A degradation product of erythromycin
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Anhydroerythromycin A

Item No. 27960

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-deoxo-6,12-dideoxy-6,9:9,12-diepoxy-erythromycin
CAS Number
23893-13-2
Synonyms
  • BRL 46355ER
  • Erythromycin Anhydride
Molecular Formula
C37H65NO12
Formula Weight
715.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
C[C@@H]1C[C@@]([C@H](O[C@@]2([H])[C@H](O)[C@@H](N(C)C)C[C@@H](C)O2)[C@@H](C)[C@H](O[C@@]3([H])C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@H]4C)(C)O[C@]51[C@H](C)[C@@H](O)[C@@](O5)(C)[C@@H](CC)OC4=O
InChi Code
InChI=1S/C37H65NO12/c1-14-25-36(10)29(40)22(6)37(50-36)18(2)16-35(9,49-37)31(48-33-27(39)24(38(11)12)15-19(3)44-33)20(4)28(21(5)32(42)46-25)47-26-17-34(8,43-13)30(41)23(7)45-26/h18-31,33,39-41H,14-17H2,1-13H3/t18-,19-,20+,21-,22-,23+,24+,25-,26+,27-,28+,29-,30+,31-,33+,34-,35-,36-,37+/m1/s1
InChi Key
YKAVHPRGGAUFDN-JTQLBUQXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Anhydroerythromycin A is a degradation product of the macrolide antibiotic erythromycin (Item No. 16486).1,2 It is formed via degradation of erythromycin in acidic aqueous solutions in vitro as well as in vivo. Anhydroerythromycin A is active against S. aureus and B. cereus in vitro (MICs = 12.5 and 6.25 μg/ml, respectively).3 It also inhibits steroid 6β-hydroxylase activity associated with the cytochrome P450 (CYP) isoform CYP3A in human liver microsomes.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cachet, T., Van den Mooter, G., Hauchecorne, R., et al. Decomposition kinetics of erythromycin A in acidic aqueous solutions. Int. J. Pharm. 55(1), 59-65 (1989).

    2. Hassanzadeh, A., Helliwell, M., and Barber, J. Determination of the stereochemistry of anhydroerythromycin A, the principal degradation product of the antibiotic erythromycin A. Org. Biomol. Chem. 4(6), 1014-1019 (2006).

    3. Sunazuka, T., Takizawa, H., Desaki, M., et al. Effects of erythromycin and its derivatives on interleukin-8 release by human bronchial epithelial cell line BEAS-2B cells. J. Antibiot. (Tokyo). 52(1), 71-74 (1999).

    4. Stupans, I., and Sansom, L.N. The inhibition of drug oxidation by anhydroerythromycin, an acid degradation product of erythromycin. Biochem. Pharmacol. 42(11), 2085-2090 (1991).