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Also known as: 1616372-41-8, Amezalpat [inn], 1eq4lqn9n3, Orb2945076, Schembl15832811, Bdbm617517

Molecular Formula

C₃₄H₄₁N₃O₄

Molecular Weight

555.7 g/mol

InChI Key

KUPVZYDOHAPPNF-UHFFFAOYSA-N

FDA UNII

1EQ4LQN9N3

Amezalpat is an orally bioavailable, small molecule, selective and competitive antagonist of peroxisome proliferator activated receptor alpha (PPARa), with potential immunomodulating and antineoplastic activities. Upon oral administration, amezalpat targets, binds to and blocks the activity of PPARa, thereby blocking transcription of PPARa target genes leading to an intracellular metabolism shift from fatty acid oxidation (FAO) to glycolysis in FAO-dependent tumors and reducing the production of fatty acids in the tumor microenvironment (TME). As fatty acids are essential for tumor cell growth in FAO-dependent tumor cells and are needed for the metabolism of suppressive immune cells in the TME, including regulatory T-cells (Tregs), reducing the amount of fatty acids leads to a direct killing of FAO-dependent tumor cells. It also skews macrophages from the immune suppressive M2 phenotype to an effector M1 phenotype and facilitates the cytotoxicity of immune effector cells, thereby stimulating an anti-tumor immune response and further killing tumor cells. Amezalpat also restores the natural inhibitor of angiogenesis thrombospondin-1 (TSP-1) and stimulator of interferon genes (STING) in the TME. PPARa, a ligand-activated nuclear transcription factor and metabolic checkpoint, regulates the expression of FAO genes and lipid metabolism. It plays a key role in immunosuppression in the TME. FAO is a metabolic pathway essential to tumor growth, survival and immunosuppression.

1 2D Structure

Amezalpat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[5-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-ethoxyphenyl]acetic acid

2.1.2 InChI

InChI=1S/C34H41N3O4/c1-6-36-31(35-37(33(36)40)23-25-14-17-29(18-15-25)34(3,4)5)13-9-11-24-10-8-12-26(20-24)27-16-19-30(41-7-2)28(21-27)22-32(38)39/h8,10,12,14-21H,6-7,9,11,13,22-23H2,1-5H3,(H,38,39)

2.1.3 InChI Key

KUPVZYDOHAPPNF-UHFFFAOYSA-N

2.2 Other Identifiers

2.2.1 UNII

1EQ4LQN9N3

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1616372-41-8

2. Amezalpat [inn]

3. 1eq4lqn9n3

4. Orb2945076

5. Schembl15832811

6. Bdbm617517

7. Us20240041837, Example 6

8. Us20240041837, Example 11

9. [1,1'-biphenyl]-3-acetic Acid, 3'-[3-[1-[[4-(1,1-dimethylethyl)phenyl]methyl]-4-ethyl-4,5-dihydro-5-oxo-1h-1,2,4-triazol-3-yl]propyl]-4-ethoxy-

10. 3'-(3-(1-((4-(1,1-dimethylethyl)phenyl)methyl)-4-ethyl-4,5-dihydro-5-oxo-1h-1,2,4-triazol-3-yl)propyl)-4-ethoxy(1,1'-biphenyl)-3-acetic Acid

2.4 Create Date

2014-07-28

3 Chemical and Physical Properties

Molecular Formula	C₃₄H₄₁N₃O₄
Molecular Weight	555.7 g/mol
XLogP3	6.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	13
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	82.4
Heavy Atom Count	41
Formal Charge	0
Complexity	891
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1