Flurithromycin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444405791

| IUPAC_name = (3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-
[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-
6-methyloxan-2-yl]oxy-14-ethyl-9-fluoro-7,12,
13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-
4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,
11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

| image = Flurithromycin.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 82664-20-8

| ATC_prefix = J01

| ATC_suffix = FA14

| PubChem = 71260

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64388

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 131719

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2106403

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

| UNII = 56C9DTE69V

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07242

| C=37 | H=66 | F=1 | N=1 | O=13

| smiles = O=C3O[C@H](CC)[C@](O)(C)[C@H](O)[C@H](C(=O)[C@](F)(C)C[C@](O)(C)[C@H](O[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O)[C@H]([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H]3C)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C37H66FNO13/c1-14-24-37(10,46)29(42)21(5)28(41)34(7,38)17-35(8,45)31(52-33-26(40)23(39(11)12)15-18(2)48-33)19(3)27(20(4)32(44)50-24)51-25-16-36(9,47-13)30(43)22(6)49-25/h18-27,29-31,33,40,42-43,45-46H,14-17H2,1-13H3/t18-,19+,20-,21+,22+,23+,24-,25+,26-,27+,29-,30+,31-,33+,34+,35-,36-,37-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XOEUHCONYHZURQ-HNUBZJOYSA-N

}}

Flurithromycin is a second generation macrolide antibiotic. It is a fluorinated derivative of erythromycin A.{{cite journal | vauthors = Gialdroni Grassi G, Alesina R, Bersani C, Ferrara A, Fietta A, Peona V | title = In vitro activity of flurithromycin, a novel macrolide antibiotic | journal = Chemioterapia | volume = 5 | issue = 3 | pages = 177–184 | date = June 1986 | pmid = 3487389 | doi = }} It is a broad spectrum antibiotic with similar bactericidal action to erythromycin. Unlike erythromycin, flurithromycin is more tolerant of acidic environments, meaning more survives the digestion process, resulting in higher serum levels, and more efficacious elimination of susceptible bacteria, including staphylococcus aureus and streptococcus pyogenes.{{cite book | vauthors = Kaneko T, Dougherty TJ, Magee TV | chapter = 7.18 - Macrolide Antibiotics |date= January 2007 | title = Comprehensive Medicinal Chemistry II |pages=519–566 | veditors = Taylor JB, Triggle DJ |place=Oxford |publisher=Elsevier |language=en |doi=10.1016/b0-08-045044-x/00219-4 |isbn=978-0-08-045044-5 }}