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Compound Detail

CHEMBL289228

TIPIFARNIB
🧪 Phase III
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🧪 Phase III
Cn1cncc1[C@@](N)(c1ccc(Cl)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL289228
Name TIPIFARNIB
Phase Phase III
Structure Type MOL
InChI Key PLHJCIYEEKOWNM-HHHXNRCGSA-N

Known Names

NSC-702818 R-11577 R-115777 R115777 Tipifarnib Zarnestra
568
Targets
719
Activities
3
Assay Types
1
PK Parameters
20
Publications
6
Known Names
20
Indications
1
Mechanisms

Molecular Properties

489.4
MW (Da)
5.50
ALogP
5
HBA
1
HBD
65.8
PSA (Ų)
0.36
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -farnib
USAN Year 2002

Extended Properties

Molecular Formula C27H22Cl2N4O
MW 489.41
Aromatic Rings 5
Heavy Atoms 34
NP-Likeness -0.73

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Protein farnesyltransferase inhibitor INHIBITOR Protein farnesyltransferase ✓ ✓

Indications

Leukemia, Monocytic, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myelomonocytic, Acute Myelodysplastic Syndromes Astrocytoma Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Colorectal Neoplasms Glioblastoma Glioblastoma Gliosarcoma Head and Neck Neoplasms Inflammatory Breast Neoplasms Leukemia, Large Granular Lymphocytic Leukemia, Lymphocytic, Chronic, B-Cell

