An internal standard for the quantification of azithromycin
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Unlabeled Version(s)
15004Azithromycin
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Azithromycin-d3

Item No. 20675

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-6-(methyl-d3)-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
CAS Number
163921-65-1
Molecular Formula
C38H69D3N2O12
Formula Weight
752.0
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 100 mg/mlDMSO: Soluble: ≥ 10 mg/mlEthanol: 100 mg/mlEthanol: Soluble: ≥ 10 mg/ml
SMILES
C[C@@H]([C@@H]([C@H](C(O[C@H](CC)[C@@](C)(O)[C@H](O)[C@H]1C)=O)C)O[C@@](O[C@@H](C)[C@@H]2O)([H])C[C@@]2(C)OC)[C@H]([C@](O)(C[C@H](CN1C([2H])([2H])[2H])C)C)O[C@@](O[C@H](C)C[C@@H]3N(C)C)([H])[C@@H]3O
InChi Code
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,2
InChi Key
MQTOSJVFKKJCRP-DAANATKPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Azithromycin-d3 is intended for use as an internal standard for the quantification of azithromycin (Item No. 15004) by GC- or LC-MS. Azithromycin is a macrolide antibiotic.1 It is active against S. pneumoniae, S. aureus, N. gonorrhoeae, M. pneumoniae, H. pylori, C. trachomatis, and H. influenzae in vitro (MIC90s = <0.01-2 mg/L). Azithromycin increases survival in mouse models of intraperitoneal S. pyogenes, S. pneumoniae, E. faecalis, or H. influenzae infection (ED50s = 0.78, 8.7, 12.7, and 30.3 mg/kg, respectively).2 It inhibits replication of severe acute respiratory coronavirus 2 (SARS-CoV-2), but not Middle East respiratory syndrome CoV (MERS-CoV), when used at concentrations of 5 and 10 µM.3 Azithromycin also decreases plasma levels of IL-6, TNF-α, and IL-1β and increases survival in a mouse model of LPS-induced sepsis when administered at a dose of 100 mg/kg.4 Formulations containing azithromycin have been used in the treatment of a variety of bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. Girard, D., Finegan, S.M., Dunne, M.W., et al. Enhanced efficacy of single-dose versus multi-dose azithromycin regimens in preclinical infection models. J. Antimicrob. Chemother. 56(2), 365-371 (2005).

    3. Mostafa, A., Kandeil, A., Elshaier, Y.A.M.M., et al. FDA-approved drugs with potent in vitro antiviral activity against severe acute respiratory syndrome coronavirus 2. Pharmaceuticals (Basel) 13(12), 443 (2020).

    4. Patel, A., Joseph, J., Periasamy, H., et al. Azithromycin in combination with ceftriaxone reduces systemic inflammation and provides survival benefit in a murine model of polymicrobial sepsis. Antimicrob. Agents Chemother. 62(9), e00752-00718 (2018).