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Tipifarnib

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Tipifarnib Basic information

Product Name:
Tipifarnib
Synonyms:
  • ipifarnib
  • CS-2330
  • ZARNESTRA; IND 58359; R115777; IND-58359; IND58359; R-115777; R 115777
  • TIPIFARNIB
  • TIPIFARNIB ZARNESTRA
  • (R)-6-(Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone
  • Zarnestra
  • (R)-(+)-R 115777
CAS:
192185-72-1
MF:
C27H22Cl2N4O
MW:
489.4
Product Categories:
  • Inhibitors
  • Amines
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Tyrosine Kinase Inhibitors
  • Inhibitor
  • Antineoplastic
Mol File:
192185-72-1.mol
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Tipifarnib Chemical Properties

Melting point:
211-213°C (dec.)
Boiling point:
681.7±55.0 °C(Predicted)
Density 
1.33±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
7.20±0.10(Predicted)
form 
powder
color 
white to beige
optical activity
[α]/D 17 to 24°, c = 1 in methanol
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Safety Information

HS Code 
2933790090
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Tipifarnib Usage And Synthesis

Chemical Properties

Off-White to Pale Beige Solid

Uses

A farnesyltransferase inhibitor. Sensitizes human multiple myeloma cell to proteasome inhibition by blocking degradation of bortezomib(B675700)-induced aggresomes. Also shown to inhibit the growth of myeloid leukemia cell lines and primary leukemia cells by inducing apoptosis and cell-cycle blockage when combined with rapamycin(R124000).

Definition

ChEBI: Tipifarnib is a quinolone that is 1-methylquinolin-2-one which carries a 3-chlorophenyl and an amino(4-chlorophenyl)(1-methyl-imidazol-5-yl)methyl groups at the 4 and 6 positions, respectively (the R-isomer). It has a role as an antineoplastic agent, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor and an apoptosis inducer. It is a quinolone, a member of monochlorobenzenes, a member of imidazoles and a primary amino compound.

General Description

Pre-clinical studies show that tipifarnib has antiproliferative effects on pancreatic cancer cell lines at clinically relevant concentrations (concentration that inhibits 50% growth [IC50] from 9.5 to 500?nmol/L). It also exhibits marked growth retardation and antiangiogenic effects in a pancreatic cancer xenograft model.

Biological Activity

tipifarnib (also known as zarnestra or r115777), an orally bioavailable quinolone analog of imidazole heterocyclics, is a potent and specific nonpeptidomimetic competitive inhibitor of farnesyltransferase (ftase), an enezyme mediating post-translational farnesylation of multiple protein substrates involved in tumor cell proliferation. it has demonstrated inhibition of growth and proliferation of a broad range of human tumor models (either wild-type or mutated ras) via cytostatic rather than cytotoxic activity both in vitro and in vivo. it cell-type dependently induces apoptosis in some neoplastic cell lineages other than acute myeloid leukemia (aml), including multiple myeloma (mm) cell lines and mm cultures from patients.p.k. epling-burnett and thomas p. loughran jr. suppression of farnesyltransferase activity in acute myeloid leukemia and myelodysplastic syndrome: current understanding and recommended use of tipifarnib. expert opin investig drugs. 2010; 19(5): 689-698jean-pierre armand, alan k. burnett, johannes drach, jean-luc harousseau, bob lowenberg and jesus san miguel. the emerging role of targeted therapy for hematologic malignancies: update on bortezomib and tipifarnib. the oncologist 2007, 12:281-290elzbieta izbicka, david campos, gilbert carrizales and amita patnaik. biomarkers of anticancer activity of r115777 (tipifarnib, zarnestra) in human breast cancer models in vitro. anticancer research 2005; 25: 3215-3224

Biochem/physiol Actions

Tipifarnib (R115777) is an orally active and potent farnesyltransferase (FTase) inhibitor that exhibits potent anti-tumorigenic effects. Tipifarnib mechanism of action is not fully understand.

target

FTase

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