Activity Summary

IC50 701 meas. best 9.35
EC50 17 meas. best 9.26
Ki 1 meas. best 9.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.35 8.356 0.5 10
Unchecked
CHEMBL612545
 Ki 9.3 9.3 0.5 1
Unchecked
CHEMBL612545
 EC50 9.26 8.7229 0.6 7
Protein farnesyltransferase
CHEMBL2095178
 IC50 9.24 9.2025 0.6 4
Protein farnesyltransferase
CHEMBL2094108
 IC50 9.1 8.8738 0.8 8
Protein farnesyltransferase
CHEMBL2096912
 EC50 8.8 8.35 1.6 4
NIH3T3
CHEMBL614822
 IC50 8.77 8.77 1.7 3
HT1197
CHEMBL614836
 IC50 8.77 6.85 1.7 2
NIH3T3
CHEMBL614822
 EC50 8.7 8.565 2.0 2
Trypanosoma cruzi
CHEMBL368
 EC50 8.4 8.4 4.0 3
RPMI-6666
CHEMBL2366187
 IC50 8.13 8.13 7.4 1
SU.86.86
CHEMBL4630707
 IC50 8.02 8.02 9.5 1
ML-2
CHEMBL614356
 IC50 7.87 7.87 13.6 1
SIG-M5
CHEMBL2366251
 IC50 7.84 7.84 14.6 1
Capan-2
CHEMBL1075417
 IC50 7.8 6.385 16.0 2
QIMR-WIL
CHEMBL2366337
 IC50 7.79 7.79 16.3 1
Protein farnesyltransferase (PFT)
CHEMBL2111381
 IC50 7.77 7.77 17.0 1
A4-Fuk
CHEMBL2366356
 IC50 7.69 7.69 20.6 1
ETK-1
CHEMBL2366116
 IC50 7.67 7.67 21.5 1
MEL-JUSO
CHEMBL1075501
 IC50 7.63 7.63 23.4 1
HCT-116
CHEMBL394
 EC50 7.62 7.62 24.0 1
NCI-H441
CHEMBL1075542
 IC50 7.44 6.155 36.0 2
NALM-6
CHEMBL614187
 IC50 7.44 7.44 36.2 1
IA-LM
CHEMBL2366366
 IC50 7.32 7.32 47.5 1
Daoy
CHEMBL612519
 IC50 7.24 7.24 57.5 1
REH
CHEMBL2366320
 IC50 7.23 7.23 59.2 1
KU812 cell line
CHEMBL613997
 IC50 7.01 7.01 97.1 1
KM12
CHEMBL614709
 IC50 6.93 6.93 116.9 1
LCLC-103H cell line
CHEMBL614066
 IC50 6.89 6.89 129.0 1
BC1 cell line
CHEMBL614277
 IC50 6.89 6.89 130.0 1
CMK
CHEMBL2366177
 IC50 6.82 6.82 151.4 1
MCF7
CHEMBL387
 IC50 6.78 6.145 166.3 2
SK-LMS-1
CHEMBL2366096
 IC50 6.74 6.74 184.1 1
Calu-1
CHEMBL613505
 IC50 6.74 6.74 181.3 1
NCI-H2122
CHEMBL1075533
 IC50 6.72 6.72 191.4 1
HH
CHEMBL2366310
 IC50 6.72 6.72 190.9 1
SNG-M
CHEMBL1075582
 IC50 6.69 6.69 203.5 1
IGROV-1
CHEMBL613984
 IC50 6.68 6.68 208.2 1
HMV-2 cell line
CHEMBL614826
 IC50 6.67 6.67 215.8 1
KYSE-270
CHEMBL1075486
 IC50 6.66 6.66 216.7 1
NTERA-2-cl-D1
CHEMBL614206
 IC50 6.62 6.62 237.4 1
LoVo
CHEMBL614721
 IC50 6.62 6.62 240.9 1
MOLT-16
CHEMBL2366362
 IC50 6.59 6.59 258.2 1
P30-OHK
CHEMBL2366165
 IC50 6.58 6.58 263.9 1
HuTu80
CHEMBL614582
 IC50 6.54 6.54 285.0 1
HCC2157
CHEMBL2366126
 IC50 6.49 6.49 323.2 1
HCT-15
CHEMBL612263
 IC50 6.49 6.49 327.1 1
MIA PaCa-2
CHEMBL614725
 IC50 6.49 6.49 320.4 1
786-0
CHEMBL613102
 IC50 6.47 6.47 341.6 1
GDM-1
CHEMBL2366157
 IC50 6.45 6.45 352.4 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 16.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.45 nM 9.35 Inhibition of recombinant human FTase incubated for 30 mins in presence of [3H]F... 16222147
Unchecked Ki = 0.5 nM 9.3 Competitive inhibition of human FPTase using K-RasB peptide as a substrate asses... 33228976
Unchecked EC50 = 0.55 nM 9.26 Inhibition of FTase in human HCT-15 cells expressing high level of P-gp1 using R... 16222147
Protein farnesyltransferase IC50 = 0.57 nM 9.24 In vitro inhibitory activity against farnesyltransferase (FTase) 12657284
Unchecked IC50 = 0.6 nM 9.22 Inhibition of FTase 20925433
Unchecked IC50 = 0.65 nM 9.19 Inhibition of bovine farnesyl transferase in presence of Tipifarnib 15911281
Protein farnesyltransferase IC50 = 0.65 nM 9.19 Inhibition of bovine farnesyltransferase 15808463
Protein farnesyltransferase IC50 = 0.65 nM 9.19 Inhibition of bovine farnesyltransferase 15454229
Protein farnesyltransferase IC50 = 0.65 nM 9.19 Inhibition of Bovine farnesyltransferase (FTase) 15454228
Unchecked EC50 = 0.69 nM 9.16 Inhibition of FTase in human DLD-1 cells expressing moderate level of P-gp1 usin... 16222147
Unchecked IC50 = 0.7 nM 9.15 Inhibition of rat recombinant PFT expressed in insect Sf9 cells by scintillation... 20429511
Unchecked IC50 = 0.7 nM 9.15 Inhibition of rat recombinant protein farnesyltransferase expressed in Sf9 cells... 19239254
Protein farnesyltransferase IC50 = 0.8 nM 9.1 Inhibition of [3H]FPP incorporation into biotinylated laminB peptide by farnesyl... 12699751
Protein farnesyltransferase IC50 = 0.86 nM 9.07 Inhibitory concentration against farnesyltransferase was determined 15055985
Protein farnesyltransferase IC50 = 0.9 nM 9.05 Inhibition of human recombinant FTase using [3H]farnesyldiphosphate 25530833
Protein farnesyltransferase IC50 = 0.9 nM 9.05 Inhibition of [3H]FPP incorporation into biotinylated laminB peptide by farnesyl... 14643327
Protein farnesyltransferase IC50 = 0.9 nM 9.05 Inhibition of Farnesyltransferase 14736242
Protein farnesyltransferase IC50 = 0.9 nM 9.05 Inhibition of [3H]FPP incorporation into biotinylated lamin B peptide by farnesy... 14643326
Unchecked EC50 = 0.98 nM 9.01 Inhibition of FTase in human HCT-116 cells expressing low level of P-gp1 using R... 16222147
Protein farnesyltransferase EC50 = 1.6 nM 8.8 Inhibition of Ras processing in H-ras transformed NIH3T3 cells in presence of Ti... 15911281

Literature References

PubMed DOI Target Context # Activities
16222147 10.1097/00001813-200511000-00004 Unchecked 14
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
16222147 10.1097/00001813-200511000-00004 HCT-116 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
15808463 10.1016/j.bmcl.2005.02.062 Protein farnesyltransferase 2
19239254 10.1021/jm801313t Unchecked 2
15911281 10.1016/j.bmcl.2005.03.049 Unchecked 2
15454229 10.1016/j.bmcl.2004.08.011 Protein farnesyltransferase 2
22497764 10.1016/j.bmcl.2012.03.070 ADMET 2
15454228 10.1016/j.bmcl.2004.08.012 Protein farnesyltransferase 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
15911281 10.1016/j.bmcl.2005.03.049 Geranylgeranyl transferase type I 2
14643327 10.1016/j.bmcl.2003.08.080 NIH3T3 2
- 10.6019/CHEMBL4651402 Vero C1008 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19239254 10.1021/jm801313t Trypanosoma cruzi 2
12699751 10.1016/s0960-894x(03)00180-x ADMET 2
33228976 10.1016/j.ejmech.2020.113006 Unchecked 2
15911281 10.1016/j.bmcl.2005.03.049 Protein farnesyltransferase 2
14643326 10.1016/j.bmcl.2003.09.043 NIH3T3 2

Data from ChEMBL 36 via Core Engine