Cenicriviroc

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Also known as: Tbr-652, 497223-25-3, Tak-652, Tbr652, Tbr 652, 15c116ua4y

Molecular Formula

C₄₁H₅₂N₄O₄S

Molecular Weight

696.9 g/mol

InChI Key

PNDKCRDVVKJPKG-WHERJAGFSA-N

FDA UNII

15C116UA4Y

Cenicriviroc is an orally bioavailable, dual inhibitor of human C-C chemokine receptor types 2 (CCR2; CD192) and 5 (CCR5; CD195), with potential immunomodulating, anti-inflammatory and antiviral activities. Upon oral administration, cenicriviroc specifically binds to and prevents the activation of both CCR2 and CCR5. This inhibits the activation of CCR2/CCR5-mediated signal transduction pathways and may inhibit inflammatory processes. The G-protein coupled chemokine receptors CCR2 and CCR5 are expressed on the surface of monocytes and macrophages and stimulate their migration and infiltration; they play key roles in inflammation and autoimmune diseases. In addition, cenicriviroc inhibits human immunodeficiency virus (HIV)-1 entry via CCR5 coreceptor interaction.

1 2D Structure

Cenicriviroc

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5E)-8-[4-(2-butoxyethoxy)phenyl]-1-(2-methylpropyl)-N-[4-[(S)-(3-propylimidazol-4-yl)methylsulfinyl]phenyl]-3,4-dihydro-2H-1-benzazocine-5-carboxamide

2.1.2 InChI

InChI=1S/C41H52N4O4S/c1-5-7-22-48-23-24-49-38-15-10-32(11-16-38)33-12-19-40-35(25-33)26-34(9-8-21-44(40)28-31(3)4)41(46)43-36-13-17-39(18-14-36)50(47)29-37-27-42-30-45(37)20-6-2/h10-19,25-27,30-31H,5-9,20-24,28-29H2,1-4H3,(H,43,46)/b34-26+/t50-/m0/s1

2.1.3 InChI Key

PNDKCRDVVKJPKG-WHERJAGFSA-N

2.1.4 Canonical SMILES

CCCCOCCOC1=CC=C(C=C1)C2=CC3=C(C=C2)N(CCCC(=C3)C(=O)NC4=CC=C(C=C4)S(=O)CC5=CN=CN5CCC)CC(C)C

2.1.5 Isomeric SMILES

CCCCOCCOC1=CC=C(C=C1)C2=CC/3=C(C=C2)N(CCC/C(=C3)/C(=O)NC4=CC=C(C=C4)[S@@](=O)CC5=CN=CN5CCC)CC(C)C

2.2 Other Identifiers

2.2.1 UNII

15C116UA4Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (-)-8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-n-(4-(((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide

2. 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-(2-methylpropyl)-n-(4-((s)-((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-1-benzazocine-5-carboxamide

3. Tak 652

4. Tak-652

5. Tbr 652

6. Tbr-652

7. Tbr652

2.3.2 Depositor-Supplied Synonyms

1. Tbr-652

2. 497223-25-3

3. Tak-652

4. Tbr652

5. Tbr 652

6. 15c116ua4y

7. 497223-25-3 (free Base)

8. (-)-8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-n-(4-(((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide

9. (s,e)-8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-n-(4-(((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydrobenzo[b]azocine-5-carboxamide

10. Cvc

11. Tak 652

12. Tak652

13. Cenicrivirocum

14. Cenicriviroc [inn]

15. Cenicriviroc (usan/inn)

16. Cenicriviroc [usan:inn]

17. Cenicriviroc [usan]

18. Cenicriviroc [who-dd]

19. Unii-15c116ua4y

20. Schembl3157748

21. Schembl3157768

22. Chembl2110727

23. Tbr-652tak-652

24. Chebi:149636

25. (5e)-8-[4-(2-butoxyethoxy)phenyl]-1-(2-methylpropyl)-n-[4-[(s)-(3-propylimidazol-4-yl)methylsulfinyl]phenyl]-3,4-dihydro-2h-1-benzazocine-5-carboxamide

26. Amy12051

27. Ex-a1608

28. Tak-652; Tbr-652

29. Bdbm50306033

30. Bdbm50422828

31. Mfcd28502076

32. S8512

33. Cs-6148

34. Db11758

35. 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-(2-methylpropyl)-n-(4-((s)-((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-1-benzazocine-5-carboxamide

36. Ac-31368

37. As-35184

38. Bc179068

39. Hy-14882

40. D09878

41. Q5058846

42. (5e)-8-[4-(2-butoxyethoxy)phenyl]-1-(2-methylpropyl)-n-(4-{(s)-[(1-propyl-1h-imidazol-5-yl)methyl]sulfinyl}phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide

43. (5e)-8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-n-[4-[(s)-(3-propylimidazol-4-yl)methylsulfinyl]phenyl]-3,4-dihydro-2h-1-benzazocine-5-carboxamide

44. (s)-8-(4-(2-butoxyethoxy)phenyl)-1-(2-methylpropyl)-n-(4-(((1-propyl-1h-imidazol-5- Yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide

45. 1-benzazocine-5-carboxamide, 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-(2- Methylpropyl)-n-(4-((s)-((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-

46. 1-benzazocine-5-carboxamide, 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-(2-methylpropyl)-n-(4-((s)-((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-

47. 1-benzazocine-5-carboxamide, 8-[4-(2-butoxyethoxy)phenyl]-1,2,3,4-tetrahydro-1-(2-methylpropyl)-n-[4-[[(1-propyl-1h-imidazol-5-yl)methyl]sulfinyl]phenyl]-, (5e)-

48. 8-(4-(2-(butoxy)ethoxy)phenyl)-1-(2-methylpropyl)-n-(4-((s)-((1-propyl-1h-imidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₅₂N₄O₄S
Molecular Weight	696.9 g/mol
XLogP3	7.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	17
Exact Mass	696.37092733 g/mol
Monoisotopic Mass	696.37092733 g/mol
Topological Polar Surface Area	105 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	1060
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1