9458. Tipifarnib

Nomenclature

CAS number: 192185-72-1; 192185-68-5 (unspecified stereo)
6-[(R)-Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone; R-115777; Zarnestra (Janssen).
C27H22Cl2N4O; mol wt 489.40.
C 66.26%, H 4.53%, Cl 14.49%, N 11.45%, O 3.27%.

Description and references

Farnesyl transferase inhibitor. Prepn: M. G. Venet et al., WO 9721701; eidem, US 6037350 (1997, 2000 both to Janssen). Review of syntheses: P. R. Angibaud et al., Eur. J. Org. Chem. 2004, 479-486. Inhibition of farnesyl protein transferase and antitumor effects in vivo: D. W. End et al., Cancer Res. 61, 131 (2001). Clinical pharmacology and pharmacokinetics: J. Zujewski et al., J. Clin. Oncol. 18, 927 (2000). Accelerator mass spec determn in biological samples: R. C. Garner et al., Drug Metab. Dispos. 30, 823 (2002). Clinical evaluation in hematologic malignancies: J. Cortes et al., Blood 101, 1692 (2003). Review of clinical experience: P. Norman, Curr. Opin. Investig. Drugs 3, 313-319 (2002).

Chemical structure

Properties

Crystals from 2-propanol, mp 234°. [α]D20 +22.86° (c = 0.98 in methanol).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Farnesyl Transferase Inhibitors