TIPIFARNIB

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII MAT637500A
EPA CompTox DTXSID5041140

Structure

InChI Key PLHJCIYEEKOWNM-HHHXNRCGSA-N
Smiles Cn1cncc1[C@@](N)(c1ccc(Cl)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H22Cl2N4O
Molecular Weight 489.41
AlogP 5.5
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 65.84
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 34.0

Bioactivity

Mechanism of Action Action Reference
Protein farnesyltransferase inhibitor INHIBITOR PubMed
Protein: Protein farnesyltransferase
Description: Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Organism : Homo sapiens
P49354 ENSG00000168522
Protein: Protein farnesyltransferase
Description: Protein farnesyltransferase subunit beta
Organism : Homo sapiens
P49356 ENSG00000257365
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 1700-4060 - - -
Enzyme Transferase
2-100 1-8 - - 2
Enzyme
2-100 1-8 - - 2
Assay Description Organism Bioactivity Reference
Inhibition of Farnesyltransferase None 0.9 nM
In vitro inhibitory activity against farnesyltransferase (FTase) Bos taurus 0.57 nM
Inhibition of [3H]FPP incorporation into biotinylated lamin B peptide by farnesyl transferase None 0.9 nM
Inhibition of [3H]FPP incorporation into biotinylated laminB peptide by farnesyl transferase None 0.9 nM
Inhibition of [3H]FPP incorporation into biotinylated laminB peptide by farnesyl transferase None 0.8 nM
Inhibitory concentration against farnesyltransferase was determined Homo sapiens 0.86 nM
In vivo inhibition of T24ras-NIH3T3 tumor growth at 25 mg/kg in mice Mus musculus 37.0 %
T24H-ras-transformed NIH3T3 cell proliferation Mus musculus 1.7 nM
In vitro inhibition of NIH3T3 cell proliferation Mus musculus 1.7 nM
Inhibition of T24F1H-ras-transformation in NIH 3T3 cells Mus musculus 1.7 nM
In vivo inhibition of T24H-ras-NIH3T3 cell proliferation in mice Mus musculus 37.0 %
Effective concentration against Ha-RAS processing in NIH3T3 ras-transformed cells Mus musculus 2.0 nM
In vivo inhibition of T24H-ras NIH3T3 tumor growth in mice Mus musculus 37.0 %
Inhibition of Bovine farnesyltransferase (FTase) Bos taurus 0.65 nM
Inhibition of bovine farnesyltransferase Bos taurus 0.65 nM
Inhibition of bovine farnesyltransferase Bos taurus 0.65 nM
Inhibition of bovine farnesyl transferase in presence of Lonafarnib Bos taurus 8.3 nM
Inhibition of bovine farnesyl transferase in presence of Tipifarnib Bos taurus 0.65 nM
Inhibitory concentration against Protein farnesyltransferase of Trypanosoma cruzi Trypanosoma cruzi 75.0 nM
Inhibition of biotinylated lamin B peptide farnesylation by Plasmodium falciparum farnesyltransferase Plasmodium falciparum 17.0 nM
Inhibition of Ras farnesylation in H-Ras transformed NIH3T3 cells Mus musculus 1.6 nM
Inhibition of H-Ras transformed NIH-3T3-cell proliferation Mus musculus 1.6 nM
Inhibition of Ras processing in H-ras transformed NIH3T3 cells in presence of Lonafarnib Mus musculus 100.0 nM
Inhibition of Ras processing in H-ras transformed NIH3T3 cells in presence of Tipifarnib Mus musculus 1.6 nM
Percent inhibition of H-ras processing in transformed NIH3T3 cells at 100 nM Mus musculus 1.6 %
Inhibition of rat recombinant protein farnesyltransferase expressed in Sf9 cells by [3H]-scintillation proximity assay Rattus norvegicus 0.7 nM
Antitrypanosomal activity against Trypanosoma cruzi Tulahuen amastigotes expressing beta-galactosidase in mouse 3T3 fibroblast after 7 days by alamar blue assay Trypanosoma cruzi 4.0 nM
Antitrypanosomal activity against Trypanosoma cruzi Tulahuen infected in mouse 3T3 cells Trypanosoma cruzi 4.0 nM
Inhibition of rat recombinant PFT expressed in insect Sf9 cells by scintillation proximity assay Rattus norvegicus 0.7 nM
