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{{short description|Chemical compound}}
{{redirect|Roxar|the Norwegian company|Roxar AS}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464384076
| verifiedrevid = 464384076
| 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-d-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-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
| image = Roxithromycin.svg
| image = Roxithromycin.svg
| image2 = Roxithromycin ball-and-stick.png


<!--Clinical data-->
<!-- Clinical data -->
| tradename =
| pronounce =
| tradename = Rulide, Biaxsig, others
| Drugs.com = {{drugs.com|international|roxithromycin}}
| Drugs.com = {{drugs.com|international|roxithromycin}}
| MedlinePlus =
| pregnancy_category = ? ([[United States|USA]]) <br /> B1 ([[Australia|Aus]])
| licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) -->
| legal_status =
| licence_EU = <!-- EMA uses INN (or special INN_EMA) -->
| routes_of_administration =
| 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-->
<!-- Pharmacokinetic data -->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism = Liver, peak concentration averaging 2 hours after ingestion.
| metabolism = Liver, peak concentration averaging 2 hours after ingestion.
| elimination_half-life = 12 hours
| elimination_half-life = 11 hours


<!--Identifiers-->
<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 80214-83-1
| CAS_number = 80214-83-1
| CAS_supplemental =
| ATC_prefix = J01
| ATC_supplemental = FA06
| PubChem = 6915744
| PubChem = 6915744
| IUPHAR_ligand = 1465
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = APRD01305
| DrugBank = DB00778
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5291557
| ChemSpiderID = 5291557
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1214185
| ChEMBL = 1214185
| NIAID_ChemDB =
| PDB_ligand = ROX
| synonyms =


<!--Chemical data-->
<!--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
| C=41 | H=76 | N=2 | O=15
| molecular_weight = 837.047 g/mol
| 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
| 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
| InChI = 1/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
| InChIKey = RXZBMPWDPOLZGW-XMRMVWPWBP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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
Line 48: Line 88:
| StdInChIKey = RXZBMPWDPOLZGW-XMRMVWPWSA-N
| 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. However, an N-oxime [[side chain]] is attached to the lactone ring. It is also currently undergoing clinical trials for the treatment of male-pattern hair loss.<ref>{{cite web| title = The Effect of 0.5% Roxithromycin Lotion for Androgenetic Alopecia - ClinicalTrials.gov | url = http://www.clinicaltrials.gov/ct/show/NCT00197379?order=8| accessdate = 2007-09-22}}</ref>
'''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 is available under several brandnames, for example, '''Xthrocin''', '''Roxl-150''', '''Roxo''', '''Surlid''', '''Rulide''', '''Biaxsig''', '''Roxar''', '''Roximycin''', '''Roxomycin''', '''Rulid''', '''Tirabicin''' and '''Coroxin'''. Roxithromycin is not available in the United States. Roxithromycin has also been tested to possess antimalarial activity.
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}}


== History ==
== 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}}
German pharmaceutical company [[Hoechst AG|Hoechst Uclaf]] brought out roxithromycin in 1987.

== 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.


== Available forms ==
== Available forms ==
Roxithromycin is commonly available as 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 ==
== History ==
French pharmaceutical company [[Roussel Uclaf]] first marketed roxithromycin in 1987.
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, and also the rarely seen rashes, abnormal liver function values and alteration in senses of smell and taste.

== Drug interactions ==
Roxithromycin has fewer interactions than [[erythromycin]] as it has a lower affinity for [[cytochrome P450]].

Roxithromycin does not 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 (international normalised ratio [INR]) in patients taking roxithromycin and [[warfarin]] concurrently. As a consequence, severe bleeding episodes have occurred.

== Drug Dosage ==
Adults: 150&nbsp;mg twice in a day, 30 minutes before meals or 2 hours after. For children, it is 2.5 - 5.0&nbsp;mg/kg of body weight, given in two divided doses per day.
<ref>Medical pharmacology, Ch.-54, ISBN-81_8448_085_7</ref>
Mode of Administration- Oral.

