(2R,4R)-2-[[4-(hydroxymethyl)phenyl]methoxy]-4-(4-oxo-1-benzopyran-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid prop-2-enyl ester, also known as **Tigecycline**, is an important antibiotic used to treat various bacterial infections.
**Here's a breakdown of its significance in research:**
* **Broad-spectrum antibiotic:** Tigecycline exhibits broad-spectrum activity against a wide range of Gram-positive and Gram-negative bacteria, including those resistant to other antibiotics.
* **Mechanism of action:** It is a **glycylcycline**, a class of antibiotics that bind to the 30S subunit of the bacterial ribosome, inhibiting protein synthesis and ultimately leading to bacterial death. This mechanism differs from other tetracyclines, making Tigecycline effective against strains resistant to other tetracyclines.
* **Resistance:** While Tigecycline has significant clinical utility, research is ongoing to understand and mitigate the emergence of bacterial resistance to it. Studying the mechanisms of resistance helps in the development of new antibiotics or strategies to overcome existing resistance.
* **Pharmacokinetics:** Understanding the pharmacokinetics (absorption, distribution, metabolism, and excretion) of Tigecycline is crucial for optimizing its dosage and administration. Research focuses on improving its bioavailability and ensuring effective drug delivery.
* **Clinical applications:** Tigecycline is used to treat complicated skin and skin structure infections (cSSSI), complicated intra-abdominal infections (cIAI), and community-acquired pneumonia (CAP). Ongoing research explores its potential in treating other infections and its efficacy in combination with other antibiotics.
**In summary, (2R,4R)-2-[[4-(hydroxymethyl)phenyl]methoxy]-4-(4-oxo-1-benzopyran-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid prop-2-enyl ester (Tigecycline) is a valuable antibiotic with broad-spectrum activity. Research into its mechanism of action, resistance mechanisms, pharmacokinetics, and clinical applications continues to expand our understanding of this important drug and its potential role in combating bacterial infections.**
| ID Source | ID |
|---|---|
| PubMed CID | 6669976 |
| CHEMBL ID | 1322279 |
| CHEBI ID | 94022 |
| Synonym |
|---|
| smr000389460 |
| MLS000766316 |
| (2r,4r)-allyl 2-(4-(hydroxymethyl)benzyloxy)-4-(4-oxo-4h-chromen-3-yl)-3,4-dihydro-2h-pyran-6-carboxylate |
| DHPC1_000782 , |
| BRD-K38690464-001-01-6 |
| prop-2-enyl (2r,4r)-2-[[4-(hydroxymethyl)phenyl]methoxy]-4-(4-oxochromen-3-yl)-3,4-dihydro-2h-pyran-6-carboxylate |
| HMS2198M19 |
| CHEMBL1322279 |
| CHEBI:94022 |
| (2r,4r)-2-[[4-(hydroxymethyl)phenyl]methoxy]-4-(4-oxo-1-benzopyran-3-yl)-3,4-dihydro-2h-pyran-6-carboxylic acid prop-2-enyl ester |
| Q27165774 |
| Class | Description |
|---|---|
| chromones | A chromenone that consists of a 1,4-benzopyrone skeleton and its substituted derivatives thereof. |
| [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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 11.2202 | 0.0447 | 17.8581 | 100.0000 | AID485341 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 44.6684 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 8.1961 | 0.0041 | 10.8903 | 31.5287 | AID504467 |
| TDP1 protein | Homo sapiens (human) | Potency | 24.5192 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 35.4813 | 0.1800 | 13.5574 | 39.8107 | AID1460 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 44.6684 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| glucocerebrosidase | Homo sapiens (human) | Potency | 14.1254 | 0.0126 | 8.1569 | 44.6684 | AID2101 |
| serine-protein kinase ATM isoform a | Homo sapiens (human) | Potency | 10.0000 | 0.7079 | 25.1119 | 41.2351 | AID485349 |
| DNA polymerase beta | Homo sapiens (human) | Potency | 89.1251 | 0.0224 | 21.0102 | 89.1251 | AID485314 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 11.2202 | 0.0079 | 8.2332 | 1,122.0200 | AID2546 |
| lethal(3)malignant brain tumor-like protein 1 isoform I | Homo sapiens (human) | Potency | 1.0000 | 0.0752 | 15.2253 | 39.8107 | AID485360 |
| geminin | Homo sapiens (human) | Potency | 0.3663 | 0.0046 | 11.3741 | 33.4983 | AID624296 |
| Guanine nucleotide-binding protein G | Homo sapiens (human) | Potency | 31.6228 | 1.9953 | 25.5327 | 50.1187 | AID624288 |
| TAR DNA-binding protein 43 | Homo sapiens (human) | Potency | 17.7828 | 1.7783 | 16.2081 | 35.4813 | AID652104 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| plasma membrane | Guanine nucleotide-binding protein G | Homo sapiens (human) |
| intracellular non-membrane-bounded organelle | TAR DNA-binding protein 43 | Homo sapiens (human) |
| nucleus | TAR DNA-binding protein 43 | Homo sapiens (human) |
| nucleoplasm | TAR DNA-binding protein 43 | Homo sapiens (human) |
| perichromatin fibrils | TAR DNA-binding protein 43 | Homo sapiens (human) |
| mitochondrion | TAR DNA-binding protein 43 | Homo sapiens (human) |
| cytoplasmic stress granule | TAR DNA-binding protein 43 | Homo sapiens (human) |
| nuclear speck | TAR DNA-binding protein 43 | Homo sapiens (human) |
| interchromatin granule | TAR DNA-binding protein 43 | Homo sapiens (human) |
| nucleoplasm | TAR DNA-binding protein 43 | Homo sapiens (human) |
| chromatin | TAR DNA-binding protein 43 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, 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] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 3 (60.00) | 24.3611 |
| 2020's | 1 (20.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.56) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||