Antitrypanosomal activity against Trypanosoma cruzi Tulahuen amastigotes infected in rat 3T3 cells after 7 days by alamar blue assay Trypanosoma cruzi 4.0 nM
Inhibition of FTase None 0.6 nM
SANGER: Inhibition of human NCI-H2009 cell growth in a cell viability assay. Homo sapiens 363.36 nM
SANGER: Inhibition of human NCI-H2122 cell growth in a cell viability assay. Homo sapiens 191.45 nM
SANGER: Inhibition of human NCI-H2342 cell growth in a cell viability assay. Homo sapiens 379.83 nM
SANGER: Inhibition of human NCI-H650 cell growth in a cell viability assay. Homo sapiens 773.09 nM
SANGER: Inhibition of human NCI-H727 cell growth in a cell viability assay. Homo sapiens 874.26 nM
SANGER: Inhibition of human NKM-1 cell growth in a cell viability assay. Homo sapiens 774.18 nM
SANGER: Inhibition of human NMC-G1 cell growth in a cell viability assay. Homo sapiens 425.05 nM
SANGER: Inhibition of human NTERA-S-cl-D1 cell growth in a cell viability assay. Homo sapiens 237.44 nM
SANGER: Inhibition of human OAW-42 cell growth in a cell viability assay. Homo sapiens 955.9 nM
SANGER: Inhibition of human OCUB-M cell growth in a cell viability assay. Homo sapiens 471.64 nM
SANGER: Inhibition of human P30-OHK cell growth in a cell viability assay. Homo sapiens 263.88 nM
SANGER: Inhibition of human QIMR-WIL cell growth in a cell viability assay. Homo sapiens 16.31 nM
SANGER: Inhibition of human REH cell growth in a cell viability assay. Homo sapiens 59.2 nM
SANGER: Inhibition of human RPMI-6666 cell growth in a cell viability assay. Homo sapiens 7.407 nM
SANGER: Inhibition of human RT-112 cell growth in a cell viability assay. Homo sapiens 381.76 nM
SANGER: Inhibition of human SIG-M5 cell growth in a cell viability assay. Homo sapiens 14.57 nM
SANGER: Inhibition of human SK-HEP-1 cell growth in a cell viability assay. Homo sapiens 714.07 nM
SANGER: Inhibition of human SK-LMS-1 cell growth in a cell viability assay. Homo sapiens 184.09 nM
SANGER: Inhibition of human SK-MEL-2 cell growth in a cell viability assay. Homo sapiens 483.73 nM
SANGER: Inhibition of human SNG-M cell growth in a cell viability assay. Homo sapiens 203.54 nM
SANGER: Inhibition of human SNU-423 cell growth in a cell viability assay. Homo sapiens 704.66 nM
SANGER: Inhibition of human SNU-449 cell growth in a cell viability assay. Homo sapiens 622.94 nM
SANGER: Inhibition of human SUP-T1 cell growth in a cell viability assay. Homo sapiens 786.79 nM
SANGER: Inhibition of human SW1710 cell growth in a cell viability assay. Homo sapiens 725.5 nM
SANGER: Inhibition of human SW620 cell growth in a cell viability assay. Homo sapiens 482.24 nM
SANGER: Inhibition of human T84 cell growth in a cell viability assay. Homo sapiens 546.2 nM
SANGER: Inhibition of human 786-0 cell growth in a cell viability assay. Homo sapiens 341.56 nM
SANGER: Inhibition of human 8305C cell growth in a cell viability assay. Homo sapiens 976.31 nM
SANGER: Inhibition of human 8505C cell growth in a cell viability assay. Homo sapiens 431.09 nM
SANGER: Inhibition of human A3-KAW cell growth in a cell viability assay. Homo sapiens 901.22 nM
SANGER: Inhibition of human A375 cell growth in a cell viability assay. Homo sapiens 616.48 nM
SANGER: Inhibition of human A388 cell growth in a cell viability assay. Homo sapiens 864.57 nM
SANGER: Inhibition of human A4-Fuk cell growth in a cell viability assay. Homo sapiens 20.59 nM
SANGER: Inhibition of human A427 cell growth in a cell viability assay. Homo sapiens 579.17 nM
SANGER: Inhibition of human A431 cell growth in a cell viability assay. Homo sapiens 655.36 nM
