Cefmetazole
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| Category | Antibiotics |
| Catalog number | BBF-00724 |
| CAS | 56796-20-4 |
| Molecular Weight | 471.53 |
| Molecular Formula | C15H17N7O5S3 |
| Purity | 95% |
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Description
It is produced by the strain of Semisynthetic second generation cephalosporin for injection. It belongs to the cephalomycin-type compound. and its sodium salt is used in preparations. Cefmeazole is an antibiotic with broad spectrum activity against gram-positive and Gram-negative bacteria. It binds to a penicillin-binding protein (PBPs) responsible for the cross-linking of peptidoglycan.
Specification
| Related CAS | 56796-39-5 (sodium) |
| Synonyms | Cefmetazolo; Cefmetazolum; U-72791A; U72791A; Zefazone; CS-1170; CS 1170; CS1170; (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Storage | −20 °C |
| IUPAC Name | (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-carboxylic acid |
| Canonical SMILES | CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O |
| InChI | InChI=1S/C15H17N7O5S3/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)/t13-,15+/m1/s1 |
| InChI Key | SNBUBQHDYVFSQF-HIFRSBDPSA-N |
Properties
| Appearance | White Powder |
| Application | Cefmetazole has antibacterial activity. |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Melting Point | 154-157 °C |
| Density | 1.75 g/cm3 |
| Solubility | Soluble in Water, Methanol (Heated), Acetone; Insoluble in Chloroform |
Reference Reading
1.Postoperative Mycoplasma hominis infection after robot-assisted laparoscopic radical prostatectomy: A case report.
Yokoyama H1, Domen T1, Hiragata S1, Ogawa T1, Matsumoto T2, Ishizuka O1. Asian J Endosc Surg. 2016 May;9(2):146-148. doi: 10.1111/ases.12258.
A 59-year-old man developed a high fever, elevated white blood cell count, elevated C-reactive protein level, and perineal pain 5 days after robot-assisted laparoscopic radical prostatectomy. Treatment with cefmetazole was ineffective. A urine specimen was submitted for culture on postoperative day 7, and Mycoplasma hominis (M. hominis) was detected 1 week later. Cefmetazole was therefore switched to quinolone. The clinical symptoms and laboratory data immediately showed marked improvement. M. hominis has been shown to inhabit the genitourinary tract. Although it is considered to induce urethritis, its pathogenicity in healthy male subjects has not been investigated. M. hominis is difficult to detect and is resistant to β-lactams because it lacks a cell wall. Urine culture sometimes results in false-negative results. In cases where empirical therapy for postoperative infection is ineffective, surgeons should recognize the possibility of M.
2.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).
3.[The Great Imitator; Clavicular Tuberculosis Mimics a Metastatic Neoplasm].
Mikawa T, Miyoshi K, Fujita K, Hase R, Hosokawa N. Kansenshogaku Zasshi. 2015 Sep;89(5):588-91.
In the same manner as syphilis, tuberculosis (TB) was often called "The Great Imitator". We have to consider not only malignancies but also TB as a differential diagnosis when we find any tumorous regions. We report herein on a rare case, clavicular osteomyelitis due to TB. A 72-year-old female, with diabetic nephropathy, was on maintenance hemodialysis. She had a fall 2 months prior to admission followed by pain around her right clavicle. Ulceration occurred in that region a month prior to admission, and CT scan revealed a fracture of the right clavicle with a tumor surrounding that area. Seven days prior to admission, she went to a neurologist because of dizziness. MRI of the brain revealed a tumor in her pons. The physician suspected the tumor was metastasis. Needle biopsies revealed only necrotic tissue so the medical oncologist consulted us because they suspected it was caused by infection of some kind. From the patient's history and the physical examination, we suspected TB osteomyelitis and grew some more cultures, but only MRSA and E.
4.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 ╳
