Cefradine (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

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

Indications

*Respiratory tract infections (such as

tonsillitis Tonsillitis is inflammation of the tonsils in the upper part of the throat. It can be acute or chronic. Acute tonsillitis typically has a rapid onset. Symptoms may include sore throat, fever, enlargement of the tonsils, trouble swallowing, and en ...

pharyngitis Pharyngitis is inflammation of the back of the throat, known as the pharynx. It typically results in a sore throat and fever. Other symptoms may include a Rhinorrhea, runny nose, cough, headache, difficulty swallowing, swollen lymph nodes, and a ...

, and

lobar pneumonia Lobar pneumonia is a form of pneumonia characterized by inflammatory exudate within the intra-alveolar space resulting in consolidation that affects a large and continuous area of the lobe of a lung. It is one of three anatomic classifications ...

) 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.

Cefuroxime Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract inf ...

is generally effective in the eradication of streptococci from the nasopharynx *Otitis media caused by group A beta-hemolytic streptococci, ''S. pneumoniae'', ''H. influenzae'', and

staphylococci ''Staphylococcus'' is a genus of Gram-positive bacteria in the family Staphylococcaceae from the order Bacillales. Under the microscope, they appear spherical ( cocci), and form in grape-like clusters. ''Staphylococcus'' species are facultati ...

. *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 ''Klebsiella'' is a genus of Gram-negative, oxidase-negative, rod-shaped bacteria with a prominent polysaccharide-based capsule. ''Klebsiella'' species are found everywhere in nature. This is thought to be due to distinct sublineages developi ...

'' 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 The Birch reduction is an organic reaction that is used to convert arenes to cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally ...

of D-α-

phenylglycine Phenylglycine is the organic compound with the formula C6H5CH(NH2)CO2H. It is a non-proteinogenic alpha amino acid related to alanine, but with a phenyl group in place of the methyl group. It is a white solid. The compound exhibits some biolog ...

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). Cefradine synthesis

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, 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 * The 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 Cefradine is known as Cefradina in Portuguese and Spanish and is produced by the following companies under this name: AC Farma, Peru; Andromaco, Chile; Anglopharma, Colombia; AZ Pharma, Colombia; Biogalenic, Venezuela; Bussié, Colombia; Elter - Medicamentos Genéricos, Venezuela; Farmindustria, Peru; Genfar, Colombia, Honduras and Peru; La Sante, Peru; La Santé, Colombia; Labesfal, Portugal; Lafrancol, Colombia; LCG, Peru; Marfan, Peru; Memphis, Colombia; Mintlab, Chile; MK, Colombia; Ophalac, Colombia; Procaps, Colombia and Vitalis, Colombia and Peru.

Notes

References