An internal standard for the quantification of erythromycin
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Unlabeled Version(s)
16486Erythromycin
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Erythromycin-13C-d3

Item No. 25310

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-6-(((2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methyl(methyl-13C-d3)amino)tetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
CAS Number
2378755-50-9
Molecular Formula
C36[13C]H64D3NO13
Formula Weight
738.0
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 15 mg/mlEthanol: 30 mg/ml
SMILES
C[C@H]1[C@H](O)[C@@](OC)(C)C[C@@](O[C@H]([C@@H](C)C(O[C@H](CC)[C@]([C@H](O)[C@H]2C)(O)C)=O)[C@H](C)[C@@H](O[C@@]3([H])[C@H](O)[C@@H](N(C)[13C]([2H])([2H])[2H])C[C@@H](C)O3)[C@](C)(O)C[C@@H](C)C2=O)([H])O1
InChi Code
InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/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/i11+1D3
InChi Key
ULGZDMOVFRHVEP-ZZKXWFBHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $395

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    Product Description

    Erythromycin-13C-d3 is intended for use as an internal standard for the quantification of erythromycin (Item No. 16486) by GC- or LC-MS. Erythromycin is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains.1 It is active against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s = 0.015-2.0 mg/l).2 Erythromycin (10-40 mg/kg) dose-dependently inhibits the growth of S. aureus in a mouse model of thigh infection.3 It also inhibits the cytochrome P450 (CYP450) isoform CYP3A4 in vitro with IC50 values of 33 and 27.3 µM for α-hydroxytriazolam and 4-hydroxytriazolam formation, respectively, following administration of triazolam, which is known to be metabolized primarily by CYP3A4.4,5 Formulations containing erythromycin have been used in the treatment of bacterial respiratory and skin infections, pertussis, and a variety of other bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

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

    3. Hoogeterp, J.J., Mattie, H., and van Furth, R. Activity of erythromycin and clindamycin in an experimental Staphylococcus aureus infection in normal and granulocytopenic mice. A comparative in vivo and in vitro study. Scand. J. Infect. Dis. 25(1), 123-132 (1993).

    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. Greenblatt, D.J., von Moltke, L.L., Harmatz, J.S., et al. Inhibition of triazolam clearance by macrolide antimicrobial agents: In vitro correlates and dynamic consequences. Clin. Pharmacol. Ther. 64(3), 278-285 (1998).