2-propylpentanoic acid

• ChemBase ID: 198
• Molecular Formular: C8H16O2
• Molecular Mass: 144.21144
• Monoisotopic Mass: 144.11502975
• SMILES: CCCC(C(=O)O)CCC
• Canonical SMILES: CCCC(C(=O)O)CCC
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-propylpentanoic acid
• IUPAC Traditional name: valproic acid
• Brand Name: Alti-Valproic; Convulex; Delepsine; Depakene; Depakine; Deproic; Dom-Valproic; Epilex; Epilim; Epival; Ergenyl; Med Valproic; Mylproin; Novo-Valproic; Nu-Valproic; PMS-Valproic Acid; Penta-Valproic; Sprinkle; Valcote; Valparin; Valproic acid USP; Valproic acid USP24; Avugane; Baceca
• Synonyms: Valproic acid; Valproic acid; 2-Propylvaleric acid; 2-Propylpentanoic acid; 2-Propylpentanoic acid; DI-n-PROPYLACETIC ACID; Di-n-propylacetic acid; Di-n-propylessigsaure; Dipropylacetic acid; DPA; Kyselina 2-propylvalerova; n-Dipropylacetic acid; n-DPA; Myproic Acid; Propylvaleric acid; Sodium hydrogen divalproate; Valproate semisodique [French]; Valproate semisodium; Valproato semisodico [Spanish]; Valproatum seminatricum [Latin]; Valproic Acid; Heptane-4-carboxylic acid; 2-n-Propylpentanoic acid; 2,2-Di-n-propylacetic acid; 2-Propyl-pentanoic Acid Sodium Salt; Depakote; Divalproex Sodium; Epival; Sodium Hydrogen Bis(2-propylpentanoate); Sodium Hydrogen Bis(2-propylvalerate); Valdisoval; Valproic Acid Semisodium Salt; 4-Heptanecarboxylic Acid; 44089; Depakine; Ergenyl; Mylproin; NSC 93819; 2-丙基戊酸; 丙戊酸; 丙戊酸; 2-丙基戊酸; 2,2-二-正丙基乙酸

Database IDs

• CAS Number: 76584-70-8; 99-66-1
• EC Number: 202-777-3
• MDL Number: MFCD00002672
• Beilstein Number: 1750447
• Merck Index: 149913
• PubChem SID: 46505925; 24898751; 160963661
• PubChem CID: 3121
• CHEBI ID: 39867
• ATC CODE: N03AG01
• CHEMBL: 109
• Chemspider ID: 3009
• DrugBank ID: DB00313
• KEGG ID: D00399
• Unique Ingredient Identifier: 614OI1Z5WI
• Wikipedia Title: Valproic_acid
• Medline Plus: a682412

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.1443896
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.2844827
• LogD (pH = 7.4): 0.5629592
• Log P: 2.7984512
• Molar Refractivity: 40.2491 cm^3
• Polarizability: 15.977569 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.54
• LOG S: -1.79
• Solubility (Water): 2.36e+00 g/l

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; Chloroform; H2O: slightly soluble; Slightly soluble (1.3 mg/mL)
• Apperance: White Solid; Yellow Liquid
• Melting Point: 99-101°C
• Boiling Point: 219-220°C; 220 °C(lit.); 220°C; 221-222°C
• Flash Point: 111 °C; 126°C(258°F); 231.8 °F
• Density: 0.9 g/mL at 25 °C(lit.); 0.905; 1.136 g/ml
• Refractive Index: 1.4250; n20/D 1.425(lit.)
• Hydrophobicity(logP): 2.7

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• RTECS: YV7875000
• European Hazard Symbols: Corrosive (C); Toxic (T); Harmful (Xn)
• UN Number: 1760; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: II; III
• Australian Hazchem: 2X
• Risk Statements: 22-36/37/38; 61-22-34; R:22-34
• Safety Statements: 26; 53-45; S:26-27/28-36/37/39-46-64
• EU Classification: C9
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H360-H314-H318-H302
• GHS Precautionary statements: P201-P309-P310; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: Rapid absorption
• Excretion: Less than 3% excreted unchanged in urine.
• Half Life: 9–16 h
• Metabolism: Hepatic—glucuronide conjugation 30–50%, mitochondrial β-oxidation over 40%
• Protein Bound: Concentration-dependent, from 90% at 40 μg/mL to 81.5% at 130 μg/mL
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: D—teratogenic
• US Licence: Valproic+acid
• Gene Information: human ... CYP1A2(1544)mouse ... Hdac1(433759)rat ... Slc6a1(79212)

Product Information

• Purity: 98%; 98+%
• Pharmacopeia Traceability: traceable to PhEur V0033000; traceable to USP 1708707
• Linear Formula: (CH3CH2CH2)2CHCO2H

DETAILS

MP Biomedicals - 05206257

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02190286

(2-Propylpentanoic acid)

