Cefteram

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (6R,7R)-7-([(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino)-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

| image = Cefteram.svg

| tradename =

| Drugs.com = {{drugs.com|international|cefteram}}

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Rx-only

| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number = 82547-58-8

| ATC_prefix = J01

| ATC_suffix = DD18

| ATC_supplemental =

| PubChem = 6537431

| DrugBank =

| ChEMBL = 2105953

| ChemSpiderID = 4576594

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 74CQ4Q3N63

| KEGG = D07655

| chemical_formula =

| C=16 | H=17 | N=9 | O=5 | S=2

| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)Cn4nc(nn4)C)C(=O)O

}}

Cefteram (INN) is a third-generation cephalosporin antibiotic.{{cite journal | vauthors = Yamaguchi K, Ohno A, Takahashi S, Hayashi M, Yamanaka K, Hirakata Y, Mitsuyama J | title = [In vitro antibacterial activities of cefteram and other beta-lactam agents against recent clinical isolates] | journal = The Japanese Journal of Antibiotics | volume = 51 | issue = 1 | pages = 11–25 | date = January 1998 | pmid = 9557273 }}

Synthesis

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The reaction of 7-aminocephalosporanic acid (1) with the methyl-substituted tetrazole (2) gives the intermediate (3). Protection with diazodiphenylmethane (4) produces (5). Amide formation with the thiazole carboxylic acid (6) gives (7), which is deprotected with trifluoroacetic acid to yield cefteram.{{cite web |url=https://www.chemdrug.com/article/8/3284/16419968.html |title=Cefteram |website=chemdrug.com |access-date=2024-07-03}}{{cite patent |country=US |number=4489072 |inventor=Hiroshi Sadaki, et al. |status=patent |gdate=1984-12-18 |fdate=1981-09-23 |pridate=1980-09-25 |assign1=Toyama Chemical Co Ltd}}

References

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{{CephalosporinAntiBiotics}}

Category:Cephalosporin antibiotics

Category:Thiazoles

Category:Tetrazoles

Category:Ketoxime ethers

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