cefazaflur
{{Short description|Cephalosporin antibiotic}}
{{Drugbox
| verifiedrevid = 443772283
| IUPAC_name = (6R,7R)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-([2-(trifluoromethylsulfanyl)acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
| image = Cefazaflur.png
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
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| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
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| index2_label = Sodium
| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 52123-49-6
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 8NJ5RWV39D
| CAS_number = 58665-96-6
| ATC_prefix = none
| ATC_suffix =
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChEMBL = 2104456
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 97I0692RNT
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03422
| PubChem = 40240
| ChemSpiderID = 36777
| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSC(F)(F)F)CSc3nnnn3C)C(=O)O
| StdInChI = 1S/C13H13F3N6O4S3/c1-21-12(18-19-20-21)28-3-5-2-27-10-7(9(24)22(10)8(5)11(25)26)17-6(23)4-29-13(14,15)16/h7,10H,2-4H2,1H3,(H,17,23)(H,25,26)/t7-,10-/m1/s1
| StdInChIKey = HGXLJRWXCXSEJO-GMSGAONNSA-N
| chemical_formula =
| C=13 | H=13 | F=3 | N=6 | O=4 | S=3
}}
Cefazaflur (INN) is a first-generation cephalosporin antibiotic.
Synthesis
Cefazaflur stands out among this group of analogues because it lacks an arylamide C-7 side chain (see cephacetrile for another example).
Cefazaflur is synthesized by reaction of 3-(1-methyl-1H-tetrazol-5-ylthiomethylene)-7-amino-cephem-4-carboxylic acid (1) with trifluoromethylthioacetyl chloride (2).