Compounds > skepinone-l
Page last updated: 2024-08-03 16:13:25

skepinone-l

Description

skepinone-L: a dibenzosuberone-type p38 MAPK inhibitor; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID45279963
CHEMBL ID2152944
SCHEMBL ID2686103
MeSH IDM0573970

Synonyms (30)

Synonym
2-(2,4-difluorophenylamino)-7-[2r-,3-dihydroxypropoxy]-10,11-dihydro-dibenzo[a,d]-cyclohepten-5-one
3ff ,
2-[(2,4-difluorophenyl)amino]-7-{[(2r)-2,3-dihydroxypropyl]oxy}-10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-one
bdbm50392175
CHEMBL2152944 ,
HY-15300
skepinone-l
CS-0941
S7214
1221485-83-1
3QUE
(r)-2-((2,4-difluorophenyl)amino)-7-(2,3-dihydroxypropoxy)-10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-one
5h-dibenzo[a,d]cyclohepten-5-one, 2-[(2,4-difluorophenyl)amino]-7-[(2r)-2,3-dihydroxypropoxy]-10,11-dihydro-
SCHEMBL2686103
skepinone l
2-(2,4-difluoroanilino)-7-[(2r)-2,3-dihydroxypropoxy]-10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-one
DTXSID30669907
AKOS027422745
cbs3830
SW219942-1
BCP04105
2-[(2,4-difluorophenyl)amino]-7-[(2r)-2,3-dihydroxypropoxy]-10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-one
AC-35955
EX-A2161
13-(2,4-difluoroanilino)-5-[(2r)-2,3-dihydroxypropoxy]tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-one
CCG-268943
Q27453778
A891204
AS-79383
Z2235802136

Protein Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Heat shock protein beta-1Homo sapiens (human)IC500.0250AID1792170
Cholesteryl ester transfer proteinHomo sapiens (human)IC500.0050AID691521
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ki3.7111AID1914141
5-hydroxytryptamine receptor 2BHomo sapiens (human)Ki0.1724AID1914142
Sodium-dependent dopamine transporter Homo sapiens (human)Ki10.0000AID1914143
Mitogen-activated protein kinase 11Homo sapiens (human)IC500.0351AID1792157; AID1912759; AID1912932
Mitogen-activated protein kinase 14Homo sapiens (human)IC500.0091AID1792156; AID1792169; AID1820047; AID1912758; AID1912931; AID1913187; AID691521; AID721305
Sigma intracellular receptor 2Homo sapiens (human)Ki3.3580AID1914146

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Chain A, Mitogen-activated protein kinase 14Homo sapiens (human)Kd0.0015AID977611

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1657791Inhibition of p38alpha MAPK (unknown origin) assessed as target residence time using ATF2 as substrate preincubated for 1 hr followed by jump dilution in presence of substrate and measured every 3 mins for 4 hrs by TR-FRET assay2020Journal of medicinal chemistry, 07-09, Volume: 63, Issue:13
ISSN: 1520-4804		Bioisosteric Replacement of Arylamide-Linked Spine Residues with
AID1899344Pro-proliferative activity in Wistar rat cardiac cells from P6 late postnatal developmental time points assessed as effect on cell number by measuring alphaAct/Ki67 cardiomyocyte nuclei at at 0.33 to 10 uM by DAPI analysis2022Journal of medicinal chemistry, 01-27, Volume: 65, Issue:2
ISSN: 1520-4804		High-Throughput Screening Platform in Postnatal Heart Cells and Chemical Probe Toolbox to Assess Cardiomyocyte Proliferation.
AID1899312Inhibition of P38betaMAPK (unknown origin) relative to control2022Journal of medicinal chemistry, 01-27, Volume: 65, Issue:2
ISSN: 1520-4804		High-Throughput Screening Platform in Postnatal Heart Cells and Chemical Probe Toolbox to Assess Cardiomyocyte Proliferation.
AID691523Inhibition of p38alpha-dependent TNFalpha production in human whole blood2012Journal of medicinal chemistry, Jun-28, Volume: 55, Issue:12
ISSN: 1520-4804		Design, synthesis, and biological evaluation of novel disubstituted dibenzosuberones as highly potent and selective inhibitors of p38 mitogen activated protein kinase.
AID721305Inhibition of p38alpha MAP kinase (unknown origin) by ELISA2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
ISSN: 1520-4804		Dibenzosuberones as p38 mitogen-activated protein kinase inhibitors with low ATP competitiveness and outstanding whole blood activity.
AID1820047Inhibition of human p38 MAPK alpha2022Journal of medicinal chemistry, 01-27, Volume: 65, Issue:2
ISSN: 1520-4804
AID721304Inhibition of p38alpha MAP kinase in whole blood (unknown origin) assessed as lipopolysaccharide-stimulated TNF-alpha release by ELISA2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
ISSN: 1520-4804		Dibenzosuberones as p38 mitogen-activated protein kinase inhibitors with low ATP competitiveness and outstanding whole blood activity.
AID691521Inhibition of p38alpha by immunosorbent based kinase assay2012Journal of medicinal chemistry, Jun-28, Volume: 55, Issue:12
ISSN: 1520-4804		Design, synthesis, and biological evaluation of novel disubstituted dibenzosuberones as highly potent and selective inhibitors of p38 mitogen activated protein kinase.
AID1899343Pro-proliferative activity in Wistar rat cardiac cells from P1 early postnatal developmental time points assessed as effect on cell number by measuring alphaAct/Ki67 cardiomyocyte nuclei at at 0.33 to 10 uM by DAPI analysis2022Journal of medicinal chemistry, 01-27, Volume: 65, Issue:2
ISSN: 1520-4804		High-Throughput Screening Platform in Postnatal Heart Cells and Chemical Probe Toolbox to Assess Cardiomyocyte Proliferation.
AID1899303Inhibition of P38alphaMAPK (unknown origin) relative to control2022Journal of medicinal chemistry, 01-27, Volume: 65, Issue:2
ISSN: 1520-4804		High-Throughput Screening Platform in Postnatal Heart Cells and Chemical Probe Toolbox to Assess Cardiomyocyte Proliferation.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2011Nature chemical biology, Dec-25, Volume: 8, Issue:2
ISSN: 1552-4469		Skepinone-L is a selective p38 mitogen-activated protein kinase inhibitor.

