A metabolite of doxycycline
Related Products
Metabolite(s)
35830Doxycycline (hydrate)
Parent Compound(s)
14422Doxycycline (hyclate)
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4-Epidoxycycline

Item No. 23225

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
CAS Number
6543-77-7
Synonyms
  • 4-ED
Molecular Formula
C22H24N2O8
Formula Weight
444.4
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
OC1=C2C([C@H](C)[C@]3([H])C(C2=O)=C(O)[C@@]4(O)[C@@]([C@@H](N(C)C)C(O)=C(C(N)=O)C4=O)([H])[C@H]3O)=CC=C1
InChi Code
InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15+,17-,22-/m0/s1
InChi Key
JBIWCJUYHHGXTC-NLJUDYQYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-Epidoxycycline is the 4-epimer hepatic metabolite of the antibiotic doxycycline (Item No. 14422).1,2 Unlike doxycycline, 4-epidoxycycline lacks antibiotic activity, therefore, it may not induce the intestinal inflammation in mice associated with doxycycline use. It is an alternative to doxycycline to inactivate the transactivator protein tTA or activate the reverse transactivator rtTA protein in Tet-Off- and Tet-On-based gene expression systems in vitro and in mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nelis, H.J.C.F., and De Leenheer, A.P. Evidence for metabolic inertness of doxycycline. J. Pharm. Sci. 70(2), 226-228 (1981).

    2. Eger, K., Hermes, M., Uhlemann, K., et al. 4-Epidoxycycline: An alternative to doxycycline to control gene expression in conditional mouse models. Biochem. Biophys. Res. Commun. 323(3), 979-986 (2004).