tipifarnib   Click here for help

GtoPdb Ligand ID: 8025

Synonyms: R-115777 | R115777
PDB Ligand
Compound class: Synthetic organic
Comment: Tipifarnib is a non-peptidomimetic competitive farnesyltransferase inhibitor (FTI) [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 65.84
Molecular weight 488.12
XLogP 6.97
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(cc1)C(c1cncn1C)(c1ccc2c(c1)c(cc(=O)n2C)c1cccc(c1)Cl)N
Isomeric SMILES Clc1ccc(cc1)[C@](c1cncn1C)(c1ccc2c(c1)c(cc(=O)n2C)c1cccc(c1)Cl)N
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
1. Angibaud P, Bourdrez X, Devine A, End DW, Freyne E, Ligny Y, Muller P, Mannens G, Pilatte I, Poncelet V et al.. (2003)
5-imidazolyl-quinolinones, -quinazolinones and -benzo-azepinones as farnesyltransferase inhibitors.
Bioorg Med Chem Lett, 13 (9): 1543-7. [PMID:12699751]
2. Downward J. (2003)
Targeting RAS signalling pathways in cancer therapy.
Nat Rev Cancer, 3 (1): 11-22. [PMID:12509763]
3. End DW, Smets G, Todd AV, Applegate TL, Fuery CJ, Angibaud P, Venet M, Sanz G, Poignet H, Skrzat S et al.. (2001)
Characterization of the antitumor effects of the selective farnesyl protein transferase inhibitor R115777 in vivo and in vitro.
Cancer Res, 61 (1): 131-7. [PMID:11196150]
4. Venet M, End D, Angibaud P. (2003)
Farnesyl protein transferase inhibitor ZARNESTRA R115777 - history of a discovery.
Curr Top Med Chem, 3 (10): 1095-102. [PMID:12769710]