cefepime

セフェピム

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/13 07:36:29」(JST)

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Cefepime

Systematic (IUPAC) name
(6R,7R,Z)- 7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)- 3-((1-methylpyrrolidinium-1-yl)methyl)-8-oxo-5-thia- 1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate
Clinical data
Trade names	Maxipime
AHFS/Drugs.com	monograph
MedlinePlus	a698021
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
Legal status	AU: Prescription Only (S4) CA: ℞-only UK: Prescription-only (POM) US: ℞-only
Routes of administration	Intravenous, intramuscular
Pharmacokinetic data
Bioavailability	100% (IM)
Metabolism	Hepatic 15%
Biological half-life	2 hours
Excretion	Renal 70–99%
Identifiers
CAS Registry Number	88040-23-7 Y
ATC code	J01DE01
PubChem	CID: 5479537
DrugBank	DB01413 Y
ChemSpider	4586395 Y
UNII	807PW4VQE3 Y
KEGG	D02376 Y
ChEBI	CHEBI:478164 Y
ChEMBL	CHEMBL186 Y
Chemical data
Formula	C19H24N6O5S2
Molecular mass	480.56 g/mol
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)C[N+]4(C)CCCC4)C([O-])=O
InChI InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1 Y Key:HVFLCNVBZFFHBT-ZKDACBOMSA-N Y
Y (what is this?)  (verify)

Cefepime (INN, AAN, BAN, USAN) (/ˈsɛfɨpiːm/ or /ˈkɛfɨpiːm/) is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. Cefepime hydrochloride was developed by Bristol-Myers Squibb and marketed beginning in 1994. It is now available as a generic drug and sold under a variety of trade names worldwide. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in patients treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration performed their own meta-analysis which found no mortality difference.

Clinical use

Main article: Cephalosporin

Cefepime is usually reserved to treat moderate to severe nosocomial pneumonia, infections caused by multiple drug-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia.

Cefepime has good activity against important pathogens including Pseudomonas aeruginosa, Staphylococcus aureus, and multiple drug-resistant Streptococcus pneumoniae. A particular strength is its activity against Enterobacteriaceae. Whereas other cephalosporins are degraded by many plasmid- and chromosome-mediated beta-lactamases, cefepime is stable and is a front-line agent when infection with Enterobacteriaceae is known or suspected.

Spectrum of bacterial susceptibility

Cefepime is a broad-spectrum cephalosporin antibiotic and has been used to treat bacteria responsible for causing pneumonia and infections of the skin and urinary tract. Some of these bacteria include Pseudomonas, Escherichia, and Streptoccus species. The following represents MIC susceptibility data for a few medically significant microorganisms.

• Escherichia coli: ≤0.007 - 128 μg/ml
• Pseudomonas aeruginosa: 0.06 - >256 μg/ml
• Streptococcus pneumoniae: ≤0.007 - >8 μg/ml

Chemistry

The combination of the syn-configuration of the methoxyimino moiety and the aminothiazolyl moiety confers extra stability to β-lactamase enzymes produced by many bacteria. The N-methylpyrrolidine moiety increases penetration into Gram-negative bacteria. These factors increase the activity of cefepime against otherwise resistant organisms including Pseudomonas aeruginosa and Staphylococcus aureus.

Trade names

Following expiration of the Bristol-Myers Squibb patent, cefepime became available as a generic and is now marketed by numerous companies worldwide under tradenames including Neopime (Neomed), Maxipime. Cepimax, Cepimex, and Axepim.

References

UpToDate Contents

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• 1. 成人における確定診断を得られていない低血圧やショックの評価および初期アプローチ evaluation of and initial approach to the adult patient with undifferentiated hypotension and shock
• 2. セフェム系 cephalosporins
• 3. 基質特異性拡張型β-ラクタマーゼ extended spectrum beta lactamases
• 4. βラクタム系抗生物質の長期注入投与 prolonged infusions of beta lactam antibiotics
• 5. 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

English Journal

• His224 Alters the R2 Drug Binding Site and Phe218 Influences the Catalytic Efficiency of the Metallo-β-Lactamase VIM-7.

