Page last updated: 2024-11-12

km-233

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

Description

KM-233: used for the treatment of high-grade glioma; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10248110
CHEMBL ID119592
SCHEMBL ID14447597
MeSH IDM0501137

Synonyms (25)

Synonym
(6ar,10ar)-6,6,9-trimethyl-3-(1-methyl-1-phenyl-ethyl)-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
6,6,9-trimethyl-3-(2-phenylpropan-2-yl)-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
bdbm50133546
(6ar,10ar)-6,6,9-trimethyl-3-(2-phenylpropan-2-yl)-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
km-233
CHEMBL119592 ,
628263-22-9
SCHEMBL14447597
Q6333245
km 233
(6ar,10ar)-6,6,9-trimethyl-3-(2-phenylpropan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
nsc-792739
nsc792739
km233
ymv7s3c3b7 ,
baj4486bwx ,
797793-15-8
HY-123410
CS-0082626
6h-dibenzo[b,d]pyran-1-ol, 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-(1-methyl-1-phenylethyl)-, (6ar,10ar)-rel-
6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-(1-methyl-1-phenylethyl)-6h-dibenzo[b,d]pyran-1-ol, (6ar,10ar)-rel-
6h-dibenzo[b,d]pyran-1-ol, 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-(1-methyl-1-phenylethyl)-, (6ar,10ar)-
(6ar,10ar)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-(1-methyl-1-phenylethyl)-6h-dibenzo[b,d]pyran-1-ol
rel-(6ar,10ar)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-(1-methyl-1-phenylethyl)-6h-dibenzo[b,d]pyran-1-ol
AKOS040745948

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The cytotoxic effects of KM-233 against human glioma cells in vitro occur as early as two hours after administration, and dosing of KM-233 can be cycled without compromising cytotoxic efficacy and while improving safety."( Safety and efficacy of a novel cannabinoid chemotherapeutic, KM-233, for the treatment of high-grade glioma.
Boehm, P; Divi, MK; Duntsch, C; Jones, T; Krishnamurthy, M; Moore, BM; Sills, A; Wood, G; Zhou, Q, 2006
)
0.88
" Dose escalation studies in the orthotopic model using U87MG cells revealed an 80 % reduction in tumor size after 12 mg/kg daily dosing for 20 days."( Mechanism of anti-glioma activity and in vivo efficacy of the cannabinoid ligand KM-233.
Abidi, AH; Allison, P; Bigner, DD; Duntsch, C; Elberger, AJ; Guan, P; Gurley, SN; Keir, ST; Kosanke, SD; Moore, BM; Robertson, JH, 2012
)
0.61
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cholesteryl ester transfer proteinHomo sapiens (human)Ki0.00090.00050.02200.0520AID311038
Cannabinoid receptor 1Homo sapiens (human)Ki0.01230.00010.50779.6000AID311037; AID406561; AID414286; AID416355; AID49314
Cannabinoid receptor 2 Homo sapiens (human)Ki0.00090.00000.415610.0000AID311038; AID406562; AID414287; AID416356; AID49845
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (58)

