同: Suprax

同: Suprax

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/13 19:40:20」(JST)

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Cefixime (under the brand name of Suprax in the USA, Triocim by BEXIMCO & under the brand name of Fixitol by Solmarc Lifesciences (P) Ltd ) is a cephalosporin antibiotic used to treat infections caused by bacteria.

Spectrum of Bacterial Susceptibility and Resistance[edit]

Generally Haemolytic streptococci, Haemophilus parainfluenzee and moraxella catarrhalis are susceptible to Cefixime. While Listeria innocua, Pseudomonas aeruginosa and Staphylococcus aureus are resistant to Cefixime. Branhamella catarrhalis, Citrobacter freundii, Haemophilus influenzae and Moraxella catarrhalis have developed resistance towards Cefixime to varying degrees.For the detailed minimum inhibition concentration information, please refer to Cefixime Susceptibilty and Resistance Data sheet.^[1]

Medical uses[edit]

Cefixime treats infections of the:
Ear: Otitis caused by Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pyogenes.
Sinuses: Sinusitis.
Throat: Tonsillitis, pharyngitis caused by Streptococcus pyogenes.
Chest and lungs: Bronchitis, pneumonia caused by Streptococcus pneumoniae and Haemophilus influenzae.

Mechanism of action[edit]

The bactericidal action of cephalosporin due to the inhibition of cell wall synthesis. It binds to one of the penicillin binding proteins (PBPs) which inhibits the final transpeptidation step of the peptidoglycan synthesis in the bacterial cell wall, thus inhibiting biosynthesis and arresting cell wall assembly resulting in bacterial cell death.

Absorption
Only 40-50% is absorbed from the GI tract (oral). Rate may be decreased if taken with food. Absorption from oral suspensions than tablet.

Distribution
It has high concentrations in bile and urine. It can cross the placenta and its protein binding capacity is 65%.

It is always better to perform appropriate cultures and susceptibility studies to determine the causative organism and its sensitivity to Cefixime.

Contraindications[edit]

Cefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics. As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy. ^[2]

Adverse effects[edit]

Adverse drug reactions include diarrhea, dyspepsia, nausea and vomiting. Hypersensitivity reactions like skin rashes, urticaria and Stevens-Johnson syndrome have been reported. There is no specific antidote for Cefixime overdosage. Gastric lavage may performed. Dialysis will not remove Cefixime in significant quantities.

History[edit]

It was sold under the trade name Suprax 125 in the USA until 2003 when it was taken off the market by drug manufacturer Wyeth after its patent expired.

The oral suspension form of Suprax 125 was re-launched by Lupin in the USA.

References[edit]

^ "Cefixime Susceptibilty and Resistance Data". Retrieved 22 July 2013.
^ http://www.cks.nhs.uk/gonorrhoea/prescribing_information/prescribing_information/cephalosporins_ceftriaxone_or_cefixime

UpToDate Contents

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1. 合併症のない淋菌感染の治療 treatment of uncomplicated gonococcal infections
2. 乳児および1ヶ月以上の小児における尿路感染症：急性期マネージメント、画像検査、および予後 urinary tract infections in infants and children older than one month acute management imaging and prognosis
3. 急性膀胱炎：2歳以上の小児および思春期におけるマネージメントおよび予後 acute cystitis management and prognosis in children older than two years and adolescents
4. セフェム系 cephalosporins
5. 腸チフスの治療および予防 treatment and prevention of typhoid fever

English Journal

Novel mechanisms of resistance to β-lactam antibiotics in Haemophilus parainfluenzae: β-lactamase-negative ampicillin resistance and inhibitor-resistant TEM β-lactamases.

García-Cobos S, Arroyo M, Campos J, Pérez-Vázquez M, Aracil B, Cercenado E, Orden B, Lara N, Oteo J.SourceAntibiotic Laboratory, Bacteriology Service, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Majadahonda, Madrid, Spain.
The Journal of antimicrobial chemotherapy.J Antimicrob Chemother.2013 May;68(5):1054-9. doi: 10.1093/jac/dks525. Epub 2013 Jan 18.
OBJECTIVES: To determine the mechanisms of resistance to β-lactam antibiotics in clinical isolates of Haemophilus parainfluenzae.METHODS: Twenty clinical isolates of H. parainfluenzae with decreased susceptibility to aminopenicillins were examined and compared with a control group of 20 fully susce
PMID 23335113

Identification of the amino acids conferring high-level resistance to expanded-spectrum cephalosporins in the penA gene from the Neisseria gonorrhoeae strain H041.

