Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Contact Supplier

SPI Pharma has been solving formulation challenges using superior functional materials.

ACCESS ALL DATA
Browse all information
CHEMISTRY
Discover Molecule Insights

DEVELOPMENTS

4 Drugs in Development

4 Drugs in Development

DIGITAL CONTENT

2 NEWS #PharmaBuzz

media
2 NEWS #PharmaBuzz

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 0

MARKET PLACE

API

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

4DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

Annual Reports (USD Million)

Finished Drug Prices

0RELATED EXCIPIENT COMPANIES

0EXCIPIENTS BY APPLICATIONS

Chemistry

Click the arrow to open the dropdown

Click the button for full data set

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.)

Drugs in Development