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{{short description|Chemical compound}}
'''Roxithromycin''' is a semi-synthetic [[macrolide]] [[antibiotic]]. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin is derived from [[erythromycin]], containing the same 14-membered lactone ring. However, an N-oxime [[side chain]] is attached to the lactone ring.
{{redirect|Roxar|the Norwegian company|Roxar AS}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 464384076
| image = Roxithromycin.svg
| image2 = Roxithromycin ball-and-stick.png

<!-- 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]]. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin is derived from [[erythromycin]], containing the same 14-membered lactone ring. but with an N-oxime [[side chain]] attached to the 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. Roxithromycin is available in Australia, France, Germany, Israel, South Korea and New Zealand, but not in the United States. It has also been shown to possess antimalarial activity.{{citation needed|date=July 2023}}

== Side effects ==
The most common side effects are gastrointestinal: diarrhoea, nausea, abdominal pain and vomiting. Less common side effects include central or peripheral nervous system events such as headaches, dizziness, 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 contraception|hormonal contraceptives]], [[prednisolone]], [[carbamazepine]], [[ranitidine]] or [[antacids]].

When roxithromycin is administered with [[theophylline]], some studies have shown an increase in the [[Blood plasma|plasma]] concentration of [[theophylline]]. A change in dosage is usually not required but patients with high levels of [[theophylline]] at the start of the [[Pharmacotherapy|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.


Roxithromycin is available under several brandnames, for example '''Surlid''' and '''Rulid'''
{| border="1" cellpadding="2" cellspacing="0" width="250px" align="right" style="border-collapse:collapse;"
|-
|bgcolor="#ffffff" align="center" colspan=2|[[Image:Roxithromycin.png|center|200px|Chemical structure of roxithromycin.]]<br><small>Roxithromycin</small>
|-
|align="center" colspan=2 style="border-bottom:3px solid gray;"|<font size="-1">'"erythromycin-9-(-o-[2-methoxyethoxy]methyloxime)"</font>
|-
|bgcolor="#efefef"|[[Molecular mass | Molecular Weight]]
|bgcolor="#dfefff"|836.94
|-
|bgcolor="#efefef"|Empiric Formula
|bgcolor="#dfefff"|C<sub>41</sub>H<sub>76</sub>N<sub>2</sub>O<sub>15</sub>
|-
|bgcolor="#efefef"|[[ATC code]]
|bgcolor="#dfefff"|J01FA06
|-
|bgcolor="#efefef"|Metabolism
|bgcolor="#dfefff"|Liver
|-
|bgcolor="#efefef"|[[Pregnancy category (pharmaceutical) | Pregnancy category]]
|bgcolor="#dfefff"|? ([[United States|USA]]) <br /> B1 ([[Australia|Aus]])
|}
== History ==
German pharmaceutical company [[Hoechst AG|Hoechst Uclaf]] brought out roxithromycin in [[1987]].
== Available forms ==
== Available forms ==
Roxithromycin is commonly administered in tablets or oral suspension.
Roxithromycin is commonly available as tablets or oral suspension.{{cn|date=March 2023}}

== Mechanism of action ==
== Mechanism of action ==
Roxithromycin prevents [[bacterium|bacteria]] from growing, by interfering with their [[protein synthesis]]. Roxithromycin binds to the subunit 50S of the bacterial [[ribosome]], and thus inhibits the translocation of [[peptide]]s. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly ''[[Legionella pneumophila]]''.
Roxithromycin prevents [[bacterium|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 [[peptide]]s. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly ''[[Legionella pneumophila]]''.{{cn|date=March 2023}}


== Pharmacokinetics ==
== Pharmacokinetics ==
When taken before a meal, roxithromycin is very rapidly absorbed, and diffused into most tissues and [[phagocyte]]s. 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.
When taken before a meal, roxithromycin is very rapidly absorbed, and diffuses into most tissues and [[phagocyte]]s. 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 ==
== 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.
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.
== Side effects ==
Most common side effects are gastrointestinal; diarrhoea, nausea, abdominal pain and vomiting. Less common side effects include headaches, rashes, abnormal liver function values and alteration in senses of smell and taste.


== History ==
[[Category:Macrolide antibiotics]]
French pharmaceutical company [[Roussel Uclaf]] first marketed roxithromycin in 1987.


==References==
[[de:Roxithromycin]]
{{Reflist}}
[[pl:Roksytromycyna]]
{{-}}
[[th:ร็อกซิโทรมัยซิน]]

[[tr:Roksitromisin]]
== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/roxithromycin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Roxithromycin }}

{{Macrolides, lincosamides and streptogramins}}
{{Ion channel modulators}}
{{Portal bar | Medicine}}

[[Category:HERG blocker]]
[[Category:Macrolide antibiotics]]
[[Category:Ketoxime ethers]]

Latest revision as of 20:57, 10 October 2024

"Roxar" redirects here. For the Norwegian company, see Roxar AS.
Roxithromycin
Clinical data
Trade namesRulide, Biaxsig, others
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B1
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismLiver, peak concentration averaging 2 hours after ingestion.
Elimination half-life11 hours
Identifiers
  • (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-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-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.121.308 Edit this at Wikidata
Chemical and physical data
FormulaC41H76N2O15
Molar mass837.058 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 checkY
  • Key:RXZBMPWDPOLZGW-XMRMVWPWSA-N checkY
  (verify)

Roxithromycin is a semi-synthetic macrolide antibiotic. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin is derived from erythromycin, containing the same 14-membered lactone ring. but with an N-oxime side chain attached to the ring.

Roxithromycin was patented in 1980 and approved for medical use in 1987.[1] It is available under several brand names. Roxithromycin is available in Australia, France, Germany, Israel, South Korea and New Zealand, but not in the United States. It has also been shown to possess antimalarial activity.[citation needed]

Side effects

[edit]

The most common side effects are gastrointestinal: diarrhoea, nausea, abdominal pain and vomiting. Less common side effects include central or peripheral nervous system events such as headaches, dizziness, vertigo.Rarely seen side effects are rashes, abnormal liver function values and alteration in the senses of smell and taste.[citation needed]

Drug interactions

[edit]

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

[edit]

Roxithromycin is commonly available as tablets or oral suspension.[citation needed]

Mechanism of action

[edit]

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.[citation needed]

Pharmacokinetics

[edit]

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.[citation needed]

Metabolism

[edit]

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

[edit]

French pharmaceutical company Roussel Uclaf first marketed roxithromycin in 1987.

References

[edit]
  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 9783527607495.
[edit]
  • "Roxithromycin". Drug Information Portal. U.S. National Library of Medicine.
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Roxithromycin&oldid=1250508078"