Cefmetazole sodium
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| Category | Antibiotics |
| Catalog number | BBF-04639 |
| CAS | 56796-39-5 |
| Molecular Weight | 493.52 |
| Molecular Formula | C15H16N7O5S3.Na |
| Purity | ≥95% |
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Description
Cefmetazole sodium, containing N-methyl thiotetrazole side chains, is a semi-synthetic, second-generation cephalosporin antibiotic with broad spectrum activity.
Specification
| Related CAS | 56796-20-4 (free acid) |
| Synonyms | (6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Sodium Salt; CS-1170 Sodium Salt; Cefmetazon Sodium; Metafar; Metazol; Sodium Cefmetazole; Zefazone; CMZ sodium |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | sodium;(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate |
| Canonical SMILES | CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)[O-].[Na+] |
| InChI | InChI=1S/C15H17N7O5S3.Na/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25;/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25);/q;+1/p-1/t13-,15+;/m1./s1 |
| InChI Key | BITQGIOJQWZUPL-PBCQUBLHSA-M |
Properties
| Appearance | White to Off-white Solid |
| Application | Anti-Bacterial Agents |
| Melting Point | >130°C (dec.) |
| Density | 1.75 g/cm3 |
| Solubility | Soluble in DMSO, Methanol |
Reference Reading
1.Multicenter retrospective study of cefmetazole and flomoxef for treatment of extended-spectrum-β-lactamase-producing Escherichia coli bacteremia.
Matsumura Y1, Yamamoto M2, Nagao M2, Komori T3, Fujita N3, Hayashi A4, Shimizu T5, Watanabe H6, Doi S7, Tanaka M2, Takakura S2, Ichiyama S2. Antimicrob Agents Chemother. 2015 Sep;59(9):5107-13. doi: 10.1128/AAC.00701-15. Epub 2015 Jun 22.
The efficacy of cefmetazole and flomoxef (CF) for the treatment of patients with extended-spectrum β-lactamase-producing Escherichia coli (ESBL-EC) bacteremia (ESBL-CF group) was compared with that of carbapenem treatment for ESBL-EC patients (ESBL-carbapenem group) and with that of CF treatment in patients with non-ESBL-EC bacteremia (non-ESBL-CF group). Adult patients treated for E. coli bacteremia in four hospitals were retrospectively evaluated. The 30-day mortality rates in patients belonging to the ESBL-CF, ESBL-carbapenem, and non-ESBL-CF groups were compared as 2 (empirical and definitive therapy) cohorts. The adjusted hazard ratios (aHRs) for mortality were calculated using Cox regression models with weighting according to the inverse probability of propensity scores for receiving CF or carbapenem treatment. The empirical-therapy cohort included 104 patients (ESBL-CF, 26; ESBL-carbapenem, 45; non-ESBL-CF, 33), and the definitive-therapy cohort included 133 patients (ESBL-CF, 59; ESBL-carbapenem, 54; non-ESBL-CF, 20).
2.In vitro activities and detection performances of cefmetazole and flomoxef for extended-spectrum β-lactamase and plasmid-mediated AmpC β-lactamase-producing Enterobacteriaceae.
Matsumura Y1, Yamamoto M2, Nagao M3, Tanaka M4, Takakura S5, Ichiyama S6. Diagn Microbiol Infect Dis. 2016 Apr;84(4):322-7. doi: 10.1016/j.diagmicrobio.2015.12.001. Epub 2015 Dec 11.
To investigate the in vitro activities of cephamycins (cefmetazole and flomoxef) for extended-spectrum β-lactamase (ESBL)- and plasmid-mediated AmpC β-lactamase (pAmpC)-producing Enterobacteriaceae, a total of 574 third-generation cephalosporin-resistant clinical isolates were collected at a Japanese multicenter study. PCR and sequencing identified 394 isolates with only ESBL genes, 63 isolates with only pAmpC genes, and 6 isolates with both ESBL and pAmpC genes. blaCTX-M types predominated 95.5% of the ESBL genes, and blaCMY-2 predominated 91.3% of the pAmpC genes. The MIC50/90 values of cefmetazole and flomoxef were ≤1/4 and ≤1/≤1μg/mL for isolates with only ESBL genes, respectively, and 16/>16 and 8/16μg/mL for isolates with only pAmpC genes, respectively. Flomoxef ≥4μg/mL had the best screening performance for the detection of isolates with pAmpC genes. Flomoxef had better in vitro activities against ESBL-producing Enterobacteriaceae and provided a clearer distinction between ESBL and pAmpC-producing Enterobacteriaceae compared to cefmetazole.
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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 ╳
