(S)-Tipifarnib | CAS# 192185-71-0 | Enantiomer of Tipifarnib

MedKoo Cat#: 565365 | Name: (S)-Tipifarnib

Description:

WARNING: This product is for research use only, not for human or veterinary use.

(S)-Tipifarnib is an inactive enantiomer of Tipifarnib to be used as a negative control.

Chemical Structure

(S)-Tipifarnib

CAS#192185-71-0

Theoretical Analysis

MedKoo Cat#: 565365

Name: (S)-Tipifarnib

CAS#: 192185-71-0

Chemical Formula: C27H22Cl2N4O

Exact Mass: 488.1171

Molecular Weight: 489.40

Elemental Analysis: C, 66.26; H, 4.53; Cl, 14.49; N, 11.45; O, 3.27

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

(S)-Zarnestra; (S)-Tipifarnib

IUPAC/Chemical Name

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

InChi Key

PLHJCIYEEKOWNM-MHZLTWQESA-N

InChi Code

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-/m0/s1

SMILES Code

O=C1N(C)C2=C(C=C([C@](C3=CC=C(Cl)C=C3)(N)C4=CN=CN4C)C=C2)C(C5=CC=CC(Cl)=C5)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 489.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: 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. Tipifarnib prevents development of hypoxia-induced pulmonary hypertension. Cardiovasc Res. 2017 Mar 1;113(3):276-287. doi: 10.1093/cvr/cvw258. PubMed PMID: 28395021; PubMed Central PMCID: PMC5408956. 2: Shirozu K, Hirai S, Tanaka T, Hisaka S, Kaneki M, Ichinose F. Farnesyltransferase inhibitor, tipifarnib, prevents galactosamine/lipopolysaccharide-induced acute liver failure. Shock. 2014 Dec;42(6):570-577. doi: 10.1097/SHK.0000000000000239. PubMed PMID: 25046541; PubMed Central PMCID: PMC4236263. 3: Ding N, Cui XX, Gao Z, Huang H, Wei X, Du Z, Lin Y, Shih WJ, Rabson AB, Conney AH, Hu C, Zheng X. A triple combination of atorvastatin, celecoxib and tipifarnib strongly inhibits pancreatic cancer cells and xenograft pancreatic tumors. Int J Oncol. 2014 Jun;44(6):2139-45. doi: 10.3892/ijo.2014.2350. Epub 2014 Mar 19. PubMed PMID: 24647860; PubMed Central PMCID: PMC4063540. 4: 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. 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. Neuro Oncol. 2014 May;16(5):707-18. doi: 10.1093/neuonc/nou004. Epub 2014 Feb 4. PubMed PMID: 24500418; PubMed Central PMCID: PMC3984559. 5: Erba HP, Othus M, Walter RB, Kirschbaum MH, Tallman MS, Larson RA, Slovak ML, Kopecky KJ, Gundacker HM, Appelbaum FR. Four different regimens of farnesyltransferase inhibitor tipifarnib in older, untreated acute myeloid leukemia patients: North American Intergroup Phase II study SWOG S0432. Leuk Res. 2014 Mar;38(3):329-33. doi: 10.1016/j.leukres.2013.12.001. Epub 2013 Dec 11. PubMed PMID: 24411921; PubMed Central PMCID: PMC4247790. 6: Bentke A, Małecki J, Ostrowska B, Krzykowska-Petitjean K, Laidler P. Tanespimycin and tipifarnib exhibit synergism in inducing apoptosis in melanoma cell lines from later stages of tumor progression. Cancer Invest. 2013 Oct;31(8):545-9. doi: 10.3109/07357907.2013.830736. Epub 2013 Sep 25. PubMed PMID: 24066674. 