Drug Details

General Information of the Drug (ID: DR0727)
Name
Valproic acid
Synonyms
VALPROIC ACID; 2-Propylpentanoic acid; 99-66-1; 2-Propylvaleric acid; Dipropylacetic acid; Depakine; Depakene; Ergenyl; Di-n-propylacetic acid; Valproate; Mylproin; Pentanoic acid, 2-propyl-; 4-Heptanecarboxylic acid; n-Dipropylacetic acid; Propylvaleric acid; Myproic Acid; n-DPA; Dipropylacetate; Convulex; Depakin; Di-n-propylessigsaure; Avugane; Baceca; Stavzor; Acido valproico; Kyselina 2-propylvalerova; Acide valproique; 2-n-Propyl-n-valeric acid; Acidum valproicum; Acetic acid, dipropyl-; 2,2-di-n-propylacetic acid; Valproinsaeure; Savicol; Depakine chrono; Depakin chrono; Abbott 44090; Acide valproique [INN-French]; Acido valproico [INN-Spanish]; Acidum valproicum [INN-Latin]; 2-PROPYL-PENTANOIC ACID; Di-n-propylessigsaure [German]; Valeric acid, 2-propyl-; divalproex; Epilim; Kyselina 2-propylvalerova [Czech]; Di-n-propylessigsaeure; VPA;2-Propylpentanoic Acid; UNII-614OI1Z5WI; MFCD00002672; NSC 93819; Delepsine; Sprinkle; Valcote; Valparin; Epilex; PEAC; VPA; Depakene (TN); Vupral; CHEMBL109; (n-C3H7)2CHCOOH; 614OI1Z5WI; CHEBI:39867; NSC-93819; NCGC00091149-01; Deproic; Alti-Valproic; Novo-Valproic; Penta-Valproic; Dom-Valproic; Med Valproic; Nu-Valproic; DSSTox_CID_3733; DSSTox_RID_77171; DSSTox_GSID_23733; Valproic acid USP; PMS-Valproic Acid; 2-Propylpentanoic acid, 99%; Valproic acid (USP); CAS-99-66-1; Depakote (TM); SMR000499581; 362049-65-8; HSDB 3582; 2 PP (base); EINECS 202-777-3; BRN 1750447; Depacane; valproic-acid; Novo-divalproex; Sandoz valproic; Dom-valproate; Gen-divalproex; Apo-valproic; A-44090; AI3-10500; APO-divalproex; DOM-divalproex; Epival er; PHL-valproate; PMS-valproate; PMS-Divalproex; Erganyl; Stavzor; Dom-valproic acid; Apo-valproic syrup; PHL-valproic acid; Epiject I.V.; 2-propyl-Pentanoate; Epical (TM); Epilim (Salt/Mix); Valproic acid [USAN:USP:INN:BAN]; Depacon (Salt/Mix); 345909-03-7; 87745-17-3; Convulex (Salt/Mix); Eurekene (Salt/Mix); G2M-777; Valparin (Salt/Mix); Valproic acid solution; Novo-Valproic - ECC; Spectrum_000521; Divalproex (Salt/Mix); Dom-valproic acid syrup; Ratio-Valproic - ECC; Valdisoval (Salt/Mix); ACMC-209sdq; 2 -propylpentanoic acid; di-n-propyl acetic acid; S(-)-4-En-valproate; Spectrum2_000946; Spectrum3_001733; Spectrum4_000376; DOM-valproic acid E.C.; Heptane-4-carboxylic acid; PHL-valproic acid E.C.; PMS-valproic acid E.C.; Novo-valproic soft gel cap; EC 202-777-3; SCHEMBL2275; S-2-n-Propyl-4-pentenoate; (S)-2-propyl-4-pentanoate; KBioGR_000871; KBioGR_002277; KBioSS_001001; KBioSS_002278; MLS001076682; MLS001335927; MLS001335928; MLS002415770; BIDD:GT0858; DivK1c_000273; SPBio_000912; GTPL7009; DTXSID6023733; 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; HMS2089J06; HMS2231E06; HMS3259C18; HMS3370C21; HMS3715B15; HMS3885G14; ACT05281; ALBB-032973; BCP33204; NSC93819; ZINC3008621; Tox21_111091; Tox21_201963; Tox21_300603; ANW-41052; BDBM50003616; LMFA01020291; s3944; SBB065764; STL445581; AKOS009156895; Tox21_111091_1; Valproic Acid 1.0 mg/ml in Methanol; CCG-221127; CS-1765; DB00313; MCULE-7136317196; NC00584; SDCCGSBI-0050864.P004; NCGC00091149-02; NCGC00091149-03; NCGC00091149-04; NCGC00091149-05; NCGC00091149-06; NCGC00091149-08; NCGC00091149-09; NCGC00162288-07; NCGC00254365-01; NCGC00259512-01; AK128830; AS-11354; HY-10585; SBI-0050864.P003; AB0009719; 791-EP2306789A1; FT-0609289; FT-0675769; P0823; 6400-EP1441224A2; 6400-EP2272537A2; 6400-EP2272827A1; 6400-EP2275420A1; 6400-EP2280008A2; 6400-EP2298764A1; 6400-EP2298765A1; 6400-EP2308867A2; 6400-EP2308870A2; 6400-EP2311494A1; 6400-EP2311840A1; 