Linezolid
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| Category | Antibiotics |
| Catalog number | BBF-04161 |
| CAS | 165800-03-3 |
| Molecular Weight | 337.35 |
| Molecular Formula | C16H20FN3O4 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04161 | 50 mg | $199 | In stock |
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Add to cartDescription
Linezolid inhibits initiation complex formation with either the 30S or the 70S ribosomal subunits from Escherichia coli. Linezolid is a synthetic oxazolidinone antibiotic active against a wide range of Gram-positive bacteria, including resistant strains of several species, such as MRSA and penicillin-resistant pneumococci.
Specification
| Synonyms | Zyvox; Zyvoxid; Zyvoxam; PNU 100766; PNU-100766; PNU100766; U 100766; U-100766; U100766 |
| Storage | Store at -20°C |
| IUPAC Name | N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide |
| Canonical SMILES | CC(=O)NCC1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F |
| InChI | InChI=1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1 |
| InChI Key | TYZROVQLWOKYKF-ZDUSSCGKSA-N |
| Source | Synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 585.5°C at 760 mmHg |
| Melting Point | 176-180°C |
| Flash Point | 307.9ºC |
| Density | 1.302 g/cm3 |
| Solubility | Soluble in DMSO |
| LogP | 0.9 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Linezolid targets the large 39S subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result Linezolid is cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. The likely target of Linezolid is the 16S rRNA molecule in the mitochondrial ribosome, which is analogous to the 23S rRNA in bacterial ribosomes. |
Reference Reading
1.Evaluation of Combination Drug Therapy for Treatment of Antibiotic-Resistant Inhalation Anthrax in a Murine Model.
Heine HS;Shadomy SV;Boyer AE;Chuvala L;Riggins R;Kesterson A;Myrick J;Craig J;Candela MG;Barr JR;Hendricks K;Bower WA;Walke H;Drusano GL Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: e00788-17. doi: 10.1128/AAC.00788-17. Print 2017 Sep.
Bacillus anthracis; is considered a likely agent to be used as a bioweapon, and the use of a strain resistant to the first-line antimicrobial treatments is a concern. We determined treatment efficacies against a ciprofloxacin-resistant strain of ;B. anthracis; (Cip;r; Ames) in a murine inhalational anthrax model. Ten groups of 46 BALB/c mice were exposed by inhalation to 7 to 35 times the 50% lethal dose (LD;50;) of ;B. anthracis; Cip;r; Ames spores. Commencing at 36 h postexposure, groups were administered intraperitoneal doses of sterile water for injections (SWI) and ciprofloxacin alone (control groups), or ciprofloxacin combined with two antimicrobials, including meropenem-linezolid, meropenem-clindamycin, meropenem-rifampin, meropenem-doxycycline, penicillin-linezolid, penicillin-doxycycline, rifampin-linezolid, and rifampin-clindamycin, at appropriate dosing intervals (6 or 12 h) for the respective antibiotics. Ten mice per group were treated for 14 days and observed until day 28. The remaining animals were euthanized every 6 to 12 h, and blood, lungs, and spleens were collected for lethal factor (LF) and/or bacterial load determinations. All combination groups showed significant survival over the SWI and ciprofloxacin controls: meropenem-linezolid (;P; = 0.
2.Comparative genomics of Clostridium bolteae and Clostridium clostridioforme reveals species-specific genomic properties and numerous putative antibiotic resistance determinants.
Dehoux P;Marvaud JC;Abouelleil A;Earl AM;Lambert T;Dauga C BMC Genomics. 2016 Oct 21;17(1):819.
BACKGROUND: ;Clostridium bolteae and Clostridium clostridioforme, previously included in the complex C. clostridioforme in the group Clostridium XIVa, remain difficult to distinguish by phenotypic methods. These bacteria, prevailing in the human intestinal microbiota, are opportunistic pathogens with various drug susceptibility patterns. In order to better characterize the two species and to obtain information on their antibiotic resistance genes, we analyzed the genomes of six strains of C. bolteae and six strains of C. clostridioforme, isolated from human infection.;RESULTS: ;The genome length of C. bolteae varied from 6159 to 6398 kb, and 5719 to 6059 CDSs were detected. The genomes of C. clostridioforme were smaller, between 5467 and 5927 kb, and contained 5231 to 5916 CDSs. The two species display different metabolic pathways. The genomes of C. bolteae contained lactose operons involving PTS system and complex regulation, which contribute to phenotypic differentiation from C. clostridioforme. The Acetyl-CoA pathway, similar to that of Faecalibacterium prausnitzii, a major butyrate producer in the human gut, was only found in C. clostridioforme. The two species have also developed diverse flagella mobility systems contributing to gut colonization.
3.In vitro activity of daptomycin versus linezolid and vancomycin against gram-positive uropathogens and ampicillin against enterococci, causing complicated urinary tract infections.
Wagenlehner FM;Lehn N;Witte W;Naber KG Chemotherapy. 2005 May;51(2-3):64-9. Epub 2005 May 4.
OBJECTIVES: ;The existing therapeutic options for complicated urinary tract infections (UTI) caused by gram-positive uropathogens are not always optimal. Therefore, newer antimicrobials have to be assessed.;METHODS: ;The antimicrobial activity of daptomycin was tested versus linezolid, vancomycin, and ampicillin (enterococci on ly), against pathogens from three different collections: (1) Uropathogens from hospitalized urological patients with complicated and/or hospital-acquired UTIs of the Urologic Clinic, Hospital St. Elisabeth, Straubing. (2) Uropathogens from a multicenter study comprising 37 urological centers throughout Germany. (3) Methicillin-resistant Staphylococcus aureus (MRSA) isolates of patients and staff within the Hospital St. Elisabeth, Straubing. Genotyping of the latter isolates was performed by pulsed-field gel electrophoresis. The minimal inhibitory concentrations (MIC) of daptomycin, linezolid, vancomycin, and ampicillin (only tested against enterococci) were determined by an agar dilution method using a multipointer with an inoculum of 10(4) CFU per point.;RESULTS: ;For all methicillin-susceptible Staphylococcus aureus (n = 25), MRSA (n = 49), methicillin-susceptible coagulase-negative staphylococci (n = 129), methicillin-resistant coagulase-negative staphylococci (n = 33), for Enterococcus faecalis (n = 289), and for Enterococcus faecium (n = 4) the MICs ranged up to 2 mg/l (daptomycin, linezolid), up to 4 mg/l (vancomycin), and up to 8 mg/l (ampicillin, enterococci only) indicating that all strains were susceptible to the antibiotics tested.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C16H20FN3O4
Molecular Weight (Monoisotopic Mass): 337.1438 Da
Molecular Weight (Avergae Mass): 337.3461 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C16H20FN3O4
Molecular Weight (Monoisotopic Mass): 337.1438 Da
Molecular Weight (Avergae Mass): 337.3461 Da
LC-MS/MS Spectrum - LC-ESI-QFT , positive
Experimental Conditions
Instrument Type: LC-ESI-QFT
Ionization Mode: positive
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C16H20FN3O4
Molecular Weight (Monoisotopic Mass): 337.1438 Da
Molecular Weight (Avergae Mass): 337.3461 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C16H20FN3O4
Molecular Weight (Monoisotopic Mass): 337.1438 Da
Molecular Weight (Avergae Mass): 337.3461 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
