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    Technical details about Mezigdomide, learn more about the structure, uses, toxicity, action, side effects and more

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    Mezigdomide

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    2D Structure
    Also known as: Cc-92480, 2259648-80-9, Unii-la88ih4o02, Mezigdomide [usan], La88ih4o02, Cc92480
    Molecular Formula
    C32H30FN5O4
    Molecular Weight
    567.6  g/mol
    InChI Key
    YTINZZFBHWSAGL-NDEPHWFRSA-N
    FDA UNII
    LA88IH4O02
    Mezigdomide is a modulator of the E3 ubiquitin ligase complex containing cereblon (CRL4-CRBN E3 ubiquitin ligase), with potential immunomodulating and antineoplastic activities. Upon administration, mezigdomide specifically binds to cereblon (CRBN), thereby affecting the ubiquitin E3 ligase activity, and targeting certain substrate proteins for ubiquitination. This induces proteasome-mediated degradation of certain transcription factors, some of which are transcriptional repressors in T-cells. This leads to modulation of the immune system, including activation of T-lymphocytes, and downregulation of the activity of other proteins, some of which play key roles in the proliferation of certain cancer cell types. CRBN, the substrate recognition component of the CRL4-CRBN E3 ubiquitin ligase complex, plays a key role in the ubiquitination of certain proteins.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-[[4-[[2-[(3S)-2,6-dioxopiperidin-3-yl]-1-oxo-3H-isoindol-4-yl]oxymethyl]phenyl]methyl]piperazin-1-yl]-3-fluorobenzonitrile
    2.1.2 InChI
    InChI=1S/C32H30FN5O4/c33-26-16-23(17-34)8-9-27(26)37-14-12-36(13-15-37)18-21-4-6-22(7-5-21)20-42-29-3-1-2-24-25(29)19-38(32(24)41)28-10-11-30(39)35-31(28)40/h1-9,16,28H,10-15,18-20H2,(H,35,39,40)/t28-/m0/s1
    2.1.3 InChI Key
    YTINZZFBHWSAGL-NDEPHWFRSA-N
    2.1.4 Canonical SMILES
    C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3OCC4=CC=C(C=C4)CN5CCN(CC5)C6=C(C=C(C=C6)C#N)F
    2.1.5 Isomeric SMILES
    C1CC(=O)NC(=O)[C@H]1N2CC3=C(C2=O)C=CC=C3OCC4=CC=C(C=C4)CN5CCN(CC5)C6=C(C=C(C=C6)C#N)F
    2.2 Other Identifiers
    2.2.1 UNII
    LA88IH4O02
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Cc-92480

    2. 2259648-80-9

    3. Unii-la88ih4o02

    4. Mezigdomide [usan]

    5. La88ih4o02

    6. Cc92480

    7. Who 11455

    8. (s)-4-(4-(4-(((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)oxy)methyl)benzyl)piperazin-1-yl)-3-fluorobenzonitrile

    9. 4-[4-[[4-[[2-[(3s)-2,6-dioxopiperidin-3-yl]-1-oxo-3h-isoindol-4-yl]oxymethyl]phenyl]methyl]piperazin-1-yl]-3-fluorobenzonitrile

    10. (83s)-12-fluoro-71,82,86-trioxo-71,73-dihydro-6-oxa-7(4,2)-isoindola-2(1,4)-piperazina-8(3)-piperidina-1(1),4(1,4)-dibenzenaoctaphane-14-carbonitrile

    11. Benzonitrile, 4-(4-((4-(((2-((3s)-2,6-dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1hisoindol-4-yl)oxy)methyl)phenyl)methyl)-1-piperazinyl)-3-fluoro-

    12. Qfc

    13. Mezigdomide [who-dd]

    14. Mezigdomide [inn]

    15. Chembl4648616

    16. Schembl20608563

    17. Gtpl12718

    18. Bcp32805

    19. Ex-a5597

    20. S8975

    21. Akos040732735

    22. At18067

    23. Compound 4 [pmid: 32130004]

    24. Ms-30267

    25. Hy-129395

    26. Cc 92480; Cc92480

    27. Cs-0105182

    28. 4-(4-((4-(((2-((3s)-2,6-dioxopiperidin-3-yl)-1-oxo-2,3-dihydro-1h-isoindol-4- Yl)oxy)methyl)phenyl)methyl)piperazin-1-yl)-3-fluorobenzonitrile

    29. 4-[4-({4-[({2-[(3s)-2,6-dioxopiperidin-3-yl]-1-oxo-2,3-dihydro-1h-isoindol-4-yl}oxy)methyl]phenyl}methyl)piperazin-1-yl]-3-fluorobenzonitrile

    30. Benzonitrile, 4-(4-((4-(((2-((3s)-2,6-dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1h-isoindol-4-yl)oxy)methyl)phenyl)methyl)-1-piperazinyl)-3-fluoro-

    2.4 Create Date
    2019-03-16
    3 Chemical and Physical Properties
    Molecular Weight 567.6 g/mol
    Molecular Formula C32H30FN5O4
    XLogP32.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count7
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area106
    Heavy Atom Count42
    Formal Charge0
    Complexity1050
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of mature B-cell neoplasms