関: cefamandole sodium

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/04 17:30:15」(JST)

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Cefamandole (INN, also known as cephamandole) is a second-generation broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.

The chemical structure of cefamandole, 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)(vitamin K supplement is recommended during therapy) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.

Cefamandole has a broad spectrum of activity and can be used to treat bacterial infections of the skin, bones and joints, urinary tract, and lower respiratory tract. The following represents cefamandole MIC susceptibility data for a few medically significant microorganisms.

Escherichia coli: 0.12 - 400 μg/ml
Haemophilus influenzae: 0.06 - >16 μg/ml
Staphylococcus aureus: 0.1 - 12.5 μg/ml

^[1]

CO₂ is generated during the normal constitution of cefamandole and ceftazidim, resulting in an explosive-like reaction in syringes.^[2]

References

^ http://www.toku-e.com/Assets/MIC/Cefamandole%20sodium%20salt.pdf
^ 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.

UpToDate Contents

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English Journal

Prospective survey of acute osteoarticular infections in a French paediatric orthopedic surgery unit.

Ferroni A, Al Khoury H, Dana C, Quesne G, Berche P, Glorion C, Péjin Z.SourceHôpital Necker Enfants-Malades, Laboratoire de Bactériologie Hôpital Necker-Enfants Malades, Unité de Chirurgie Orthopédique Pédiatrique, Paris, France.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases.Clin Microbiol Infect.2013 Sep;19(9):822-8. doi: 10.1111/clm.12031.
The epidemiology of acute paediatric osteoarticular infections (OAI) has recently evolved, mainly due to the improvement of microbiological diagnosis. We conducted a prospective study to analyse the recent epidemiology and the clinical evolution of paediatric OAI in order to validate the adequacy of
PMID 23957786

Validation of the cephalosporin intradermal skin test for predicting immediate hypersensitivity: a prospective study with drug challenge.

Yoon SY, Park SY, Kim S, Lee T, Lee YS, Kwon HS, Cho YS, Moon HB, Kim TB.SourceDivision of Allergy and Clinical Immunology, Department of Internal Medicine, Asan Medical Center, University of Ulsan College of Medicine, Seoul, Korea.
Allergy.Allergy.2013 Jul;68(7):938-44. doi: 10.1111/all.12182. Epub 2013 Jun 10.
BACKGROUND: Cephalosporin is a major offending agent in terms of drug hypersensitivity along with penicillin. Cephalosporin intradermal skin tests (IDTs) have been widely used; however, their validity for predicting immediate hypersensitivity has not been studied. This study aimed to determine the p
PMID 23751142

Hemophagocytic syndrome as uncommon presentation of disseminated toxoplasmosis in an immunocompetent adult from Chinese Kunming.

Yang Y, Zuo W, Hu J, Esch GW, Zuo Y.SourceKey Laboratory for Animal Genetic Diversity and Evolution of High Education in Yunnan Province, Yunnan University, Kunming, China. 12011000936@mail.ynu.edu.cn
The American journal of tropical medicine and hygiene.Am J Trop Med Hyg.2013 Jun;88(6):1209-11. doi: 10.4269/ajtmh.12-0556. Epub 2013 Mar 18.
Hemophagocytic syndrome is a rare disease that is often fatal, despite treatment. An immunocompetent patient was presented with fever, hepatosplenomegaly, cytopenias, hypertriglyceridemia, hypofibrinogenemia, and hyperferritinemia, which conformed to a hemophagocytic syndrome diagnosis. Despite broa
PMID 23509123

Japanese Journal

Effects of antineoplastics, antibiotics and antidiabetics on acetaldehyde metabolism after alcohol ingestion.

Acta Medica Okayama 52(1), 9-17, 1998-02
NAID 120002312418

メチシリン感受性および耐性黄色ブドウ球菌へのセフメタゾールとセフォチァム,セファマンドールまたはセフォペラゾンの併用による相乗的in vitro抗菌力増強作用 : II. 接種菌量の影響

The Japanese journal of antibiotics 48(4), 563-570, 1995-04-01
NAID 10008464733

メチシリン感受性および耐性黄色ブドウ球菌へのセフメタゾールとセファゾリン,セフォチァム,セファマンドールまたはセフォペラゾンの併用による相乗的 in vitro抗菌力増強作用 : I.NaC1の影響

The Japanese journal of antibiotics 48(4), 553-562, 1995-04-01
NAID 10008464701

「セファマンドール」

Cefamandole
Systematic (IUPAC) name
	(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-; 3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-; 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	former Mandol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
Pregnancy; category	AU: B1;
Legal status	UK: Prescription-only (POM); Discontinued (US);
Routes of; administration	Intramuscular, intravenous
Pharmacokinetic data
Protein binding	75%
Half-life	48 minutes
Excretion	Mostly renal, as unchanged drug
Identifiers
CAS Registry Number	34444-01-4 42540-40-9
ATC code	J01DC03
PubChem	CID 456255
DrugBank	DB01326
ChemSpider	401748
UNII	5CKP8C2LLI
KEGG	D02344
ChEBI	CHEBI:3480
ChEMBL	CHEMBL1146
Chemical data
Formula	C18H18N6O5S2
Molecular mass	462.505 g/mol
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4C)C(=O)O;
	InChI InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1 ; Key:OLVCFLKTBJRLHI-AXAPSJFSSA-N ;
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