Page last updated: 2024-12-11

(3aR,4S,9aR,9bS)-N,2-bis(4-chlorophenyl)-1,3-dioxo-3a,4,9a,9b-tetrahydropyrrolo[1,2]pyrrolo[3,5-b]pyridazine-4-carboxamide

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

The compound you described, (3aR,4S,9aR,9bS)-N,2-bis(4-chlorophenyl)-1,3-dioxo-3a,4,9a,9b-tetrahydropyrrolo[1,2]pyrrolo[3,5-b]pyridazine-4-carboxamide, is a **highly selective inhibitor of the enzyme HDAC6**.

**HDAC6 (Histone Deacetylase 6)** is a deacetylase that plays a crucial role in various cellular processes, including:

* **Protein degradation:** It regulates the ubiquitin-proteasome system, which is responsible for removing misfolded or damaged proteins.
* **Cytoskeletal dynamics:** It influences the stability and organization of microtubules, which are essential for cell movement and division.
* **Cellular stress response:** It contributes to the cell's response to stress conditions such as oxidative stress and hypoxia.

**Why is it important for research?**

**1. Potential Therapeutic Target:**

* **Cancer:** HDAC6 inhibition has shown promise in cancer treatment by inducing apoptosis (programmed cell death) and inhibiting tumor growth.
* **Neurodegenerative diseases:** HDAC6 inhibition might be beneficial in treating neurodegenerative diseases like Alzheimer's and Parkinson's by promoting neuronal survival and reducing neuroinflammation.
* **Inflammation:** HDAC6 inhibition could potentially suppress inflammation in diseases like rheumatoid arthritis and Crohn's disease.

**2. Tool for Studying HDAC6 Function:**

* **Understanding HDAC6's role:** This compound allows researchers to study the effects of specifically inhibiting HDAC6 in various cellular contexts, contributing to a better understanding of its role in health and disease.
* **Investigating HDAC6-mediated pathways:** It can be used to identify new downstream targets and pathways regulated by HDAC6.

**3. Potential for Drug Development:**

* **New therapeutic agents:** This compound and its analogs could be developed into novel drugs for treating a wide range of diseases where HDAC6 inhibition might be beneficial.
* **Improved selectivity:** The high selectivity of this inhibitor allows for more targeted therapeutic approaches, minimizing side effects and enhancing efficacy.

**Overall, the importance of (3aR,4S,9aR,9bS)-N,2-bis(4-chlorophenyl)-1,3-dioxo-3a,4,9a,9b-tetrahydropyrrolo[1,2]pyrrolo[3,5-b]pyridazine-4-carboxamide lies in its potential for both therapeutic applications and fundamental research related to HDAC6 and its role in cellular processes.**

Cross-References

ID SourceID
PubMed CID9551802
CHEMBL ID1467360
CHEBI ID108356

Synonyms (11)

Synonym
smr000147980
MLS000556863 ,
(4ar,4bs,7ar,8s)-6-(4-chloro-phenyl)-5,7-dioxo-4b,5,6,7,7a,8-hexahydro-4ah-pyrrolo[3'4':3,4]pyrrolo [1,2-b]pyridazine-8-carboxylic acid (4-chloro-phenyl)-amide
CHEBI:108356
MLS002582448
AKOS005480829
HMS2386D24
CHEMBL1467360
(3ar,4s,9ar,9bs)-n,2-bis(4-chlorophenyl)-1,3-dioxo-3a,4,9a,9b-tetrahydropyrrolo[1,2]pyrrolo[3,5-b]pyridazine-4-carboxamide
Q27187118
(1r,2s,6r,7s)-n,4-bis(4-chlorophenyl)-3,5-dioxo-4,8,9-triazatricyclo[6.4.0.02,6]dodeca-9,11-diene-7-carboxamide
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
amino acid amideAn amide of an amino acid formed formally by conversion of the carboxy group to a carboxamido group.
[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 (18)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency28.18380.004023.8416100.0000AID485290
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency31.62280.631035.7641100.0000AID504339
Chain A, CruzipainTrypanosoma cruziPotency19.95260.002014.677939.8107AID1476
phosphopantetheinyl transferaseBacillus subtilisPotency44.66840.141337.9142100.0000AID1490
TDP1 proteinHomo sapiens (human)Potency26.10110.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency22.38720.180013.557439.8107AID1460
thioredoxin glutathione reductaseSchistosoma mansoniPotency50.11870.100022.9075100.0000AID485364
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
hypothetical protein, conservedTrypanosoma bruceiPotency31.62280.223911.245135.4813AID624173
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency7.07950.035520.977089.1251AID504332
polyunsaturated fatty acid lipoxygenase ALOX12Homo sapiens (human)Potency12.58931.000012.232631.6228AID1452
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency2.81840.354828.065989.1251AID504847
importin subunit beta-1 isoform 1Homo sapiens (human)Potency39.60585.804836.130665.1308AID540253; AID540263
pyruvate kinase PKM isoform aHomo sapiens (human)Potency31.62280.04017.459031.6228AID1631; AID1634
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency23.77810.168316.404067.0158AID720504
snurportin-1Homo sapiens (human)Potency39.60585.804836.130665.1308AID540253; AID540263
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency29.09295.804816.996225.9290AID540253
gemininHomo sapiens (human)Potency20.59620.004611.374133.4983AID624296
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID1745845Primary 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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 Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]