Cefradine

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

Indications

 * Respiratory tract infections (such as tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia).
 * 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
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.

It is not approved by the FDA for use in the United States.

Synthesis
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).



Production names
The antibiotic is produced under many brand names across the world.
 * 🇧🇩 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
 * 🇨🇳 China: Cefradine, Cephradine, Kebili, Saifuding, Shen You, Taididing, Velosef, Xianyi, and Xindadelei
 * 🇨🇴 Colombia: Cefagram, Cefrakov, Cefranil, Cefrex, and Kliacef
 * 🇪🇬 Egypt: Cefadrin, Cefadrine, Cephradine, Cephraforte, Farcosef, Fortecef, Mepadrin, Ultracef, and Velosef
 * 🇫🇷 France: Dexef
 * 🇭🇰 Hong Kong: Cefradine and ChinaQualisef-250
 * 🇮🇩 Indonesia: Dynacef, Velodine, and Velodrom
 * 🇱🇧 Lebanon: Eskacef, Julphacef, and Velosef
 * 🇱🇹 Lithuania: Tafril
 * 🇲🇲 Myanmar: Sinaceph
 * 🇴🇲 Oman: Ceframed, Eskasef, Omadine, and Velocef
 * 🇵🇰 Pakistan: Abidine, Ada-Cef, Ag-cef, Aksosef, Amspor, Anasef, Antimic, Atcosef, Bactocef, Biocef, Biodine, Velora, Velosef
 * 🇵🇪 Peru: Abiocef, Cefradinal, Cefradur, Cefrid, Terbodina II, Velocef, Velomicin
 * 🇵🇭 Philippines: Altozef, Racep, Senadex, Solphride, Yudinef, Zefadin, Zefradil, and Zolicef
 * 🇵🇱 Poland: Tafril
 * 🇵🇹 Portugal: Cefalmin, Cefradur
 * 🇿🇦 South Africa: Cefril A
 * 🇰🇷 South Korea: Cefradine and Tricef
 * 🇹🇼 Taiwan: Cefadin, Cefamid, Cefin, Cekodin, Cephradine, Ceponin, Lacef, Licef-A, Lisacef, Lofadine, Recef, S-60, Sefree, Sephros, Topcef, Tydine, Unifradine, and U-Save
 * 🇬🇧 UK: Cefradune (Kent)
 * Vietnam: Eurosefro and Incef