Processvia Protein(s)Taxonomy
triglyceride metabolic processCholesteryl ester transfer proteinHomo sapiens (human)
lipid transportCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol metabolic processCholesteryl ester transfer proteinHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationCholesteryl ester transfer proteinHomo sapiens (human)
regulation of cholesterol effluxCholesteryl ester transfer proteinHomo sapiens (human)
phospholipid transportCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol transportCholesteryl ester transfer proteinHomo sapiens (human)
positive regulation of cholesterol transportCholesteryl ester transfer proteinHomo sapiens (human)
triglyceride transportCholesteryl ester transfer proteinHomo sapiens (human)
very-low-density lipoprotein particle remodelingCholesteryl ester transfer proteinHomo sapiens (human)
low-density lipoprotein particle remodelingCholesteryl ester transfer proteinHomo sapiens (human)
high-density lipoprotein particle remodelingCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
reverse cholesterol transportCholesteryl ester transfer proteinHomo sapiens (human)
phosphatidylcholine metabolic processCholesteryl ester transfer proteinHomo sapiens (human)
lipid homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
phospholipid homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
triglyceride homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
positive regulation of phospholipid transportCholesteryl ester transfer proteinHomo sapiens (human)
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
phospholipid transporter activityCholesteryl ester transfer proteinHomo sapiens (human)
lipid bindingCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol bindingCholesteryl ester transfer proteinHomo sapiens (human)
triglyceride bindingCholesteryl ester transfer proteinHomo sapiens (human)
phosphatidylcholine bindingCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol transfer activityCholesteryl ester transfer proteinHomo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
extracellular regionCholesteryl ester transfer proteinHomo sapiens (human)
extracellular spaceCholesteryl ester transfer proteinHomo sapiens (human)
vesicleCholesteryl ester transfer proteinHomo sapiens (human)
extracellular exosomeCholesteryl ester transfer proteinHomo sapiens (human)
high-density lipoprotein particleCholesteryl ester transfer proteinHomo sapiens (human)
mitochondrial outer membraneCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
actin cytoskeletonCannabinoid receptor 1Homo sapiens (human)
growth coneCannabinoid receptor 1Homo sapiens (human)
presynaptic membraneCannabinoid receptor 1Homo sapiens (human)
membrane raftCannabinoid receptor 1Homo sapiens (human)
glutamatergic synapseCannabinoid receptor 1Homo sapiens (human)
GABA-ergic synapseCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
cytoplasmCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID416355Binding affinity to CB1 receptor2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Quantitative structure-activity relationship (QSAR) for a series of novel cannabinoid derivatives using descriptors derived from semi-empirical quantum-chemical calculations.
AID49845Binding affinity towards Cannabinoid receptor 2 using CP-55940 as radioligand in HEK293 EBNA cells2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and testing of novel phenyl substituted side-chain analogues of classical cannabinoids.
AID311038Binding affinity to CB2 receptor2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
The application of 3D-QSAR studies for novel cannabinoid ligands substituted at the C1' position of the alkyl side chain on the structural requirements for binding to cannabinoid receptors CB1 and CB2.
AID416356Binding affinity to CB2 receptor2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Quantitative structure-activity relationship (QSAR) for a series of novel cannabinoid derivatives using descriptors derived from semi-empirical quantum-chemical calculations.
AID414287Binding affinity to human CB2 receptor transfected in HEK293 cells2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands.
AID49314Binding affinity towards Cannabinoid receptor 1 using CP-55940 as radioligand in HEK293 EBNA cells2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and testing of novel phenyl substituted side-chain analogues of classical cannabinoids.
AID414286Binding affinity to human CB1 receptor transfected in HEK293 cells2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands.
AID406568Cytotoxicity against human DBTRG-O5MG cells assessed as cell death after 18 hrs2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID406564Cytotoxicity against human U87 cells by side flank model relative to control2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID311037Binding affinity to CB1 receptor2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
The application of 3D-QSAR studies for novel cannabinoid ligands substituted at the C1' position of the alkyl side chain on the structural requirements for binding to cannabinoid receptors CB1 and CB2.
AID406561Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID49327Ratio of binding affinity towards cannabinoid receptor-1 (CB1) to that of cannabinoid receptor-2 (CB2)2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and testing of novel phenyl substituted side-chain analogues of classical cannabinoids.
AID406569Cytotoxicity against human MT310 cells assessed as cell death after 18 hrs2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID414288Selectivity ratio of Ki for human CB1 receptor to Ki for human CB2 receptor2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands.
AID406565Cytotoxicity against human U87MG cells assessed as cell death after 18 hrs2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID406567Cytotoxicity against human LN229 cells assessed as cell death after 18 hrs2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID406566Cytotoxicity against human T98G cells assessed as cell death after 18 hrs2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID406562Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO-K1 cells2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
AID406563Selectivity ratio of Ki for human CB1 receptor to Ki for human CB2 receptor2008Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13
Exploring the substituent effects on a novel series of C1'-dimethyl-aryl Delta8-tetrahydrocannabinol analogs.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (85.71)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.43

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.43 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (24.43)

All Compounds (24.57)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]