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99-66-1 molecular structure
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2-propylpentanoic acid

ChemBase ID: 198
Molecular Formular: C8H16O2
Molecular Mass: 144.21144
Monoisotopic Mass: 144.11502975
SMILES and InChIs

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

Cite this record

CBID:198 http://www.chembase.cn/molecule-198.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
99-66-1
76584-70-8
EC Number
202-777-3
MDL Number
MFCD00002672
Beilstein Number
1750447
Merck Index
149913
PubChem SID
160963661
46505925
24898751
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.1443896  H Acceptors
H Donor LogD (pH = 5.5) 2.2844827 
LogD (pH = 7.4) 0.5629592  Log P 2.7984512 
Molar Refractivity 40.2491 cm3 Polarizability 15.977569 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.54  LOG S -1.79 
Solubility (Water) 2.36e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
alcohol: soluble expand Show data source
Chloroform expand Show data source
H2O: slightly soluble expand Show data source
Slightly soluble (1.3 mg/mL) expand Show data source
Apperance
White Solid expand Show data source
Yellow Liquid expand Show data source
Melting Point
99-101°C expand Show data source
Boiling Point
219-220°C expand Show data source
220 °C(lit.) expand Show data source
220°C expand Show data source
221-222°C expand Show data source
Flash Point
111 °C expand Show data source
126°C(258°F) expand Show data source
231.8 °F expand Show data source
Density
0.9 g/mL at 25 °C(lit.) expand Show data source
0.905 expand Show data source
1.136 g/ml expand Show data source
Refractive Index
1.4250 expand Show data source
n20/D 1.425(lit.) expand Show data source
Hydrophobicity(logP)
2.7 expand Show data source
Storage Condition
2-8°C expand Show data source
Refrigerator expand Show data source
RTECS
YV7875000 expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1760 expand Show data source
UN3265 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
8 expand Show data source
Packing Group
II expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
22-36/37/38 expand Show data source
61-22-34 expand Show data source
R:22-34 expand Show data source
Safety Statements
26 expand Show data source
53-45 expand Show data source
S:26-27/28-36/37/39-46-64 expand Show data source
EU Classification
C9 expand Show data source
EU Hazard Identification Number
8B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
H360-H314-H318-H302 expand Show data source
GHS Precautionary statements
P201-P309-P310 expand Show data source
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Admin Routes
Oral, intravenous expand Show data source
Bioavailability
Rapid absorption expand Show data source
Excretion
Less than 3% excreted unchanged in urine. expand Show data source
Half Life
9–16 h expand Show data source
Metabolism
Hepatic—glucuronide conjugation 30–50%, mitochondrial β-oxidation over 40% expand Show data source
Protein Bound
Concentration-dependent, from 90% at 40 μg/mL to 81.5% at 130 μg/mL expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
D—teratogenic expand Show data source
US Licence
Valproic+acid expand Show data source
Gene Information
human ... CYP1A2(1544)mouse ... Hdac1(433759)rat ... Slc6a1(79212) expand Show data source
Purity
98% expand Show data source
98+% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Pharmacopeia Traceability
traceable to PhEur V0033000 expand Show data source
traceable to USP 1708707 expand Show data source
Linear Formula
(CH3CH2CH2)2CHCO2H expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05206257 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02190286 external link
(2-Propylpentanoic acid)
DrugBank - DB00313 external link
Item Information
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 external link
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 external link
Biochem/physiol Actions
Anticonvulsant that also has efficacy as a mood stabilizer in bipolar disorder
Sigma Aldrich - 05194 external link
Biochem/physiol Actions
Anticonvulsant that also has efficacy as a mood stabilizer in bipolar disorder
Toronto Research Chemicals - V094750 external link
Antiepileptic; Anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.
Toronto Research Chemicals - V094755 external link
Antiepileptic; Anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

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