Together with cephamycins they constitute a subgroup of β-lactam antibiotics called cephems.
The commonly quoted figure of 10% of patients with allergic hypersensitivity to penicillins and/or carbapenems also having cross-reactivity with cephalosporins originated from a 1975 study looking at the original cephalosporins, and subsequent "safety first" policy meant this was widely quoted and assumed to apply to all members of the group. Hence it was commonly stated that they are contraindicated in patients with a history of severe, immediate allergic reactions (urticaria, anaphylaxis, interstitial nephritis, etc.) to penicillins, carbapenems or cephalosporins. This, however, should be viewed in the light of recent epidemiological work suggesting that, for many second-generation (or later) cephalosporins, the cross-reactivity rate with penicillin is much lower, having no significantly increased risk of reactivity in the studies examined. The British National Formulary previously issued blanket warnings of 10% cross reactivity, but, since the September 2008 edition, suggests in the absence of suitable alternatives that oral cefixime or cefuroxime and injectable cefotaxime, ceftazidine, and ceftriaxone can be used with caution, but to avoid cefaclor, cefadrocil, cefalexin, and cefradine.
Several cephalosporins are associated with hypoprothrombinemia and a disulfiram-like reaction with ethanol. These include latamoxef, cefmenoxime, moxalactam, cefoperazone, cefamandole, cefmetazole, and cefotetan. This is thought to be due to the N-methylthiotetrazole (NMTT) side-chain of these cephalosporins, which blocks the enzyme vitamin K epoxide reductase (likely causing hypothrombinemia) and aldehyde dehydrogenase (causing alcohol intolerance).
The classification of cephalosporins into "generations" is commonly practised, although the exact categorization of cephalosporins is often imprecise. For example, the fourth generation of cephalosporins is not recognized as such, in Japan. In Japan, cefaclor is classed as a first-generation cephalosporin, even though in the United States it is a second-generation one; and cefbuperazone, cefminox, and cefotetan are classed as second-generation cephalosporins. Cefmetazole and cefoxitin are classed as third-generation cephems. Flomoxef, latamoxef are in a new class called oxacephems.
Most first-generation cephalosporins were originally spelled "ceph-" in English-speaking countries. This continues to be the preferred spelling in the United States and Australia, while European countries (including the United Kingdom) have adopted the International Nonproprietary Names, which are always spelled "cef-". Newer first-generation cephalosporins and all cephalosporins of later generations are spelled "cef-", even in the United States.
Some state that, although cephalosporins can be divided into five or even six generations, the usefulness of this organization system is of limited clinical relevance.
Fourth-generation Cephalosporins as of March, 2007 were considered to be "a class of highly potent antibiotics that are among medicine's last defenses against several serious human infections" according to the Washington Post.
! # | ! Members | ! Description |
1 | Cefacetrile (cephacetrile), Cefadroxil (cefadroxyl; Duricef), Cephalexin (cephalexin; Keflex), Cefaloglycin (cephaloglycin), Cefalonium (cephalonium), Cefaloridine (cephaloradine), Cefalotin (cephalothin; Keflin), Cefapirin (cephapirin; Cefadryl), Cefatrizine, Cefazaflur, Cefazedone, Cefazolin (cephazolin; Ancef, Kefzol), Cefradine (cephradine; Velosef), Cefroxadine, Ceftezole. | Gram-positive: Activity against penicillinase-producing, methicillin-susceptible staphylococci and streptococci (though they are not the drugs of choice for such infections). No activity against methicillin-resistant staphylococci or enterococci. Gram-negative: Activity against Proteus mirabilis, some Escherichia coli, and Klebsiella pneumoniae ("PEcK"), but have no activity against Bacteroides fragilis, Pseudomonas, Acinetobacter, Enterobacter, indole-positive Proteus, or Serratia. |
2 | Cefaclor (Ceclor, Distaclor, Keflor, Raniclor), Cefonicid (Monocid), Cefprozil (cefproxil; Cefzil), Cefuroxime (Zefu, Zinnat, Zinacef, Ceftin, Biofuroksym, Xorimax), Cefuzonam. Second generation cephalosporins with antianaerobe activity: Cefmetazole, Cefotetan, Cefoxitin. The following cephems are also sometimes grouped with second-generation cephalosporins: Carbacephems: loracarbef (Lorabid); Cephamycins: cefbuperazone, cefmetazole (Zefazone), cefminox, cefotetan (Cefotan), cefoxitin (Mefoxin). | Gram-positive: Less than first-generation. Gram-negative: Greater than first-generation: HEN (Haemophilus influenzae, Enterobacter aerogenes and some Neisseria + the PEcK described above. |
3 | Cefcapene, Cefdaloxime, Cefdinir (Zinir, Omnicef, Kefnir), Cefditoren, Cefetamet, Cefixime (Zifi, Suprax), Cefmenoxime, Cefodizime, Cefotaxime (Claforan), Cefovecin (Convenia), Cefpimizole, Cefpodoxime (Vantin, PECEF), Cefteram, Ceftibuten (Cedax), Ceftiofur, Ceftiolene, Ceftizoxime (Cefizox), Ceftriaxone (Rocephin). Third-generation cephalosporins with antipseudomonal activity: Cefoperazone (Cefobid), Ceftazidime (Fortum, Fortaz). The following cephems are also sometimes grouped with third-generation cephalosporins: Oxacephems: latamoxef (moxalactam). | Gram-positive: Some members of this group (in particular, those available in an oral formulation, and those with anti-pseudomonal activity) have decreased activity against Gram-positive organisms. Gram-negative: Third-generation cephalosporins have a broad spectrum of activity and further increased activity against Gram-negative organisms. They may be particularly useful in treating nosocomial infection |
4 | [[Cefclidine, Cefepime (Maxipime), Cefluprenam, Cefoselis, Cefozopran, Cefpirome (Cefrom), Cefquinome. The following cephems are also sometimes grouped with fourth-generation cephalosporins: Oxacephems: flomoxef | |
