Page last updated: 2024-12-06

dipropylacetamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Dipropylacetamide is a synthetic compound that has been investigated for its potential therapeutic properties. It exhibits anticonvulsant activity and has been studied for its effects on epilepsy and other neurological conditions. The compound's mechanism of action is thought to involve modulation of neurotransmitter release and activity. Dipropylacetamide has been synthesized through various methods, including the reaction of propionic acid with dipropylamine. Research on dipropylacetamide aims to explore its efficacy and safety as a potential treatment for neurological disorders, with studies focusing on its pharmacokinetic profile, potential side effects, and therapeutic potential.'

dipropylacetamide: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

valpromide : A fatty amide derived from valproic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID71113
CHEMBL ID93836
CHEBI ID74562
SCHEMBL ID35392
MeSH IDM0045784

Synonyms (67)

Synonym
CHEMBL93836
chebi:74562 ,
2,2-di-n-propylacetamide
D02766
depamide (tn)
valpromide (inn)
2430-27-5
2-propylpentanamide
valpromide
DB04165
1NU3
valpromide [inn]
2-ethylvaleramide
2-propylpentamide
valeramide, 2-propyl-
valpromidum [inn-latin]
depamide
propyl-2 valeramide
einecs 219-394-2
valpramide
brn 1750444
dipropylacetamide
valpromida [inn-spanish]
alpha-propylvaleramide
2-propylvaleramide
pentanamide, 2-propyl-
AKOS005068257
NCGC00182080-02
valpromidum
rua6cwu76g ,
unii-rua6cwu76g
valpromida
dtxcid203734
dtxsid1023734 ,
cas-2430-27-5
tox21_113134
A817204
FT-0609288
valproic acid impurity f [ep impurity]
valpromide [mi]
valpromide [mart.]
valpromide [who-dd]
S4991
SCHEMBL35392
3G0I
di-n-propyl acetamide
NCGC00182080-03
depamid
di-n-propylacetamide
.alpha.-propylvaleramide
W-107334
mfcd00051534
sr-01000944932
SR-01000944932-1
AS-58130
valpromide, >=97% (nmr)
2-propylpentanamide; valproic acid imp. f (ep); valproic acid impurity f
CS-8176
SY096545
HY-B2117
Q847560
A16980
HMS3886C09
CCG-266167
NCGC00182080-04
Z995089344
valpromide, 1mg/ml in methanol

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" At the time of deterioration, serum valproate was at toxic level in the three reported cases."( Delayed toxicity following acute ingestion of valpromide.
Descotes, J; Frantz, P; Martin, O; Moulsma, M; Parant, F; Payen, C; Pulce, C, 2004
)
0.32

Pharmacokinetics

ExcerptReferenceRelevance
" It also had the lowest clearance and the longest half-life and mean residence time."( Pharmacokinetic analysis of the structural requirements for forming "stable" analogues of valpromide.
Bialer, M; Hadad, S; Haj-Yehia, A, 1992
)
0.28
" MPD, the least-branched compound had the largest clearance and shortest half-life of all the amides investigated and was the least active."( Structure-pharmacokinetic relationships in a series of valpromide derivatives with antiepileptic activity.
Bialer, M; Haj-Yehia, A, 1989
)
0.28
"Only valproyl glycinamide showed a good anticonvulsant profile in both mice and rats due to its better pharmacokinetic profile."( Pharmacokinetic analysis and antiepileptic activity of N-valproyl derivatives of GABA and glycine.
Bialer, M; Hadad, S, 1995
)
0.29
" The current study demonstrates the benefit of the SPPR approach in developing and selecting a potent antiepileptic compound in intact animals based not only on its intrinsic pharmacodynamic activity, but also on its better pharmacokinetic profile."( Pharmacokinetic analysis and antiepileptic activity of N-valproyl derivatives of GABA and glycine.
Bialer, M; Hadad, S, 1995
)
0.29
"The described structure pharmacokinetic pharmacodynamic relationships (SPPR) study explored the utilization of tetramethylcyclopropane analogues of valpromide (VPD), or tetramethylcyclopropane carboxamide derivatives of valproic acid (VPA) as new antiepileptics."( Pharmacokinetic analysis and antiepileptic activity of tetra-methylcyclopropane analogues of valpromide.
Abdul-Hai, A; Bialer, M; Hadad, S; Haj-Yehia, A; Herzig, Y; Kadry, B; Sterling, J; Yagen, B, 1996
)
0.29
" VPA-HA and HEV showed improved anticonvulsant activity over VPA because of their greater intrinsic activity and not due to better pharmacokinetic characteristics."( Pharmacokinetics and antiepileptic activity of valproyl hydroxamic acid derivatives.
Bialer, M; Levi, M; Yagen, B, 1997
)
0.3
" We utilized pharmacokinetic considerations in designing various amide derivatives of VPA which are more potent as anticonvulsants than VPA and have the potential to be nonteratogenic and nonhepatotoxic."( Pharmacokinetic considerations in the design of better and safer new antiepileptic drugs.
Bialer, M, 1999
)
0.3