==Assay of Roxithromycin<ref>Analytical Method development by Liquid Chromatography, ISBN 978-3-8443-2869-1, LAP LAMBERT Academic Publishing GmbH & Co. KG, Germany. Published on 25-11-2011.[http://books.google.co.in/books?id=oHvXygAACAAJ&dq=prafulla+kumar+sahu&hl=en&sa=X&ei=wwJnT_mGI4HprQeQluG8Bw&ved=0CDQQ6AEwAA]</ref>==
Stability of roxithromycin was studied by Wei Zhenping et al<ref>Wei Zhenping and Bi Dianzhou, A Comparative Study on the Stability of Roxithromycin in Different pH Solutions by Colorimetry, TLC and HPLC, Journal of Chinese Pharmaceutical Sciences 2000, 9 (4), 204-207.</ref> in solutions of different pH values were determined separately by colorimetry, TLC and HPLC.
Oh-Seung Kwon et al<ref>Oh-Seung Kwon, Hey-Jung Kim, Heesoo Pyo and Youn Bok Chung, Bioequivalence assessment of Roxithromycin Tablets in healthy Korean volunteers, The Journal of Applied Pharmacology, 2006, 14, 50-55.</ref> evaluated the bioequivalency between different brands of Roxithromycin Tablets administered to healthy Korean male volunteers using HPLC with fluorescence detector.
The reversed-phase (RP) chromatographic behaviour of the macrolide antibiotics clarithromycin (Clari) and roxithromycin (Roxi) was extensively studied by A. Pappa-louisi et al<ref>A. Pappa-louisi, p. Agrafiotou, g. Zissopoulou, p. Liatsi, Influence of temperature and mobile phase composition on retention properties of the macrolide antibiotics clarithromycin and roxithromycin in reversed-phase liquid chromatography, BAÜ Fen Bil. Enst. Dergisi, 2002. 4.2, 17-19.</ref> as a function of mobile phase composition - modified with one, two or three of organic solvents - and column temperature.
A rapid and sensitive reverse phase high performance liquid chromatographic method with UV detection was developed by Prafulla Sahu et al<ref>Prafulla Kumar Sahu*, K.Ravi Sankar, M.Mathrusri Annapurna, Reverse phase high performance liquid chromatographic method for the analysis of Roxithromycin in bulk and pharmaceutical dosage forms”, Analytical Chemistry: An Indian Journal, 2009, 8(1).</ref> for the determination of Roxithromycin present in bulk and pharmaceutical dosage forms.
A selective HPLC method with fluorescence detection for the determination of roxithromycin (ROX) in human plasma was described by Franciszek K. Główka et al.<ref>Franciszek K. Główka and Marta Karaźniewicz-Łada, Determination of roxithromycin in human plasma by HPLC with fluorescence and UV absorbance detection: Application to a pharmacokinetic study, Journal of Chromatography B, Volume 852, Issues 1-2, 1 June 2007, Pages 669-673.</ref> After solid-phase extraction (SPE), ROX and erythromycin (internal standard, I.S.) were derivatized by treatment with 9-fluorenylmethyl chloroformate (FMOC-Cl). Optimal resolution of fluorescence derivatives of ROX and I.S. was obtained during one analytical run using reversed phase, C18 column. The mobile phase was composed of potassium dihydrogenphosphate solution, pH 7.5 and acetonitrile. Fluorescence of the compounds was measured at the maximum excitation, 255&nbsp;nm and emission, 313&nbsp;nm, of ROX derivatives.
A method for the determination of Roxithromycin in the flounder muscle by LC–MS was developed by Jong-hwan Lim et al.<ref>Jong-hwan Lim, Beom-su Jang, Rae-kyung Lee, Seung-chun Park and Hyo-in Yun, Determination of roxithromycin residues in the flounder muscle with electrospray liquid chromatography–mass spectrometry, Journal of Chromatography B: Biomedical Sciences and Applications, Volume 746, Issue 2, 15 September 2000, Pages 219-225.</ref> A dichloromethane extract of the sample was separated on C18 reversed-phase column with acetonitrile–50 mM ammonium acetate (80:20, v/v) as the mobile phase and analyzed by LC–MS via atmospheric pressure ionization/ electrospray ionization interface.
Jin Sun et al<ref>Jin Sun, Tianhong Zhang, Feng Qiu, Yu Liu, Jingling Tang, Haihua Huang and Zhonggui He, Impact of pharmaceutical dosage forms on the pharmacokinetics of roxithromycin in healthy human volunteers, Journal of Antimicrobial Chemotherapy, 2011, 55, 5, 796-799.</ref> described the impact of pharmaceutical dosage forms on the pharmacokinetics of roxithromycin in healthy human volunteers and characterization of roxithromycin degradation in simulated gastric fluid and simulated intestinal fluid using high performance liquid chromatography (HPLC)-tandem MS.
