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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/12/30 22:15:44」(JST)

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Cefroxadine (INN, trade names Oraspor and Cefthan-DS) is a cephalosporin antibiotic. It is structurally related to cefalexin, and both drugs share a similar spectrum of activity.^[1]

It is available in Italy.^[2]

Synthesis

Cefroxadine can be prepared by several routes, including one in which the enol is methylated with diazomethane as a key step. A rather more involved route starts with compatively readily available phenoxymethylpenicillin sulfoxide benzhydryl ester (1).

Synthesis of cefroxadine^[3]^[4]

This undergoes fragmentation when treated with benzothiazole-2-thiol to give 2. Ozonolysis (reductive work-up) cleaves the olefinic linkage and the unsymmetrical disulfide moiety is converted to a tosyl thioester (3). The enol moiety is methylated with diazomethane, the six-membered ring is closed by reaction with 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU), and the ester protection is removed with trifluoroacetic acid to give 4. The amide side chain is removed by the usual PCl₅/dimethylaniline sequence followed by reamidation with the appropriate acid chloride to give cefroxadine (5).

References

^ Yasuda K, Kurashige S, Mitsuhashi S (July 1980). "Cefroxadine (CGP-9000), an orally active cephalosporin". Antimicrobial Agents and Chemotherapy. 18 (1): 105–10. PMC 283947 . PMID 6998373.
^ [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.
^ R. Scartazzini, H. Bickel, DE 2331133 ; eidem, U.S. Patent 4,073,902 (1974, 1978 both to Ciba-Geigy).
^ R. B. Woodward and H. Bickel, U.S. Patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).

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1. セフェム系 cephalosporins
2. セファロスポリン-アレルギー患者：セファロスポリンおよび関連抗菌薬のその後の使用 cephalosporin allergic patients subsequent use of cephalosporins and related antibiotics
3. セファロスポリンアレルギー：臨床症状および診断 cephalosporin allergy clinical manifestations and diagnosis
4. Anesthesia for renal transplantation
5. ペニシリン-アレルギー患者：セフェム系、カルバペネム系、およびモノバクタム系の使用 penicillin allergic patients use of cephalosporins carbapenems and monobactams

English Journal

Cephalosporin-induced recurrent aplastic anemia.

Han J, Lee H, Lee YS, Bae YJ, Cho YS, Moon HB, Kim TB.PMID: 20963403 [PubMed - indexed for MEDLINE] PMCID: PMC3043250 Free PMC ArticleImages from this publication.See all images (1)Free text
European journal of clinical pharmacology.Eur J Clin Pharmacol.2011 Mar;67(3):317-8. doi: 10.1007/s00228-010-0913-3. Epub 2010 Oct 12.
PMID 20963403

A specific and rapid HPLC assay for the determination of cefroxadine in human plasma and its application to pharmacokinetic study in Korean.

Kang YS, Lee SY, Kim NH, Choi HM, Park JS, Kim W, Lee HJ.SourceCollege of Pharmacy, Sookmyung Women's University, Chungpa-dong, Yongsan-ku, Seoul 140-742, Republic of Korea.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2006 Feb 13;40(2):369-74. Epub 2005 Aug 30.
A specific and rapid high performance liquid chromatographic (HPLC) method with UV detection (254 nm) was developed for the determination of cefroxadine in human plasma. The sample extraction was performed by a simple procedure, vortexing and centrifugation of sample following addition of 60% trichl
PMID 16137854

[Antibacterial activity of oral cephems against various clinically isolated strains and evaluation of efficacy based on the pharmacokinetics/pharmacodynamics theory].