5 | Ceftobiprole, Ceftaroline | Ceftobiprole has been described as "fifth-generation" cephalosporin, though acceptance for this terminology is not universal. Ceftobiprole (and the soluble prodrug medocaril) are on the FDA fast-track. Ceftobiprole has powerful antipseudomonal characteristics and appears to be less susceptible to development of resistance. Ceftaroline has also been described as "fifth-generation" cephalosporin. |
These cephems have progressed far enough to be named, but have not been assigned to a particular generation: Cefaloram, Cefaparole, Cefcanel, Cefedrolor, Cefempidone, Cefetrizole, Cefivitril, Cefmatilen, Cefmepidium, Cefoxazole, Cefrotil, Cefsumide, Ceftioxide, Cefuracetime
ar:سيفالوسبورين ca:Cefalosporina cs:Cefalosporin de:Cephalosporine el:Κεφαλοσπορίνες es:Cefalosporina eu:Zefalosporina fa:سفالوسپورین fr:Céphalosporine hi:सेफालोस्पोरिन hr:Cefalosporin it:Cefalosporine he:צפלוספורין nl:Cefalosporine ja:セファロスポリン pl:Cefalosporyny pt:Cefalosporina ru:Цефалоспорины sk:Cefalosporín sl:Cefalosporini sr:Цефалоспорини fi:Kefalosporiini sv:Cefalosporiner th:Cephalosporin tr:Sefalosporin wuu:头孢菌素 zh:頭孢菌素
This text is licensed under the Creative Commons CC-BY-SA License. This text was originally published on Wikipedia and was developed by the Wikipedia community.
The World News (WN) Network, has created this privacy statement in order to demonstrate our firm commitment to user privacy. The following discloses our information gathering and dissemination practices for wn.com, as well as e-mail newsletters.
We do not collect personally identifiable information about you, except when you provide it to us. For example, if you submit an inquiry to us or sign up for our newsletter, you may be asked to provide certain information such as your contact details (name, e-mail address, mailing address, etc.).
When you submit your personally identifiable information through wn.com, you are giving your consent to the collection, use and disclosure of your personal information as set forth in this Privacy Policy. If you would prefer that we not collect any personally identifiable information from you, please do not provide us with any such information. We will not sell or rent your personally identifiable information to third parties without your consent, except as otherwise disclosed in this Privacy Policy.
Except as otherwise disclosed in this Privacy Policy, we will use the information you provide us only for the purpose of responding to your inquiry or in connection with the service for which you provided such information. We may forward your contact information and inquiry to our affiliates and other divisions of our company that we feel can best address your inquiry or provide you with the requested service. We may also use the information you provide in aggregate form for internal business purposes, such as generating statistics and developing marketing plans. We may share or transfer such non-personally identifiable information with or to our affiliates, licensees, agents and partners.
We may retain other companies and individuals to perform functions on our behalf. Such third parties may be provided with access to personally identifiable information needed to perform their functions, but may not use such information for any other purpose.
In addition, we may disclose any information, including personally identifiable information, we deem necessary, in our sole discretion, to comply with any applicable law, regulation, legal proceeding or governmental request.
We do not want you to receive unwanted e-mail from us. We try to make it easy to opt-out of any service you have asked to receive. If you sign-up to our e-mail newsletters we do not sell, exchange or give your e-mail address to a third party.
E-mail addresses are collected via the wn.com web site. Users have to physically opt-in to receive the wn.com newsletter and a verification e-mail is sent. wn.com is clearly and conspicuously named at the point of
collection.If you no longer wish to receive our newsletter and promotional communications, you may opt-out of receiving them by following the instructions included in each newsletter or communication or by e-mailing us at michaelw(at)wn.com
The security of your personal information is important to us. We follow generally accepted industry standards to protect the personal information submitted to us, both during registration and once we receive it. No method of transmission over the Internet, or method of electronic storage, is 100 percent secure, however. Therefore, though we strive to use commercially acceptable means to protect your personal information, we cannot guarantee its absolute security.
If we decide to change our e-mail practices, we will post those changes to this privacy statement, the homepage, and other places we think appropriate so that you are aware of what information we collect, how we use it, and under what circumstances, if any, we disclose it.
If we make material changes to our e-mail practices, we will notify you here, by e-mail, and by means of a notice on our home page.
The advertising banners and other forms of advertising appearing on this Web site are sometimes delivered to you, on our behalf, by a third party. In the course of serving advertisements to this site, the third party may place or recognize a unique cookie on your browser. For more information on cookies, you can visit www.cookiecentral.com.
As we continue to develop our business, we might sell certain aspects of our entities or assets. In such transactions, user information, including personally identifiable information, generally is one of the transferred business assets, and by submitting your personal information on Wn.com you agree that your data may be transferred to such parties in these circumstances.