関: cefapirin、cefapirin sodium

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/21 23:15:46」(JST)

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Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.^[1]

It also has a role in veterinary medicine as Metricure, an intrauterine preparation, and combined with prednisolone in Mastiplan, an intramammary preparation. Both are licenced in cattle.

Synthesis

Cephapirin synthesis:^[2] U.S. Patent 3,422,100 U.S. Patent 3,503,967 U.S. Patent 3,578,661

In one of the syntheses, 7-aminocephalosporanic acid (7-ACA) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine.^[2]

References

^ http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL
^ ^a ^b Crast, L. B.; Graham, R. G.; Cheney, L. C. (1973). "Synthesis of cephapirin and related cephalosporins from 7-(.alpha.-bromoacetamido)cephalosporanic acid". Journal of Medicinal Chemistry 16 (12): 1413. doi:10.1021/jm00270a025.

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1. セフェム系 cephalosporins

English Journal

Elimination kinetics of cephapirin sodium in milk after an 8-day extended therapy program of daily intramammary infusion in healthy lactating Holstein-Friesian cows.

Gorden PJ, van der List M, Lehman FD, Lantz RK, Constable PD.SourceDepartment of Veterinary Diagnostic and Production Animal Medicine, Iowa State University, Ames 50011-1250.
Journal of dairy science.J Dairy Sci.2013 May 15. pii: S0022-0302(13)00375-5. doi: 10.3168/jds.2012-6487. [Epub ahead of print]
The objective of this study was to determine the elimination kinetics of extended therapy with intramammary (IMM) cephapirin in lactating dairy cattle. Eight healthy Holstein-Friesian cows were administered cephapirin (200 mg) into all 4 mammary glands every 24 h after milking. Cows were milked 3 ti
PMID 23684021

Minimum inhibitory concentrations of cephalosporin compounds and their active metabolites for selected mastitis pathogens.

Cortinhas CS, Oliveira L, Hulland CA, Santos MV, Ruegg PL.SourceDepartment of Animal Nutrition and Production, School of Veterinary Medicine, University of São Paulo, Pirassununga, SP-17 13635-900, Brazil.
American journal of veterinary research.Am J Vet Res.2013 May;74(5):683-90. doi: 10.2460/ajvr.74.5.683.
Objective-To compare the minimum inhibitory concentration (MIC) of cephapirin and ceftiofur with MICs of their active metabolites (desacetylcephapirin and desfuroylceftiofur) for selected mastitis pathogens. Sample-488 mastitis pathogen isolates from clinically and subclinically affected cows in com
PMID 23627380

Clinical trial of treatment programs for purulent vaginal discharge in lactating dairy cattle in New Zealand.

McDougall S, de Boer M, Compton C, Leblanc SJ.SourceCognosco, Anexa Animal Health, Morrinsville, New Zealand. Electronic address: smcdougall@anexa.co.nz.
Theriogenology.Theriogenology.2013 May;79(8):1139-45. doi: 10.1016/j.theriogenology.2013.02.002. Epub 2013 Mar 15.
Studies of treatment of postpartum endometritis in dairy cows indicate that prostaglandin (PGF2α) might result in similar outcomes as intrauterine antibiotics, but the effect might depend on the presence of a CL. The objective was to compare reproductive performance in cows with purulent vaginal di
PMID 23499414

Japanese Journal

ENHANCED RECTAL ABSORPTION OF β-LACTAM ANTIBIOTICS IN RAT BY MONODESMOSIDES ISOLATED FROM PERICARPS OF SAPINDUS MUKUROSSI (ENMEI-HI)

YATA NOBORU,SUGIHARA NARUMI,YAMAJO RYOKO,MURAKAMI TERUO,HIGASHI YUTAKA,KIMATA HIROKO,NAKAYAMA KEISO,KUZUKI TATSUO,TANAKA OSAMU
Journal of pharmacobio-dynamics 8(12), 1041-1047, 1985-12
Monodesmosides, saponin A, B and C, isolated from pericarps of Sapindus mukurossi(Enmei-hi) were shown to promote the rectal absorption of β-lactam antibiotics in rat, using an in situ loop method and …
NAID 110003637881

EPILEPTOGENIC ACTIVITY INDUCED BY INTRAVENOUS INJECTION OF CERTAIN CEPHALOSPORINS IN RATS

HAIYU QUING,KITAZUMI KAZUHIRO,KAMEI CHIAKI,TASAKA KENJI
Journal of pharmacobio-dynamics 7(8), 586-592, 1984-08
… On the other hand, cephapirin, cefmetazole and cefoxitin did not evoke any changes in EEG nor in behavior. …
NAID 110003637794

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リンク元	「セファピリン」「cefapirin sodium」「cefapirin」

「セファピリン」

Cefapirin
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Pregnancy; category	US: B (No risk in non-human studies);
Legal status	US: ℞-only;
Routes of; administration	Intravenous, intramuscular
Identifiers
CAS Registry Number	21593-23-7
ATC code	J01DB08 QG51AA05 QJ51DB08
PubChem	CID: 30699
DrugBank	DB01139
ChemSpider	28486
UNII	89B59H32VN
KEGG	D07636
ChEBI	CHEBI:554446
ChEMBL	CHEMBL1599
Chemical data
Formula	C17H17N3O6S2
Molecular mass	423.466 g/mol
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O ;
	InChI InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 ; Key:UQLLWWBDSUHNEB-CZUORRHYSA-N ;
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