Bioavailability

ExcerptReferenceRelevance
" The complete oral bioavailability of VPD and the fact that the AUC of VPA obtained after oral administration of VPD was not higher than that obtained after the iv injection of VPD indicates that the gastrointestinal tract is not one of the metabolic sites of VPD to VPA conversion."( The disposition of valpromide in rats and the isolated perfused rat liver.
Bar-On, H; Bialer, M; Billig, H; Ziv, E,
)
0.13
" Following oral administration, the absolute bioavailability of VCD was 94 +/- 14%, and the terminal half-life was similar to that obtained after iv administration."( Pharmacokinetics of a valpromide isomer, valnoctamide, in dogs.
Bialer, M; Haj-Yehia, A, 1988
)
0.27
" The average fraction of valpromide that was transformed to valproic acid (fm) ranged from 30-55 per cent after all the oral and parenteral administrations, except for the enteric-coated tablet, which showed a very low bioavailability of valpromide."( Pharmacokinetics of valpromide in dogs after various modes of administration.
Bialer, M; Rubinstein, A,
)
0.13
" The relative bioavailability of the amide was 81."( Some clinical pharmacological aspects of n-dipropylacetamide.
Di Perri, R; Pisani, F, 1980
)
0.52
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
" VPM summary of product characteristics and pharmacokinetic studies revealed a lower bioavailability (80% vs."( Valproate, divalproex, valpromide: Are the differences in indications justified?
Besson, VC; Blaise, N; Bloch, V; Chouchana, M; Delage, C; Etain, B; Hagenimana, M; Palayer, M; Smati, J, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
" One group (n = 6) received sodium valproate (1,100 mg/day) for 2 weeks, while the other group (n = 6) was given, for the same period, a dosage of VPM (1,200 mg/day) expected to produce VPA levels equivalent to those achieved with valproate."( Sodium valproate and valpromide: differential interactions with carbamazepine in epileptic patients.
Fazio, A; Gitto, C; Oteri, G; Perucca, E; Pisani, F; Ruello, C; Russo, F,
)
0.13
" The dosage was 900 mg per day, administered orally."( [Preventive effect of dipropylacetamide in bipolar manic-depressive psychoses].
Kabes, J; Peterová, E; Vencovský, E, 1987
)
0.59
" Dosage should be reduced when valpromide is used in combination with these drugs."( [Use of valpromide in psychiatric therapeutics].
Lambert, PA; Venaud, G,
)
0.13
" The adequate dosage of VPD (Depamide, 300 mg) is 4 to 6 tablets in acute manic phases, 2 to 4 tablets in long term treatment, 1 to 3 tablets in depressive episode."( [Valpromide, Valproic acid and removal of small intestine in the treatment of a chronic depression: a case report].
Benjelloun, G; Blandin, K; Fossati, P,
)
0.13
" VPM would require a closer dosing schedule and a 20% reduction in dosage when switching to valproate."( Valproate, divalproex, valpromide: Are the differences in indications justified?
Besson, VC; Blaise, N; Bloch, V; Chouchana, M; Delage, C; Etain, B; Hagenimana, M; Palayer, M; Smati, J, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
teratogenic agentA role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
geroprotectorAny compound that supports healthy aging, slows the biological aging process, or extends lifespan.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
fatty amideA monocarboxylic acid amide derived from a fatty acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
limonene degradation I (D-limonene)326
limonene degradation II (L-limonene)325