Nakamura T, Takahashi H.SourceClinical Central Laboratory, Kansai Medical University Hospital, 10-15 Fumizono, Moriguchi, Osaka, 570-8507, Japan.
The Japanese journal of antibiotics.Jpn J Antibiot.2004 Dec;57(6):465-74.
We compared the antimicrobial activity of commercially available oral cephem agents, cefaclor (CCL), cefroxadine (CXD), cefdinir (CFDN), cefixime (CFIX), cefpodoxime (CPDX), cefteram (CFTM), cefcapene (CFPN), and cefditoren (CDTR), against Streptococcus pneumoniae, Haemophilus influenzae, Escherichi
PMID 15747584

Japanese Journal

各種臨床分離株の経口セフェム系薬に対する薬剤感受性とPharmacokinetics/Pharmacodynamics (PK/PD) 理論を用いたその有効性について

中村竜也,高橋伯夫
The Japanese Journal of Antibiotics 57(6), 465-474, 2004
… ら2003年にかけて関西医科大学附属病院にて臨床材料より分離された<I>Streptococcus pneumoniae, Haemophilus influenzae, Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Streptococcus agalactiae, Streptococcus pyogenes</I>およびExtended spectrumβ-lactamase (ESBL) 産生菌について, 現在上市されている経口セフェム系薬cefaclor (CCL), cefroxadine (CXD), cefdinir (CFDN), cefixime (CFIX), cefpodoxime (CPDX), cefteram (CFTM), cefcapene (CFPN), cefditoren (CDTR) の抗菌力を比較した。 …
NAID 130004131052

pH-Dependent Inhibitory Effects of Angiotensin-Converting Enzyme Inhibitors on Cefroxadine Uptake by Rabbit Small Intestinal Brush-Border Membrane Vesicles and Their Relationship with Hydrophobicity and the Ratio of Zwitterionic Species

Kitagawa Shuji,Takeda Junko,Sato Shinji
Biological & pharmaceutical bulletin 22(7), 721-724, 1999-07-15
… The inhibitory effects of five angiotensin-converting enzyme (ACE) inhibitors on the uptake of an aminocephalosporin antibiotic, cefroxadine, by rabbit small intestinal brush-border membrane vesicles were examined in the presence of an inward H^+ gradient. … Dixon plot analysis showed that all these ACE inhibitors inhibited the uptake of cefroxadine, which is transported by a H^+/oligopeptide transporter in the membrane, in the order of enalapril<quinapril, benazepril<temocapril, trandolapril at extravesicular pH 6.0. …
NAID 110003639744

Inhibitory Effects of Angiotensin-Converting Enzyme Inhibitors on Cefroxadine Uptake by Rabbit Small Intestinal Brush Border Membrane Vesicles

Kitagawa Shuji,Takeda Junko,Kaseda Yoshiyuki [他],SATO Shinji
Biological & pharmaceutical bulletin 20(4), 449-451, 1997-04-15
… Effects of angiotensin-converting enzyme (ACE) inhibitors, captopril, enalapril maleate and quinapril, on the uptake of aminocephalosporin antibiotic, cefroxadine, by rabbit small intestinal brush border membrane vesicles were examined. … These ACE inhibitors significantly inhibited the uptake of cefroxadine, which is transported by H^+/dipeptide transporter in the membrane, in the order of captopril<enalapril<quinapril in the presence of an inward H^+ gradient. …
NAID 110003639076

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「セフロキサジン」

Cefroxadine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	J01DB11 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Biological half-life	~1 hour
Excretion	Renal
Identifiers
	IUPAC name (6R,7R)-7-{[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino}-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid;
CAS Number	51762-05-1;
PubChem CID	443991;
ChemSpider	4447587;
UNII	B908C4MV2R;
KEGG	D01528;
ChEMBL	CHEMBL2104150;
ECHA InfoCard	100.052.157
Chemical and physical data
Formula	C16H19N3O5S
Molar mass	365.405 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(/OC)CS[C@@H]1[C@@H]2NC(=O)[C@@H](C/3=C/C\C=C/C\3)N)C(=O)O ;

　　[★]

英: cefroxadine, CXD
ラ: cefroxadinum
商: オラスポア
関: 抗菌薬

[1] Yasuda K, Kurashige S, Mitsuhashi S (July 1980). "Cefroxadine (CGP-9000), an orally active cephalosporin". Antimicrobial Agents and Chemotherapy. 18 (1): 105–10. PMC 283947 . PMID 6998373.

[2] [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.

[3] R. Scartazzini, H. Bickel, DE 2331133 ; eidem, U.S. Patent 4,073,902 (1974, 1978 both to Ciba-Geigy).

[4] R. B. Woodward and H. Bickel, U.S. Patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).

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cefroxadine