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    Quemliclustat

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: Ab-680, 2105904-82-1, Ab680, Quemliclustat [usan], J6k8wsv73a, Chembl4471306
    Molecular Formula
    C20H24ClFN4O9P2
    Molecular Weight
    580.8  g/mol
    InChI Key
    MFYLCAMJNGIULC-KCVUFLITSA-N
    FDA UNII
    J6K8WSV73A
    Quemliclustat is a small molecule, competitive inhibitor of the ectoenzyme CD73 (cluster of differentiation 73; 5'-ecto-nucleotidase; 5'-NT; ecto-5'-nucleotidase), with potential immunomodulating and antineoplastic activities. Upon administration, quemliclustat targets and binds to CD73, leading to clustering of and internalization of CD73. This prevents CD73-mediated conversion of adenosine monophosphate (AMP) to adenosine and decreases the amount of free adenosine in the tumor microenvironment (TME). This prevents adenosine-mediated lymphocyte suppression and increases the activity of CD8-positive effector cells and natural killer (NK) cells. This also activates macrophages and reduces the activity of myeloid-derived suppressor cells (MDSCs) and regulatory T-lymphocytes (Tregs). By abrogating the inhibitory effect on the immune system and enhancing the cytotoxic T-cell-mediated immune response against cancer cells, tumor cell growth decreases. In addition, clustering and internalization of CD73 decreases the migration of cancer cells and prevents metastasis. CD73, a plasma membrane protein belonging to the 5'-nucleotidase (NTase) family, upregulated on a number of cancer cell types, catalyzes the conversion of extracellular nucleotides, such as AMP, to membrane-permeable nucleosides, such as adenosine; it plays a key role in adenosine-mediated immunosuppression within the TME.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [[(2R,3S,4R,5R)-5-[6-chloro-4-[[(1S)-1-(2-fluorophenyl)ethyl]amino]pyrazolo[3,4-b]pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]methylphosphonic acid
    2.1.2 InChI
    InChI=1S/C20H24ClFN4O9P2/c1-10(11-4-2-3-5-13(11)22)24-14-6-16(21)25-19-12(14)7-23-26(19)20-18(28)17(27)15(35-20)8-34-37(32,33)9-36(29,30)31/h2-7,10,15,17-18,20,27-28H,8-9H2,1H3,(H,24,25)(H,32,33)(H2,29,30,31)/t10-,15+,17+,18+,20+/m0/s1
    2.1.3 InChI Key
    MFYLCAMJNGIULC-KCVUFLITSA-N
    2.1.4 Canonical SMILES
    CC(C1=CC=CC=C1F)NC2=CC(=NC3=C2C=NN3C4C(C(C(O4)COP(=O)(CP(=O)(O)O)O)O)O)Cl
    2.1.5 Isomeric SMILES
    C[C@@H](C1=CC=CC=C1F)NC2=CC(=NC3=C2C=NN3[C@H]4[C@@H]([C@@H]([C@H](O4)COP(=O)(CP(=O)(O)O)O)O)O)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    J6K8WSV73A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ab680

    2.3.2 Depositor-Supplied Synonyms

    1. Ab-680

    2. 2105904-82-1

    3. Ab680

    4. Quemliclustat [usan]

    5. J6k8wsv73a

    6. Chembl4471306

    7. [[(2~{r},3~{s},4~{r},5~{r})-5-[6-chloranyl-4-[[(1~{s})-1-(2-fluorophenyl)ethyl]amino]pyrazolo[3,4-b]pyridin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl]methylphosphonic Acid

    8. [[(2r,3s,4r,5r)-5-[6-chloro-4-[[(1s)-1-(2-fluorophenyl)ethyl]amino]pyrazolo[3,4-b]pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]methylphosphonic Acid

    9. Unii-j6k8wsv73a

    10. Quemliclustat [inn]

    11. Cd73 Inhibitor Ab-680

    12. Schembl19100484

    13. Gtpl10707

    14. Ex-a4998

    15. Bdbm50527134

    16. Who 11621

    17. Ac-36768

    18. Ba178946

    19. Hy-125286

    20. Cs-0090231

    21. F78354

    22. (((((2r,3s,4r,5r)-5-(6-chloro-4-(((s)-1-(2-fluorophenyl)ethyl)amino)-1h-pyrazolo[3,4-b]pyridin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)methyl)phosphonic Acid

    23. (((2r,3s,4r,5r)-5-(6-chloro-4-((s)-1-(2-fluorophenyl)ethylamino)-1h-pyrazolo[3,4-b]pyridin-1-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethoxy)(hydroxy)phosphorylmethyl)phosphonic Acid

    24. 1h-pyrazolo[3,4-b]pyridin-4-amine, 6-chloro-n-[(1s)-1-(2-fluorophenyl)ethyl]-1-[5-o-[hydroxy(phosphonomethyl)phosphinyl]-beta-d-ribofuranosyl]-

    25. 2-chloro-n6 -[(1s)-1-(2-fluorophenyl)ethyl]-8-aza-1,7- Dicarbaadenosine 5'- (trihydrogen 2-carbadiphosphate)

    26. Qdh

    2.4 Create Date
    2017-10-07
    3 Chemical and Physical Properties
    Molecular Weight 580.8 g/mol
    Molecular Formula C20H24ClFN4O9P2
    XLogP3-0.7
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count9
    Exact Mass580.0691082 g/mol
    Monoisotopic Mass580.0691082 g/mol
    Topological Polar Surface Area197 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity893
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Immune Checkpoint Inhibitors

    Drugs that block negative regulator IMMUNE CHECKPOINT proteins (e.g., PD-1 RECEPTOR and CTLA-4 ANTIGEN) thereby increasing suppressed immune activation in immunotherapies. (See all compounds classified as Immune Checkpoint Inhibitors.)