View source for Chemistry:Flurithromycin

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444405791
| IUPAC_name = (3''R'',4''S'',5''S'',6''R'',7''R'',9''S'',11''R'',12''R'',13''S'',14''R'')-6-<br>[(2''S'',3''R'',4''S'',6''R'')-4-dimethylamino-3-hydroxy-<br>6-methyloxan-2-yl]oxy-14-ethyl-9-fluoro-7,12,<br>13-trihydroxy-4-[(2''R'',4''R'',5''S'',6''S'')-5-hydroxy-<br>4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,<br>11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
| image = Flurithromycin.svg

<!--Clinical data-->
| tradename = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!--Identifiers-->
| 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

<!--Chemical data-->
| 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 [[Chemistry:Macrolide|macrolide]] antibiotic. It is a [[Chemistry:Fluorine|fluorinated]] derivative of [[Chemistry:Erythromycin|erythromycin]] A.<ref name="pmid3487389">{{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 =  }}</ref> 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 [[Medicine:Staphylococcus aureus|staphylococcus aureus]] and [[Biology:Streptococcus pyogenes|streptococcus pyogenes]].<ref>{{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 }}</ref>

== References ==
{{Reflist}}

{{Macrolides, lincosamides and streptogramins}}

[[Category:Macrolide antibiotics]]


{{Sourceattribution|Flurithromycin}}