6400-EP2314585A1; 6400-EP2374790A1; A19450; C07185; D00399; AB00698315-06; 2-(Propyl-3,3,3-d3)pentanoic-5,5,5-d3 Acid; Q240642; Q-200321; Sodium valproate; 2-Propylpentanoic acid sodium salt; SR-01000075242-7; F2191-0115; Z1511532065; Valproic acid, European Pharmacopoeia (EP) Reference Standard; Valproic acid, United States Pharmacopeia (USP) Reference Standard; Valproic acid for system suitability, European Pharmacopoeia (EP) Reference Standard; Valproic acid solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material; Valproic acid, Pharmaceutical Secondary Standard; Certified Reference Material
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Molecular Type
Small molecule
Disease Epilepsy/seizure [ICD-11: 8A60] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C8H16O2
PubChem CID
3121
Canonical SMILES
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)
InChIKey
NIJJYAXOARWZEE-UHFFFAOYSA-N
CAS Number
CAS 99-66-1
ChEBI ID
CHEBI:39867
TTD Drug ID
D0Y3KG
DrugBank ID
DB00313
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP8  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
NCI-H1299 CVCL_0060 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combination of arsenic trioxide and valproic acid efficiently inhibits growth of lung cancer cells via G2/M-phase arrest and apoptotic cell death.
          Metformin      Galega officinalis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 MET + VPA induced a significant decrease in proliferation and an increase in apoptosis in tumor cells.
          Xanthotoxin      Cullen corylifolium     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Adult male Albino Swiss mice weighing 22-26 g were used in this study.
                    Experimental
                    Result(s)		 XANT in combination with levetiracetam exerts beneficial anticonvulsant pharmacodynamic interactions in the 6 Hz mouse psychomotor seizure model.
Target and Pathway
Target(s) Glycogen synthase kinase-3 alpha (GSK-3A)  Molecule Info  [5]
Histone deacetylase (HDAC)  Molecule Info  [6]
NetPath Pathway TGF_beta_Receptor Signaling Pathway Click to Show/Hide
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Insulin/IGF pathway-protein kinase B signaling cascade
3 PDGF signaling pathway
4 Ras Pathway
Pathway Interaction Database Degradation of beta catenin Click to Show/Hide
2 Canonical Wnt signaling pathway
3 FOXM1 transcription factor network
4 Class I PI3K signaling events mediated by Akt
Reactome AKT phosphorylates targets in the cytosol Click to Show/Hide
2 XBP1(S) activates chaperone genes
3 Constitutive Signaling by AKT1 E17K in Cancer
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7009).
Reference 2 Combination of Arsenic Trioxide and Valproic Acid Efficiently Inhibits Growth of Lung Cancer Cells via G2/M-Phase Arrest and Apoptotic Cell Death. Int J Mol Sci. 2020 Apr 10;21(7):2649.
Reference 3 The Combination of Metformin and Valproic Acid Induces Synergistic Apoptosis in the Presence of p53 and Androgen Signaling in Prostate Cancer. Mol Cancer Ther. 2017 Dec;16(12):2689-2700.
Reference 4 Xanthotoxin enhances the anticonvulsant potency of levetiracetam and valproate in the 6-Hz corneal stimulation model in mice. Fundam Clin Pharmacol. 2021 Jul 2.
Reference 5 Challenges and new opportunities in the investigation of new drug therapies to treat frontotemporal dementia. Expert Opin Ther Targets. 2008 Nov;12(11):1367-76.
Reference 6 Transcription-independent heritability of induced histone modifications in the mouse preimplantation embryo. PLoS One. 2009 Jun 30;4(6):e6086.
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