Cefradine Explained

Cefradine (INN) or cephradine (BAN) is a first generation cephalosporin antibiotic.^[1]

Indications

Respiratory tract infections (such as tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia).^[2]
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.^[3]

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