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Also known as: 923564-51-6, Abt-263, Abt 263, Abt263, Abt-263 (navitoclax), Navitoclax (abt-263)
Molecular Formula
C47H55ClF3N5O6S3
Molecular Weight
974.6  g/mol
InChI Key
JLYAXFNOILIKPP-KXQOOQHDSA-N
FDA UNII
XKJ5VVK2WD

Navitoclax
Navitoclax is an orally active, synthetic small molecule and an antagonist of a subset of the B-cell leukemia 2 (Bcl-2) family of proteins with potential antineoplastic activity. Navitoclax selectively binds to apoptosis suppressor proteins Bcl-2, Bcl-XL, and Bcl-w, which are frequently overexpressed in a wide variety of cancers, including those of the lymph, breast, lung, prostate, and colon, and are linked to tumor drug resistance. Inhibition of these apoptosis suppressors prevents their binding to the apoptotic effectors Bax and Bak proteins, thereby triggering apoptotic processes in cells overexpressing Bcl-2, Bcl-XL, and Bcl-w. This eventually reduces tumor cell proliferation.
1 2D Structure

Navitoclax

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-N-[4-[[(2R)-4-morpholin-4-yl-1-phenylsulfanylbutan-2-yl]amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonylbenzamide
2.1.2 InChI
InChI=1S/C47H55ClF3N5O6S3/c1-46(2)20-18-42(34-8-12-37(48)13-9-34)36(31-46)32-55-22-24-56(25-23-55)39-14-10-35(11-15-39)45(57)53-65(60,61)41-16-17-43(44(30-41)64(58,59)47(49,50)51)52-38(19-21-54-26-28-62-29-27-54)33-63-40-6-4-3-5-7-40/h3-17,30,38,52H,18-29,31-33H2,1-2H3,(H,53,57)/t38-/m1/s1
2.1.3 InChI Key
JLYAXFNOILIKPP-KXQOOQHDSA-N
2.1.4 Canonical SMILES
CC1(CCC(=C(C1)CN2CCN(CC2)C3=CC=C(C=C3)C(=O)NS(=O)(=O)C4=CC(=C(C=C4)NC(CCN5CCOCC5)CSC6=CC=CC=C6)S(=O)(=O)C(F)(F)F)C7=CC=C(C=C7)Cl)C
2.1.5 Isomeric SMILES
CC1(CCC(=C(C1)CN2CCN(CC2)C3=CC=C(C=C3)C(=O)NS(=O)(=O)C4=CC(=C(C=C4)N[C@H](CCN5CCOCC5)CSC6=CC=CC=C6)S(=O)(=O)C(F)(F)F)C7=CC=C(C=C7)Cl)C
2.2 Other Identifiers
2.2.1 UNII
XKJ5VVK2WD
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Abt 263

2. Abt-263

3. Abt263

2.3.2 Depositor-Supplied Synonyms

1. 923564-51-6

2. Abt-263

3. Abt 263

4. Abt263

5. Abt-263 (navitoclax)

6. Navitoclax (abt-263)

7. Unii-xkj5vvk2wd

8. Xkj5vvk2wd

9. A-855071.0

10. Chembl443684

11. (r)-4-(4-((4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)-n-((4-((4-morpholino-1-(phenylthio)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

12. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[4-[[(1r)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]phenyl]sulfonyl]benzamide

13. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[(2r)-4-morpholin-4-yl-1-phenylsulfanylbutan-2-yl]amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonylbenzamide

14. (r)-4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-n-(4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)p

15. (r)-4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-n-(4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

16. 4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-n-({4-({(1r)-3-morpholin-4-yl-1-[(phenylsulfanyl)methyl]propyl}amino)-3-[(trifluoromethyl)sulfonyl]phenyl}sulfonyl)benzamide

17. 4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-n-[(4-{[(2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl]amino}-3-[(trifluoromethyl)sulfonyl]phenyl)sulfonyl]benzamide

18. Navitoclax [usan]

19. Navitoclax [usan:inn]

20. Navitoclaxum

21. C47h55clf3n5o6s3

22. 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((4-(((2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

23. Abt-263,navitoclax

24. Navitoclax [mi]

25. Abt-263 In Bulk

26. Navitoclax, Abt-263

27. Navitoclax; Abt-263

28. Navitoclax [inn]

29. Navitoclax [jan]

30. Navitoclax (usan/inn)

31. Abt-263 - Navitoclax

32. Navitoclax [who-dd]

33. Mls006011021

34. Schembl522847

35. Gtpl8319

36. Dtxsid2042640

37. Chebi:94128

38. Ex-a055

39. Chebi:131174

40. Bdbm50270877

41. Mfcd12756219

42. Nsc759659

43. S1001

44. Akos015896297

45. Zinc150338726

46. Db12340

47. Nsc-759659

48. Rg-7433

49. Ncgc00188344-01

50. Ncgc00188344-02

51. Ncgc00188344-03

52. Ncgc00188344-05

53. Ncgc00188344-08

54. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[4-[[(1r)-3-(4-mo

55. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-cyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[(1r)-3-morpholino-1-(phenylsulfanylmethyl)propyl]amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonyl-benzamide

