Cefradine is distributed in the form of capsules containing 250 mg or 500 mg, as a syrup containing 250 mg/5 ml, or in vials for injection containing 500 mg or 1 g.[citation needed]
It is not approved by the FDA for use in the United States.[citation needed]
Synthesisedit
Birch reduction of D-α-phenylglycine led to diene (2). This was N-protected using tert-butoxycarbonylazide and activated for amide formation via the mixed anhydride method using isobutylchloroformate to give 3. Mixed anhydride 3 reacted readily with 7-aminodesacetoxycephalosporanic acid to give, after deblocking, cephradine (5).
^Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefuroxime is generally effective in the eradication of streptococci from the nasopharynx
Referencesedit
^British National Formulary (45 ed.). London: British Medical Association. 2003.
^Dolfini JE, Applegate HE, Bach G, Basch H, Bernstein J, Schwartz J, Weisenborn FL (February 1971). "A new class of semisynthetic penicillins and cephalosporins derived from D-2-(1,4-cyclohexadienyl)glycine". Journal of Medicinal Chemistry. 14 (2): 117–9. doi:10.1021/jm00284a008. PMID 5544394.
^DE 1931722, Weisenborn, Frank L.; Dolfini, Joseph E. & Bach, Georges G. et al., "α-Amino-cyclohexadienyl-alkylen-penicilline und -cephalosporine, ihre Salze, und Verfahren zu ihrer Herstellung [Alpha-amino-cyclohexadienyl-alkylene-penicillins and cephalosporins, their salts, and processes for their preparation]", published 1970-01-08, assigned to E. R. Squibb & Sons Inc.
cefradine, cephradine, first, generation, cephalosporin, antibiotic, clinical, datatrade, namesintracef, velocefahfs, drugs, cominternational, drug, namesmedlineplusa601206routes, ofadministrationoral, ivatc, codej01db09, legal, statuslegal, statusin, general,. Cefradine INN or cephradine BAN is a first generation cephalosporin antibiotic 1 CefradineClinical dataTrade namesIntracef VelocefAHFS Drugs comInternational Drug NamesMedlinePlusa601206Routes ofadministrationOral IM IVATC codeJ01DB09 WHO Legal statusLegal statusIn general Prescription only Pharmacokinetic dataBioavailabilityWell absorbedProtein binding lt 10 MetabolismNilElimination half life0 9 hoursExcretionRenal unchangedIdentifiersIUPAC 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 acidCAS Number38821 53 3 YPubChem CID38103IUPHAR BPS4830DrugBankDB01333 YChemSpider34933 YUNII9YA6SX5S4DKEGGD00264 YChEBICHEBI 3547 YChEMBLChEMBL1604 YCompTox Dashboard EPA DTXSID4022785ECHA InfoCard100 049 199Chemical and physical dataFormulaC 16H 19N 3O 4SMolar mass349 41 g mol 13D model JSmol Interactive imageMelting point140 to 142 C 284 to 288 F dec 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 OInChI 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 YKey RDLPVSKMFDYCOR UEKVPHQBSA N Y verify Contents 1 Indications 2 Formulations 3 Synthesis 4 Production names 5 See also 6 Notes 7 ReferencesIndications editRespiratory tract infections such as tonsillitis pharyngitis and lobar pneumonia caused by group A beta hemolytic streptococci and S pneumoniae formerly D pneumonia note 1 Otitis media caused by group A beta hemolytic streptococci S 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 and Klebsiella species Formulations editCefradine is distributed in the form of capsules containing 250 mg or 500 mg as a syrup containing 250 mg 5 ml or in vials for injection containing 500 mg or 1 g citation needed It is not approved by the FDA for use in the United States citation needed Synthesis editBirch reduction of D a phenylglycine led to diene 2 This was N protected using tert butoxycarbonylazide and activated for amide formation via the mixed anhydride method using isobutylchloroformate to give 3 Mixed anhydride 3 reacted readily with 7 aminodesacetoxycephalosporanic acid to give after deblocking cephradine 5 nbsp Cefradin synthesis 2 3 4 Production names editThe antibiotic is produced under many brand names across the world 5 nbsp Bangladesh Ancef Ancef forte Aphrin Avlosef Cefadin Cephadin Cephran Cephran DS Cusef Cusef DS Dicef Dicef forte Dolocef Efrad Elocef Extracef Extracef DS Intracef Kefdrin Lebac Lebac Forte Medicef Mega Cef Megacin Polycef Procef Procef Procef forte Rocef Rocef Forte DS Sefin Sefin DS Sefnin Sefrad Sefrad DS Sefril Sefril DS Sefro Sefro HS Sephar Sephar DS Septa Sinaceph SK Cef Sk Cef DS Supracef and Supracef F Torped Ultrasef Vecef Vecef DS Velogen Sinaceph Velox nbsp China Cefradine Cephradine Kebili Saifuding Shen You Taididing Velosef Xianyi and Xindadelei nbsp Colombia Cefagram Cefrakov Cefranil Cefrex and Kliacef nbsp Egypt Cefadrin Cefadrine Cephradine Cephraforte Farcosef Fortecef Mepadrin Ultracef and Velosef nbsp France Dexef nbsp Hong Kong Cefradine and ChinaQualisef 250 nbsp Indonesia Dynacef Velodine and Velodrom nbsp Lebanon Eskacef Julphacef and Velosef nbsp Lithuania Tafril nbsp Myanmar Sinaceph nbsp Oman Ceframed Eskasef Omadine and Velocef nbsp Pakistan Abidine Ada Cef Ag cef Aksosef Amspor Anasef Antimic Atcosef Bactocef Biocef Biodine Velora Velosef nbsp Peru Abiocef Cefradinal Cefradur Cefrid Terbodina II Velocef Velomicin nbsp Philippines Altozef Racep Senadex Solphride Yudinef Zefadin Zefradil and Zolicef nbsp Poland Tafril nbsp Portugal Cefalmin Cefradur nbsp South Africa Cefril A nbsp South Korea Cefradine and Tricef nbsp Taiwan Cefadin Cefamid Cefin Cekodin Cephradine Ceponin Lacef Licef A Lisacef Lofadine Recef S 60 Sefree Sephros Topcef Tydine Unifradine and U Save nbsp UK Cefradune Kent nbsp Vietnam Eurosefro and IncefSee also editCephapirin Cephacetrile Cefamandole Ampicillin Has the same chemical formula Notes edit Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections including the prophylaxis of rheumatic fever Cefuroxime is generally effective in the eradication of streptococci from the nasopharynxReferences edit British National Formulary 45 ed London British Medical Association 2003 Dolfini JE Applegate HE Bach G Basch H Bernstein J Schwartz J Weisenborn FL February 1971 A new class of semisynthetic penicillins and cephalosporins derived from D 2 1 4 cyclohexadienyl glycine Journal of Medicinal Chemistry 14 2 117 9 doi 10 1021 jm00284a008 PMID 5544394 U S patent 3 485 819 DE 1931722 Weisenborn Frank L Dolfini Joseph E amp Bach Georges G et al a Amino cyclohexadienyl alkylen penicilline und cephalosporine ihre Salze und Verfahren zu ihrer Herstellung Alpha amino cyclohexadienyl alkylene penicillins and cephalosporins their salts and processes for their preparation published 1970 01 08 assigned to E R Squibb amp Sons Inc Cefradine Retrieved 5 May 2016 Retrieved from https en wikipedia org w index php title Cefradine amp oldid 1179953645, wikipedia, wiki, book, books, library,
