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Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.

Cefotetan was developed by Yamanouchi. It is marketed outside Japan by AstraZeneca with the brand names Apatef and Cefotan.

Adverse effects

The chemical structure of cefotetan, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.^[1]

Spectrum of bacterial susceptibility

Cefotetan has a broad spectrum of activity and has been used to treat bacterial infections of the bone, skin, urinary tract, and lower respiratory tract. Notable species include Bacteroides, Streptococcus, and Escherichia. The following represents MIC susceptibility data for a few medically significant bacteria.^[2]

Escherichia coli: 0.06 µg/mL
Bacteroides fragilis: ≤0.06 µg/mL - 512 µg/mL
Clostridium perfringins: 1 µg/mL - 4 µg/mL

References

^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
^ "Cefotetan Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). Toku-e.

External links

Cefotan official web site run by AstraZeneca US
Cefotetan entry in RxList

UpToDate Contents

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1. セフェム系 cephalosporins
2. 成人における手術部位感染症予防のための予防的抗菌薬投与 antimicrobial prophylaxis for prevention of surgical site infection in adults
3. 基質特異性拡張型β-ラクタマーゼ extended spectrum beta lactamases
4. 小児における急性虫垂炎：管理 acute appendicitis in children management
5. 慢性副鼻腔炎の微生物学的および抗菌薬によるマネージメント microbiology and antibiotic management of chronic rhinosinusitis

English Journal

Immunologic evaluation of patients with cefotetan-induced anaphylaxis.

Nam YH1, Hwang EK2, Ban GY2, Jin HJ3, Yoo HS2, Shin YS2, Ye YM2, Nahm DH2, Park HS2, Lee SK4.
Allergy, asthma & immunology research.Allergy Asthma Immunol Res.2015 May;7(3):301-3. doi: 10.4168/aair.2015.7.3.301. Epub 2014 Oct 8.
Cefotetan is a commonly prescribed second-generation cephalosporin that acts against a wide range of bacteria. However, cefotetan-induced hypersensitivity has rarely been reported. We report 2 cases of cefotetan-induced anaphylaxis with immunologic evaluation. The first case was a 70-year-old asthma
PMID 25749763

Oral and intramuscular treatment options for early postpartum endometritis in low-resource settings: a systematic review.

Meaney-Delman D1, Bartlett LA, Gravett MG, Jamieson DJ.
Obstetrics and gynecology.Obstet Gynecol.2015 Apr;125(4):789-800. doi: 10.1097/AOG.0000000000000732.
OBJECTIVE: To suggest options for oral and intramuscular antibiotic treatment of early postpartum endometritis in low-resource community settings where intravenous antibiotics are unavailable.DATA SOURCES: Studies were identified through MEDLINE from inception through December 2014. Search terms inc
PMID 25751198

Recent evolution of antibiotic resistance in the anaerobes as compared to previous decades.

Boyanova L1, Kolarov R2, Mitov I3.
Anaerobe.Anaerobe.2015 Feb;31:4-10. doi: 10.1016/j.anaerobe.2014.05.004. Epub 2014 May 27.
Evolution of antibiotic resistance in the anaerobes was reviewed using recent data covering 2000-2013 as compared to previous years. All studies reported growing moxifloxacin resistance in Bacteroides/Parabacteroides spp. in Europe and USA and in Clostridium difficile in Europe. In half or more stud
PMID 24875330

Japanese Journal

S94 抗生物質Cefotetanの合成原料、Organomycinの発酵生産とLCA

永木英雄
日本生物工学会大会講演要旨集平成11年度, 364, 1999-08-16
NAID 110002921356

セフォテタン合成の工程開発と工業化

藤本正治
有機合成化学協会誌 57(5), 374-381, 1999-05-01
… Cefotetan (YM09330) is a semi-synthetic injectable antibiotic which was discovered and developed by Yamanouchi Pharmaceutical Co., Ltd. and has been on the market since 1983. …
NAID 10009347556

In Vitro Susceptibility of Escherichia coli O157 to Several Antimicrobial Agents

OIE Shigeharu,KAMIYA Akira,TOMITA Masaaki,MATSUSAKI Shizue,KATAYAMA Atsushi,IWASAKI Akira
Biological & pharmaceutical bulletin 20(5), 584-585, 1997-05-15
… When oral administration is impossible, bile excreting cephem antibiotics (such as cefoperazone, cefriaxone, and cefotetan) may be useful. …
NAID 110003639105

Related Pictures

★リンクテーブル★

リンク元	「セファロスポリン系抗菌薬」「セフォテタン」
拡張検索	「cefotetan sodium」

「セファロスポリン系抗菌薬」

Cefotetan
Systematic (IUPAC) name
	(7S)-7-{[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene); 1,3-dithietane-2-carbonyl]amino}-7-methoxy-; 3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-; 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy; category	US: B (No risk in non-human studies);
Legal status	US: ℞-only;
Routes of; administration	Injection
Identifiers
CAS Registry Number	69712-56-7
ATC code	J01DC05
PubChem	CID: 53025
DrugBank	DB01330
ChemSpider	47904
UNII	48SPP0PA9Q
KEGG	D00260
ChEBI	CHEBI:3499
ChEMBL	CHEMBL474579
Chemical data
Formula	C17H17N7O8S4
Molecular mass	575.623 g/mol
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)C3S/C(S3)=C(/C(=O)N)C(=O)O)CSc4nnnn4C)C(=O)O ;
	InChI InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1 ; Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N ;
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　　[★]

英: cephalosporin antibiotics, cephalosporin, cephalosporins
同: セフェム系抗菌薬？、セフェム系抗生物質？ cephem antibiotic？ cephem antibiotics
関: 抗菌薬、βラクタム系抗菌薬、第三世代抗生物質

特徴

抗菌スペクトルが広い

グラム陽性菌、グラム陰性菌

酸に対して安定である
ペニシリナーゼに対して安定である

構造

副作用

過敏症(ペニシリン系抗菌薬と同様であるが、頻度はペニシリン系に比べ低い)
(1)ジスルフィラム様作用、(2)ビタミンK依存性の凝固因子の産生低下(cefotetanとcefoperazoneに特徴的。共通点はN-methylthiotetrazole(NMTT) side chainを持つこと)。(PPC.612)

セフェム系抗菌薬

第三世代セフェム

セフォタキシム	cefotaxime
セフトリアキソン	ceftriaxone
セフジニル	cefdinir
セフジトレンピボキシル	cefditoren pivoxil
セフチブテン	ceftibuten
セフポドキシムプロキセチル	cefpodoxime proxetil
セフチゾキシム	ceftizoxime
セフォペラゾン	cefoperazone
セフタジジム	ceftazidime