Roxithromycin

Title: Roxithromycin
CAS Registry Number: 80214-83-1
CAS Name: Erythromycin 9-[O-[(2-methoxyethoxy)methyl]oxime]
Additional Names: oxacyclotetradecane erythromycin deriv; 9-(2¢,5¢-dioxahexyloxyimino)erythromycin
Manufacturers' Codes: RU-28965; RU-965
Trademarks: Assoral (Glaxo); Claramid (Jouveinal); Forilin (Novo); Overal (Lusofarmaco); Rossitrol (Corvi); Rotramin (Glaxo-Allen); Rulid (Hoechst); Surlid (HMR)
Molecular Formula: C41H76N2O15
Molecular Weight: 837.05
Percent Composition: C 58.83%, H 9.15%, N 3.35%, O 28.67%
Literature References: Semisynthetic erythromycin derivative. Prepn: S. Gouin d¢Ambrieres et al., FR 2473525; eidem, US 4349545 (1981, 1982 both to Roussel-UCLAF). In vitro antibacterial spectrum: R. N. Jones et al., Antimicrob. Agents Chemother. 24, 209 (1983); Y. J. Drabu et al., Drugs Exp. Clin. Res. 13, 201 (1987). Antiprotozoal activity in mice: B. J. Luft, Eur. J. Clin. Microbiol. 6, 479 (1987); H. R. Chang, J.-C. R. Pechere, Antimicrob. Agents Chemother. 31, 1147 (1987). Pharmacokinetics: R. Wise et al., ibid. 1051. Bioassay in biological fluids: A. L. Barry, R. R. Packer, Eur. J. Clin. Microbiol. 5, 536 (1986). Clinical evaluations in respiratory tract infections: J. M. Lachat et al., Schweiz. Med. Wochenschr. 116, 1739 (1986); C. Grassi et al., Chemioterapia 6, 41 (1987). Series of articles on antimicrobial activity, pharmacokinetics and clinical efficacy: J. Antimicrob. Chemother. 20, Suppl. B, 1-185 (1987).
Properties: [a]D25 -77.5 ±2° (c = 0.45 in chloroform).
Optical Rotation: [a]D25 -77.5 ±2° (c = 0.45 in chloroform)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.
Royal Jelly Rubber Rubeanic Acid Ruberythric Acid Rubiadin

This article is about the antibiotic Roxithromycin. For the Norwegian company see Roxar AS.

Roxithromycin
Roxithromycin.svg
Roxithromycin ball-and-stick.png
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.  ? (USA)
B1 (Aus)
Legal status  ?
Pharmacokinetic data
Metabolism Liver, peak concentration averaging 2 hours after ingestion.
Half-life 11 hours
Identifiers
CAS number 80214-83-1 YesY
ATC code J01FA06
PubChem CID 6915744
DrugBank DB00778
ChemSpider 5291557 YesY
UNII 21KOF230FA YesY
KEGG D01710 YesY
ChEBI CHEBI:48935 YesY
ChEMBL CHEMBL1214185 YesY
Chemical data
Formula C41H76N2O15 
Mol. mass 837.047 g/mol
 YesY (what is this?)  (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. 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.[1]

Roxithromycin is available under several brandnames, for example, Biaxsig, Coroxin, Romac, Roxar, Roximycin, Roxl-150, Roxo, Roxomycin, Rulid, Rulide, Surlid, Tirabicin and Xthrocin. Roxithromycin is not available in the United States. Roxithromycin is available in Australia. Roxithromycin has also been tested to possess antimalarial activity.