Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/25 07:40:32」(JST)

wiki en

Cefradine (INN) (formerly cephradine BAN) is a first generation cephalosporin antibiotic.

Indications

It has similar spectrum of activity to cefalexin. RESPIRATORY TRACT INFECTIONS (e.g., tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia). (Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Velosef is generally effective in the eradication of streptococci from the nasopharynx; substantial data establishing the efficacy of Velosef in the subsequent prevention of rheumatic fever are not available at present.) OTITIS MEDIA caused by group A beta-hemolytic streptococci, S. pneumoniae (formerly D. pneumoniae), H. influenzae, and staphylococci. SKIN AND SKIN STRUCTURE INFECTIONS caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. URINARY TRACT INFECTIONS, including prostatitis, caused by E. coli, P. mirabilis, Klebsiella species, and enterococci (S. faecalis). The high concentrations of cephradine achievable in the urinary tract will be effective against many strains of enterococci for which disc susceptibility studies indicate relative resistance. It is to be noted that among beta-lactam antibiotics, ampicillin is the drug of choice for enterococcal urinary tract (E. faecalis) infection.

Formulations

Capsules containing 250 mg or 500 mg, Syrup containing 250 mg/5 ml, or vials for injection containing 500 mg or 1 g.

Brand Names

International Brands Velocef, Infexin (by Merck Pvt, Ltd) Intracef (by Beximco Pharma) SEFRIL(The ACME laboratories Ltd., Bangladesh), REOCEF(Rephco Pharmaceuticals Ltd., Bangladesh). Lebac (by Square pharmaceuticals Ltd., Bangladesh).^{[promotional language]}

Synthesis

Noting that 1,4-cyclohexadiene rings are nearly as planar as benzene rings but of greatly different reactivity, a cephalosporin was synthesized with such a moiety.

Cefradin synthesis:^[1] U.S. Patent 3,485,819 DE 1931722

Birch reduction of D-α-phenylglycine led to diene (2). This was N-protected using tert-Butoxycarbonylazide and activated for amide fromation via the mixed anhydride method using isobutylchloroformate to give 3. Mixed anhydride 3 reacted readily with 7-Aminodesacetoxycephalosporanic acid to give, after deblocking, cephadrine (5).

References

^ doi:10.1021/jm00284a008
This citation will be automatically completed in the next few minutes. You can jump the queue or expand by hand

British National Formulary 45 March 2003

This systemic antibacterial-related article is a stub. You can help Wikipedia by expanding it.

English Journal

A medusa-like β-cyclodextrin with 1-methyl-2-(2'-carboxyethyl) maleic anhydrides, a potential carrier for pH-sensitive drug delivery.

Kang S1, Park E, Kim Y, Lee S, Kwon J, Cho H, Lee Y.
Journal of drug targeting.J Drug Target.2014 Aug;22(7):658-68. doi: 10.3109/1061186X.2014.928718. Epub 2014 Jun 23.
We developed a new pH-sensitive drug delivery carrier based on β-cyclodextrin (β-CD) and 1-methyl-2-(2'-carboxyethyl) maleic anhydrides (MCM). The primary hydroxyl groups of β-CD were successfully attached to MCM residues to produce a medusa-like β-CD-MCM. The MCM residue was conjugated with cep
PMID 24955615

Isolation and antibiotic susceptibility of E. coli from urinary tract infections in a tertiary care hospital.

Sabir S1, Ahmad Anjum A2, Ijaz T3, Asad Ali M4, Ur Rehman Khan M5, Nawaz M6.
Pakistan journal of medical sciences.Pak J Med Sci.2014 Mar;30(2):389-92.
OBJECTIVE: The study was conducted to isolate and determine the antibiotic resistance in E. coli from urinary tract infections in a tertiary care hospital, Lahore.METHODS: Urine samples (n=500) were collected from patients with signs and symptoms of Urinary tract infections. Bacteria were isolated a
PMID 24772149

32 years' experience of peritoneal dialysis-related peritonitis in a university hospital.

van Esch S1, Krediet RT, Struijk DG.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis.Perit Dial Int.2014 Mar-Apr;34(2):162-70. doi: 10.3747/pdi.2013.00275. Epub 2014 Mar 1.
BACKGROUND: Peritonitis in peritoneal dialysis (PD) patients can lead to technique failure and contributes to infection-related mortality. Peritonitis prevention and optimization of treatment are therefore important in the care for PD patients. In the present study, we analyzed the incidence of peri
PMID 24584620

Japanese Journal

成人で多数の多核巨細胞の出現をみた薬剤性肝炎の1例

福井実,杉村巌,成沢恒男,関谷千尋,並木正義
肝臓 26(4), 500-505, 1985
… 薬剤によって多数の多核巨細胞の出現をみた肝炎の1例を経験した.症例は62歳の主婦.cefradine, ibuprofenを8日間服用後,嘔気・黄疸が出現.肝腫大と肝機能異常が認められ,急性肝炎の疑いで入院.第14病日の腹腔鏡下肝生検で多核巨細胞化した肝細胞を多数認めた.輸血歴,飲酒歴はなく,HAV, HBV, EBVの感染は血清学的検査により否定された.CMVのLA (Late Antigen)抗体の有意な変動,尿からのCMVの分離などでCMV感染は認められたが,CMV-Lymphocyt …
NAID 130000880575

Physicochemical Properties of Amphoteric β-Lactam Antibiotics. III. Stability, Solubility, and Dissolution Behavior of Cefatrizine and Cefadroxil as a Function of pH

辻彰,中島恵美,西出和憲,出口芳春,浜野正一郎,山名月中
Chemical & pharmaceutical bulletin 31(11), 4057-4069, 1983-11-25
… The intramolecular reaction rate was very similar to that of cephaloglycin, but ten times faster than those for cefadroxil, cephalexin, and cefradine under the same conditions. …
NAID 110003624151

Related Pictures

★リンクテーブル★

リンク元

「セフラジン」

Cefradine
Systematic (IUPAC) name
	(6R,7R)-7-{[(2R)-2-amino-2-(1-cyclohexa-1,4-; dienyl)acetyl]amino}-3-methyl-8-oxo-5-thia-; 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Intracef, Velocef
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Legal status	℞ (Prescription only);
Routes of; administration	Oral, IM, IV
Pharmacokinetic data
Bioavailability	Well absorbed
Protein binding	<10%
Metabolism	Nil
Biological half-life	0.9 hours
Excretion	Renal, unchanged
Identifiers
CAS Registry Number	38821-53-3
ATC code	J01DB09
PubChem	CID: 38103
IUPHAR/BPS	4830
DrugBank	DB01333
ChemSpider	34933
UNII	9YA6SX5S4D
KEGG	D00264
ChEBI	CHEBI:3547
ChEMBL	CHEMBL1604
Chemical data
Formula	C16H19N3O4S
Molecular mass	349.406 g/mol
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](C/3=C/C\C=C/C\3)N)C)C(=O)O ;
	InChI InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1 ; Key:RDLPVSKMFDYCOR-UEKVPHQBSA-N ;
(what is this?) (verify)

　　[★]

英: cephradine、cefradine, CED
関: 抗菌薬

[1] :10.1021/jm00284a008
This citation will be automatically completed in the next few minutes. You can jump the queue or expand by hand

匿名

検索

案内

案内

cefradine