(3R,4S,5S,6R,7R,9R,10Z,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

• ChemBase ID: 658
• Molecular Formular: C41H76N2O15
• Molecular Mass: 837.04654
• Monoisotopic Mass: 836.52456974
• SMILES: [C@@H]1([C@@](C[C@H](/C(=N/OCOCCOC)/[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]([C@H]([C@@H]1C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(OC)C)C)CC)(C)O)O)C)C)(O)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O
• Canonical SMILES: COCCOCO/N=C\1/[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)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
• InChIKey: RXZBMPWDPOLZGW-HEWSMUCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,10Z,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; (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
• IUPAC Traditional name: (Z)-roxithromycin; roxiβ
• Brand Name: ROX; Rulid; Rulide; Surlid
• Synonyms: Roxithromycin

Database IDs

• CAS Number: 80214-83-1
• PubChem SID: 160964121
• PubChem CID: 5480431; 6915744
• CHEBI ID: 48935
• ATC CODE: J01FA06
• CHEMBL: 1214185
• Chemspider ID: 5291557
• DrugBank ID: DB00778
• KEGG ID: D01710
• Unique Ingredient Identifier: 21KOF230FA
• Wikipedia Title: Roxithromycin

CALCULATED PROPERTIES

JChem

• Rotatable Bonds: 13
• Lipinski's Rule of Five: false
• Acid pKa: 12.454023
• H Acceptors: 16
• H Donor: 5
• LogD (pH = 5.5): -0.23886713
• LogD (pH = 7.4): 1.3162447
• Log P: 2.9999793
• Molar Refractivity: 211.2376 cm^3
• Polarizability: 85.90249 Å^3
• Polar Surface Area: 216.89 Å^2

ALOGPS 2.1

• Solubility (Water): 1.87e-01 g/l
• Log P: 2.9
• LOG S: -3.65

PROPERTIES

Physical Property

• Solubility: 0.0189 mg/L at 25 oC (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))
• Hydrophobicity(logP): 1.7

Pharmacology Properties

• Half Life: 11 hours
• Metabolism: Liver, peak concentration averaging 2 hours after ingestion.
• Pregnancy Category: ? (USA) ; B1 (Aus)

DETAILS

DrugBank - DB00778

• Drug Groups: approved
• Description: Roxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. 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 translocation of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila. It can treat respiratory tract, urinary and soft tissue infections.
• Indication: Used to treat respiratory tract, urinary and soft tissue infections.
• Pharmacology: Roxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. Roxithromycin has the following antibacterial spectrum in vitro: Streptococcus agalactiae, Streptococcus pneumoniae (Pneumococcus), Neisseria meningitides (Meningococcus), Listeria monocytogenes, Mycoplasma pneumoniae, Chlamydia trachomatis, Ureaplasma urealyticum, Legionella pneumophila, Helicobacter (Campylobacter), Gardnerella vaginalis, Bordetella pertussis, Moraxella catarrhalis (Branhamella Catarrhalis), and Haemophilus ducreyi. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.
• Toxicity: 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.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.
• Absorption: Very rapidly absorbed and diffused into most tissues and phagocytes.
• Half Life: 12 hours
• Protein Binding: 96%, mainly to alpha1-acid glycoproteins
• References: [Link] ; Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Link
• Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. Pubmed