A stability indicating reverse phase high performance liquid chromatographic method is developed by Dhiraj S. Nikam et al<ref>Dhiraj S. Nikam, Swapnil C. Aswale, Stability indicating RP-HPLC method for simultaneous estimation of ambroxol hydrochloride and roxithromycin in bulk and tablet dosage form, International Journal of Pharmaceutical Research and Development, 2010, 2, 10.</ref> for simultaneous estimation of ambroxol hydrochloride and roxithromycin in bulk and pharmaceutical formulation using water: acetonitrile: orthophosphoric acid (50:50:0.1) as a mobile phase. Detection was carried out at 210&nbsp;nm.
An isocratic liquid chromatographic method has been developed by H. K. Chepkwony et al<ref>H. K. Chepkwony, F. N. Kamau, E. Rodriguez, E. Roets and J. Hoogmartens, Isocratic liquid chromatographic method for the analysis of roxithromycin and structurally related substances in bulk samples, Chromatographia, Volume 54, Numbers 11-12, 725-729.</ref> for the analysis of bulk samples of Roxithromycin using acetonitrile-2.0M (NH4)2HPO4, pH 6.4-water, 25∶30∶45, (v/v) as mobile phase detection was by UV absorbance at 215&nbsp;nm. Sufficient separation of roxithromycin from its homolog containing one more methyleneoxy group (roxithromycin G) and from other related substances was achieved.
Valéria de Oliveira et al<ref>Valéria de Oliveira; Ana Maria Bergold; Elfrides Eva Scherman Schapoval, High-Performance Liquid Chromatographic Determination of Roxithromycin in Tablets, Analytical Letters, 1996, 29, 13, 2377–2382.</ref> described a High-Performance Liquid Chromatographic method for the determination of Roxithromycin in Tablets using 0.067 M phosphate buffer, pH 4.0 and methanol (65:35) as mobile phase and UV detection at 210&nbsp;nm.
A liquid chromatography–mass spectrometry (LC–MS) method for the determination of roxithromycin in rat lung tissue is described by Peng Wang et al.<ref>Peng Wang, Meiling Qi, and Xin Jin, Determination of roxithromycin in rat lung tissue by liquid chromatography–mass spectrometry, Journal of Pharmaceutical and Biomedical Analysis, Volume 39, Issues 3-4, 15 September 2005, Pages 618-623.</ref>
Chen Nai-jiang et al<ref>Chen Nai-jiang and Zhang Hong, HPLC-ELSD method for content determination of Roxithromycin, Chinese Journal of Antibiotics, 2009, doi: CNKI:SUN:ZKSS.0.2009-05-012.</ref> described a HPLC-ELSD method for content determination of Roxithromycinusing methanol-0.2% trifluoroacetic acid(TFA) solution(50:50)(pH was adjusted to 6.5 with triethylamine) as mobile phase at room temperature and ELSD as detector.
Dafang Zhong et al<ref>Dafang Zhong, Xueqing Li, Aimin Wang, Youjun Xu and Shuodong Wu, Identification of the Metabolites of Roxithromycin in Humans, Drug Metabolism and Disposition 2000, 28 5, 552-559.</ref> identified various metabolites of Roxithromycin in human biological fluids. A total of 15 metabolites were found in bile, urine, and plasma by HPLC with ion trap mass spectrometric and electrochemical detection.


==References==
==References==
{{Reflist}}
{{Reflist}}
{{-}}
{{-}}

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


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

[[de:Roxithromycin]]
[[dv:ރޮކްސިތްރޯމައިސިން]]
[[es:Roxitromicina]]
[[fr:Roxithromycine]]
[[ja:ロキシスロマイシン]]
[[pl:Roksytromycyna]]
[[ru:Рокситромицин]]
[[fi:Roksitromysiini]]
[[th:ร็อกซิโทรมัยซิน]]
[[tr:Roksitromisin]]
[[zh:罗红霉素]]

Latest revision as of 20:57, 10 October 2024

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

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

Mechanism of action

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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

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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

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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

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French pharmaceutical company Roussel Uclaf first marketed roxithromycin in 1987.

References

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  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 9783527607495.
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  • "Roxithromycin". Drug Information Portal. U.S. National Library of Medicine.