7: 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. Farnesyltransferase inhibitor tipifarnib inhibits Rheb prenylation and stabilizes Bax in acute myelogenous leukemia cells. Haematologica. 2014 Jan;99(1):60-9. doi: 10.3324/haematol.2013.087734. Epub 2013 Aug 30. PubMed PMID: 23996484; PubMed Central PMCID: PMC4007940. 8: Ducassou A, Uro-Coste E, Verrelle P, Filleron T, Benouaich-Amiel A, Lubrano V, Sol JC, Delisle MB, Favre G, Ken S, Laprie A, De Porre P, Toulas C, Poublanc M, Cohen-Jonathan Moyal E. αvβ3 Integrin and Fibroblast growth factor receptor 1 (FGFR1): Prognostic factors in a phase I-II clinical trial associating continuous administration of Tipifarnib with radiotherapy for patients with newly diagnosed glioblastoma. Eur J Cancer. 2013 Jun;49(9):2161-9. doi: 10.1016/j.ejca.2013.02.033. Epub 2013 Apr 6. PubMed PMID: 23566417. 9: Buckner FS, Bahia MT, Suryadevara PK, White KL, Shackleford DM, Chennamaneni NK, Hulverson MA, Laydbak JU, Chatelain E, Scandale I, Verlinde CL, Charman SA, Lepesheva GI, Gelb MH. Pharmacological characterization, structural studies, and in vivo activities of anti-Chagas disease lead compounds derived from tipifarnib. Antimicrob Agents Chemother. 2012 Sep;56(9):4914-21. doi: 10.1128/AAC.06244-11. Epub 2012 Jul 9. PubMed PMID: 22777048; PubMed Central PMCID: PMC3421879. 10: Burnett AK, Russell NH, Culligan D, Cavanagh J, Kell J, Wheatley K, Virchis A, Hills RK, Milligan D; AML Working Group of the UK National Cancer Research Institute. The addition of the farnesyl transferase inhibitor, tipifarnib, to low dose cytarabine does not improve outcome for older patients with AML. Br J Haematol. 2012 Aug;158(4):519-22. doi: 10.1111/j.1365-2141.2012.09165.x. Epub 2012 May 29. PubMed PMID: 22639959. 11: Li T, Guo M, Gradishar WJ, Sparano JA, Perez EA, Wang M, Sledge GW. A phase II trial of capecitabine in combination with the farnesyltransferase inhibitor tipifarnib in patients with anthracycline-treated and taxane-resistant metastatic breast cancer: an Eastern Cooperative Oncology Group Study (E1103). Breast Cancer Res Treat. 2012 Jul;134(1):345-52. doi: 10.1007/s10549-012-2071-z. Epub 2012 May 1. PubMed PMID: 22547107; PubMed Central PMCID: PMC4596817. 12: Krzykowska-Petitjean K, Małecki J, Bentke A, Ostrowska B, Laidler P. Tipifarnib and tanespimycin show synergic proapoptotic activity in U937 cells. J Cancer Res Clin Oncol. 2012 Mar;138(3):537-44. doi: 10.1007/s00432-011-1131-9. Epub 2011 Dec 31. PubMed PMID: 22209975; PubMed Central PMCID: PMC3278622. 13: Karp JE, Vener TI, Raponi M, Ritchie EK, Smith BD, Gore SD, Morris LE, Feldman EJ, Greer JM, Malek S, Carraway HE, Ironside V, Galkin S, Levis MJ, McDevitt MA, Roboz GR, Gocke CD, Derecho C, Palma J, Wang Y, Kaufmann SH, Wright JJ, Garret-Mayer E. Multi-institutional phase 2 clinical and pharmacogenomic trial of tipifarnib plus etoposide for elderly adults with newly diagnosed acute myelogenous leukemia. Blood. 2012 Jan 5;119(1):55-63. doi: 10.1182/blood-2011-08-370825. Epub 2011 Oct 14. PubMed PMID: 22001391; PubMed Central PMCID: PMC3251236. 