Page last updated: 2024-12-09

(5-phenyl-3-isoxazolyl)-(1-pyrrolidinyl)methanone

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

(5-phenyl-3-isoxazolyl)-(1-pyrrolidinyl)methanone is a chemical compound, also known by its more common name **ISX-9**. It is a **potent and selective inhibitor of the enzyme histone deacetylase 6 (HDAC6)**.

**What is HDAC6?**

HDAC6 is an enzyme that plays a crucial role in regulating the acetylation of proteins, a process that is involved in various cellular functions, including cell growth, differentiation, and stress response.

**How does ISX-9 work?**

ISX-9 specifically binds to and inhibits HDAC6, preventing it from removing acetyl groups from proteins. This leads to an accumulation of acetylated proteins, which can have a number of effects on cellular processes.

**Why is ISX-9 important for research?**

ISX-9 has shown promising therapeutic potential in various research settings, including:

* **Cancer research:** By inhibiting HDAC6, ISX-9 can induce cell death in cancer cells and inhibit tumor growth.
* **Neurodegenerative disease research:** HDAC6 is implicated in the progression of neurodegenerative diseases like Alzheimer's and Parkinson's. ISX-9 might be useful in protecting against neuronal damage and improving cognitive function.
* **Inflammation research:** HDAC6 is involved in regulating inflammation. ISX-9 may be beneficial in treating inflammatory conditions.
* **Other areas:** Research is ongoing to explore ISX-9's potential in other areas such as wound healing and heart disease.

**Important Notes:**

* ISX-9 is currently **not approved for clinical use** in humans.
* The research on ISX-9 is ongoing, and further studies are needed to understand its full potential and any potential side effects.

**In summary,** (5-phenyl-3-isoxazolyl)-(1-pyrrolidinyl)methanone (ISX-9) is a powerful research tool that offers potential for treating various diseases by targeting the enzyme HDAC6.

Cross-References

ID SourceID
PubMed CID973874
CHEMBL ID1408325
CHEBI ID109085

Synonyms (18)

Synonym
SDCCGMLS-0018553.P002
TIMTEC1_008361
MLS000064968
smr000078290
5-phenyl-3-(1-pyrrolidinylcarbonyl)isoxazole
CHEBI:109085
HMS1557M01
(5-phenyl-1,2-oxazol-3-yl)-pyrrolidin-1-ylmethanone
AKOS000559506
HMS2478D21
(5-phenyl-1,2-oxazol-3-yl)(pyrrolidin-1-yl)methanone
STL176908
5-phenyl-3-[(pyrrolidin-1-yl)carbonyl]-1,2-oxazole
JDBDMIPWPHEKEQ-UHFFFAOYSA-N
CHEMBL1408325
Q27188122
(5-phenyl-3-isoxazolyl)-(1-pyrrolidinyl)methanone
(5-phenyl-3-isoxazolyl)(1-pyrrolidinyl)methanone
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
heteroareneA heterocyclic compound formally derived from an arene by replacement of one or more methine (-C=) and/or vinylene (-CH=CH-) groups by trivalent or divalent heteroatoms, respectively, in such a way as to maintain the continuous pi-electron system characteristic of aromatic systems and a number of out-of-plane pi-electrons corresponding to the Hueckel rule (4n+2).
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
[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]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency9.52830.007215.758889.3584AID588342
ATAD5 protein, partialHomo sapiens (human)Potency4.91780.004110.890331.5287AID504466; AID504467
P53Homo sapiens (human)Potency79.43280.07319.685831.6228AID504706
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency0.79430.01262.451825.0177AID485313
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency14.12540.001815.663839.8107AID894
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency1.03230.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency12.58933.548119.542744.6684AID743266
ras-related protein Rab-9AHomo sapiens (human)Potency0.89130.00022.621531.4954AID485297
survival motor neuron protein isoform dHomo sapiens (human)Potency11.22020.125912.234435.4813AID1458
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
[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's1 (14.29)29.6817
2010's5 (71.43)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

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 Index12.20 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.28 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

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]