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Valproic acid is an analog of the natural fatty acid valeric acid. The sodium salt of valproic acid has long been used as an anticonvulsant to prevent many kinds of seizures. It is an inhibitor of histone deacetylases (HDACs), inhibiting Class I HDACs with an IC50 of ~2 mM.1 Valproic acid also inhibits glycogen synthase kinase 3 (GSK3) and depletes cellular inositol-1,4,5-trisphosphate (1,4,5-IP3).2 Because of these actions, valproic acid shows promise in combination therapy for cancer and in treating Alzheimer’s disease.3,4 Valproic acid (1 mM) also has pronounced effects on stem cell differentiation and self-renewal.5,6
1
Göttlicher, M., Minucci, S., Zhu, P., et al. Valproic acid defines a novel class of HDAC inhibitors inducing differentiation of transformed cells. EMBO J20(24)6969-6978(2001).
2
Williams, R.S.B., Cheng, L., Mudge, A.W., et al. A common mechanism of action for three mood-stabilizing drugs. Nature417292-295(2002).
3
Noguchi, H., Yamashita, H., Murakami, T., et al. Successful treatment of anaplastic thyroid carcinoma with a combination of oral valproic acid, chemotherapy, radiation and surgery. Endocr J56(2)245-249(2009).
4
Qing, H., He, G., Ly, P.T.T., et al. Valproic acid inhibits Aβproduction, neuritic plaque formation, and behavioral deficits in Alzheimer’s disease mouse models. J Exp Med205(12)2781-2789(2008).
5
Bug, G., Gül, H., Schwarz, K., et al. Valproic acid stimulates proliferation and self-renewal of hematopoietic stem cells. Cancer Res65(7)2537-2541(2005).
6
Jung, G., Yoon, J., Moon, B., et al. Valproic acid induces differentiation and inhibition of proliferation in neural progenitor cells via the beta-catenin-Ras-ERK-p21Cip/WAFI pathway. BMC Cell Biol9(66)(2008).
Synonyms
Sodium Valproate
2-Propylvaleric Acid
Formal Name
2-propyl-pentanoic acid, monosodium salt
CAS Number
1069-66-5
Molecular Formula
C8H16O2 · Na
Formula Weight
167.2
Formulation
A crystalline solid
Purity
≥95%
Stability
2 years
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCC(CCC)C(=O)O
Background Reading
Jung, G., Yoon, J., Moon, B., et al. Valproic acid induces differentiation and inhibition of proliferation in neural progenitor cells via the beta-catenin-Ras-ERK-p21Cip/WAFI pathway. BMC Cell Biol9(66)(2008).
Bug, G., Gül, H., Schwarz, K., et al. Valproic acid stimulates proliferation and self-renewal of hematopoietic stem cells. Cancer Res65(7)2537-2541(2005).
Göttlicher, M., Minucci, S., Zhu, P., et al. Valproic acid defines a novel class of HDAC inhibitors inducing differentiation of transformed cells. EMBO J20(24)6969-6978(2001).
Williams, R.S.B., Cheng, L., Mudge, A.W., et al. A common mechanism of action for three mood-stabilizing drugs. Nature417292-295(2002).
Qing, H., He, G., Ly, P.T.T., et al. Valproic acid inhibits Aβproduction, neuritic plaque formation, and behavioral deficits in Alzheimer’s disease mouse models. J Exp Med205(12)2781-2789(2008).