Ensifentrine

Synopsis, Chemistry

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Also known as: Rpl-554, 298680-25-8, Rpl554, 1884461-72-6, Ensifentrine [inn], Ensifentrine [usan]

Molecular Formula

C₂₆H₃₁N₅O₄

Molecular Weight

477.6 g/mol

InChI Key

CSOBIBXVIYAXFM-UHFFFAOYSA-N

FDA UNII

3E3D8T1GIX

Ensifentrine is an inhaled inhibitor of the phosphodiesterase (PDE) types 3 (PDE3) and 4 (PDE4), with potential anti-inflammatory and bronchodilator activities. Upon administration, ensifentrine targets, binds to and inhibits PDE3 and PDE4, which leads to an increase of both intracellular levels of cyclic-3',5'-adenosine monophosphate (cAMP) and cAMP-mediated signaling. This may lead to bronchial smooth muscle relaxation and modulate inflammatory responses. PDE3 and PDE4, members of the PDE superfamily, hydrolyze cAMP and 3',5'-cyclic guanosine monophosphate (cGMP) to their inactive 5' monophosphates. PDE3 is the most expressed PDE isoenzyme in bronchial smooth muscle. PDE4 is expressed in immune cells including T-cells, monocytes, macrophages, neutrophils, dendritic cells and eosinophils. It plays an important role in inflammation, especially in inflammatory airway diseases.

1 2D Structure

Ensifentrine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[9,10-dimethoxy-4-oxo-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-3-yl]ethylurea

2.1.2 InChI

InChI=1S/C26H31N5O4/c1-15-10-16(2)24(17(3)11-15)29-23-14-20-19-13-22(35-5)21(34-4)12-18(19)6-8-30(20)26(33)31(23)9-7-28-25(27)32/h10-14H,6-9H2,1-5H3,(H3,27,28,32)

2.1.3 InChI Key

CSOBIBXVIYAXFM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=C(C(=C1)C)N=C2C=C3C4=CC(=C(C=C4CCN3C(=O)N2CCNC(=O)N)OC)OC)C

2.2 Other Identifiers

2.2.1 UNII

3E3D8T1GIX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9,10-dimethoxy-2-(2,4,6-trimethylphenylimino)-3-(n-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2h-pyrimidino(6,1-a)isoquinolin-4-one

2. Rpl 554

3. Rpl-554

4. Rpl554

2.3.2 Depositor-Supplied Synonyms

1. Rpl-554

2. 298680-25-8

3. Rpl554

4. 1884461-72-6

5. Ensifentrine [inn]

6. Ensifentrine [usan]

7. Ls-193855

8. 3e3d8t1gix

9. Ls-193,855

10. A]isoquinolin-3(4h)-yl}ethyl)urea

11. (e)-1-(2-(2-(mesitylimino)-9,10-dimethoxy-4-oxo-6,7-dihydro-2h-pyrimido[6,1-a]isoquinolin-3(4h)-yl)ethyl)urea

12. 2-[9,10-dimethoxy-4-oxo-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-3-yl]ethylurea

13. Trimethylphenyl)imino]-6,7-dihydro-2h-pyrimido[6,1-

14. N-(2-{(2e)-9,10-dimethoxy-4-oxo-2-[(2,4,6-

15. 2-(9,10-dimethoxy-4-oxo-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido(6,1-a)isoquinolin-3-yl)ethylurea

16. N-(2-((2e)-9,10-dimetoxi-4-oxo-2-((2,4,6-trimetilfenil)imino)-6,7-dihidro-2h-pirimido(6,1-a)isoquinolein-3(4h)-il)etil)urea

17. Urea, N-(2-(6,7-dihydro-9,10-dimethoxy-4-oxo-2-((2,4,6-trimethylphenyl)imino)-2h-pyrimido(6,1-a)isoquinolin-3(4h)-yl)ethyl)-

18. Unii-3e3d8t1gix

19. Vmx-554

20. Rpl-554;ensifentrinum

21. Ensifentrine (usan/inn)

22. Ensifentrine [who-dd]

23. Schembl625876

24. Chembl4594287

25. Schembl20720900

26. Gtpl11865

27. Dtxsid00183983

28. Bcp31840

29. Ex-a6633

30. Who 10726

31. Sb19810

32. D11743

33. A937318

34. Q7277486

35. Ensifentrina; Ensifentrinum;rpl-554;rpl554;rpl 554

36. 9,10-dimethoxy-2-(2,4,6-trimethylphenylimino)-3-(n-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2h-pyrimidino(6,1-a)isoquinolin-4-one

37. 9,10-dimethoxy-2-(2,4,6-trimethylphenylimino)-3-(n-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2h-pyrimido[6,1-a]isoquinolin-4-one

38. 9,10-dimethoxy-2-(2,4,6-trimethylphenylimino)3-(n-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2h-pyrimido[6,1-a]isoquinolin-4-one

39. 9,10-dimethoxy-2-(2.4.6-trimethylphenylimino)-3-(n-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2h-pyrimido[6.1-a]isoquinolin-4-one

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₁N₅O₄
Molecular Weight	477.6 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	477.23760449 g/mol
Monoisotopic Mass	477.23760449 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	849
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