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Quemliclustat

Quemliclustat

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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

Quemliclustat

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 Formula	C₂₀H₂₄ClFN₄O₉P₂
Molecular Weight	580.8 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	9
Exact Mass	580.0691082 g/mol
Monoisotopic Mass	580.0691082 g/mol
Topological Polar Surface Area	197 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	893
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)