A macrolide antibiotic
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Azathramycin

Item No. 46202

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-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
CAS Number
76801-85-9
Synonyms
  • Azaerythromycin A
  • N-desmethyl Azithromycin
Molecular Formula
C37H70N2O12
Formula Weight
Purity
≥95%
A solid
Ethanol: Sparingly soluble: 1-10 mg/ml
SMILES
C[C@@H]1O[C@@H](O[C@@H]2[C@H](C(O[C@@H]([C@](C)([C@@H]([C@H](NC[C@@H](C[C@](C)([C@@H]([C@H]2C)O[C@@H]3O[C@@H](C[C@@H]([C@H]3O)N(C)C)C)O)C)C)O)O)CC)=O)C)C[C@@](C)(OC)[C@H]1O
InChi Code
InChI=1S/C37H70N2O12/c1-14-26-37(10,45)30(41)23(6)38-18-19(2)16-35(8,44)32(51-34-28(40)25(39(11)12)15-20(3)47-34)21(4)29(22(5)33(43)49-26)50-27-17-36(9,46-13)31(42)24(7)48-27/h19-32,34,38,40-42,44-45H,14-18H2,1-13H3/t19-,20-,21+,22-,23-,24+,25+,26-,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
InChi Key
HRKNNHYKWGYTEN-HOQMJRDDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Azathramycin is a macrolide antibiotic.1 It is active against S. pyogenes, S. aureus, E. coli, and several strains of H. influenzae (MICs = ≤0.025, 0.78, 0.78, and 0.78-1.56 µg/ml, respectively). Azathramycin is also active against T. gondii (IC50 = 65 µM).2 Subcutaneous administration of azathramycin protects mice against an acutely fatal S. aureus infection with a half-maximal protective dose (PD50) value of 9 mg/kg.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bright, G.M., Nagel, A.A., Bordner, J., et alSynthesis, in vitro and in vivo activity of novel 9-deoxo-9a-AZA-9a-homoerythromycin A derivatives; a new class of macrolide antibiotics, the azalides. J. Antibiot. 41(8), 1029-1047 (1988).

    2. Lee, Y., Choi, J.Y., Fu, H., et alChemistry and biology of macrolide antiparasitic agents. J. Med. Chem. 54(8), 2792-2804 (2011).