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's13 (76.47)24.3611
2020's4 (23.53)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
sb 239063
1
imidazoles202220222.0low000001
1-ethyl-2-benzimidazolinone
1
imidazoles202220222.0low000001
birb 796
1
aromatic ether;
morpholines;
naphthalenes;
pyrazoles;
ureas		EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
immunomodulator		2013201311.0low000010
sb 203580
2
imidazoles;
monofluorobenzenes;
pyridines;
sulfoxide		EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent		2012201311.5low000020
ml 3403
1
202220222.0high000001
4-[4-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-1H-imidazol-5-yl]pyridine
1
imidazoles202220222.0high000001
chir 99021
1
aminopyridine;
aminopyrimidine;
cyanopyridine;
diamine;
dichlorobenzene;
imidazoles;
secondary amino compound		EC 2.7.11.26 (tau-protein kinase) inhibitor202220222.0low000001
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
hydrazine
1
azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor2014201410.0low000010
fluorobenzenes
1
monofluorobenzenesNMR chemical shift reference compound202020204.0low000010
dibenzsuberone
1
2012201212.0low000010
misonidazole
1
201920195.0low000010
fura-2
1
2013201311.0low000010
fluoromisonidazole
1
201920195.0low000010
kt 5823
1
gamma-lactam;
hemiaminal;
indolocarbazole;
methyl ester;
organic heterooctacyclic compound		EC 2.7.11.12 (cGMP-dependent protein kinase) inhibitor202020204.0low000010
sclareol
1
labdane diterpenoidantifungal agent;
antimicrobial agent;
apoptosis inducer;
fragrance;
plant metabolite		201620168.0low000010
ouabain
1
11alpha-hydroxy steroid;
14beta-hydroxy steroid;
5beta-hydroxy steroid;
alpha-L-rhamnoside;
cardenolide glycoside;
steroid hormone		anti-arrhythmia drug;
cardiotonic drug;
EC 2.3.3.1 [citrate (Si)-synthase] inhibitor;
EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
ion transport inhibitor;
plant metabolite		2014201410.0low000010
wogonin
2
dihydroxyflavone;
monomethoxyflavone		angiogenesis inhibitor;
antineoplastic agent;
cyclooxygenase 2 inhibitor;
plant metabolite		201420178.5low000020
thromboxane b2
1
thromboxanes Bhuman metabolite;
mouse metabolite		2013201311.0low000010
ly 344864
1
carbazoles202020204.0low000010
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid
1
2013201311.0low000010
bay 63-2521
1
aminopyrimidine;
carbamate ester;
organofluorine compound;
pyrazolopyridine		antihypertensive agent;
soluble guanylate cyclase activator		202020204.0low000010
cyclic gmp
1
3',5'-cyclic purine nucleotide;
guanyl ribonucleotide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite		202020204.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Adjuvant Arthritis0
1
201920195.0low000010
Atherogenesis0
1
201720177.0low000010
Atherosclerosis0
1
201720177.0low000010
Blood Clot0
1
2013201311.0low000010
Disease Models, Animal0
2
201620196.5medium000020
Extravascular Hemolysis0
1
201620168.0low000010
Graft Occlusion, Vascular0
1
2014201410.0low000010
Hemolysis0
1
201620168.0low000010
Hyperplasia0
1
2014201410.0low000010
Inflammation0
1
201620168.0low000010
Innate Inflammatory Response0
1
201620168.0low000010
Nerve Pain0
1
201620168.0low000010
Neuralgia0
1
201620168.0low000010
Thrombosis0
1
2013201311.0low000010

Dosage (1)

ArticleYear
Anti-inflammatory and anti-proliferative effects of CBS3830 in arterialized vein grafts in rats.
Immunopharmacology and immunotoxicology, , Volume: 36, Issue:6		2014