A potential impurity in commercial preparations of erythromycin
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Erythromycin A N-oxide

Item No. 23642

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
erythromycin N-oxide
CAS Number
992-65-4
Molecular Formula
C37H67NO14
Formula Weight
749.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
C[C@@H]([C@@H]([C@H](C(O[C@@H]1CC)=O)C)O[C@@]2([H])C[C@](OC)(C)[C@@H](O)[C@H](C)O2)[C@H]([C@@](O)(C)C[C@H](C([C@@H]([C@@H](O)[C@]1(C)O)C)=O)C)O[C@@](O[C@H](C)C[C@@H]3[N+](C)([O-])C)([H])[C@@H]3O
InChi Code
InChI=1S/C37H67NO14/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(52-34-28(40)24(38(11,12)46)15-19(3)48-34)21(5)29(22(6)33(43)50-25)51-26-17-36(9,47-13)31(42)23(7)49-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
InChi Key
LUIPOVCSQJTWHA-RWJQBGPGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $121

    Add

    25 mg

    $477

    Add
    Cayman Chemical
    Neutrophil Biology Wall Poster

    Explore how neutrophils shape the immune response in health and disease. This poster highlights neutrophil pathogen defense mechanisms, including phagocytosis, degranulation, and NETosis, as well as neutrophil roles in inflammation and NET-associated pathologies.

    DOWNLOAD NOW
    Product Description

    Erythromycin A N-oxide is a potential impurity found in commercial preparations of erythromycin.1 Erythromycin (Item No. 16486) is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains.2 It is effective against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s = 0.015-2.0 mg/l).3 Erythromycin is known to potently inhibit the cytochrome P450 isoform CYP3A4, which can affect the metabolism of numerous clinically relevant medications.4,5 Erythromycin A N-oxide is also a precursor in the synthesis of clarithromycin (Item No. 19455).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Deubel, A., Fandino, A.S., Sorgel, F., et al. Determination of erythromycin and related substances in commercial samples using liquid chromatography/ion trap mass spectrometry. J. Chromatogr. A 1136(1), 39-47 (2006).

    2. Wilson, D.N. The A-Z of bacterial translation inhibitors. Crit. Rev. Biochem. Mol. Biol. 44(6), 393-433 (2009).

    3. Kanatani, M.S., and Guglielmo, B.J. The new macrolides. Azithromycin and clarithromycin. Western J. Med. 160(1), 31-37 (1994).

    4. Westphal, J.F. Macrolide - induced clinically relevant drug interactions with cytochrome P-450A (CYP) 3A4: An update focused on clarithromycin, azithromycin and dirithromycin. Br. J. Clin. Pharmacol. 50(4), 285-295 (2000).

    5. Bibi, Z. Role of cytochrome P450 in drug interactions. Nutr. Metab. (Lond) 5(27), (2008).

    6. Suh, K.-H., Seong, M.-R., Kim, N.-D., et al. Method of preparing clarithromycin. US 6,809,188 B1, (2004).