Compounds > (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
Page last updated: 2024-12-11

(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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
miconazole
Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.		2.2110dichlorobenzene;
ether;
imidazoles
norfloxacin
Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.		2.5820fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug;
DNA synthesis inhibitor;
environmental contaminant;
xenobiotic
ofloxacin
Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.		2.21103-oxo monocarboxylic acid;
N-arylpiperazine;
N-methylpiperazine;
organofluorine compound;
oxazinoquinoline
ampicillin
Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.		2.2110beta-lactam antibiotic;
penicillin allergen;
penicillin		antibacterial drug
erythromycin
Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.		2.2110cyclic ketone;
erythromycin
vancomycin
Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.		2.5820glycopeptideantibacterial drug;
antimicrobial agent;
bacterial metabolite
streptomycin
[no description available]		2.2110antibiotic antifungal drug;
antibiotic fungicide;
streptomycins		antibacterial drug;
antifungal agrochemical;
antimicrobial agent;
antimicrobial drug;
bacterial metabolite;
protein synthesis inhibitor
iodophthalein
iodophthalein: RN given refers to parent cpd; structure		2.2110
gentamicin c1a
[no description available]		2.2110gentamycin C
fulvestrant
Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.		2.211017beta-hydroxy steroid;
3-hydroxy steroid;
organofluorine compound;
sulfoxide		antineoplastic agent;
estrogen antagonist;
estrogen receptor antagonist
imipenem, anhydrous
Imipenem: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.. imipenem : A broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup.		2.2110beta-lactam antibiotic allergen;
carbapenems;
zwitterion		antibacterial drug
meropenem
Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.		2.5820alpha,beta-unsaturated monocarboxylic acid;
carbapenemcarboxylic acid;
organic sulfide;
pyrrolidinecarboxamide		antibacterial agent;
antibacterial drug;
drug allergen
linezolid
[no description available]		2.1710acetamides;
morpholines;
organofluorine compound;
oxazolidinone		antibacterial drug;
protein synthesis inhibitor
fosfomycin
Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.		2.2110epoxide;
phosphonic acids		antimicrobial agent;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.2110cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310
Extravascular Hemolysis
[description not available]		02.1710
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.1710