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    Technical details about Tipifarnib, learn more about the structure, uses, toxicity, action, side effects and more

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    Tipifarnib

    APIs // Active Pharmaceutical Ingredients

    DEVELOPMENTS

    PRICE INFORMATION

    DIGITAL CONTENT

    PharmaCompass

    Inke S.A: APIs manufacturing plant.

    ChemWerth works in generic API development & supply, non-infringement patent strategy development and regulatory support.

    2D Structure
    1. 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

    2D Structure

    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 Weight 489.4 g/mol
    Molecular Formula C27H22Cl2N4O
    XLogP34.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass488.1170667 g/mol
    Monoisotopic Mass488.1170667 g/mol
    Topological Polar Surface Area64.2 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity785
    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

    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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