Tipifarnib, Free base

  • CAT Number: I002461
  • CAS Number: 192185-72-1
  • Molecular Formula: C₂₇H₂₂Cl₂N₄O
  • Molecular Weight: 489.4
  • Purity: ≥95%
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Tipifarnib (Cat No.: I002461) is a highly potent and selective inhibitor of farnesyltransferase (FTase), an enzyme involved in protein prenylation. It exerts its most significant antiproliferative effects in cells with mutations in H-ras or N-ras genes. By inhibiting FTase, Tipifarnib disrupts the prenylation process critical for the activation of Ras proteins, which are involved in cell signaling and growth. This specific targeting of mutant Ras-driven pathways makes Tipifarnib a promising candidate for cancer therapy, particularly in cases where Ras mutations play a prominent role in the disease’s progression. If you need to, please contact us in time, and we will reply to you as soon as possible within 24 hours.

Catalog Number I002461
CAS Number 192185-72-1
Synonyms

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

Molecular Formula

C₂₇H₂₂Cl₂N₄O

Purity 95%
Target Transferase
Solubility 10 mM in DMSO
Storage -20°C
IC50 0.6 nM
IUPAC Name 6-[(R)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one
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
InChIKey PLHJCIYEEKOWNM-HHHXNRCGSA-N
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
Reference

</br>1:Tipifarnib prevents development of hypoxia-induced pulmonary hypertension. Duluc L, Ahmetaj-Shala B, Mitchell J, Abdul-Salam VB, Mahomed AS, Aldabbous L, Oliver E, Iannone L, Dubois OD, Storck EM, Tate EW, Zhao L, Wilkins MR, Wojciak-Stothard B.Cardiovasc Res. 2017 Mar 1;113(3):276-287. doi: 10.1093/cvr/cvw258. PMID: 28395021 Free PMC Article</br>2:Voxel-based evidence of perfusion normalization in glioblastoma patients included in a phase I-II trial of radiotherapy/tipifarnib combination. Ken S, Deviers A, Filleron T, Catalaa I, Lotterie JA, Khalifa J, Lubrano V, Berry I, Péran P, Celsis P, Moyal EC, Laprie A.J Neurooncol. 2015 Sep;124(3):465-73. doi: 10.1007/s11060-015-1860-8. Epub 2015 Jul 19. PMID: 26189058 </br>3:Simvastatin interacts synergistically with tipifarnib to induce apoptosis in leukemia cells through the disruption of RAS membrane localization and ERK pathway inhibition. Ahmed TA, Hayslip J, Leggas M.Leuk Res. 2014 Nov;38(11):1350-7. doi: 10.1016/j.leukres.2014.09.002. Epub 2014 Sep 16. PMID: 25262449 </br>4:Farnesyltransferase inhibitor, tipifarnib, prevents galactosamine/lipopolysaccharide-induced acute liver failure. Shirozu K, Hirai S, Tanaka T, Hisaka S, Kaneki M, Ichinose F.Shock. 2014 Dec;42(6):570-7. doi: 10.1097/SHK.0000000000000239. PMID: 25046541 Free PMC Article</br>5:A triple combination of atorvastatin, celecoxib and tipifarnib strongly inhibits pancreatic cancer cells and xenograft pancreatic tumors. Ding N, Cui XX, Gao Z, Huang H, Wei X, Du Z, Lin Y, Shih WJ, Rabson AB, Conney AH, Hu C, Zheng X.Int J Oncol. 2014 Jun;44(6):2139-45. doi: 10.3892/ijo.2014.2350. Epub 2014 Mar 19. PMID: 24647860 Free PMC Article</br>6:Phase 2 randomized, flexible crossover, double-blinded, placebo-controlled trial of the farnesyltransferase inhibitor tipifarnib in children and young adults with neurofibromatosis type 1 and progressive plexiform neurofibromas. Widemann BC, Dombi E, Gillespie A, Wolters PL, Belasco J, Goldman S, Korf BR, Solomon J, Martin S, Salzer W, Fox E, Patronas N, Kieran MW, Perentesis JP, Reddy A, Wright JJ, Kim A, Steinberg SM, Balis FM.Neuro Oncol. 2014 May;16(5):707-18. doi: 10.1093/neuonc/nou004. Epub 2014 Feb 4. PMID: 24500418 Free PMC Article</br>7:Four different regimens of farnesyltransferase inhibitor tipifarnib in older, untreated acute myeloid leukemia patients: North American Intergroup Phase II study SWOG S0432. Erba HP, Othus M, Walter RB, Kirschbaum MH, Tallman MS, Larson RA, Slovak ML, Kopecky KJ, Gundacker HM, Appelbaum FR.Leuk Res. 2014 Mar;38(3):329-33. doi: 10.1016/j.leukres.2013.12.001. Epub 2013 Dec 11. PMID: 24411921 Free PMC Article</br>8:Phase I-II study of the farnesyl transferase inhibitor tipifarnib plus sequential weekly paclitaxel and doxorubicin-cyclophosphamide in HER2/neu-negative inflammatory carcinoma and non-inflammatory estrogen receptor-positive breast carcinoma. Andreopoulou E, Vigoda IS, Valero V, Hershman DL, Raptis G, Vahdat LT, Han HS, Wright JJ, Pellegrino CM, Cristofanilli M, Alvarez RH, Fehn K, Fineberg S, Sparano JA.Breast Cancer Res Treat. 2013 Oct;141(3):429-35. doi: 10.1007/s10549-013-2704-x. Epub 2013 Sep 26. PMID: 24068539 Free PMC Article</br>9:Tanespimycin and tipifarnib exhibit synergism in inducing apoptosis in melanoma cell lines from later stages of tumor progression. Bentke A, Małecki J, Ostrowska B, Krzykowska-Petitjean K, Laidler P.Cancer Invest. 2013 Oct;31(8):545-9. doi: 10.3109/07357907.2013.830736. Epub 2013 Sep 25. PMID: 24066674 </br>10:Farnesyltransferase inhibitor tipifarnib inhibits Rheb prenylation and stabilizes Bax in acute myelogenous leukemia cells. Ding H, McDonald JS, Yun S, Schneider PA, Peterson KL, Flatten KS, Loegering DA, Oberg AL, Riska SM, Huang S, Sinicrope FA, Adjei AA, Karp JE, Meng XW, Kaufmann SH.Haematologica. 2014 Jan;99(1):60-9. doi: 10.3324/haematol.2013.087734. Epub 2013 Aug 30. PMID: 23996484 Free PMC Article

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