1.0 2011-09-21 00:18:28 UTC 2015-10-09 22:31:14 UTC FDB022722 Valproic acid Valproic acid (VPA) is considered to be a drug of first choice and one of the most frequently-prescribed antiepileptic drugs worldwide for the therapy of generalized and focal epilepsies, including special epileptic. It is a broad-spectrum antiepileptic drug and is usually well tolerated. Rarely, serious complications may occur in some patients, including hemorrhagic pancreatitis, coagulopathies, bone marrow suppression, VPA-induced hepatotoxicity and encephalopathy, but there is still a lack of knowledge about the incidence and occurrence of these special side effects. VPA has been approved for stabilization of manic episodes in patients with bipolar disorder. It is also used to treat migraine headaches and schizophrenia. As the use of VPA increases, the number of both accidental and intentional exposures increases. This is paralleled by more reports of VPA-induced toxicity. VPA is relatively contraindicated in pregnancy due to its teratogenicity. It is a known folate antagonist, which can cause neural tube defects. Thus, folic acid supplements may alleviate teratogenic problems. Women who become pregnant whilst taking valproate should be counselled as to its risks. VPA is an inhibitor of the enzyme histone deacetylase 1 (HDAC1). HDAC1 is needed for HIV to remain in infected cells. Patients treated with valproic acid in addition to highly active antiretroviral therapy (HAART) showed a median 75% reduction in latent HIV infection. VPA is believed to affect the function of the neurotransmitter GABA (as a GABA transaminase inhibitor) in the human brain. Valproic Acid dissociates to the valproate ion in the gastrointestinal tract. (PMID: 18201150, 17496767) [HMDB] (n-C3H7)2CHCOOH (S)-2-propyl-4-pentanoate (S)-2-propyl-4-pentanoic acid 2 PP (base) 2-N-Propyl-N-valerate 2-n-Propyl-n-valeric acid 2-propyl-Pentanoate 2-propyl-Pentanoic acid 2-Propylpentanoate 2-Propylpentanoic acid 2-propylpentanoic acid (ACD/Name 4.0) 2-Propylvalerate 2-Propylvaleric acid 4-Heptanecarboxylate 4-Heptanecarboxylic acid Acide valproique acide valproique [inn-french] Acido valproico acido valproico [inn-spanish] Acidum valproicum acidum valproicum [inn-latin] Alti-valproic APO-divalproex Apo-valproic Apo-valproic syrup Avugane Baceca Convulex Delepsine Depakene Depakene Cap 250mg Depakene Cap 500mg Depakin Depakin chrono Depakine Depakine chrono Deproic Di-N-propylacetate Di-n-propylacetic acid Di-N-propylessigsaeure Di-n-propylessigsaure Di-n-propylessigsaure [german] Dipropylacetate Dipropylacetic acid Divalproex Divalproex-125 Divalproex-250 Divalproex-500 DOM-divalproex Dom-valproate DOM-valproic Dom-valproic acid DOM-valproic acid E.C. Dom-valproic acid syrup DPA (van) Epiject I.V. Epilex Epilim Epival Epival Ect 125mg Epival Ect 250mg Epival Ect 500mg Epival er Ergenyl Gen-divalproex Gen-Valproic - Cap 250mg Kyselina 2-propylvalerova Kyselina 2-propylvalerova [Czech] Med valproic Mylproin N-dipropylacetic acid N-DPA nchembio815-comp21 Novo-divalproex Novo-valproic Novo-Valproic - ECC Novo-valproic soft gel cap Nu-Divalproex 125mg Nu-Divalproex 250mg Nu-Divalproex 500mg Nu-valproic PEAC Penta-valproic