An internal standard for the quantification of doxycycline
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Unlabeled Version(s)
14422Doxycycline (hyclate) 35830Doxycycline (hydrate)
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Doxycycline-d3 (hyclate)

Item No. 28528

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-(6-methyl-d)-1,11-dioxo-2-naphthacene-4,6-d2-carboxamide, hydrochloride, compd. with ethanol, hydrate (2:2:1:X)
Molecular Formula
2[C22H21D3N2O8] • 2HCl • XH2O • C2H6O
Formula Weight
894.9
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
CCO.OC1=C2C([C@@](C([2H])([H])[H])([2H])[C@]3([H])C(C2=O)=C(O)[C@@]4(O)[C@@]([C@@](N(C)C)([2H])C(O)=C(C(N)=O)C4=O)([H])[C@H]3O)=CC=C1.OC5=C6C([C@@](C([2H])([H])[H])([2H])[C@]7([H])C(C6=O)=C(O)[C@@]8(O)[C@@]([C@@](N(C)C)([2H])C(O)=C(C(N)=O)C8=O)([H])[C@H]7O)=CC=C5.Cl.O.Cl
InChi Code
InChI=1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(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;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10+,14+,15-,17-,22-;;;;/m00..../s1/i2*1D,7D,15D;;;;
InChi Key
HALQELOKLVRWRI-SFNMZOGZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $325

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    Product Description

    Doxycycline-d3 is intended for use as an internal standard for the quantification of doxycycline (Item No. 14422) by GC- or LC-MS. Doxycycline is a broad-spectrum tetracycline antibiotic.1,2 It inhibits bacterial protein synthesis by binding to ribosomes.2,3 Doxycycline also selectively inhibits human matrix metalloproteinase-8 (MMP-8) and MMP-13 over MMP-1 with 50, 60, and 5% inhibition, respectively, when used at a concentration of 30 μM.4 It can be used as a regulator for inducible gene expression systems where expression depends on either the presence (Tet-On) or absence (Tet-Off) of doxycycline.5,6 Formulations containing doxycycline have been used in the treatment of bacterial infections and the prevention of malaria.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Williamson, G.M. The in vitro activity of vibramycin (doxycycline). Chemotherapia (Basel) 13(Suppl. 1), 1-6 (1968).

    2. Griffin, M.O., Ceballos, G., and Villarreal, F.J. Tetracycline compounds with non-antimicrobial organ protective properties: Possible mechanisms of action. Pharmacol. Res. 63(2), 102-107 (2011).

    3. Chopra, I. Tetracycline analogs whose primary target is not the bacterial ribosome. Antimicrob. Agents Chemother. 38(4), 637-640 (1994).

    4. Smith, G.N., Jr., Mickler, E.A., Hasty, K.A., et al. Specificity of inhibition of matrix metalloproteinase activity by doxycycline: Relationship to structure of the enzyme. Arthritis Rheum. 42(6), 1140-1146 (1999).

    5. Gould, D.J., Berenstein, M., Dreja, H., et al. A novel doxycycline inducible autoregulatory plasmid which displays “on”/“off” regulation suited to gene therapy applications. Gene Ther. 7(24), 2061-2070 (2000).

    6. Li, Z., Michael, I.P., Zhou, D., et al. Simple piggyBac transposon-based mammalian cell expression system for inducible protein production. Proc. Natl. Acad. Sci. USA 110(13), 5004-5009 (2013).