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 =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

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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

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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).

File:Cefazaflur synthesis.svg

Cefazaflur is synthesized by reaction of 3-(1-methyl-1H-tetrazol-5-ylthiomethylene)-7-amino-cephem-4-carboxylic acid (1) with trifluoromethylthioacetyl chloride (2).

References