Cefradine

Cefradine
Clinical data
Trade namesIntracef, Velocef
AHFS/Drugs.comInternational Drug Names
MedlinePlusa601206
Routes of
administration		Oral, IM, IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityWell absorbed
Protein binding<10%
MetabolismNil
Elimination half-life0.9 hours
ExcretionRenal, 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 InfoCard100.049.199 Edit this at Wikidata
Chemical and physical data
FormulaC16H19N3O4S
Molar mass349.41 g·mol−1
3D model (JSmol)
Melting point140 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 checkY
  • Key:RDLPVSKMFDYCOR-UEKVPHQBSA-N checkY
  (verify)

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

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:

Production names

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

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. ↑ 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.