Cefradine

Last updated
Cefradine
Cefradine.svg
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
Elimination half-life 0.9 hours
Excretion Renal, unchanged
Identifiers
  • (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 acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.049.199 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H19N3O4S
Molar mass 349.41 g·mol−1
3D model (JSmol)
Melting point 140 to 142 °C (284 to 288 °F) (dec.)
  • 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)O
  • 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 Yes check.svgY
  • Key:RDLPVSKMFDYCOR-UEKVPHQBSA-N Yes check.svgY
   (verify)

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

Contents

Indications

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.[ citation needed ]

It is not approved by the FDA for use in the United States.[ citation needed ]

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).

Cefradin synthesis: Cefradine synthesis.svg
Cefradin synthesis:

Production names

The antibiotic is produced under many brand names across the world. [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

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References

  1. British National Formulary (45 ed.). London: British Medical Association. 2003.
  2. 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.
  3. U.S. Patent 3,485,819
  4. 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.
  5. "Cefradine" . Retrieved 5 May 2016.