An internal standard for the quantification of acitretin
Related Products
Parent Compound(s)
19878Etretinate
Unlabeled Version(s)
20853Acitretin
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Acitretin-d3

Item No. 28696

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4E,6E,8E)-9-(4-(methoxy-d3)-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Molecular Formula
C21H23D3O3
Formula Weight
329.5
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
CC1=C(OC([2H])([2H])[2H])C=C(C)C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)=C1C
InChi Code
InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+/i6D3
InChi Key
IHUNBGSDBOWDMA-FDNRGZQGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $561

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    Product Description

    Acitretin-d3 is intended for use as an internal standard for the quantification of acitretin (Item No. 20853) by GC- or LC-MS. Acitretin is a retinoid and an active metabolite of the retinoid etretinate (Item No. 19878) that has antiproliferative activities.1,2 It binds to cellular retinoic acid binding protein I (CRABP-I) and CRABP-II (Kds = 3 and 15 nM, respectively, for the mouse recombinant proteins) but has low affinity for human recombinant retinoic acid receptor-retinoid X receptor (RAR-RXR) heterocomplexes.3,4 Acitretin inhibits proliferation (IC50 = 6.6 µM) and suppresses TNF-α- and IFN-γ-induced protein levels of STAT1, NF-ĸB, and RANTES in HaCaT keratinocytes when used at concentrations up to 50 µM.5 It inhibits proliferation of HL-60, SCC-4, SCC-15, and A431, but not MCF-7, cancer cells, when used at a concentration of 30 µM.1 Acitretin (20 µg per mouse) decreases the severity of psoriatic-like skin lesions in K14-VEGF transgenic mice.2 Formulations containing acitretin have been used in the treatment of psoriasis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Frey, J.R., Peck, R., and Bollag, W. Antiproliferative activity of retinoids, interferon α and their combination in five human transformed cell lines. Cancer Lett. 57(3), 223-227 (1991).

    2. An, J., Zhang, D., Wu, J., et al. The acitretin and methotrexate combination therapy for psoriasis vulgaris achieves higher effectiveness and less liver fibrosis. Pharmacol. Res. 121, 158-168 (2017).

    3. Norris, A.W., Cheng, L., Giguère, V., et al. Measurement of subnanomolar retinoic acid binding affinities for cellular retinoic acid binding proteins by fluorometric titration. Biochim. Biophys. Acta 1209(1), 10-18 (1994).

    4. Tian, K., Norris, A.W., Lin, C.L., et al. The isolation and characterization of purified heterocomplexes of recombinant retinoic acid receptor and retinoid X receptor ligand binding domains. Biochemistry 36(19), 5669-5676 (1997).

    5. Zhang, M., Zhu, L., Feng, Y., et al. Effects of acitretin on proliferative inhibition and RANTES production of HaCaT cells. Arch. Dermatol. Res. 300(10), 575-581 (2008).