Page last updated: 2024-11-08

acylfulvene

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

Description

acylfulvene: an antineoplastic agent; structure given in first source; an analog of illudin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID365701
CHEMBL ID121987
SCHEMBL ID17168188
MeSH IDM0212601

Synonyms (19)

Synonym
acylfulvene
NSC633555 ,
nsc-633555
NCI60_011189
(-)-acylfulvene
CHEMBL121987
bdbm50410833
125392-76-9
SCHEMBL17168188
DTXSID30327131
Q4678004
spiro[cyclopropane-1,5'-[5h]inden]-7'(6'h)-one, 6'-hydroxy-2',4',6'-trimethyl-, (6'r)-
acylfulvene, (-)-
(6'r)-6'-hydroxy-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one
illudofulvene
unii-g4t2fa57q6
g4t2fa57q6 ,
spiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one, 6'-hydroxy-2',4',6'-trimethyl-, (r)-
(6'r)-6'-hydroxy-2',4',6'-trimethyl-6',7'-dihydrospiro(cyclopropane-1,5'-indene)-7'-one

Research Excerpts

Overview

Acylfulvenes (AFs) are a class of antitumor agents derived from illudin S, a sesquiterpenoid toxin isolated from mushrooms of the genus Omphalotus. Clinical trials are ongoing for (-)-(hydroxymethyl)AF.

ExcerptReferenceRelevance
"Acylfulvenes are a class of antitumor agents derived from illudin S, a sesquiterpenoid toxin isolated from mushrooms of the genus Omphalotus. "( Sulfotransferase-independent genotoxicity of illudin S and its acylfulvene derivatives in bacterial and mammalian cells.
Glatt, H; Meinl, W; Pietsch, KE; Sturla, SJ, 2014
)
2.08
"Acylfulvenes (AFs) are a class of antitumor agents with favorable cytotoxic selectivity profiles compared to their natural product precursor, illudin S. "( Profiling patterns of glutathione reductase inhibition by the natural product illudin S and its acylfulvene analogues.
Liu, X; Sturla, SJ, 2009
)
2.01
"Acylfulvenes (AFs) are a class of semisynthetic agents with high toxicity toward certain tumor cells, and for one analogue, hydroxymethylacylfulvene (HMAF), clinical trials are in progress. "( Depurinating acylfulvene-DNA adducts: characterizing cellular chemical reactions of a selective antitumor agent.
Gong, J; Kensler, TW; Peterson, LA; Sturla, SJ; Vaidyanathan, VG; Yu, X, 2007
)
2.15
"Acylfulvenes (AFs) are a class of antitumor agents that exert their cytotoxic effects by forming covalent adducts with biomolecules, including DNA and proteins; clinical trials are ongoing for (-)-(hydroxymethyl)AF. "( Quantitative correlation of drug bioactivation and deoxyadenosine alkylation by acylfulvene.
Gong, J; Neels, JF; Sturla, SJ; Yu, X, 2007
)
2.01

Toxicity

ExcerptReferenceRelevance
" In vitro killing of tumor cells by acylfulvene required up to a 30-fold increase in molecules per cell, as compared with illudin S, indicating that acylfulvene was less toxic on a cellular level."( Characterization of acylfulvene histiospecific toxicity in human tumor cell lines.
Bagnell, RD; Estes, L; Kelner, MJ; McMorris, TC; Montoya, MA; Rutherford, M; Samson, KM; Taetle, R; Uglik, SF, 1998
)
0.9
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin reductase 1Rattus norvegicus (Norway rat)IC50 (µMol)0.09500.05500.07500.0950AID262580
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID262581Affinity towards rat NADP-dependent AOR, leukotriene B4 12-hydroxydehydrogenase2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity.
AID355132Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion method1996Journal of natural products, Sep, Volume: 59, Issue:9
(Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties.
AID262579Cytotoxicity against HEK293 cells by MTT assay2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity.
AID262580Cytotoxicity against HEK293 cells transfected with recombinant AOR by MTT assay2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity.
AID7788Concentration required for 50% toxicity in metastatic lung carcinoma (MV522) cells.2000Journal of medicinal chemistry, Sep-21, Volume: 43, Issue:19
Preparation and biological activity of amino acid and peptide conjugates of antitumor hydroxymethylacylfulvene.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (22.73)18.2507
2000's7 (31.82)29.6817
2010's9 (40.91)24.3611
2020's1 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.03

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 Index22.03 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.03)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]