Cefamandole

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Cefamandole
Category Antibiotics
Catalog number BBF-00708
CAS 34444-01-4
Molecular Weight 462.50
Molecular Formula C18H18N6O5S2
Purity ≥98%

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Description

It is produced by the strain of Semisynthetic second generation cephalosporin for injection. The activity of gram-positive bacteria was similar to cefthiophene, and it is sensitive to gram-negative bacteria including Escherichia coli, Pneumococci, Proteus, influenzae, typhoid, dysentery and enterobacter, but has no effect on pseudomonas aeruginosa and Serratia. All anaerobic bacteria were sensitive except the fragile bacilli and Clostridium difficile.

Specification

Related CAS 30034-03-8 (sodium salt)
Synonyms (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid; Cefadole; Cephadole; CEPHAMANDOLE; Cefamandol; Cefamandolum; L-Cefamandole
Shelf Life As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage Store at -20 °C
IUPAC Name (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-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)C(C4=CC=CC=C4)O)SC2)C(=O)O
InChI 1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChI Key OLVCFLKTBJRLHI-AXAPSJFSSA-N

Properties

Appearance White to Yellowish White Powder
Application A broad-spectrum cephalosporin antibiotic
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Density 1.75 g/cm3
Solubility Soluble in DMSO

Reference Reading

1.Development of a Novel Chromogenic Medium for Improved Campylobacter Detection from Poultry Samples.
Teramura H1, Iwasaki M2, Ogihara H3. J Food Prot. 2015 Sep;78(9):1750-5. doi: 10.4315/0362-028X.JFP-15-115.
The presence of expanded-spectrum β-lactamase (ESBL)-producing Escherichia coli is a common problem in the isolation of Campylobacter from poultry samples using conventional cefoperazone-based selective media. A novel chromogenic medium (CM-HT), based on modified charcoal cefoperazone deoxycholate agar (mCCDA), has been developed as a solution for improved Campylobacter detection from poultry samples. Although the basic components of CM-HT are the same as mCCDA, CM-HT uses both granular charcoal and sodium cefoxitin to enhance viewability and inhibit ESBL-producing bacteria. All tested Campylobacter jejuni (n = 31) and Campylobacter coli (n = 6) strains grew and formed purple-colored colonies on CM-HT. In contrast, the growth of all other tested microorganisms, including ESBL-producing E. coli strains, was suppressed by this medium. Additionally, 84 poultry samples were examined for the presence of Campylobacter using the ISO 10272-1 method (enrichment with Bolton broth) and the NIHSJ-02 method (enrichment with Preston broth) with mCCDA and CM-HT media for the isolation.
2.Restoring the selectivity of modified charcoal cefoperazone deoxycholate agar for the isolation of Campylobacter species using tazobactam, a β-lactamase inhibitor.
Smith S1, Meade J1, McGill K1, Gibbons J1, Bolton D2, Whyte P3. Int J Food Microbiol. 2015 Oct 1;210:131-5. doi: 10.1016/j.ijfoodmicro.2015.06.014. Epub 2015 Jun 23.
Extended spectrum β-lactamase (ESBL) producing Escherichia coli have emerged as a contaminant on modified charcoal cefoperazone deoxycholate agar (mCCDA) when attempting to selectively isolate Campylobacter spp. from poultry. E. coli are particularly problematic given their ability to grow under microaerophilic conditions and have been shown to outcompete Campylobacter species making Campylobacter detection or enumeration difficult. This paper recommends a novel method for restoring the selectivity of mCCDA using tazobactam, a β-lactamase inhibitor. The method significantly inhibited ESBL E. coli growth in spiked or naturally contaminated broiler caecal samples (p≤0.01) when compared to conventional mCCDA. This effect was seen at concentrations as low as 1mg/L tazobactam. TmCCDA(1) was found to inhibit up to 8 log10 CFU/mL of ESBL E. coli in mixed pure cultures and 7.5 log10 CFU/mL in caecal samples. Furthermore TmCCDA concentrations up to 10 mg/L had no statistically significant inhibitory effect (p≥0.
3.Drug concentrations in the serum and cerebrospinal fluid of patients treated with cefoperazone/sulbactam after craniotomy.
Wang Q1, Wu Y1, Chen B2, Zhou J1. BMC Anesthesiol. 2015 Mar 13;15:33. doi: 10.1186/s12871-015-0012-1. eCollection 2015.
BACKGROUND: To identify changes in cefoperazone/sulbactam penetration into cerebrospinal fluid (CSF) after craniotomy and to investigate preliminarily whether cefoperazone/sulbactam CSF concentration can reach therapeutic level when administered intravenously after neurosurgical operation.
4.Achromobacter respiratory infections.
Swenson CE1, Sadikot RT. Ann Am Thorac Soc. 2015 Feb;12(2):252-8. doi: 10.1513/AnnalsATS.201406-288FR.
Achromobacteria are ubiquitous environmental organisms that may also become opportunistic pathogens in certain conditions, such as cystic fibrosis, hematologic and solid organ malignancies, renal failure, and certain immune deficiencies. Some members of this genus, such as xylosoxidans, cause primarily nosocomially acquired infections affecting multiple organ systems, including the respiratory tract, urinary tract, and, less commonly, the cardiovascular and central nervous systems. Despite an increasing number of published case reports and literature reviews suggesting a global increase in achromobacterial disease, most clinicians remain uncertain of the organism's significance when clinically isolated. Moreover, effective treatment can be challenging due to the organism's inherent and acquired multidrug resistance patterns. We reviewed all published cases to date of non-cystic fibrosis achromobacterial lung infections to better understand the organism's pathogenic potential and drug susceptibilities.

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