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Core structure of the cephamycins.

Cephamycins are a group of beta-lactam antibiotics. They are very similar to cephalosporins, and the cephamycins are sometimes classified as cephalosporins.

Like cephalosporins, cephamycins are based upon the cephem nucleus. Unlike most cephalosporins, cephamycins are a very efficient antibiotic against anaerobic microbes.

Cephamycins were originally produced by Streptomyces, but synthetic ones have been produced as well.

Cephamycins possess a methoxy group at the 7-alpha position.^[1]

In addition, cephamycins have been shown to be stable against extended-spectrum beta-lactamase (ESBL) producing organisms, although their use in clinical practice is lacking for this indication.

Examples

Cephamycins include:

Cefoxitin^[2]
Cefotetan^[3]
Cefmetazole^[4]

References

^ Oreste A. Mascaretti (2003). Bacteria Versus Antibacterial Agents: An Integrated Approach. American Society Microbiology. p. 144. ISBN 1-55581-258-9.
^ Little PJ, Peddie BA (July 1978). "Clinical use of cefoxitin, a new semisynthetic cephamycin". N. Z. Med. J. 88 (616): 46–9. PMID 279853.
^ Clarke AM, Zemcov SJ (January 1983). "Antibacterial activity of the cephamycin cefotetan: an in-vitro comparison with other beta-lactam antibiotics". J. Antimicrob. Chemother. 11. Suppl: 67–72. doi:10.1093/jac/11.suppl_A.67. PMID 6404881.
^ Benlloch M, Torres A, Soriano F (October 1982). "Cefmetazole (CS-1170): a new cephamycin with activity against gram-negative bacilli and staphylococci". J. Antimicrob. Chemother. 10 (4): 347–50. doi:10.1093/jac/10.4.347. PMID 6958672.

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UpToDate Contents

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1. セフェム系 cephalosporins
2. 基質特異性拡張型β-ラクタマーゼ extended spectrum beta lactamases
3. β-ラクタム系抗生物質：作用機序、耐性および有害作用 beta lactam antibiotics mechanisms of action and resistance and adverse effects
4. セラチア種による感染症 infections due to serratia species

English Journal

Nosocomial spread of Klebsiella pneumoniae isolates producing blaGES-4 carbapenemase at a Japanese hospital.

Yamasaki K1, Komatsu M2, Ono T3, Nishio H4, Sueyoshi N5, Kida K6, Satoh K7, Toda H7, Nishi I8, Akagi M9, Mizutani T9, Nakai I10, Kofuku T10, Orita T11, Zikimoto T12, Nakamura T12, Wada Y13.
Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy.J Infect Chemother.2016 Oct 18. pii: S1341-321X(16)30184-2. doi: 10.1016/j.jiac.2016.09.006. [Epub ahead of print]
Six Klebsiella pneumoniae clinical isolates resistant to various cephalosporins and cephamycins were identified in a Japanese general hospital, a tertiary care hospital, between November 2009 and April 2010. All K. pneumoniae isolates carried blaGES-4 and blaSHV-1, while 2 K. pneumoniae isolates a
PMID 27769645

Cefmetazole for bacteremia caused by ESBL-producing enterobacteriaceae comparing with carbapenems.

Fukuchi T1,2, Iwata K3,4, Kobayashi S5, Nakamura T5, Ohji G3,4,5.
BMC infectious diseases.BMC Infect Dis.2016 Aug 18;16(1):427. doi: 10.1186/s12879-016-1770-1.
BACKGROUND: ESBL (Extended spectrum beta-lactamase) producing enterobacteriaceae are challenging organisms with little treatment options. Carbapenems are frequently used, but the emergence of carbapenem resistant enterobacteriaceae is a concerning issue, which may hinder the use of carbapenems. Alth
PMID 27538488

β-Lactams and β-Lactamase Inhibitors: An Overview.

Bush K1, Bradford PA2.
Cold Spring Harbor perspectives in medicine.Cold Spring Harb Perspect Med.2016 Aug 1;6(8). pii: a025247. doi: 10.1101/cshperspect.a025247.
β-Lactams are the most widely used class of antibiotics. Since the discovery of benzylpenicillin in the 1920s, thousands of new penicillin derivatives and related β-lactam classes of cephalosporins, cephamycins, monobactams, and carbapenems have been discovered. Each new class of β-lactam has bee
PMID 27329032

Japanese Journal

生産を志向した新規合成反応の開発研究 : セファロスポリンの新規7α-メトキシ化反応開発を例として

有機合成化学協会誌 69(5), 571-578, 2011-05-01
NAID 10028293687

Identification of transcriptional activators for thienamycin and cephamycin C biosynthetic genes within the thienamycin gene cluster from Streptomyces cattleya

Mol. Microbiol. 69, 633-645, 2008
NAID 80019684085

胆道疾患におけるMT-141の胆汁および胆嚢壁への移行について

福岡大学医学紀要 32(3), 99-103, 2005-09
NAID 110001391501

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