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{{Short description|Cephalosporin antibiotic}} |
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{{drugbox |
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{{Drugbox |
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| verifiedrevid = 443772283 |
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| IUPAC_name = (6''R'',7''R'')-3--8-oxo-7-(amino)-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid |
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| image = Cefazaflur.png |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| index2_label = Sodium |
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| CAS_number2_Ref = {{cascite|correct|CAS}} |
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| CAS_number2 = 52123-49-6 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 8NJ5RWV39D |
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| CAS_number = 58665-96-6 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_supplemental = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChEMBL = 2104456 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 97I0692RNT |
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| UNII = 97I0692RNT |
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| verifiedrevid = 437173695 |
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| ⚫ |
| IUPAC_name = (6R,7R)-3--8-oxo-7-(amino)-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid |
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| image = Cefazaflur.png |
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| CAS_number = 52123-49-6 |
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| CAS_supplemental = |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_supplemental = |
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| PubChem = 23702658 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D03422 |
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| KEGG = D03422 |
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| PubChem = 40240 |
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| chemical_formula = |
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| ChemSpiderID = 36777 |
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| C=13 | H=12 | F=3 | N=6 | Na=1 | O=4 | S=3 |
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| smiles = O=C2N1/C(=C(\CS12NC(=O)CSC(F)(F)F)CSc3nnnn3C)C(=O)O |
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| molecular_weight = 492.45 g/mol |
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| 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 |
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| smiles = CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)CSC(F)(F)F)SC2)C(=O). |
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| StdInChIKey = HGXLJRWXCXSEJO-GMSGAONNSA-N |
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| bioavailability = |
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<!--Chemical data--> |
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| protein_bound = |
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| chemical_formula = |
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| metabolism = |
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| C=13 | H=13 | F=3 | N=6 | O=4 | S=3 |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| ⚫ |
| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| ⚫ |
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| ⚫ |
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| ⚫ |
| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Cefazaflur''' (]) is a first-generation ] antibiotic. |
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'''Cefazaflur''' (]) is a first-generation ] antibiotic. |
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== Synthesis == |
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Cefazaflur stands out among this group of analogues because it lacks an arylamide C-7 side chain (see ] for another example). |
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acetic acid and their sulfoxides and sulfones | journal = Journal of Medicinal Chemistry | volume = 20 | issue = 1 | pages = 30–5 | date = January 1977 | pmid = 319233 | doi = 10.1021/jm00211a006 }}</ref>]] |
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Cefazaflur is synthesized by reaction of 3-(1-methyl-1<u>H</u>-tetrazol-5-ylthiomethylene)-7-amino-cephem-4-carboxylic acid ('''1''') with trifluoromethylthioacetyl chloride ('''2'''). |
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== References == |
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{{reflist}} |
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{{antibiotic-stub}} |
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{{antibiotic-stub}} |
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{{CephalosporinAntiBiotics}} |
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{{CephalosporinAntiBiotics}} |
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] |
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] |
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] |
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] |