(10E)-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(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: 132692
• Molecular Formular: C41H76N2O15
• Molecular Mass: 837.04654
• Monoisotopic Mass: 836.52456974
• SMILES: CCC1C(C(C(/C(=N/OCOCCOC)/C(CC(C(C(C(C(C(=O)O1)C)OC1CC(C(C(O1)C)O)(C)OC)C)OC1C(C(CC(O1)C)N(C)C)O)(C)O)C)C)O)(C)O
• Canonical SMILES: COCCOCO/N=C/1\C(C)CC(C)(O)C(OC2OC(C)CC(C2O)N(C)C)C(C)C(OC2OC(C)C(C(C2)(C)OC)O)C(C(=O)OC(C(C(C1C)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+
• InChIKey: RXZBMPWDPOLZGW-FEMONOMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10E)-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(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: roxithromycin
• Synonyms: Erythromycin 9-(-O-[2-methoxyethoxy]methyloxime); Roxithromycin

Database IDs

• CAS Number: 80214-83-1
• MDL Number: MFCD00214389
• PubChem SID: 24899369; 162226969
• PubChem CID: 5353933

CALCULATED PROPERTIES

• 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
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: KF4990000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Suitability: suitable for 1694 per US EPA

DETAILS

Sigma Aldrich - R4393

Biochem/physiol Actions
Semisynthetic erythromycin derivative. Impairs NADPH oxidase activation and alters translocation of its cytosolic components to the neutrophil membrane.
Roxithromycin impairs NADPH oxidase activation and alters translocation of its cytosolic components to the neutrophil membrane. It is similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, and clarithromycin. Roxithromycin binds to the subunit 50S of the bacterial ribosome, inhibiting the translocation of peptides1.
Application
Roxithromycin is a semi-synthetic macrolide antibiotic. Roxithromycin is used to block bacterial protein synthesis. Clinically, it is used to treat respiratory tract, urinary and soft tissue infections. It has a similar antimicrobial spectrum as erythromycin, but is the preferred treatment for certain gram-negative bacteria, such as Legionella pneumophila1.