Cephamycin C
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| Category | Antibiotics |
| Catalog number | BBF-00760 |
| CAS | 38429-35-5 |
| Molecular Weight | 446.43 |
| Molecular Formula | C16H22N4O9S |
| Purity | 95% |
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Description
It is produced by the strain of Streptomyces lactamdurans, Str. chartrensis, Str. griseus, Str. cinnamonensis, Str. fimbiiatus, Str. halstddii, Str. rochei, Str. vuridochromogene. Cephalomycin C was resistant to gram-positive bacteria (weak) and negative bacteria, with low toxicity, and mice could tolerate intraperitoneal injection of 10 g/kg. Used as raw material for semisynthetic cephalosporin.
Specification
| Related CAS | 34279-54-4 (sodium salt) |
| Synonyms | Cephemimycin; 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) |
| InChI Key | LXWBXEWUSAABOA-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.61g/cm3 |
Reference Reading
1.Evaluation of cephamycins as supplements to selective agar for detecting Campylobacter spp. in chicken carcass rinses.
Chon JW1, Kim YJ2, Kim HS2, Kim DH2, Kim H3, Song KY2, Sung K1, Seo KH4. Int J Food Microbiol. 2016 Apr 16;223:75-8. doi: 10.1016/j.ijfoodmicro.2016.01.019. Epub 2016 Jan 28.
Although cefoperazone is the most commonly used antibiotic in Campylobacter-selective media, the distribution of cefoperazone-resistant bacteria such as extended-spectrum beta-lactamase (ESBL)-producing Escherichia coli is increasing. Here we evaluated the potential of cephamycins for use as supplements to improve modified charcoal-cefoperazone-deoxycholate agar (mCCDA) by replacing cefoperazone with the same concentrations (32mg/L) of cefotetan (modified charcoal-cefotetan-deoxycholate agar, mCCtDA) and cefoxitin (modified charcoal-cefoxitin-deoxycholate agar, mCCxDA). In chicken carcass rinse samples, the number of mCCDA plates detecting for Campylobacter (18/70, 26%) was significantly lower than that of mCCtDA (42/70, 60%) or mCCxDA plates (40/70, 57%). The number of mCCDA plates (70/70, 100%) that were contaminated with non-Campylobacter species was significantly higher than that of mCCtDA (20/70, 29%) or mCCxDA plates (21/70, 30%). The most common competing species identified using mCCDA was ESBL-producing E.
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.
3.Analysis of the Structure and Function of FOX-4 Cephamycinase.
Lefurgy ST1, Malashkevich VN2, Aguilan JT2, Nieves E2, Mundorff EC1, Biju B1, Noel MA1, Toro R2, Baiwir D3, Papp-Wallace KM4, Almo SC2, Frere JM5, Bou G6, Bonomo RA7. Antimicrob Agents Chemother. 2015 Nov 2;60(2):717-28. doi: 10.1128/AAC.01887-15.
Class C β-lactamases poorly hydrolyze cephamycins (e.g., cefoxitin, cefotetan, and moxalactam). In the past 2 decades, a new family of plasmid-based AmpC β-lactamases conferring resistance to cefoxitin, the FOX family, has grown to include nine unique members descended from the Aeromonas caviae chromosomal AmpC. To understand the basis for the unique cephamycinase activity in the FOX family, we determined the first X-ray crystal structures of FOX-4, apo enzyme and the acyl-enzyme with its namesake compound, cefoxitin, using the Y150F deacylation-deficient variant. Notably, recombinant expression of N-terminally tagged FOX-4 also yielded an inactive adenylylated enzyme form not previously observed in β-lactamases. The posttranslational modification (PTM), which occurs on the active site Ser64, would not seem to provide a selective advantage, yet might present an opportunity for the design of novel antibacterial drugs. Substantial ligand-induced changes in the enzyme are seen in the acyl-enzyme complex, particularly the R2 loop and helix H10 (P289 to N297), with movement of F293 by 10.
4.Dissociation of cephamycin C and clavulanic acid biosynthesis by 1,3-diaminopropane in Streptomyces clavuligerus.
Leite CA1, Cavallieri AP2, Baptista AS2, Araujo ML2. FEMS Microbiol Lett. 2016 Jan;363(1):fnv215. doi: 10.1093/femsle/fnv215. Epub 2015 Nov 11.
Streptomyces clavuligerus produces simultaneously cephamycin C (CephC) and clavulanic acid (CA). Adding 1,3-diaminopropane to culture medium stimulates production of beta-lactam antibiotics. However, there are no studies on the influence of this diamine on coordinated production of CephC and CA. This study indicates that 1,3-diaminopropane can dissociate CephC and CA productions. Results indicated that low diamine concentrations (below 1.25 g l(-1)) in culture medium increased CA production by 200%, but not that of CephC. Conversely, CephC production increased by 300% when 10 g l(-1) 1,3-diaminopropane was added to culture medium. Addition of just L-lysine (18.3 g l(-1)) to culture medium increased both biocompounds. On the other hand, while L-lysine plus 7.5 g l(-1) 1,3-diaminopropane increased volumetric production of CephC by 1100%, its impact on CA production was insignificant. The combined results suggest that extracellular concentration of 1,3-diaminopropane may trigger the dissociation of CephC and CA biosynthesis in S.
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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 ╳
