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Chemistry

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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
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 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.)


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ABOUT THIS PAGE

Quemliclustat Manufacturers

A Quemliclustat manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Quemliclustat, including repackagers and relabelers. The FDA regulates Quemliclustat manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Quemliclustat API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Quemliclustat Suppliers

A Quemliclustat supplier is an individual or a company that provides Quemliclustat active pharmaceutical ingredient (API) or Quemliclustat finished formulations upon request. The Quemliclustat suppliers may include Quemliclustat API manufacturers, exporters, distributors and traders.

Quemliclustat GMP

Quemliclustat Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Quemliclustat GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Quemliclustat GMP manufacturer or Quemliclustat GMP API supplier for your needs.

Quemliclustat CoA

A Quemliclustat CoA (Certificate of Analysis) is a formal document that attests to Quemliclustat's compliance with Quemliclustat specifications and serves as a tool for batch-level quality control.

Quemliclustat CoA mostly includes findings from lab analyses of a specific batch. For each Quemliclustat CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Quemliclustat may be tested according to a variety of international standards, such as European Pharmacopoeia (Quemliclustat EP), Quemliclustat JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Quemliclustat USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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