Cefradine

Cefradine
Clinical data
Trade names Intracef, Velocef
AHFS/Drugs.com International Drug Names
MedlinePlus a601206
Routes of
administration		 Oral, IM, IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability Well absorbed
Protein binding <10%
Metabolism Nil
Biological half-life 0.9 hours
Excretion Renal, unchanged
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.049.199
Chemical and physical data
Formula C16H19N3O4S
Molar mass 349.406 g/mol
3D model (JSmol)
  (verify)

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

Indications

Cefradine has similar spectrum of activity to cefalexin. It is used in the following instances:

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.

Production Names

The antibiotic is produced under a wide number of brand names across the world.[2]

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.

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

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:[3] 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 formation 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).

See also

Notes

  1. ↑ 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

References

  1. ↑ British National Formulary (45 ed.). London: British Medical Association. 2003.
  2. ↑ {cite web|url=http://www.drugs.com/international/cefradine.html%7Ctitle=Cefradine%7Caccess-date=5 May 2016}
  3. ↑ Dolfini, Joseph E.; Applegate, Harold E.; Bach, Georges; Basch, Harold; Bernstein, Jack; Schwartz, Joseph; Weisenborn, Frank L. (1971). "New class of semisynthetic penicillins and cephalosporins derived from D-2-(1,4-cyclohexadienyl)glycine". Journal of Medicinal Chemistry. 14 (2): 117. PMID 5544394. doi:10.1021/jm00284a008.
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