Compound: VALPROIC ACID
SMILES: O=C(O)C(CCC)CCC
InChIKey: NIJJYAXOARWZEE-UHFFFAOYSA-N
Synonyms: VALPROIC ACID, 2-Propylpentanoic acid, 99-66-1, 2-Propylvaleric acid, Dipropylacetic acid, Depakene, Depakine, Mylproin, Di-n-propylacetic acid, Propylvaleric acid, n-Dipropylacetic acid, 4-Heptanecarboxylic acid, Myproic Acid, Convulex, n-DPA, Acido valproico, Acide valproique, Di-n-propylessigsaure, Stavzor, Kyselina 2-propylvalerova, Acidum valproicum, 2-n-Propyl-n-valeric acid, Acetic acid, dipropyl-, Epilim, 2-PROPYL-PENTANOIC ACID, Valeric acid, 2-propyl-, pentanoic acid, 2-propyl, Valproic acid extended release, 614OI1Z5WI, DTXSID6023733, DTXCID803733, CHEBI:39867, 3-02-00-00807 (Beilstein Handbook Reference), NSC93819, 2 Propylpentanoic Acid, Valproic, RefChem:6343, 202-777-3, Ergenyl, Pentanoic acid, 2-propyl-, Dipropylacetate, Depakin, Avugane, Baceca, 2,2-di-n-propylacetic acid, Valproinsaeure, Savicol, Depakine chrono, Depakin chrono, Acide valproique [INN-French], Acido valproico [INN-Spanish], Acidum valproicum [INN-Latin], Di-n-propylessigsaure [German], Kyselina 2-propylvalerova [Czech], Di-n-propylessigsaeure, VPA;2-Propylpentanoic Acid, MFCD00002672, NSC 93819, Sprinkle, Valcote, PEAC, VPA, Depakene (TN), CHEMBL109, (n-C3H7)2CHCOOH, Vupral, Valerin, NSC-93819, s3944, NCGC00091149-01, Deproic, Alti-Valproic, Novo-Valproic, Penta-Valproic, Dom-Valproic, Med Valproic, Nu-Valproic, Valproic acid USP, PMS-Valproic Acid, Valproic acid (USP), CAS-99-66-1, Depakote (TM), SMR000499581, VALPROICACID, HSDB 3582, 2 PP (base), EINECS 202-777-3, BRN 1750447, UNII-614OI1Z5WI, valproic-acid, Novo-divalproex, Sandoz valproic, Dom-valproate, Gen-divalproex, Apo-valproic, Vaproic acid, AI3-10500, APO-divalproex, DOM-divalproex, Epival er, PHL-valproate, PMS-valproate, PMS-Divalproex, Erganyl; Stavzor, Dom-valproic acid, Valproic acid RS, PHL-valproic acid, Valproic acid CRS, Epiject I.V., 2-propyl-Pentanoate, Epical (TM), Epilim (Salt/Mix), Valproic acid [USAN:USP:INN:BAN], Depacon (Salt/Mix), Convulex (Salt/Mix), Eurekene (Salt/Mix), G2M-777, Valparin (Salt/Mix), Valproic acid (GMP), Novo-Valproic - ECC, Spectrum_000521, VPA +TNFa, Divalproex (Salt/Mix), Ratio-Valproic - ECC, Valdisoval (Salt/Mix), 2 -propylpentanoic acid, di-n-propyl acetic acid, S(-)-4-En-valproate, Spectrum2_000946, Spectrum3_001733, Spectrum4_000376, Valproic acid (Standard), DOM-valproic acid E.C., PHL-valproic acid E.C., PMS-valproic acid E.C., Novo-valproic soft gel cap, EC 202-777-3, SCHEMBL2275, VALPROIC ACID [MI], VALPROIC ACID [INN], S-2-n-Propyl-4-pentenoate, (S)-2-propyl-4-pentanoate, KBioGR_000871, KBioGR_002277, KBioSS_001001, KBioSS_002278, VALPROIC ACID [HSDB], VALPROIC ACID [USAN], MLS001076682, MLS001335927, MLS001335928, MLS002415770, BIDD:GT0858, DivK1c_000273, SCHEMBL515242, VALPROIC ACID [VANDF], SPBio_000912, VALPROIC ACID [MART.], GTPL7009, orb1300101, orb3141166, SCHEMBL1261583, SCHEMBL7618217, SCHEMBL9405011, VALPROIC ACID [USP-RS], VALPROIC ACID [WHO-DD], WLN: QVY3 & 3, KBio1_000273, KBio2_001001, KBio2_002277, KBio2_003569, KBio2_004845, KBio2_006137, KBio2_007413, KBio3_002626, KBio3_002757, NIJJYAXOARWZEE-UHFFFAOYSA-, Valproic acid [USAN:BAN:INN], NINDS_000273, GLXC-02555, HMS2089J06, HMS2231E06, HMS3259C18, HMS3370C21, HMS3715B15, HMS3885G14, HMS5082N05, Valproic acid, 1mg/ml in Methanol, ALBB-032973, VALPROIC ACID [EP IMPURITY], VALPROIC ACID [ORANGE BOOK], Tox21_111091, Tox21_201963, Tox21_300603, BDBM50003616, EBC-13795, HY-10585G, HY-10585R, LMFA01020291, SBB065764, STL445581, VALPROIC ACID [EP MONOGRAPH], VALPROIC ACID [USP IMPURITY], VALPROIC ACID [USP MONOGRAPH], AKOS009156895, Tox21_111091_1, Valproic Acid 1.0 mg/ml in