• Leiros HK1, Skagseth S2, Edvardsen KS2, Lorentzen MS2, Bjerga GE2, Leiros I2, Samuelsen O3.
• Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2014 Aug;58(8):4826-4836. Epub 2014 Jun 9.
• Metallo-β-lactamases (MBLs) are the causative mechanism for resistance to β-lactams, including carbapenems, in many Gram-negative pathogenic bacteria. One important family of MBLs is the Verona integron-encoded MBLs (VIM). In this study, the importance of residues Asp120, Phe218, and His224 in the
• PMID 24913158

• Convulsive Liability of Cefepime and Meropenem in Normal and Corneal Kindled Mice.

• Tanaka A1, Takechi K2, Watanabe S2, Tanaka M2, Suemaru K3, Araki H2.
• Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2014 Aug;58(8):4380-4383. Epub 2014 May 19.
• We have reported significantly higher convulsion prevalence in patients treated with cefepime than in those treated with meropenem. Additionally, cefepime-associated convulsions were found only in patients with brain disorders, not renal failure. Here, we compared the convulsive liability of cefepim
• PMID 24841261

• Identifying Critically Ill Patients at Risk for Inappropriate Antibiotic Therapy: A Pilot Study of a Point-of-Care Decision Support Alert*.

• Micek ST1, Heard KM, Gowan M, Kollef MH.
• Critical care medicine.Crit Care Med.2014 Aug;42(8):1832-8. doi: 10.1097/CCM.0000000000000337.
• OBJECTIVE: To develop an automated alert aimed at reducing inappropriate antibiotic therapy of serious healthcare-associated infections.DESIGN: Single-center cohort study from November 2011 to November 2012.SETTING: Barnes-Jewish Hospital (1,250-bed academic hospital).PATIENTS: A total of 3,616 crit
• PMID 24751497

Japanese Journal

• 当院において分離された緑膿菌に対する広域抗菌薬の感受性調査とモンテカルロシミュレーションを用いた最適投与方法の検討

• 平野 龍一,坂本 勇一,手代森 隆一,赤平 恵美,今 めぐみ,立花 直樹
• 日本環境感染学会誌 28(4), 235-239, 2013
• …   当院で検出された緑膿菌の約9割がpiperacillin/tazobactam (PIPC/TAZ)やmeropenem (MEPM)に感受性を示したが，imipenem (IPM)やcefepime (CFPM)に対する感受性は他の2剤と比べ低下していた．緑膿菌感染症例に対する広域抗菌薬の使用状況を調査し，モンテカルロシミュレーションによって最大殺菌効果が得られる投与方法を検討した．MEPMやPIPC/TAZによって最大殺菌効果を得られる投与方法は1日3回以上であり，当院で広く用いられている投 …
• NAID 130003385524

• Active Screening of Group B Streptococci with Reduced Penicillin Susceptibility and Altered Serotype Distribution Isolated from Pregnant Women in Kobe, Japan

• Kimura Kouji,Matsubara Kousaku,Yamamoto Go,Shibayama Keigo,Arakawa Yoshichika
• Japanese Journal of Infectious Diseases 66(2), 158-160, 2013
• … All 139 isolates were susceptible to penicillin G, ampicillin, cefotaxime, cefepime, and meropenem; …
• NAID 130003381661

• 症例報告 セフェピム塩酸塩投与により周期性あるいは律動性脳波所見を呈した2症例

• 代田 悠一郎,大友 亮,花島 律子 [他]
• 臨床神経学 52(5), 356-359, 2012-05
• NAID 40019325495

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Cefepime [CFPM] セフェピム, セフェム系 1. 商品名 先発品 注射用マキシピーム 0.5g／注射用マキシピーム 1g／マキシピーム点滴静注用バッグ1g 【ブリストル・マイヤーズ】 後発品 後発品2件 を表示 セフェピム塩酸塩静注用0.5g ...

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★リンクテーブル★

リンク元	「セフェピム」「maxipime」
拡張検索	「cefepime hydrochloride」

「セフェピム」

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cefepime CFPM

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塩酸セフェピム cefepime hydrochloride セフェピム塩酸塩

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マキシピーム, Maxipime

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抗菌薬。主としてグラム陽性・陰性菌に作用するもの、その他の診断用薬

• 第四世代セフェム系抗生物質

「maxipime」

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cefepime

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cefepime

「cefepime hydrochloride」

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• 塩酸セフェピム

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cefepime