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a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11

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ソジウム,ナトリウム(金属元素;化学記号はNa)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/23 15:21:21」(JST)

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Cefoxitin is a cephamycin antibiotic developed by Merck & Co., Inc., often grouped with the second−generation cephalosporins. It is sold under the brand name Mefoxin.

Microbiology

Cefoxitin acts by interfering with cell wall synthesis. Its activity spectrum includes a broad range of gram-negative and gram-positive bacteria including anaerobes. It is inactive in vitro to most strains of Pseudomonas aeruginosa and many strains of Enterobacter cloacae. Staphylococci resistant to methicillin/oxacillin should be considered resistant to cefoxitin. ^[1]

Cefoxitin is considered to be a strong beta-lactamase inducer, as are certain other antibiotics (such as imipenem).^[2]

Spectrum of Bacterial Susceptibility

Cefoxitin has a broad spectrum of activity and has been used in the treatment of skin, bone, respiratory and urinary tract infections. Susceptible bacteria include some Staphylococci, Enterococci, Streptococci, and others. The following represents MIC susceptibility data for a few medically significant microorganisms.

Escherichia coli: 0.2 μg/ml - 64 μg/ml
Haemophilus influenzae: 0.5 μg/ml - 12.5 μg/ml
Streptococcus pneumoniae: 0.2 μg/ml - 1 μg/ml

^[3]

Syntheses

Cefoxitin synthesis 1: DE 2318829 DE 2365582 DE 2129675 DE 2143331 DE 2203653 DE 2258278 US 3775410 U.S. Patent 3,843,641 ^[4]

The benzhydryl ester of 7-aminocephalosporanic acid (7-ACA) 2 is prepared by previous tosylation of the amino group of the initial 7-ACA, esterification of the carboxyl group with diphenyldiazomethane, and subsequent removal of the tosyl protection. When reacted with nitrous acid, the product is diazotized, and a subsequent reaction of the resulting compound with triethylammonium azide in DCM and then with bromine azide gives the diphenyl methyl ester of 7-bromo-7-azidocephalosporanic acid (4). Treating this with methanol in the presence of silver borofluoride results in the replacement of the bromine atom, giving the diphenylmethyl ester of 7-methoxy-7-azidocephalosporanic acid (5). The resulting azide is reduced by hydrogen in the presence of a platinum oxide catalyst, forming the diphenyl methyl ester of 7-methoxy-7-aminocephalosporanic acid (6). Acylation of this compound with 2-(2-thienyl)acetylchloride gives the benzyhydryl ester of 7-methoxy-7-[2-(2-thienyl)-acetamido]cephalosporanic acid (7), the ester group of which is hydrolyzed using trifluoroacetic acid and then upon reacting the resulting acid with potassium bicarbonate, it is transformed into the potassium salt (8). The resulting product is then hydrolyzed by the enzyme Citrusi acetylesterase (9). Initial reaction with chlorosulfonyl isocyanate followed with water, the resulting compound is transformed into the desired cefoxitin (11).

References

^ Mefoxin Official FDA information at Drugs.com
^ Phillips I, Shannon K (1993). "Importance of beta-lactamase induction". Eur J Clin Microbiol Infect Dis. 12 Suppl 1: S19–26. PMID 8477758.
^ http://www.toku-e.com/Assets/MIC/Cefoxitin.pdf
^ doi:10.3987/S(S)-1977-01-0719
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UpToDate Contents

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1. セフェム系 cephalosporins
2. 骨盤内炎症性疾患：治療 pelvic inflammatory disease treatment
3. 小児における急性虫垂炎：管理 acute appendicitis in children management
4. メチシリン耐性黄色ブドウ球菌の迅速な検出 rapid detection of methicillin resistant staphylococcus aureus
5. 成人における非結核性抗酸菌による骨髄炎の治療 treatment of osteomyelitis due to nontuberculous mycobacteria in adults

English Journal

Prevalence of multiple antibiotic-resistant Gram-negative bacteria on bagged, ready-to-eat baby spinach.

Walia S, Rana SW, Maue D, Rana J, Kumar A, Walia SK.Sourcea Department of Biological Sciences , Oakland University , Rochester , MI , USA.
International journal of environmental health research.Int J Environ Health Res.2013 Apr;23(2):108-18. doi: 10.1080/09603123.2012.708916. Epub 2012 Jul 27.
In this study, multiple antibiotic-resistant (MAR) Gram-negative bacteria (GNB) were isolated from triple-washed, bagged, ready-to-eat (RTE) baby spinach. Biochemical identification of randomly selected bacterial colonies showed the predominance of cytochrome oxidase-positive Pseudomonas species. Am
PMID 22838727

Towards a phenotypic screening strategy for emerging β-lactamases in Gram-negative bacilli.

Willems E, Verhaegen J, Magerman K, Nys S, Cartuyvels R.SourceDepartment of Clinical Microbiology, University Hospital Leuven, Herestraat 49, 3000 Leuven, Belgium.
International journal of antimicrobial agents.Int J Antimicrob Agents.2013 Feb;41(2):99-109. doi: 10.1016/j.ijantimicag.2012.07.006. Epub 2012 Dec 29.
The purpose of this manuscript was to review recent literature and guidelines regarding phenotypic detection of emerging β-lactamases [extended-spectrum β-lactamases (ESBLs), AmpC β-lactamases and carbapenemases] in Gram-negative bacilli (GNB) in order to formulate recommendations on best practic
PMID 23280443

Japanese Journal

The Enhancing Mechanism of Capric Acid (C10) from a Suppository on Rectal Drug Absorption through a Paracellular Pathway

Takahashi Hideyuki,Shibasaki Tamayo,Takeshita Kenichi [他],KAIHO Fusao,HAYASHI Masahiro
Biological & pharmaceutical bulletin 20(4), 446-448, 1997-04-15
… Capric acid (C10) enhanced the absorption of cefoxitin sodium in a concentration-dependent manner following the rectal administration as a suppository in rats. …
NAID 110003639075

ラットにおけるセフォキシチンナトリウムの腸管吸収 : 剤型の影響(発表論文抄録(1986年))

西畑利明,吉富博則,HIGUCHI Takeru
福山大学薬学部研究年報 5, 104, 1987
NAID 110007408189

サリチル酸ナトリウム,エチレンジアミン四酢酸ニナトリウム,及びポリオキシエチレン(23)ラウリルエーテルのセフォキシチンナトリウム直腸吸収促進効果の比較(発表論文抄録(1985年))

西畑利明,冨田久夫,FREDERICK Gregory,RYTTING J. Howard,HIGUCHI Takeru
福山大学薬学部研究年報 4, 85-86, 1986
NAID 110007408130

「セフォキシチン」

Cefoxitin
Systematic (IUPAC) name
	(6S,7R)-4-(carbamoyloxymethyl)-7-methoxy-; 8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-; 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Mefoxin
AHFS/Drugs.com	monograph
MedlinePlus	a682737
Pregnancy; category	B;
Routes of; administration	IV
Pharmacokinetic data
Metabolism	minimal
Biological half-life	41-59 min
Excretion	85% urine
Identifiers
CAS Registry Number	35607-66-0
ATC code	J01DC01
PubChem	CID: 441199
DrugBank	DB01331
ChemSpider	389981
UNII	6OEV9DX57Y
KEGG	D02345
ChEBI	CHEBI:209807
ChEMBL	CHEMBL996
Chemical data
Formula	C16H17N3O7S2
Molecular mass	427.454 g/mol
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)Cc3sccc3)COC(=O)N)C(=O)O ;
	InChI InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1 ; Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N ;
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