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Chemistry

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Also known as: Ab928, 2239273-34-6, Ab-928, Etrumadenant, 3-(2-amino-6-(1-((6-(2-hydroxypropan-2-yl)pyridin-2-yl)methyl)-1h-1,2,3-triazol-4-yl)pyrimidin-4-yl)-2-methylbenzonitrile, Etrumadenant [usan]
Molecular Formula
C23H22N8O
Molecular Weight
426.5  g/mol
InChI Key
BUXIAWLTBSXYSW-UHFFFAOYSA-N
FDA UNII
W0ZE0NT8IF

Etrumadenant
Etrumadenant is an orally bioavailable antagonist of both the immunomodulatory checkpoint molecules adenosine A2A receptor (A2AR; ADORA2A) and A2B receptor (A2BR; ADORA2B), with potential immunomodulating and antineoplastic activities. Upon administration, etrumadenant competes with tumor-released adenosine for binding to A2AR and A2BR expressed on numerous intra-tumoral immune cells, such as dendritic cells (DCs), natural killer (NK) cells, macrophages and T-lymphocytes. The binding of AB928 to A2AR and A2BR inhibits A2AR/A2BR activity and prevents adenosine-A2AR/A2BR-mediated signaling. A2AR/A2BR inhibition activates and enhances the proliferation of various immune cells, abrogates the adenosine-mediated immunosuppression in the tumor microenvironment (TME) and activates the immune system to exert anti-tumor immune responses against cancer cells, which leads to tumor cell killing. A2AR and A2BR, G protein-coupled signaling receptors, are expressed on the cell surfaces of numerous immune cells. Adenosine is often overproduced by tumor cells and plays a key role in immunosuppression and tumor cell proliferation.
1 2D Structure

Etrumadenant

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[2-amino-6-[1-[[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl]triazol-4-yl]pyrimidin-4-yl]-2-methylbenzonitrile
2.1.2 InChI
InChI=1S/C23H22N8O/c1-14-15(11-24)6-4-8-17(14)18-10-19(28-22(25)27-18)20-13-31(30-29-20)12-16-7-5-9-21(26-16)23(2,3)32/h4-10,13,32H,12H2,1-3H3,(H2,25,27,28)
2.1.3 InChI Key
BUXIAWLTBSXYSW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C=CC=C1C2=CC(=NC(=N2)N)C3=CN(N=N3)CC4=NC(=CC=C4)C(C)(C)O)C#N
2.2 Other Identifiers
2.2.1 UNII
W0ZE0NT8IF
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Ab928

2. 2239273-34-6

3. Ab-928

4. Etrumadenant

5. 3-(2-amino-6-(1-((6-(2-hydroxypropan-2-yl)pyridin-2-yl)methyl)-1h-1,2,3-triazol-4-yl)pyrimidin-4-yl)-2-methylbenzonitrile

6. Etrumadenant [usan]

7. W0ze0nt8if

8. 3-[2-amino-6-[1-[[6-(1-hydroxy-1-methylethyl)-2-pyridinyl]methyl]-1h-1,2,3-triazol-4-yl]-4-pyrimidinyl]-2-methylbenzonitrile

9. Trumadenant

10. Unii-w0ze0nt8if

11. A2ar/a2br Antagonist-1

12. Etrumadenant [inn]

13. Etrumadenant [who-dd]

14. Chembl4740383

15. Schembl20401465

16. Gtpl11154

17. Bcp33220

18. Ex-a3172

19. Mfcd32263040

20. Nsc823658

21. S9608

22. Who 11620

23. Zb1610

24. Akos037649091

25. Ab928 ; Ab 928

26. Nsc-823658

27. Ac-36346

28. Bs-16547

29. Hy-129393

30. Cs-0105184

31. D81385

32. Q66977586

33. Benzonitrile, 3-[2-amino-6-[1-[[6-(1-hydroxy-1-methylethyl)-2-pyridinyl]methyl]-1h-1,2,3-triazol-4-yl]-4-pyrimidinyl]-2-methyl-

2.4 Create Date
2018-12-15
3 Chemical and Physical Properties
Molecular Weight 426.5 g/mol
Molecular Formula C23H22N8O
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass426.19165736 g/mol
Monoisotopic Mass426.19165736 g/mol
Topological Polar Surface Area139 Ų
Heavy Atom Count32
Formal Charge0
Complexity680
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

Drugs in Development

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Details:

Under the license agreement, Taiho will further support the development & commercialization of AB680 (quemliclustat) & will operationalize the PRISM-1 study in Japan as part of its mission.


Lead Product(s): Quemliclustat,Zimberelimab,Etrumadenant

Therapeutic Area: Oncology Brand Name: AB680

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Taiho Pharmaceutical

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Licensing Agreement July 08, 2024

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Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Under the license agreement, Taiho will further support the development & commercialization of AB680 (quemliclustat) & will operationalize the PRISM-1 study in Japan as part of its mission.

Brand Name : AB680

Molecule Type : Small molecule

Upfront Cash : Undisclosed

July 08, 2024

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Details:

Domvanalimab is an Fc-silent investigational monoclonal antibody that is designed to bind to TIGIT, a protein receptor on immune cells that acts as a brake on the immune response.


