{{MCN|date=April 2025}} {{short description|Chemical compound}} {{redirect|Roxar|the Norwegian company|Roxar AS}} {{Drugbox | Watchedfields = changed | verifiedrevid = 464384076 | image = Roxithromycin.svg | image_class = skin-invert-image | image2 = Roxithromycin ball-and-stick.png | image_class2 = bg-transparent
<!-- Clinical data --> | pronounce = | tradename = Rulide, Biaxsig, others | Drugs.com = {{drugs.com|international|roxithromycin}} | MedlinePlus = | licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) --> | licence_EU = <!-- EMA uses INN (or special INN_EMA) --> | DailyMedID = <!-- DailyMed may use generic or brand name (generic name preferred) --> | licence_US = <!-- FDA may use generic or brand name (generic name preferred) --> | pregnancy_AU = B1 | pregnancy_AU_comment = | pregnancy_US = <!-- A / B / C / D / X / N --> | pregnancy_US_comment = | pregnancy_category= | dependency_liability = | addiction_liability = | routes_of_administration = | class = | ATCvet = | ATC_prefix = J01 | ATC_suffix = FA06 | ATC_supplemental =
<!-- Legal status --> | legal_AU = S4 | legal_AU_comment = | legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> | legal_BR_comment = | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA_comment = | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_DE_comment = | legal_NZ = <!-- Class A, B, C --> | legal_NZ_comment = | legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> | legal_UK_comment = | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> | legal_UN_comment = | legal_status = Rx-only
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = Liver, peak concentration averaging 2 hours after ingestion. | elimination_half-life = 11 hours
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 80214-83-1 | CAS_supplemental = | PubChem = 6915744 | IUPHAR_ligand = 1465 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00778 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5291557 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 21KOF230FA | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01710 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 48935 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1214185 | NIAID_ChemDB = | PDB_ligand = ROX | synonyms =
<!--Chemical data--> | IUPAC_name = (3''R'',4''S'',5''S'',6''R'',7''R'',9''R'',11''S'',12''R'',13''S'',14''R'')-6-{[(2''S'',3''R'',4''S'',6''R'')-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2''R'',4''R'',5''S'',6''S'')-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one | C=41 | H=76 | N=2 | O=15 | smiles = O=C3O[C@H](CC)[C@](O)(C)[C@H](O)[C@H](\C(=N\OCOCCOC)[C@H](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/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RXZBMPWDPOLZGW-XMRMVWPWSA-N }} <!-- Definition and medical uses --> '''Roxithromycin''' is a semi-synthetic macrolide antibiotic used to treat respiratory tract, urinary and soft tissue infections. It is a derivative of erythromycin - comprising the same 14-membered lactone ring - with an oxime-based side chain attached to the macrolide ring.
<!-- Society and culture --> Roxithromycin was patented in 1980 and approved for medical use in 1987.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=498 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA498 |language=en}}</ref> It is available under several brand names in Australia, France, Germany, Israel, South Korea and New Zealand, but not in the United States. Roxithromycin has also been shown to possess antimalarial activity.{{citation needed|date=July 2023}}
== Side effects == The most common side effects are gastrointestinal: diarrhea, nausea, abdominal pain and vomiting. Less common side effects include central or peripheral nervous system events such as headaches, dizziness, and vertigo. Rarely seen side effects are rashes, abnormal liver function values and alteration in the senses of smell and taste.{{cn|date=March 2023}}
== Drug interactions == {{unreferenced|section|date=March 2023}} Roxithromycin has fewer interactions than erythromycin as it has a lower affinity for cytochrome P450.
Roxithromycin is not known to interact with hormonal contraceptives, prednisolone, carbamazepine, ranitidine or antacids.
When roxithromycin is administered with theophylline, some studies have shown an increase in the plasma concentration of theophylline. A change in dosage is usually not required but patients with high levels of theophylline at the start of the treatment should have their plasma levels monitored.
Roxithromycin appears to interact with warfarin. This is shown by an increase in prothrombin time and/or international normalised ratio (INR) in patients taking roxithromycin and warfarin concurrently. As a consequence, severe bleeding episodes have occurred.
== Available forms == Roxithromycin is commonly available as tablets or oral suspension.{{cn|date=March 2023}}
== Mechanism of action == Roxithromycin prevents bacteria from growing, by interfering with their protein synthesis. Roxithromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the synthesis of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly ''Legionella pneumophila''.{{cn|date=March 2023}}
== Pharmacokinetics == When taken before a meal, roxithromycin is very rapidly absorbed, and diffuses into most tissues and phagocytes. Due to the high concentration in phagocytes, roxithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations of roxithromycin are released.{{cn|date=March 2023}}
== Metabolism == Only a small portion of roxithromycin is metabolised. Most of roxithromycin is secreted unchanged into the bile and some in expired air. Under 10% is excreted into the urine. Roxithromycin's half-life is 12 hours.
== History == French pharmaceutical company Roussel Uclaf first marketed roxithromycin in 1987.
==References== {{Reflist}} {{-}}
== External links == * {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/roxithromycin | archive-url = https://web.archive.org/web/20210724112119/https://druginfo.nlm.nih.gov/drugportal/name/roxithromycin | url-status = dead | archive-date = July 24, 2021 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Roxithromycin }}
{{Macrolides, lincosamides and streptogramins}} {{Ion channel modulators}} {{Portal bar | Medicine}}
Category:Macrolide antibiotics Category:Ketoxime ethers Category:Dimethylamino compounds Category:Fourteen-membered rings