Cephemimycin
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| Category | Antibiotics |
| Catalog number | BBF-00514 |
| CAS | 34279-51-1 |
| Molecular Weight | 446.43 |
| Molecular Formula | C16H22N4O9S |
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Description
It is produced by the strain of Streptomyces jumonjinensis (NRRL 5741). It has weak antibacterial and antifungal activity. The removed side chain can be used as raw material for semisynthetic cephalosporin.
Specification
| Synonyms | Cephamycin C; antibiotic 842A; (6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7alpha-[[(R)-5-amino-5-carboxy-1-oxopentyl]amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; A16886B; A 16886B; A-16886B |
| IUPAC Name | (6R,7S)-7-[[(5R)-5-amino-5-carboxypentanoyl]amino]-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CCCC(C(=O)O)N |
| InChI | InChI=1S/C16H22N4O9S/c1-28-16(19-9(21)4-2-3-8(17)11(22)23)13(26)20-10(12(24)25)7(5-29-15(18)27)6-30-14(16)20/h8,14H,2-6,17H2,1H3,(H2,18,27)(H,19,21)(H,22,23)(H,24,25)/t8-,14-,16+/m1/s1 |
| InChI Key | LXWBXEWUSAABOA-VXSYNFHWSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Preliminary studies for cephamycin C purification technique
Alvaro de Baptista Neto, Maritza Catalina Condori Bustamante, Jaine Honorata Hortolan Luiz de Oliveira, Ana Cláudia Granato, Carolina Bellão, Alberto Coli Badino, Marlei Barboza, Carlos Osamu Hokka Appl Biochem Biotechnol. 2012 Jan;166(1):208-21. doi: 10.1007/s12010-011-9417-6. Epub 2011 Nov 5.
A study was made for purification of cephamycin C from fermentation of Streptomyces clavuligerus. Initially, the culture broth was clarified by microfiltration and ultrafiltration, after which the resulting permeates were subjected to nonspecific adsorption and ion-exchange chromatography on resin columns. The antibiotic activity was measured by the biological method at each stage by assaying its activity against the Escherichia coli ESS, super sensitive to β-lactam antibiotic. The purification processes were assessed in relation to the variables affecting each step. The purification efficiency by nonspecific adsorption was monitored by UV spectrophotometry, while the ion-exchange adsorption fractions were assessed by NMR spectroscopy. Some of the fractions obtained during purification were also analyzed by mass spectrometry (LC/MS and LC/MS/MS) to identify the cephamycin C molecule. These preliminary results proved the process feasibility.
2. [Clinical value of cefmetazole and other cephamycin antibiotics]
D Simada Antibiot Khimioter. 1995 Jan;40(1):13-21.
The review is concerned with the description of the antibiotics belonging to cephamycins. The data on the chemical structure of cefmetazole and other cephamycins and the mechanisms of their action are presented. The peculiarities of the binding to penicillin-binding proteins and the stability to the action of various beta-lactamases are discussed. The spectrum of the antibacterial activity of cefmetazole against gram-positive and gram-negative aerobes and anaerobes, as well as the antibiotic pharmacokinetics is described. The literature data on the clinical efficacy of cefmetazole in the treatment of infectious diseases of various etiology and localization and the data on the drug tolerance and the incidence of adverse reactions are summarized. The indications to the use of cefmetazole and other cephamycins are substantiated.
3. Kinetic study on cephamycin C degradation
Luciana M Brites, Liliane M Oliveira, Marlei Barboza Appl Biochem Biotechnol. 2013 Dec;171(8):2121-8. doi: 10.1007/s12010-013-0502-x. Epub 2013 Sep 12.
Cephamycin C (CepC) is a β-lactam antibiotic that belongs to the cephalosporin class of drugs. This compound stands out from other cephalosporins for its greater resistance to β-lactamases, which are enzymes produced by pathogenic microorganisms that present a major mechanism of bacterial resistance to β-lactam antibiotics. Cephamycin C is produced by the bacterium Streptomyces clavuligerus. Knowledge about the stability of the compound under different values of pH is important for the development of the process of production, extraction, and purification aimed at obtaining higher yields. Therefore, the stability of cephamycin C under different pH levels (2.2, 6.0, 7.0, 7.6, and 8.7) at 20 °C was evaluated in this study. Ultrafiltered broth from batch fermentations of S. clavuligerus was used in the trials. The results indicated that cephamycin C is a more stable compound than other β-lactam compounds such as penicillin and clavulanic acid. A higher degradation rate was observed at very acidic or basic pH levels, while this rate was lower at quasi-neutral pH levels. After 100 h of trial, the initial CepC showed 46 % degradation at pH 2.2, 71 % degradation at pH 8.7, and varied from 15 to 20 % at quasi-neutral pH levels.
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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 ╳