DrugBank - DB00313

• Drug Groups: approved; investigational
• Description: A fatty acid with anticonvulsant properties used in the treatment of epilepsy. The mechanisms of its therapeutic actions are not well understood. It may act by increasing gamma-aminobutyric acid levels in the brain or by altering the properties of voltage dependent sodium channels. Typically supplied in the sodium salt form (76584-70-8). Valproic Acid is also a histone deacetylase inhibitor and is under investigation for treatment of HIV and various cancers.
• Indication: For treatment and management of seizure disorders, mania, and prophylactic treatment of migraine headache.
• Pharmacology: Valproic Acid is an anticonvulsant and mood-stabilizing drug used primarily in the treatment of epilepsy and bipolar disorder. It is also used to treat migraine headaches and schizophrenia. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures associated with Lennox-Gastaut syndrome. Valproic Acid 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. Valproic acid has also been shown to be an inhibitor of an enzyme called histone deacetylase 1 (HDAC1). HDAC1 is needed for HIV to remain in infected cells. A study published in August 2005 revealed that patients treated with valproic acid in addition to highly active antiretroviral therapy (HAART) showed a 75% reduction in latent HIV infection.
• Toxicity: Oral, mouse: LD₅₀ = 1098 mg/kg; Oral, rat: LD₅₀ = 670 mg/kg. Symptoms of overdose may include coma, extreme drowsiness, and heart problems.
• Affected Organisms: Humans and other mammals
• Biotransformation: Valproic Acid is metabolized almost entirely by the liver. In adult patients on monotherapy, 30-50% of an administered dose appears in urine as a glucuronide conjugate. Mitochondrial ß-oxidation is the other major metabolic pathway, typically accounting for over 40% of the dose. Usually, less than 15-20% of the dose is eliminated by other oxidative mechanisms. Less than 3% of an administered dose is excreted unchanged in urine.
• Absorption: Rapid absorption from gastrointestinal tract.
• Half Life: 9-16 hours
• Protein Binding: Concentration-dependent, from 90% at 40 μg/mL to 81.5% at 130 μg/mL.
• Elimination: Valproate is metabolized almost entirely by the liver. Less than 3% of an administered dose is excreted unchanged in urine. Mitochondrial ?-oxidation is the other major metabolic pathway, typically accounting for over 40% of the dose.
• Distribution: * 11 L/1.73 m2 [total valproate]; * 92 L/1.73 m2 [free valproate]
• Clearance: * total valproate cl=0.56 L/hr/1.73 m2; * free valproate cl=4.6 L/hr/1.73 m2; * 4.8 +/- 0.17 L/hr/1.73 m2 [males, unbound clearance]; * 4.7+/- 0.07 L/hr/1.73 m2 [females, unbound clearance]
• References: Rosenberg G: The mechanisms of action of valproate in neuropsychiatric disorders: can we see the forest for the trees? Cell Mol Life Sci. 2007 Aug;64(16):2090-103. [Pubmed] ; Lehrman G, Hogue IB, Palmer S, Jennings C, Spina CA, Wiegand A, Landay AL, Coombs RW, Richman DD, Mellors JW, Coffin JM, Bosch RJ, Margolis DM: Depletion of latent HIV-1 infection in vivo: a proof-of-concept study. Lancet. 2005 Aug 13-19;366(9485):549-55. [Pubmed] ; Schwartz C, Palissot V, Aouali N, Wack S, Brons NH, Leners B, Bosseler M, Berchem G: Valproic acid induces non-apoptotic cell death mechanisms in multiple myeloma cell lines. Int J Oncol. 2007 Mar;30(3):573-82. [Pubmed] ; Valentini A, Gravina P, Federici G, Bernardini S: Valproic acid induces apoptosis, p16INK4A upregulation and sensitization to chemotherapy in human melanoma cells. Cancer Biol Ther. 2007 Feb;6(2):185-91. Epub 2007 Feb 5. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P6273

Biochem/physiol Actions
抗惊厥药，同时还具有双相障碍症情绪稳定剂的功效
包装
100 mL in glass bottle

Sigma Aldrich - 224251

Biochem/physiol Actions
Anticonvulsant that also has efficacy as a mood stabilizer in bipolar disorder

Sigma Aldrich - 05194

Biochem/physiol Actions
Anticonvulsant that also has efficacy as a mood stabilizer in bipolar disorder

Toronto Research Chemicals - V094750

Antiepileptic; Anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.

Toronto Research Chemicals - V094755

Antiepileptic; Anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.

REFERENCES

• Rosenberg G: The mechanisms of action of valproate in neuropsychiatric disorders: can we see the forest for the trees? Cell Mol Life Sci. 2007 Aug;64(16):2090-103. Pubmed
• Lehrman G, Hogue IB, Palmer S, Jennings C, Spina CA, Wiegand A, Landay AL, Coombs RW, Richman DD, Mellors JW, Coffin JM, Bosch RJ, Margolis DM: Depletion of latent HIV-1 infection in vivo: a proof-of-concept study. Lancet. 2005 Aug 13-19;366(9485):549-55. Pubmed
• Schwartz C, Palissot V, Aouali N, Wack S, Brons NH, Leners B, Bosseler M, Berchem G: Valproic acid induces non-apoptotic cell death mechanisms in multiple myeloma cell lines. Int J Oncol. 2007 Mar;30(3):573-82. Pubmed
• Valentini A, Gravina P, Federici G, Bernardini S: Valproic acid induces apoptosis, p16INK4A upregulation and sensitization to chemotherapy in human melanoma cells. Cancer Biol Ther. 2007 Feb;6(2):185-91. Epub 2007 Feb 5. Pubmed
• Chang, Z.L., et al.: Anal. Profiles Drug Subs., 8, 529 (1979)
• Della Paschoa, O.E., et al.: Br. J. Pharmacol., 125, 1610 (1979)
• Grimes, C.A., et al.: J. Neirochem., 73, 1384 (1979)
• Loscher, W., Prog. Neurobiol., 58, 31 (1979)
• Chang, Z.L., et al.: Anal. Profiles Drug Subs., 8, 529 (1979)
• Della Paschoa, O.E., et al.: Br. J. Pharmacol., 125, 1610 (1979)
• Grimes, C.A., et al.: J. Neirochem., 73, 1384 (1979)
• Loscher, W., Prog. Neurobiol., 58, 31 (1979)