |doi=}}</ref>, and even (reversible) pseudoatrophic brain changes<ref name="pmid3117347">{{cite journal |author=McLachlan RS |title=Pseudoatrophy of the brain with valproic acid monotherapy |journal=The Canadian journal of neurological sciences. Le journal canadien des sciences neurologiques |volume=14 |issue=3 |pages=294–6 |year=1987 |pmid=3117347 |doi=}}</ref> in long-term treatment with valproic acid.
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==Pharmacology==
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Valproate is believed to affect the function of the [[neurotransmitter]] [[GABA]] (as a [[transaminase|GABA transaminase]] inhibitor) in the human brain, making it an alternative to [[Lithium pharmacology|lithium salt]]s in treatment of bipolar disorder.In addition to blocking transamination of GABA, Valproate is believed to reverse the transamination process to form more GABA. However, several other mechanisms of action in neuropsychiatric disorders have been proposed for valproic acid in recent years.<ref>{{cite journal | author = Rosenberg G | title = The mechanisms of action of valproate in neuropsychiatric disorders: can we see the forest for the trees? | journal = [[Cellular and Molecular Life Sciences]] | year =2007 | pmid = 17514356 | volume = 64 | pages = 2090 | doi = 10.1007/s00018-007-7079-x}}</ref>.
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Valproic acid also blocks the [[voltage-gated sodium channel]]s and T-type Calcium channels.These mechanisms make Valproic Acid a Broad Spectrum Anticonvulsant drug.
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Valproic acid is an [[Enzyme inhibitor|inhibitor]] of the [[enzyme]] [[histone deacetylase 1]] (HDAC1). It is a member of a larger class of [[histone deacetylase inhibitor]]s.
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==Interactions==
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Valproic acid may interact with [[carbamazepine]], as valproates inhibit [[epoxide hydrolase|microsomal epoxide hydrolase]] (mEH), the [[enzyme]] responsible for the breakdown of carbamazepine-10,11 epoxide (the main active metabolite of carbamazepine) into inactive metabolites.<ref>{{cite book |last=Gonzalez |first=Frank J. |coauthors=Robert H. Tukey |editor=Laurence Brunton, John Lazo, Keith Parker (eds.) |title=[[Goodman & Gilman's The Pharmacological Basis of Therapeutics]] |edition=11<sup>th</sup> ed. |year=2006 |publisher=[[McGraw-Hill]] |location=New York |isbn=978-0071422802|pages=p. 79 |chapter=Drug Metabolism }}</ref> By inhibiting mEH, valproic acid causes a buildup of the active metabolite, prolonging the effects of carbamazepine and delaying its excretion.
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Valproic acid also decreases the [[clearance (medicine)|clearance]] of [[amitriptyline]] and [[nortriptyline]].<ref name="RxList">{{cite web | url = http://www.rxlist.com/cgi/generic/depakene_ad.htm | title = Depakene side effects (Valproic Acid) and drug interactions | year = 2007 | accessdate = 2007-06-07 | publisher = RxList.com}}</ref>
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Also, Valproic acid should be used with caution with drugs like benzodiazopines and aspirin to avoid adverse effects.
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{{CF/Current peer reviews|Peer review/Holywell, Eastbourne/archive1|4|2008-09-27T07:07:40Z|extra={{{extra|}}}}}
==Formulations==
{{CF/Current peer reviews|Peer review/Meads/archive1|4|2008-09-27T07:05:00Z|extra={{{extra|}}}}}
<!-- Please do not add sodium valproate-based products to this list. That drug has its own article -->
{{CF/Current peer reviews|Peer review/Interstate 82/archive1|4|2008-09-25T21:50:37Z|extra={{{extra|}}}}}
Branded products include:<br />
{{CF/Current peer reviews|Peer review/Bad Blood (2004)/archive1|4|2008-09-25T19:52:59Z|extra={{{extra|}}}}}
'''Depakene''' ([[Abbott Laboratories]] in U.S. & Canada)<br />
{{CF/Current peer reviews|Peer review/List of PGA Championship champions/archive1|4|2008-09-25T19:39:01Z|extra={{{extra|}}}}}
'''Convulex''' ([[Pfizer]] in the UK and Byk Madaus in South Africa)<br />
{{CF/Current peer reviews|Peer review/Olaf the Peacock/archive1|4|2008-09-25T01:56:39Z|extra={{{extra|}}}}}
'''Stavzor''' ([[Noven Pharmaceuticals|Noven Pharmaceuticals Inc.]])<br />
{{CF/Current peer reviews|Peer review/List of National Historic Landmarks in New York/archive2|4|2008-09-25T00:19:53Z|extra={{{extra|}}}}}
'''Depakine''' ([[Sanofi Aventis|Sanofi Aventis.]]) <br />
{{CF/Current peer reviews|Peer review/Batman Returns/archive1|4|2008-09-25T00:10:39Z|extra={{{extra|}}}}}
'''Epival''' ([[Abbott Laboratories]] U.S. & Canada)
{{CF/Current peer reviews|Peer review/Discipline (Janet Jackson album)/archive1|4|2008-09-24T15:47:09Z|extra={{{extra|}}}}}