14: Bai F, Villagra AV, Zou J, Painter JS, Connolly K, Blaskovich MA, Sokol L, Sebti S, Djeu JY, Loughran TP, Wei S, Sotomayor E, Epling-Burnette P. Tipifarnib-mediated suppression of T-bet-dependent signaling pathways. Cancer Immunol Immunother. 2012 Apr;61(4):523-33. doi: 10.1007/s00262-011-1109-0. Epub 2011 Oct 9. PubMed PMID: 21983879; PubMed Central PMCID: PMC4612510. 15: Witzig TE, Tang H, Micallef IN, Ansell SM, Link BK, Inwards DJ, Porrata LF, Johnston PB, Colgan JP, Markovic SN, Nowakowski GS, Thompson CA, Allmer C, Maurer MJ, Gupta M, Weiner G, Hohl R, Kurtin PJ, Ding H, Loegering D, Schneider P, Peterson K, Habermann TM, Kaufmann SH. Multi-institutional phase 2 study of the farnesyltransferase inhibitor tipifarnib (R115777) in patients with relapsed and refractory lymphomas. Blood. 2011 Nov 3;118(18):4882-9. doi: 10.1182/blood-2011-02-334904. Epub 2011 Jul 1. PubMed PMID: 21725056; PubMed Central PMCID: PMC3208296. 16: Marcuzzi A, De Leo L, Decorti G, Crovella S, Tommasini A, Pontillo A. The farnesyltransferase inhibitors tipifarnib and lonafarnib inhibit cytokines secretion in a cellular model of mevalonate kinase deficiency. Pediatr Res. 2011 Jul;70(1):78-82. doi: 10.1203/PDR.0b013e31821b581c. PubMed PMID: 21430599. 17: Yanamandra N, Buzzeo RW, Gabriel M, Hazlehurst LA, Mari Y, Beaupre DM, Cuevas J. Tipifarnib-induced apoptosis in acute myeloid leukemia and multiple myeloma cells depends on Ca2+ influx through plasma membrane Ca2+ channels. J Pharmacol Exp Ther. 2011 Jun;337(3):636-43. doi: 10.1124/jpet.110.172809. Epub 2011 Mar 4. PubMed PMID: 21378206; PubMed Central PMCID: PMC3101005. 18: Haas-Kogan DA, Banerjee A, Poussaint TY, Kocak M, Prados MD, Geyer JR, Fouladi M, Broniscer A, Minturn JE, Pollack IF, Packer RJ, Boyett JM, Kun LE. Phase II trial of tipifarnib and radiation in children with newly diagnosed diffuse intrinsic pontine gliomas. Neuro Oncol. 2011 Mar;13(3):298-306. doi: 10.1093/neuonc/noq202. PubMed PMID: 21339191; PubMed Central PMCID: PMC3064607. 19: Hong DS, Cabanillas ME, Wheler J, Naing A, Tsimberidou AM, Ye L, Busaidy NL, Waguespack SG, Hernandez M, El Naggar AK, Bidyasar S, Wright J, Sherman SI, Kurzrock R. Inhibition of the Ras/Raf/MEK/ERK and RET kinase pathways with the combination of the multikinase inhibitor sorafenib and the farnesyltransferase inhibitor tipifarnib in medullary and differentiated thyroid malignancies. J Clin Endocrinol Metab. 2011 Apr;96(4):997-1005. doi: 10.1210/jc.2010-1899. Epub 2011 Feb 2. Erratum in: J Clin Endocrinol Metab. 2012 Apr;97(4):1399. J Clin Endocrinol Metab. 2011 Jul;96(7):2286. Busaidy, Naifa L [added]; El Naggar, Alder K [corrected to El Naggar, Adel K]. PubMed PMID: 21289252; PubMed Central PMCID: PMC3070247. 20: David E, Kaufman JL, Flowers CR, Schafer-Hales K, Torre C, Chen J, Marcus AI, Sun SY, Boise LH, Lonial S. Tipifarnib sensitizes cells to proteasome inhibition by blocking degradation of bortezomib-induced aggresomes. Blood. 2010 Dec 9;116(24):5285-8. doi: 10.1182/blood-2010-03-272393. Epub 2010 Sep 15. PubMed PMID: 20844234; PubMed Central PMCID: PMC4347258.