56. Ac-31055

57. As-16690

58. Hy-10087

59. Smr004702817

60. 4-[4-[[2-(4-chlorophenyl)-5,5-dimet

61. Sw218055-2

62. D09935

63. 564a516

64. J-519525

65. Brd-k82746043-001-01-1

66. Brd-k82746043-001-02-9

67. Brd-k82746043-001-03-7

68. Brd-k82746043-001-04-5

69. Q18002993

70. (r)-4-(4-((4-chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)methyl)piperazin-1-yl)-n-((4-((4-morpholino-1-(phenylthio)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

71. 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((4-(((1r)-3-(morpholin-4-yl)-1-((phenylsulfanyl)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

72. 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-(4-(((2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl)amino)-3-(trifluoromethanesulfonyl)benzenesulfonyl)benzamide

73. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[4-[[(1r)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]phenyl]sulfonyl]benzamide;abt 263;benzamide, 4-(4-((2-(4-chlorophenyl)-5,5-dime

74. 4-{4-[(4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro[biphenyl]-2-yl)methyl]piperazin-1-yl}-n-[(4-{[(2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl]amino}-3-[(trifluoromethyl)sulfonyl]phenyl)sulfonyl]benzamide

75. Benzamide, 4-(4-((2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl)methyl)-1- Piperazinyl)-n-((4-(((1r)-3-(4-morpholinyl)-1-((phenylthio)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)-

76. Benzamide, 4-(4-((2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl)methyl)-1-piperazinyl)-n-((4-(((1r)-3-(4-morpholinyl)-1-((phenylthio)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)-

77. N-(4-{4-[2-(4-chlorophenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzoyl)-4-((r)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide

2.4 Create Date
2008-10-27
3 Chemical and Physical Properties
Molecular Weight 974.6 g/mol
Molecular Formula C47H55ClF3N5O6S3
XLogP39.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count14
Rotatable Bond Count16
Exact Mass973.2955102 g/mol
Monoisotopic Mass973.2955102 g/mol
Topological Polar Surface Area170 Ų
Heavy Atom Count65
Formal Charge0
Complexity1800
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Treatment of myelofibrosis


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


5.2 Mechanism of Action

Navitoclax targets the Bcl-2 family of proteins, the major negative regulators of apoptosis. The Bcl-2 proteins, including Bcl-2, Bcl-xL, and Bcl-w, work by binding to two other groups of proteins-the executioners (Bax, Bak) that actually start the destruction pathway, and the sentinel proteins. Cancer cells frequently overexpress the Bcl-2-like proteins, and thus, when they sustain DNA damage-from radiation, for example-they continue growing. Preventing the Bcl-2-like proteins from binding to the executioners might be able to trigger cell death in the tumor.


Drugs in Development

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Details:

Results are from an exploratory analysis of ABT-263 (navitoclax) plus ruxolitinib from Cohort 3 of the Phase 2 REFINE study in JAK inhibitor naïve myelofibrosis patients.


Lead Product(s): Navitoclax,Ruxolitinib Phosphate

Therapeutic Area: Oncology Brand Name: ABT-263

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 10, 2022

Abbvie Company Banner

01

AbbVie Inc

U.S.A
arrow
World Vaccine Congress
Not Confirmed

Details : Results are from an exploratory analysis of ABT-263 (navitoclax) plus ruxolitinib from Cohort 3 of the Phase 2 REFINE study in JAK inhibitor naïve myelofibrosis patients.

Brand Name : ABT-263

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 10, 2022

Abbvie Company Banner

Details:

Navitoclax is an investigational, oral BCL-XL/BCL-2 inhibitor. The BCL-2 family of proteins are known regulators of the apoptosis pathway. Its safety and efficacy are under evaluation as part of ongoing Phase 2 and registrational Phase 3 studies.


Lead Product(s): Navitoclax,Ruxolitinib Phosphate

Therapeutic Area: Oncology Brand Name: ABT-263

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable April 12, 2022

Abbvie Company Banner

02

AbbVie Inc

U.S.A
arrow
World Vaccine Congress
Not Confirmed

Details : Navitoclax is an investigational, oral BCL-XL/BCL-2 inhibitor. The BCL-2 family of proteins are known regulators of the apoptosis pathway. Its safety and efficacy are under evaluation as part of ongoing Phase 2 and registrational Phase 3 studies.

Brand Name : ABT-263

Molecule Type : Small molecule

Upfront Cash : Not Applicable

April 12, 2022

Abbvie Company Banner

Details:

In the Phase 1 study, Venetoclax with Navitoclax and chemotherapy was well tolerated and had promising efficacy in heavily pretreated pediatric patients with ALL and LL.


Lead Product(s): Venetoclax,Navitoclax

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IProduct Type: Small molecule

Sponsor: AbbVie Inc

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable December 06, 2020

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03

World Vaccine Congress
Not Confirmed
World Vaccine Congress
Not Confirmed

Details : In the Phase 1 study, Venetoclax with Navitoclax and chemotherapy was well tolerated and had promising efficacy in heavily pretreated pediatric patients with ALL and LL.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

December 06, 2020

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