Methanol, CCG-221127, CS-1765, DB00313, FV30281, NC00584, SDCCGSBI-0050864.P004, SDCCGSBI-0050864.P012, MSK001227-1000M, NCGC00091149-02, NCGC00091149-03, NCGC00091149-04, NCGC00091149-05, NCGC00091149-06, NCGC00091149-08, NCGC00091149-09, NCGC00091149-21, NCGC00091149-26, NCGC00162288-07, NCGC00254365-01, NCGC00259512-01, Valproic acid for system suitability CRS, AS-11354, DA-78822, HY-10585, SBI-0050864.P003, NS00010277, P0823, EN300-64925, C07185, D00399, Valproic acid Solution in Methanol, 1000ug/mL, Valproic Acid(Discontinued,See C4X-116648), Valproic Acid; Sodium Caprylate EP Impurity E, AB00698315-06, F386761, Q240642, SR-01000075242-7, BRD-K41260949-001-18-2, BRD-K41260949-236-15-0, BRD-K41260949-236-16-8, BRD-K41260949-236-17-6, BRD-K41260949-236-18-4, BRD-K41260949-236-19-2, BRD-K41260949-236-20-0, F2191-0115, Z756391526, Valproic acid, European Pharmacopoeia (EP) Reference Standard, Valproic acid, United States Pharmacopeia (USP) Reference Standard, InChI=1/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10), Valproic acid for system suitability, European Pharmacopoeia (EP) Reference Standard, Valproic acid, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C8H16O2
molecular_weight: 144.21 g/mol
exact_mass: 144.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 10
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless liquid
color: Colorless liquid
odor: Characteristic odor
boiling_point: 428 °F at 760 mmHg (NTP, 1992)
density: 0.922 at 32 °F (NTP, 1992) - Less dense than water; will float
solubility: less than 1 mg/mL at 72 °F (NTP, 1992)
flash_point: 232 °F (NTP, 1992)
Descriptions:
{"pubchem": "Valproate (Valproic acid) can cause developmental toxicity according to an independent committee of scientific and health experts.", "chebi": "A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.", "chembl": "VALPROIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Valproate (valproic acid, VPA, sodium valproate, and valproate semisodium forms) are medications primarily used to treat epilepsy and as a mood stabilizer in the treatment of bipolar disorder. 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.\nCommon side effects of valproate include nausea, vomiting, somnolence, 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.\nValproate is known to cause serious abnormalities or birth defects in the fetus if taken during pregnancy, and is contra-indicated for women of childbearing age unless the drug is essential to their medical condition and the person is also prescribed a contraceptive. Reproductive warnings have also been issued for men using the drug.\nValproate is restricted in the United Kingdom for both women and men under age 55 due to teratogenicity in pregnant women and fertility problems in men. It is also restricted in the European Union. The United States Food and Drug Administration has indicated a black box warning given the frequency and severity of the side effects and teratogenicity. Additionally, there is also a black box warning due to risk of hepatotoxicity and pancreatitis.\nValproate has been in use in Japan for the prophylaxis of migraine since 2011. It is approved as an antimanic and antiseizure in Japan as well. In UK, valproate is approved for bipolar mania and epilepsy, and both valproate and divalproex are approved, although divalproex sodium is known as valproate semisodium.\nValproate's precise mechanism of action is unclear. Proposed mechanisms include affecting GABA levels, blocking voltage-gated sodium channels, inhibiting histone deacetylases, and increasing LEF1. Valproic acid is a branched short-chain fatty acid (SCFA), a derivative of valeric acid.\nValproate was originally synthesized in 1881 and came into medical use in 1962. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 160th most commonly prescribed medication in the United States, with more than 3 million prescriptions.\n\n"}