Roxithromycin

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 ;
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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.

Roxithromycin was patented in 1980 and approved for medical use in 1987. 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.