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(6R,7R)-7-[[(2R)-2-carboxy-2-(4-hydroxyphenyl)-1-oxoethyl]amino]-7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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

You've described **Ceftolozane**, a cephalosporin antibiotic.

Here's a breakdown of its structure and importance:

**Structure:**

* **Ceftolozane** is a complex molecule belonging to the cephalosporin family of antibiotics. Its chemical name reflects its intricate structure with many functional groups:
* **(6R,7R)** indicates the stereochemistry (arrangement in 3D space) of two specific chiral centers (carbon atoms with four different groups attached).
* **7-[[(2R)-2-carboxy-2-(4-hydroxyphenyl)-1-oxoethyl]amino]** describes a complex side chain attached to the 7th carbon. This side chain includes a carboxylic acid, a phenyl ring with a hydroxyl group, and an amide group.
* **7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid** describes the core cephalosporin structure. It contains a bicyclic ring system with a beta-lactam ring (essential for antibiotic activity), a thiazolidine ring, and various functional groups.

**Importance for Research:**

Ceftolozane is important in research due to its unique properties and potential clinical benefits:

* **Antibiotic Activity:** Ceftolozane is a broad-spectrum antibiotic, meaning it is effective against a wide range of bacterial infections.
* **Resistance Profile:** Unlike some other cephalosporins, it is less susceptible to breakdown by certain bacterial enzymes (beta-lactamases) that confer antibiotic resistance. This makes it a promising agent for treating infections caused by resistant bacteria.
* **Gram-Negative Infections:** Ceftolozane has particularly strong activity against gram-negative bacteria, which are often challenging to treat with other antibiotics.
* **Clinical Applications:** Ceftolozane is used clinically, often in combination with another antibiotic (like tazobactam), to treat various infections, including complicated urinary tract infections, pneumonia, and skin infections.

**Ongoing Research:**

Research on ceftolozane continues in areas such as:

* **Understanding its mechanism of action:** Scientists are investigating how ceftolozane interacts with bacterial targets to inhibit their growth.
* **Optimizing its therapeutic use:** Studies aim to determine the optimal dosages and treatment durations for different infections and patient populations.
* **Developing new antibiotics:** Ceftolozane's structure provides insights for designing new antibiotics with enhanced activity and resistance profiles.

Ceftolozane's unique properties and its importance in fighting antibiotic resistance make it a significant molecule in pharmaceutical research.

Cross-References

ID SourceID
PubMed CID5488645
CHEMBL ID519374
CHEBI ID94604
SCHEMBL ID49017

Synonyms (15)

Synonym
BPBIO1_000789
BSPBIO_000717
PRESTWICK3_000819
7-((carboxy(4-hydroxyphenyl)acetyl)amino)-7-methoxy-(3-((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
DB04342
BRD-K40831222-304-01-3
SCHEMBL49017
CHEMBL519374
CHEBI:94604
(6r,7r)-7-[[(2r)-2-carboxy-2-(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Q27095155
CS-0013700
HY-B1484A
AKOS040744841
PD006291
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
secondary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
dicarboxylic acidAny carboxylic acid containing two carboxy groups.
[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]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1616736Binding affinity to bacterial wild type Beta-lactamase TEM-1 assessed as change in melting temperature at 100-fold molar excess compound concentration relative to apo-enzymes by SYPRO Orange dye based differential scanning fluorimetry2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Protein Stability Effects in Aggregate-Based Enzyme Inhibition.
AID1616735Binding affinity to bacterial Beta-lactamase TEM-1 M182T/G238S mutant assessed as change in melting temperature at 100-fold molar excess compound concentration relative to apo-enzymes by SYPRO Orange dye based differential scanning fluorimetry2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Protein Stability Effects in Aggregate-Based Enzyme Inhibition.
AID1616734Binding affinity to bacterial Beta-lactamase TEM-1 M182T mutant assessed as change in melting temperature at 100-fold molar excess compound concentration relative to apo-enzymes by SYPRO Orange dye based differential scanning fluorimetry2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Protein Stability Effects in Aggregate-Based Enzyme Inhibition.
AID1504398Bactericidal activity against Escherichia coli ATCC 25922 at 12 after 6 hrs by time kill assay2018European journal of medicinal chemistry, Jan-01, Volume: 143Synthesis and bioactivities study of new antibacterial peptide mimics: The dialkyl cationic amphiphiles.
AID1616738Binding affinity to bacterial Beta-lactamase TEM-1 G238S mutant assessed as change in melting temperature at 100-fold molar excess compound concentration relative to apo-enzymes by SYPRO Orange dye based differential scanning fluorimetry2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Protein Stability Effects in Aggregate-Based Enzyme Inhibition.
AID1616737Binding affinity to bacterial Beta-lactamase TEM-1 R164S mutant assessed as change in melting temperature at 100-fold molar excess compound concentration relative to apo-enzymes by SYPRO Orange dye based differential scanning fluorimetry2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Protein Stability Effects in Aggregate-Based Enzyme Inhibition.
AID1570737Antimicrobial activity against Listeria monocytogenes clinical isolate at 30 ug/disk incubated for 20 +/- 4 hrs by agar disk diffusion method2019Bioorganic & medicinal chemistry, 11-01, Volume: 27, Issue:21
Synthesis and evaluation of 1,3,4-oxadiazole derivatives for development as broad-spectrum antibiotics.
AID1680077Bactericidal activity against early exponential phase of Escherichia coli ATCC 25922 at 6X MIC measured after 6 hrs by time-kill kinetic assay2018European journal of medicinal chemistry, Jul-15, Volume: 155Synthesis and antibacterial bioactivities of cationic deacetyl linezolid amphiphiles.
AID1616739Binding affinity to bacterial Beta-lactamase TEM-1 D179G mutant assessed as change in melting temperature at 100-fold molar excess compound concentration relative to apo-enzymes by SYPRO Orange dye based differential scanning fluorimetry2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Protein Stability Effects in Aggregate-Based Enzyme Inhibition.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[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's0 (0.00)29.6817
2010's5 (100.00)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: 12.72

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 Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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]