Roxithromycin: Difference between revisions

Roxithromycin
Clinical data
Trade names	Rulide, Biaxsig, others
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B1; ;
ATC code	J01FA06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver, peak concentration averaging 2 hours after ingestion.
Elimination half-life	11 hours
Identifiers
	IUPAC name (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	80214-83-1 ;
PubChem CID	6915744;
IUPHAR/BPS	1465;
DrugBank	DB00778 ;
ChemSpider	5291557 ;
UNII	21KOF230FA;
KEGG	D01710 ;
ChEBI	CHEBI:48935 ;
ChEMBL	ChEMBL1214185 ;
PDB ligand	ROX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8041117 ;
ECHA InfoCard	100.121.308
Chemical and physical data
Formula	C41H76N2O15
Molar mass	837.058 g·mol−1
3D model (JSmol)	Interactive image;
	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 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 ; Key:RXZBMPWDPOLZGW-XMRMVWPWSA-N ;
	(verify)

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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

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

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.^{[citation needed]}

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.^{[citation needed]}

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.^{[citation needed]}

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

^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 9783527607495.

External links

"Roxithromycin". Drug Information Portal. U.S. National Library of Medicine.

[Fis2006-1] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 9783527607495.

[1]

@@ Line 1: / Line 1: @@
+{{short description|Chemical compound}}
 {{redirect|Roxar|the Norwegian company|Roxar AS}}
 {{Drugbox
 | Watchedfields = changed
 | 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-(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
 | 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}}
+| 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 =
-| legal_status =
+| 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  =
-<!--Pharmacokinetic data-->
+<!-- Legal status -->
+| legal_AU          = S4
-| bioavailability =
+| legal_AU_comment  =
-| protein_bound =
+| 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-->
+<!-- Identifiers -->
 | CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 80214-83-1
+| CAS_supplemental =
-| ATC_prefix = J01
-| ATC_suffix = FA06
 | PubChem = 6915744
+| IUPHAR_ligand = 1465
 | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
- | DrugBank = DB00778
+| DrugBank = DB00778
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 5291557
-| IUPHAR_ligand = 1465
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 21KOF230FA
@@ Line 39: / Line 75: @@
 | 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
+| 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
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
@@ Line 49: / Line 88: @@
 | 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. Roxithromycin is not available in the United States. Roxithromycin is available in Australia, Israel and New Zealand. 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 [[Roussel Uclaf]] first marketed 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 ==
-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 ==
-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]]''.
+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 ==
-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.
+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 ==
 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 and/or international normalised ratio (INR) in patients taking roxithromycin and [[warfarin]] concurrently. As a consequence, severe bleeding episodes have occurred.
 ==References==
@@ Line 84: / Line 126: @@
 {{-}}
-==External links==
+== 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 }}
-* [http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=ROX Roxithromycin bound to proteins] in the [[Protein Data Bank|PDB]]
 {{Macrolides, lincosamides and streptogramins}}
+{{Ion channel modulators}}
+{{Portal bar | Medicine}}
+[[Category:HERG blocker]]
 [[Category:Macrolide antibiotics]]
+[[Category:Ketoxime ethers]]