Tomberg J, Unemo M, Ohnishi M, Davies C, Nicholas RA.SourceDepartment of Pharmacology, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, USA.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2013 Apr 15. [Epub ahead of print]
The recent identification of a high-level ceftriaxone-resistant (MIC=2-4 μg/ml) isolate of Neisseria gonorrhoeae from Japan (H041) portends the loss of ceftriaxone as an effective treatment for gonococcal infections. This is of grave concern because ceftriaxone is the last remaining option for firs
PMID 23587946

Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles.

Aggarwal R, Kumar S, Kaushik P, Kaushik D, Gupta GK.SourceDepartment of Chemistry, Kurukshetra University, Kurukshetra 136119, India. Electronic address: ranjanaaggarwal67@gmail.com.
European journal of medicinal chemistry.Eur J Med Chem.2013 Apr;62:508-14. doi: 10.1016/j.ejmech.2012.11.046. Epub 2013 Jan 26.
A series of novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles (6) were synthesized by condensing 3-(2-bromoacetyl)coumarins (4) with various 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-thiocarboxamides (5), obtained by the reaction of thiosemicarbazide wit
PMID 23416192

Japanese Journal

A Simple and Rapid Method to Measure Residue of Cefexime – a Cephalosporin Antibiotic in the Wastewater of Pharmaceutical Production Plant

Hue Tran Thi Thanh,Son Doan Cao,Anh Nguyen Thi Lan,Phong Thai Khanh,Hiramatsu Kazuaki
Journal of the Faculty of Agriculture, Kyushu University 59(1), 169-175, 2014-02-29
… A simple and rapid HPLC method was developed to analyse cefixime, and potentially other cephalosporin antibiotic in wastewater of pharmaceutical production industry. … The analytical method was first validated using cefixime– spiked samples. … Absorbance response to cefixime concentrations is linear from 23 to 1100 ppb with a correlation coefficient > … The method was then applied to determine concentrations of cefixime in real wastewater samples. …
NAID 120005411080

主要な血清型の大腸菌を検出する酵素基質培地の開発

北川真喜,市石卓,葛原繁明 [他],江成博
日本臨床微生物学雑誌 = The journal of the Japanese Society for Clinical Microbiology 22(3), 214-220, 2012-09-25
NAID 10031123914

関東地方で分離されたNeisseria gonorrhoeaeの抗菌薬感受性とセファロスポリン感受性の低下

大神田敬,眞野容子,後藤美江子 [他]
文京学院大学保健医療技術学部紀要 5, 1-6, 2012
NAID 40019837282

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Cefixime
Systematic (IUPAC) name
	(6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxy; methoxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-; 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Fixitol, Suprax,Fixbac by RAK Pharma, Triocim(BEXIMCO) Hebixime, Zenicef, Posicef, Cefacef or Eficef
AHFS/Drugs.com	monograph
MedlinePlus	a690007
Pregnancy cat.	B
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Bioavailability	40% to 50%
Protein binding	Approximately 60%
Half-life	Variable; Average 3 to 4 hours
Excretion	Renal and biliary
Identifiers
CAS number	79350-37-1
ATC code	J01DD08
PubChem	CID 5362065
DrugBank	DB00671
ChemSpider	4514923
UNII	97I1C92E55
KEGG	D00258
ChEBI	CHEBI:472657
ChEMBL	CHEMBL1541
Chemical data
Formula	C16H15N5O7S2
Mol. mass	453.452 g/mol
	SMILES O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\OCC(=O)O)/c3nc(sc3)N)C(=O)O;
	InChI InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1 ; Key:OKBVVJOGVLARMR-QSWIMTSFSA-N ;
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英: cefixime
同: CFIX, Suprax
商: セキスパノン、セフィーナ、セフスパン
関: 抗菌薬

[1] "Cefixime Susceptibilty and Resistance Data". Retrieved 22 July 2013.

[2] ttp://www.cks.nhs.uk/gonorrhoea/prescribing_information/prescribing_information/cephalosporins_ceftriaxone_or_cefixime

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