| Identification | Back Directory | [Name]
Tipifarnib | [CAS]
192185-72-1 | [Synonyms]
CS-2330
R115777
IND 58359
Zarnestra
ipifarnib
TIPIFARNIB
(R)-(+)-R 115777
Tipifarnib(R115777)
Tipifarnib USP/EP/BP
TIPIFARNIB ZARNESTRA
Tipifarnib (IND 58359
Tipifarnib(Zarnestra,NSC-702818, R-115777)
Tipifarnib (Zarnestra) IND 58359, R115777
ZARNESTRA; IND 58359; R115777; IND-58359; IND58359; R-115777; R 115777
(R)-6-(Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone
6-[(R)-AMino(4-chlorophenyl)(1-Methyl-1H-iMidazol-5-yl)Methyl]-4-(3-chlorophenyl)-1-Methyl-2(1H)-quinolinone
(R)-6-(amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one
2(1H)-Quinolinone, 6-[(R)-amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl- | [Molecular Formula]
C27H22Cl2N4O | [MDL Number]
MFCD07772347 | [MOL File]
192185-72-1.mol | [Molecular Weight]
489.4 |
| Chemical Properties | Back Directory | [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) | [form ]
powder | [pka]
7.20±0.10(Predicted) | [color ]
white to beige | [optical activity]
[α]/D 17 to 24°, c = 1 in methanol |
| Hazard Information | Back Directory | [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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