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Tipifarnib

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Also known as: 192185-72-1, Zarnestra, R115777, R-115777, Tipifarnib (zarnestra), (r)-6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1h)-quinolinone

Molecular Formula

C₂₇H₂₂Cl₂N₄O

Molecular Weight

489.4 g/mol

InChI Key

PLHJCIYEEKOWNM-HHHXNRCGSA-N

FDA UNII

MAT637500A

Tipifarnib is a nonpeptidomimetic quinolinone with potential antineoplastic activity. Tipifarnib binds to and inhibits the enzyme farnesyl protein transferase, an enzyme involved in protein processing (farnesylation) for signal transduction. By inhibiting the farnesylation of proteins, this agent prevents the activation of Ras oncogenes, inhibits cell growth, induces apoptosis, and inhibits angiogenesis. (NCI04)

1 2D Structure

Tipifarnib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-[(R)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one

2.1.2 InChI

InChI=1S/C27H22Cl2N4O/c1-32-16-31-15-25(32)27(30,18-6-9-20(28)10-7-18)19-8-11-24-23(13-19)22(14-26(34)33(24)2)17-4-3-5-21(29)12-17/h3-16H,30H2,1-2H3/t27-/m1/s1

2.1.3 InChI Key

PLHJCIYEEKOWNM-HHHXNRCGSA-N

2.1.4 Canonical SMILES

CN1C=NC=C1C(C2=CC=C(C=C2)Cl)(C3=CC4=C(C=C3)N(C(=O)C=C4C5=CC(=CC=C5)Cl)C)N

2.1.5 Isomeric SMILES

CN1C=NC=C1[C@@](C2=CC=C(C=C2)Cl)(C3=CC4=C(C=C3)N(C(=O)C=C4C5=CC(=CC=C5)Cl)C)N

2.2 Other Identifiers

2.2.1 UNII

MAT637500A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (r)-6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1h)-quinolinone

2. 2 (1h))-quinolinone,6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-,(+)-

3. R 115777

4. R-115777

5. R115777

6. Zarnestra

2.3.2 Depositor-Supplied Synonyms

1. 192185-72-1

2. Zarnestra

3. R115777

4. R-115777

5. Tipifarnib (zarnestra)

6. (r)-6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1h)-quinolinone

7. Ind 58359

8. 6-[(r)-amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2(1h)-one

9. R-11577

10. Nsc-702818

11. (r)-6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methylquinolin-2(1h)-one

12. Mat637500a

13. 6-[(r)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one

14. 6-[(s)-amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2(1h)-one

15. Tipifarnib [usan]

16. R115777;ind 58359

17. Jan

18. Tipifarnib (usan/inn)

19. Tipifarnib [usan:inn]

20. Tipifarnibum

21. Tipifarneb

22. Unii-mat637500a

23. Ccris 9329

24. Tipifarnib - Zarnestra

25. Tipifarnib [mi]

26. (r)-tipifarnib

27. Tipifarnib [inn]

28. D03720

29. Schembl8097

30. Tipifarnib [mart.]

31. Tipifarnib (r115777)

32. Tipifarnib [who-dd]

33. Mls006011105

34. Gtpl8025

35. Dtxsid5041140

36. Schembl21544535

37. Tipifarnib, >=98% (hplc)

38. R115777; Tipifarnib

39. 1x81

40. Chebi:141969

41. Bcpp000044

42. Hms3654b10

43. Hms3748e21

44. 6-[(r)-amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl}-4-(3-chlorophenyl)-1-methyl-2(1h)-quinolinone

45. Amy20627

46. Bcp02262

47. Ex-a2346

48. Bdbm50370385

49. Nsc760444

50. S1453

51. Zinc24809155

52. Akos027326864

53. Ccg-264893

54. Cs-0475

55. Db04960

56. Nsc-760444

57. Sb16693

58. Ncgc00250406-01

59. Ncgc00250406-02

60. 2 (1h))-quinolinone,6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-, (+)-

61. 2 (1h))-quinolinone,6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-,(+)-

62. 2(1h)-quinolinone,6-[(r)-amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-

63. Ac-33171

64. Bs-15758

65. Hy-10502

66. Smr002530065

67. Tipifarnib; Ind 58359; R115777

68. Sw219749-1

69. D70631

70. (r)-(+)-r115777

71. 185t721

72. Q-102509

73. Brd-k62965247-001-01-5

74. Ind 58359;r115777;ind-58359;ind58359;r-115777;r 115777

75. (+)-(r)-6-[amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1h)-quinolinone

76. 2 (1h))-quinolinone,6-(amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-

77. 2(1h)-quinolinone, 6-[(r)-amino(4-chlorophenyl)(1-methyl-1h-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₂Cl₂N₄O
Molecular Weight	489.4 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	488.1170667 g/mol
Monoisotopic Mass	488.1170667 g/mol
Topological Polar Surface Area	64.2 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	785
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

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in colorectal cancer, leukemia (myeloid), pancreatic cancer, and solid tumors.

Treatment of head and neck epithelial malignant neoplasms

5 Pharmacology and Biochemistry

5.1 Pharmacology

R115777, a nonpeptidomimetic farnesyl transferase inhibitor, suppresses the growth of human pancreatic adenocarcinoma cell lines. This growth inhibition is associated with modulation in the phosphorylation levels of signal transducers and activators of transcription 3 (STAT3) and extracellular signal-regulated kinases (ERK).

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

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

5.3 Mechanism of Action

The farnesyltransferase inhibitors (FTIs) are a class of experimental cancer drugs that target protein farnesyltransferase with the downstream effect of preventing the proper functioning of the Ras protein, which is commonly abnormally active in cancer. After translation, RAS goes through four steps of modification: isoprenylation, proteolysis, methylation and palmitoylation. Isoprenylation involves the enzyme farnesyltransferase (FTase) transferring a farnesyl group from farnesyl pyrophosphate (FPP) to the pre-RAS protein. Also, a related enzyme geranylgeranyltransferase I (GGTase I) has the ability to transfer a geranylgeranyl group to K and N-RAS. Farnesyl is necessary to attach RAS to the cell membrane. Without attachment to the cell membrane, RAS is not able to transfer signals from membrane receptors (Reuter et al., 2000).

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