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, limonene-1,2-epoxide hydrolaseRhodococcus erythropolisKi100.0000100.0000100.0000100.0000AID977610
Chain A, Epoxide hydrolaseAspergillus nigerKi250.0000250.0000250.0000250.0000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2003The EMBO journal, Jun-02, Volume: 22, Issue:11
Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site.
AID112306Compound was tested for anticonvulsant activity in maximal electroshock seizure(MES) test after 3 hours upon intraperitoneal administration to mice at a dose of 750 mg/kg1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID470104Ratio of ED50 for antiallodynic activity in rat assessed as protection against spinal nerve ligation-induced neuropathic pain to ED50 for antiepileptic activity in rat by maximal electroshock-induced seizures assay2009Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22
Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues.
AID353917Anticonvulsant activity in ip dosed CF1 albino mouse assessed as protection against 32 mA current-induced seizure by 6Hz psychomotor seizure test2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID470102Antiallodynic activity in ip dosed rat assessed as protection against spinal nerve ligation-induced neuropathic pain2009Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22
Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues.
AID353900Protective index, ratio of TD50 for CF1 albino mouse to ED50 for maximal electroshock-induced CF1 albino seizure mouse model2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID353901Anticonvulsant activity in ip dosed CF1 albino mouse assessed as protection against scMet-induced seizures2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID353903Neurotoxicity in ip dosed CF1 albino mouse assessed as minimal motor impairment2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID227699Virtual screen for compounds with anticonvulsant activity2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.
AID304127Solubility in water2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Potent anticonvulsant urea derivatives of constitutional isomers of valproic acid.
AID353912Anticonvulsant activity in po dosed albino Sprague-Dawley rat assessed as protection against maximal electroshock-induced seizures2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID470103Antiepileptic activity in ip dosed CF1 mouse assessed as inhibition of maximal electroshock-induced seizures2009Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22
Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues.
AID353902Protective index, ratio of TD50 for CF1 albino mouse to ED50 for scMet-induced CF1 albino seizure mouse model2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID353914Anticonvulsant activity in po dosed albino Sprague-Dawley rat assessed as protection against scMet-induced seizures2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID243251Inhibitory activity against Glycogen synthase kinase-3 beta, expressed as percent control2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds.
AID409960Inhibition of bovine brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID353920Protective index, ratio of TD50 for CF1 albino mouse to ED50 for 44 mA-current-induced CF1 albino mouse seizure model2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID1303016Inhibition of soluble epoxide hydrolase (unknown origin) using 14,15-EET as substrate incubated for 20 mins by LC-MS/MS analysis2016European journal of medicinal chemistry, Jul-19, Volume: 117Discovery of enantioselectivity of urea inhibitors of soluble epoxide hydrolase.
AID112452Compound was tested for anticonvulsant activity in maximal electroshock seizure(MES) test after 30 min upon intraperitoneal administration to mice at a dose of 750 mg/kg1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID353913Protective index, ratio of TD50 for albino Sprague-Dawley rat to ED50 for maximal electroshock-induced albino Sprague-Dawley rat seizure model2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID250341Anti-convulsant activity in experimental animal model; +++ = more effective2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds.
AID1303017Inhibition of microsomal epoxide hydrolase in pooled human liver microsomes assessed as enzyme activity using styrene oxide as substrate at 10 uM incubated for 10 mins by UV-HPLC analysis relative to control2016European journal of medicinal chemistry, Jul-19, Volume: 117Discovery of enantioselectivity of urea inhibitors of soluble epoxide hydrolase.
AID353916Neurotoxicity in po dosed albino Sprague-Dawley rat assessed as minimal motor impairment2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID243252Inhibitory activity against Glycogen synthase kinase-3 alpha, expressed as percent control2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds.
AID353915Protective index, ratio of TD50 for albino Sprague-Dawley rat to ED50 for scMet-induced albino Sprague-Dawley rat seizure model2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID409958Inhibition of bovine brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID353919Anticonvulsant activity in ip dosed CF1 albino mouse assessed as protection against 44 mA-current-induced seizure by 6Hz psychomotor seizure test2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID353899Anticonvulsant activity in ip dosed CF1 albino mouse assessed as protection against maximal electroshock-induced seizures2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID353918Protective index, ratio of TD50 for CF1 albino mouse to ED50 for 32 mA current-induced CF1 albino mouse seizure model2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2009Journal of the American Chemical Society, Jun-03, Volume: 131, Issue:21
Directed evolution of an enantioselective epoxide hydrolase: uncovering the source of enantioselectivity at each evolutionary stage.
AID1745854NCATS anti-infectives library activity on HEK293 viability as a counter-qHTS vs the C. elegans viability qHTS2023Disease models & mechanisms, 03-01, Volume: 16, Issue:3
In vivo quantitative high-throughput screening for drug discovery and comparative toxicology.
AID1745855NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay2023Disease models & mechanisms, 03-01, Volume: 16, Issue:3
In vivo quantitative high-throughput screening for drug discovery and comparative toxicology.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (124)

TimeframeStudies, This Drug (%)All Drugs %
pre-199050 (40.32)18.7374
1990's20 (16.13)18.2507
2000's34 (27.42)29.6817
2010's13 (10.48)24.3611
2020's7 (5.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.40 (24.57)
Research Supply Index5.03 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (5.56%)5.53%
Reviews6 (4.17%)6.00%
Case Studies12 (8.33%)4.05%
Observational0 (0.00%)0.25%
Other118 (81.94%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]