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    Thalidomide (Immunoprin, Contergan and Thalomid)
    Thalidomide (Immunoprin, Contergan and Thalomid)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0036
    CAS #: 50-35-1 Purity ≥98%

    Description: Thalidomide (trade names Immunoprin, Contergan and Thalomid among others) is a potent immunomodulatory agent and a drug approved in the 1950s.  It is commonly used as the ligand of E3 ligase in PROTACs (proteolysis targeting chimeras), a protein degradation technology. Thalidomide is the prototypic drug of the thalidomide class of drugs that are used primarily for the treatment of certain cancers (e.g. MM-multiple myeloma) and of a complication of leprosy. It was introduced as a sedative drug, immunomodulatory agent in 1950s by the German pharmaceutical company Grunenthal and also is investigated for treating symptoms of many cancers. Nowadays, Thalidomide is often times used as a PROTAC (Proteolysis Targeting Chimera) building block which acts as a ligand for the E3 ubiquitin ligase cereblon. PROTAC is a technology utilizes hetero-bifunctional small molecules whereby one end of the molecule recruits an E3 ubiquitin ligase while the other end engages the target protein. Thalidomide inhibits an E3 ubiquitin ligase, which is a CRBN-DDB1-Cul4A complex. Thalidomide is a potent costimulator of primary human T cells in vitro, synergizing with stimulation via the T cell receptor complex to increase interleukin 2-mediated T cell proliferation and interferon gamma production.

    References: [1] Hideshima T, et al. Blood, 2000, 96(9), 2943-2950.[2] Haslett PA, et al. J Exp Med, 1998, 187(11), 1885-1892.

    Related CAS: 841-67-8 [(S)-Thalidomide]; 2098488-36-7 (Azido-Thalidomide)

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    Molecular Weight (MW)258.23
    CAS No.50-35-1
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 52 mg/mL (201.37 mM)
    Water:<1 mg/mL (slightly soluble or insoluble)
    Ethanol: 2 mg/mL (7.74 mM)
    Solubility (In vivo)30% PEG400+0.5% Tween80+5% Propylene glycol: 5 mg/mL
    Chemical Name

    Chemical Name: 2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione


    InChi Code: InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)

    SMILES Code: O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC=C3)=O

    SynonymsBrand names: Synovir; Thalomid (US); Foreign brand names: Contergan; Distaval; Kevadon; Neurosedyn; Pantosediv; Sedoval K17; Softenon Talimol; alphaphthalimidoglutarimide. Nphthaloylglutamimide; Nphthalylglutamic acid imide.

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    In VitroThalidomide must be metabolized by the liver to form an epoxide that may be the active teratogenic metabolite. Thalidomide selectively inhibits the production of human monocyte tumor necrosis factor alpha (TNF-alpha) when human monocytes are triggered with lipopolysaccharide and other agonists in culture.
    In VivoThalidomide (100 mg/kg, p.o.) inhibits the collagen deposition, down-regulates the mRNA expression level of α-SMA and collagen I, and significantly reduces the pro-inflammatory cytokines in RILF mice. Thalidomide alleviates RILF via suppression of ROS and down-regulation of TGF-β/Smad pathway dependent on Nrf2 status. Thalidomide (200 mg/kg, p.o.) combined with icotinib shows synergistic anti-tumor effects in nude mice bearing PC9 cells, suppressing tumor growth and promoting tumor death.
    Animal modelC57BL/6 mice
    Formulation & Dosage100 mg/kg, p.o.
    References[1] D Amato RJ, et al. Proc Natl Acad Sci U S A, 1994, 91(9), 4082-4085. ; Free Radic Biol Med. 2018 Dec;129:446-453.

    These protocols are for reference only. InvivoChem does not independently validate these methods.


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