Palupiprant

Synopsis, Chemistry

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Also known as: 1369489-71-3, E7046, E-7046, Er-886046, Palupiprant, Ywy620gu8i

Molecular Formula

C₂₂H₁₈F₅N₃O₄

Molecular Weight

483.4 g/mol

InChI Key

MKLKAQMPKHNQPR-NSHDSACASA-N

FDA UNII

YWY620GU8I

Palupiprant is an orally bioavailable antagonist of the prostaglandin E2 (PGE2) receptor type 4 (EP4; EP-4), with potential immunomodulating and antineoplastic activities. Upon oral administration, palupiprant selectively targets, binds to and blocks the activity of immunosuppressive tumor-associated myeloid cells (TAMCs) in the microenvironment. This abolishes TAMC-dependent immunosuppression and reduces tumor cell proliferation. The presence of immunosuppressive myeloid cells in certain tumors is associated with a poor prognosis.

1 2D Structure

Palupiprant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(1S)-1-[[3-(difluoromethyl)-1-methyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbonyl]amino]ethyl]benzoic acid

2.1.2 InChI

InChI=1S/C22H18F5N3O4/c1-11(12-6-8-13(9-7-12)21(32)33)28-19(31)16-17(18(23)24)29-30(2)20(16)34-15-5-3-4-14(10-15)22(25,26)27/h3-11,18H,1-2H3,(H,28,31)(H,32,33)/t11-/m0/s1

2.1.3 InChI Key

MKLKAQMPKHNQPR-NSHDSACASA-N

2.1.4 Canonical SMILES

CC(C1=CC=C(C=C1)C(=O)O)NC(=O)C2=C(N(N=C2C(F)F)C)OC3=CC=CC(=C3)C(F)(F)F

2.1.5 Isomeric SMILES

C[C@@H](C1=CC=C(C=C1)C(=O)O)NC(=O)C2=C(N(N=C2C(F)F)C)OC3=CC=CC(=C3)C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

YWY620GU8I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-((1s)-1-((3-(difluoromethyl)-1-methyl-5-(3-(trifluoromethyl)phenoxy)pyrazole-4-carbonyl)amino)ethyl)benzoic Acid

2. E7046

2.3.2 Depositor-Supplied Synonyms

1. 1369489-71-3

2. E7046

3. E-7046

4. Er-886046

5. Palupiprant

6. Ywy620gu8i

7. (s)-4-(1-(3-(difluoromethyl)-1-methyl-5-(3-(trifluoromethyl)phenoxy)-1h-pyrazole-4-carboxamido)ethyl)benzoic Acid

8. 4-[(1s)-1-[[3-(difluoromethyl)-1-methyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbonyl]amino]ethyl]benzoic Acid

9. 4-[(1s)-1-[[[3-(difluoromethyl)-1-methyl-5-[3-(trifluoromethyl)phenoxy]-1h-pyrazol-4-yl]carbonyl]amino]ethyl]-benzoic Acid

10. Unii-ywy620gu8i

11. Palupiprant [inn]

12. Schembl881212

13. Chembl3670685

14. Bdbm119448

15. E 7046 [who-dd]

16. Bcp25989

17. Ex-a1726

18. Nsc804040

19. S6649

20. Er 886046 [who-dd]

21. Akos037644995

22. Cs-7559

23. Nsc-804040

24. E7046 Pound Er-886406 Pound(c)

25. Ac-30338

26. As-55893

27. Er 886046

28. Hy-103088

29. E 7046

30. Us8686018, 107

31. Q27294756

32. 4-((1s)-1-(((3-(difluoromethyl)-1-methyl-5-(3-(trifluoromethyl)phenoxy)-1h-pyrazol-4-yl)carbonyl)amino)ethyl)benzoic Acid

33. 4-[(1s)-1-{[3-(difluoromethyl)-1-methyl-5-[3-(trifluoromethyl)phenoxy]pyrazol-4-yl]formamido}ethyl]benzoic Acid

2.4 Create Date

2012-04-23

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₈F₅N₃O₄
Molecular Weight	483.4 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	93.4
Heavy Atom Count	34
Formal Charge	0
Complexity	717
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1