R4393

Sigma-Aldrich

Roxithromycin

95.0-102.0% (HPLC)

Synonym(s):
Erythromycin 9-(-O-[2-methoxyethoxy]methyloxime)
Empirical Formula (Hill Notation):
C41H76N2O15
CAS Number:
Molecular Weight:
837.05
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

assay

95.0-102.0% (HPLC)

form

powder or crystals

solubility

chloroform: soluble 10 mg/mL

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

storage temp.

2-8°C

SMILES string

CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC3OC(C)CC(C3O)N(C)C)C(C)(O)CC(C)C(=N/OCOCCOC)\C(C)C(O)C1(C)O

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+

InChI key

RXZBMPWDPOLZGW-FEMONOMJSA-N

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General description

Chemical structure: macrolide

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 pneumophila.

Biochem/physiol Actions

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 peptides.
Semisynthetic erythromycin derivative. Impairs NADPH oxidase activation and alters translocation of its cytosolic components to the neutrophil membrane.

Packaging

1g,10g

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Patorn Piromchai et al.
The Cochrane database of systematic reviews, (5)(5), CD008233-CD008233 (2011-05-13)
Chronic rhinosinusitis (CRS) is a common health problem which significantly affects quality of life. A wide range of medical and surgical therapies have been used to treat CRS. Both systemic and topical antibiotics are used with the aim of eliminating...
K Adrjanowicz et al.
Molecular pharmaceutics, 9(6), 1748-1763 (2012-05-01)
Antibiotics are chemical compounds of extremely important medical role. Their history can be traced back more than one hundred years. Despite the passing time and significant progress made in pharmacy and medicine, treatment of many bacterial infections without antibiotics would...
X Wang et al.
Journal of veterinary pharmacology and therapeutics, 35(3), 282-289 (2011-07-14)
Tulathromycin is a macrolide antimicrobial agent proposed for therapeutic use in treatment of porcine and bovine respiratory disease. In this study, the absolute bioavailability of tulathromycin solution was investigated in pigs. Eight pigs, with body weight of 20.5 ± 1.6...
Z Samra et al.
Journal of chemotherapy (Florence, Italy), 23(2), 77-79 (2011-05-17)
The in vitro activity of tetracycline, doxycycline, erythromycin, roxithromycin, clarithromycin, azithromycin, levofloxacin and moxifloxacin was tested against 63 clinical isolates of Ureaplasma urealyticum. The minimal inhibitory concentrations (MICs) and the minimal bactericidal concentrations (MBCs) were determined by the broth microdilution...
Nikola Marjanović et al.
Pharmacological research, 63(5), 389-397 (2011-02-15)
Macrolide antibiotics are known to exert anti-inflammatory actions in vivo, including certain effects in COPD patients. In order to investigate the immunomodulatory profile of activity of macrolide antibiotics, we have studied the effects of azithromycin, clarithromycin, erythromycin and roxithromycin on...

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