{{CF/Current peer reviews|Peer review/United States Academic Decathlon/archive3|4|2008-09-23T17:37:36Z|extra={{{extra|}}}}}
==References==
{{CF/Current peer reviews|Peer review/United Nations/archive2|4|2008-09-23T10:06:33Z|extra={{{extra|}}}}}
{{Reflist|2}}
{{CF/Current peer reviews|Peer review/Jack the Ripper: The Final Solution/archive1|4|2008-09-23T08:02:17Z|extra={{{extra|}}}}}

{{CF/Current peer reviews|Peer review/Flag of Japan/archive2|4|2008-09-23T06:31:01Z|extra={{{extra|}}}}}
==Further reading==
{{CF/Current peer reviews|Peer review/The Sword of Shannara/archive2|4|2008-09-23T03:17:28Z|extra={{{extra|}}}}}
*T.R. Henry, "The History of Valproate in Clinical Neuroscience." [http://www.medworksmedia.com/psychopharmbulletin/pdf/19/1-PB_VOL%2037%20SUPPL%202.pdf ''Psychopharmacology bulletin'' (2003) 37 (Suppl 2):5-16] (More details on history)
{{CF/Current peer reviews|Peer review/Family Moving Day/archive1|4|2008-09-23T02:51:13Z|extra={{{extra|}}}}}

{{CF/Current peer reviews|Peer review/Anniemal/archive1|4|2008-09-23T00:43:04Z|extra={{{extra|}}}}}
==External links==
{{CF/Current peer reviews|Peer review/Meshuggah/archive2|4|2008-09-21T10:41:34Z|extra={{{extra|}}}}}
* [http://www.psychotropics.dk/usr_view_molecule.asp?ID=2372&backurl=Alphaindex%2Fview%5Falpha%2Easp%3FStartchar%3DD&backurlname=Alphabetical+index&historyline=&Catalogtype=A The Lundbeck Institute Guide to Psychotropics - Valproic acid]
{{CF/Current peer reviews|Peer review/Jean-Hilaire Aubame/archive1|4|2008-09-20T21:39:27Z|extra={{{extra|}}}}}
* http://www.psycheducation.org/depression/meds/moodstabilizers.htm
{{CF/Current peer reviews|Peer review/Chiprovtsi/archive1|4|2008-09-19T16:46:59Z|extra={{{extra|}}}}}
* http://www.psycheducation.org/depression/meds/valproate.htm
{{CF/Current peer reviews|Peer review/Bunnies & Burrows/archive1|4|2008-09-19T05:23:27Z|extra={{{extra|}}}}}
* [http://ctd.mdibl.org/voc.go?voc=chem&termUI=Valproic+Acid The Comparative Toxicogenomics Database:Valproic Acid]
{{CF/Current peer reviews|Peer review/Napoleon I of France/archive1|4|2008-09-19T00:07:17Z|extra={{{extra|}}}}}
* [http://www.chemicalland21.com/lifescience/phar/VALPROIC%20ACID.htm Chemical Land21: Valproic Acid]
{{CF/Current peer reviews|Peer review/Juno (film)/archive1|4|2008-09-18T23:50:33Z|extra={{{extra|}}}}}
* [http://www.rxlist.com/cgi/generic2/depakene.htm RXList.com: Depakene (Valproic Acid)] (U.S.)
{{CF/Current peer reviews|Peer review/Louvre Abu Dhabi/archive1|4|2008-09-18T07:52:12Z|extra={{{extra|}}}}}
* [http://home.intekom.com/pharm/byk/convulex.html South African Electronic Package Inserts: Convulex]
{{CF/Current peer reviews|Peer review/Davenport, Iowa/archive1|4|2008-09-14T02:18:49Z|extra={{{extra|}}}}}
* [http://www.medbroadcast.com/drug_info_list.asp?search_letter=VALPROIC%20ACID Med Broadcast.com: Valproic Acid] (Canadian)
{{CF/Current peer reviews|Peer review/Buckeye Check Cashing, Inc. v. Cardegna/archive1|4|2008-09-12T20:23:27Z|extra={{{extra|}}}}}

{{CF/Current peer reviews|Peer review/Rudolf Wanderone/archive1|4|2008-09-09T05:07:57Z|extra={{{extra|}}}}}
{{Anticonvulsants}}

[[Category:Anticonvulsants]]
[[Category:Mood stabilizers]]
[[Category:Teratogens]]
[[Category:Carboxylic acids]]

[[de:Valproinsäure]]
[[es:Ácido valproico]]
[[fr:Acide valproïque]]
[[it:Acido valproico]]
[[no:Valproat]]
[[pl:Kwas walproinowy]]
[[pt:Valproato]]
[[ru:Вальпроевая кислота]]
[[sv:Valproinsyra]]

Revision as of 22:00, 13 October 2008











































































































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