A macrolide antibiotic
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Labeled Version(s)
30653Azithromycin-13C-d3 20675Azithromycin-d3
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Azithromycin

Item No. 15004

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-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
CAS Number
83905-01-5
Synonyms
  • CP 62,993
Molecular Formula
C38H72N2O12
Formula Weight
749.0
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMSO: 5 mg/mlEthanol: 16 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.50 mg/ml
SMILES
C[C@@H]([C@@H]([C@@](C(O[C@H](CC)[C@@](C)(O)[C@H](O)[C@H]1C)=O)([H])C)O[C@@](O[C@@H](C)[C@@H]2O)([H])C[C@@]2(C)OC)[C@H]([C@](O)(C[C@H](CN1C)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-BICOPXKESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    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).