PHL-valproate PHL-valproic acid PHL-valproic acid E.C. PMS-Divalproex PMS-Divalproex (125mg) PMS-Divalproex (500mg) PMS-valproate PMS-valproic acid PMS-valproic acid E.C. Propylvaleric acid Ratio-Valproic - ECC Ratio-Valproic 50mg/mL Syrup Ratio-Valproic-Cap 250mg S-2-n-Propyl-4-pentenoate S-2-n-Propyl-4-pentenoic acid S(-)-4-En-valproate S(-)-4-En-valproic acid Sandoz valproic Savicol Sodium hydrogen divalproate Sodium hydrogen divalproic acid Sprinkle Valcote Valparin Valproate semisodique [french] Valproate semisodium Valproato semisodico [spanish] Valproatum seminatricum [latin] Valproic acid [usan:ban:inn] Valproic acid USP Valproic acid USP24 Valproic-250 Valproinsaeure VPA C8H16O2 144.2114 144.115029756 2-propylpentanoic acid valproic acid 99-66-1 CCCC(CCC)C(O)=O InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) NIJJYAXOARWZEE-UHFFFAOYSA-N belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Methyl-branched fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Branched fatty acids branched-chain fatty acid branched-chain saturated fatty acid Solid logp 2.54 ALOGPS logs -1.79 ALOGPS solubility 2.36e+00 g/l ALOGPS logp 2.8 ChemAxon pka_strongest_acidic 5.14 ChemAxon iupac 2-propylpentanoic acid ChemAxon average_mass 144.2114 ChemAxon mono_mass 144.115029756 ChemAxon smiles CCCC(CCC)C(O)=O ChemAxon formula C8H16O2 ChemAxon inchi InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) ChemAxon inchikey NIJJYAXOARWZEE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 40.25 ChemAxon polarizability 17 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 938 Specdb::NmrTwoD 1714 Specdb::MsIr 1423 Specdb::MsIr 1424 Specdb::MsIr 1425 Specdb::CMs 8728 Specdb::CMs 38164 Specdb::CMs 132993 Specdb::CMs 140727 Specdb::NmrOneD 1774 Specdb::NmrOneD 2745 Specdb::NmrOneD 3439 Specdb::NmrOneD 148480 Specdb::NmrOneD 148481 Specdb::NmrOneD 148482 Specdb::NmrOneD 148483 Specdb::NmrOneD 148484 Specdb::NmrOneD 148485 Specdb::NmrOneD 148486 Specdb::NmrOneD 148487 Specdb::NmrOneD 148488 Specdb::NmrOneD 148489 Specdb::NmrOneD 148490 Specdb::NmrOneD 148491 Specdb::NmrOneD 148492 Specdb::NmrOneD 148493 Specdb::NmrOneD 148494 Specdb::NmrOneD 148495 Specdb::NmrOneD 148496 Specdb::NmrOneD 148497 Specdb::NmrOneD 148498 Specdb::NmrOneD 148499 Specdb::MsMs 1771 Specdb::MsMs 1772 Specdb::MsMs 1773 Specdb::MsMs 5533 Specdb::MsMs 5534 Specdb::MsMs 5535 Specdb::MsMs 5536 Specdb::MsMs 5537 Specdb::MsMs 5538 Specdb::MsMs 5539 Specdb::MsMs 261363 Specdb::MsMs 261364 Specdb::MsMs 261365 Specdb::MsMs 281298 Specdb::MsMs 281299 Specdb::MsMs 281300 Specdb::MsMs 438591 Specdb::MsMs 438592 Specdb::MsMs 438593 Specdb::MsMs 438594 Specdb::MsMs 438595 Specdb::MsMs 438596 Specdb::MsMs 438597 Specdb::MsMs 439969 Specdb::MsMs 2247401 HMDB01877 39867 2PP #<Reference:0x000055ce32c10678> #<Reference:0x000055ce32c10498> #<Reference:0x000055ce32c102e0> #<Reference:0x000055ce32c10128> #<Reference:0x000055ce32c0fed0> #<Reference:0x000055ce32c0fca0> #<Reference:0x000055ce32c0fa70> #<Reference:0x000055ce32c0f840> #<Reference:0x000055ce32c0f638> #<Reference:0x000055ce32c0f480> #<Reference:0x000055ce32c0f2c8> Cytochrome P450 2D6 Q6NWU0 CYP2D6 Cytochrome P450, family 1, subfamily A, polypeptide 1 A0N0X8 CYP1A1