Lead Product(s): Etrumadenant,Zimberelimab

Therapeutic Area: Oncology Brand Name: AB154

Study Phase: Phase IIIProduct Type: Large molecule

Sponsor: Arcus Biosciences

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable December 19, 2022

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02

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Domvanalimab is an Fc-silent investigational monoclonal antibody that is designed to bind to TIGIT, a protein receptor on immune cells that acts as a brake on the immune response.

Brand Name : AB154

Molecule Type : Large molecule

Upfront Cash : Not Applicable

December 19, 2022

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Details:

Domvanalimab is an Fc-silent investigational monoclonal antibody that is designed to bind to TIGIT, a protein receptor on immune cells that acts as a brake on the immune response.


Lead Product(s): Etrumadenant,Zimberelimab

Therapeutic Area: Oncology Brand Name: AB154

Study Phase: Phase IIIProduct Type: Large molecule

Sponsor: Arcus Bioscience

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable November 28, 2022

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Duphat
Not Confirmed
Duphat
Not Confirmed

Lead Product(s) : Etrumadenant,Zimberelimab

Therapeutic Area : Oncology

Highest Development Status : Phase III

Partner/Sponsor/Collaborator : Arcus Bioscience

Deal Size : Not Applicable

Deal Type : Not Applicable

Details : Domvanalimab is an Fc-silent investigational monoclonal antibody that is designed to bind to TIGIT, a protein receptor on immune cells that acts as a brake on the immune response.

Brand Name : AB154

Molecule Type : Large molecule

Upfront Cash : Not Applicable

November 28, 2022

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Details:

ARC-7 and the ongoing ARC-10 Phase 3 registrational study will continue to enroll as planned, and preparations for additional Phase 3 studies are underway for domvanalimab-based combinations across various cancer types.


Lead Product(s): Domvanalimab,Zimberelimab,Etrumadenant

Therapeutic Area: Oncology Brand Name: AB154

Study Phase: Phase IIProduct Type: Large molecule

Sponsor: Gilead Sciences

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 24, 2021

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Duphat
Not Confirmed
Duphat
Not Confirmed

Details : ARC-7 and the ongoing ARC-10 Phase 3 registrational study will continue to enroll as planned, and preparations for additional Phase 3 studies are underway for domvanalimab-based combinations across various cancer types.

Brand Name : AB154

Molecule Type : Large molecule

Upfront Cash : Not Applicable

June 24, 2021

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Details:

The Phase 1b clinical trial is a global multi-center, open-label trial of CERC-007 that will enroll around 12 subjects with active adult onset Still’s disease with a primal goal of the study will be to determine the safety and tolerability of CERC-007 in AOSD patients.


Lead Product(s): Eganelisib,Etrumadenant

Therapeutic Area: Oncology Brand Name: IPI-549

Study Phase: Phase IProduct Type: Small molecule

Sponsor: Arcus Biosciences

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 05, 2021

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Duphat
Not Confirmed
Duphat
Not Confirmed

Details : The Phase 1b clinical trial is a global multi-center, open-label trial of CERC-007 that will enroll around 12 subjects with active adult onset Still’s disease with a primal goal of the study will be to determine the safety and tolerability of CERC-007 ...

Brand Name : IPI-549

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 05, 2021

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Details:

Under this agreement, Gilead Gains Broad Access to Arcus’s Clinical and Preclinical Pipeline of Immuno-Oncology Product Candidates that Target Critical Biological Pathways. Arcus to continue to independently conduct research on New Targets.


Lead Product(s): Zimberelimab,Etrumadenant,AB154

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Large molecule

Sponsor: Gilead Sciences

Deal Size: $2,000.0 million Upfront Cash: $175.0 million

Deal Type: Collaboration May 27, 2020

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Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Under this agreement, Gilead Gains Broad Access to Arcus’s Clinical and Preclinical Pipeline of Immuno-Oncology Product Candidates that Target Critical Biological Pathways. Arcus to continue to independently conduct research on New Targets.

Brand Name : Undisclosed

Molecule Type : Large molecule

Upfront Cash : $175.0 million

May 27, 2020

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Details:

Taiho’s in-licensing facilitates global development and commercialization of zimberelimab as a monotherapy and as a combination backbone for Arcus’s and Taiho’s oncology portfolios.


Lead Product(s): Zimberelimab,Etrumadenant,AB154

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Large molecule

Sponsor: Taiho Pharmaceutical

Deal Size: $275.0 million Upfront Cash: Undisclosed

Deal Type: Licensing Agreement February 26, 2020

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07

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Taiho’s in-licensing facilitates global development and commercialization of zimberelimab as a monotherapy and as a combination backbone for Arcus’s and Taiho’s oncology portfolios.

Brand Name : Undisclosed

Molecule Type : Large molecule

Upfront Cash : Undisclosed

February 26, 2020

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ABOUT THIS PAGE

Etrumadenant Manufacturers

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

Etrumadenant Suppliers

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

Etrumadenant GMP

Etrumadenant 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 Etrumadenant 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 Etrumadenant GMP manufacturer or Etrumadenant GMP API supplier for your needs.

Etrumadenant CoA

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

Etrumadenant CoA mostly includes findings from lab analyses of a specific batch. For each Etrumadenant 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.

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