SANGER: Inhibition of human ALL-PO cell growth in a cell viability assay. Homo sapiens 554.56 nM
SANGER: Inhibition of human BB30-HNC cell growth in a cell viability assay. Homo sapiens 585.23 nM
SANGER: Inhibition of human BC-1 cell growth in a cell viability assay. Homo sapiens 129.96 nM
SANGER: Inhibition of human CAL-12T cell growth in a cell viability assay. Homo sapiens 760.04 nM
SANGER: Inhibition of human CAL-148 cell growth in a cell viability assay. Homo sapiens 884.2 nM
SANGER: Inhibition of human CAL-39 cell growth in a cell viability assay. Homo sapiens 962.32 nM
SANGER: Inhibition of human TE-10 cell growth in a cell viability assay. Homo sapiens 811.79 nM
SANGER: Inhibition of human TE-15 cell growth in a cell viability assay. Homo sapiens 364.62 nM
SANGER: Inhibition of human TE-8 cell growth in a cell viability assay. Homo sapiens 928.47 nM
SANGER: Inhibition of human TUR cell growth in a cell viability assay. Homo sapiens 871.19 nM
SANGER: Inhibition of human YKG-1 cell growth in a cell viability assay. Homo sapiens 526.2 nM
SANGER: Inhibition of human CHL-1 cell growth in a cell viability assay. Homo sapiens 805.46 nM
SANGER: Inhibition of human CMK cell growth in a cell viability assay. Homo sapiens 151.45 nM
SANGER: Inhibition of human COLO-679 cell growth in a cell viability assay. Homo sapiens 985.06 nM
SANGER: Inhibition of human Calu-1 cell growth in a cell viability assay. Homo sapiens 181.34 nM
SANGER: Inhibition of human DMS-273 cell growth in a cell viability assay. Homo sapiens 719.89 nM
SANGER: Inhibition of human Daoy cell growth in a cell viability assay. Homo sapiens 57.53 nM
SANGER: Inhibition of human EFO-27 cell growth in a cell viability assay. Homo sapiens 713.73 nM
SANGER: Inhibition of human ES6 cell growth in a cell viability assay. Homo sapiens 539.35 nM
SANGER: Inhibition of human ETK-1 cell growth in a cell viability assay. Homo sapiens 21.52 nM
SANGER: Inhibition of human EW-18 cell growth in a cell viability assay. Homo sapiens 457.91 nM
SANGER: Inhibition of human G-401 cell growth in a cell viability assay. Homo sapiens 502.61 nM
SANGER: Inhibition of human GDM-1 cell growth in a cell viability assay. Homo sapiens 352.39 nM
SANGER: Inhibition of human HCC2157 cell growth in a cell viability assay. Homo sapiens 323.16 nM
SANGER: Inhibition of human HCC2998 cell growth in a cell viability assay. Homo sapiens 384.36 nM
SANGER: Inhibition of human HCT-15 cell growth in a cell viability assay. Homo sapiens 327.05 nM
SANGER: Inhibition of human HEL cell growth in a cell viability assay. Homo sapiens 394.49 nM
SANGER: Inhibition of human HH cell growth in a cell viability assay. Homo sapiens 190.89 nM
SANGER: Inhibition of human HLE cell growth in a cell viability assay. Homo sapiens 448.11 nM
SANGER: Inhibition of human HMV-II cell growth in a cell viability assay. Homo sapiens 215.78 nM
SANGER: Inhibition of human HT-29 cell growth in a cell viability assay. Homo sapiens 546.7 nM
SANGER: Inhibition of human HUTU-80 cell growth in a cell viability assay. Homo sapiens 285.02 nM
SANGER: Inhibition of human IA-LM cell growth in a cell viability assay. Homo sapiens 47.52 nM
SANGER: Inhibition of human IGROV-1 cell growth in a cell viability assay. Homo sapiens 208.23 nM
SANGER: Inhibition of human KGN cell growth in a cell viability assay. Homo sapiens 452.49 nM
SANGER: Inhibition of human KM12 cell growth in a cell viability assay. Homo sapiens 116.86 nM
SANGER: Inhibition of human KS-1 cell growth in a cell viability assay. Homo sapiens 770.35 nM
SANGER: Inhibition of human KU812 cell growth in a cell viability assay. Homo sapiens 97.06 nM
SANGER: Inhibition of human KYSE-270 cell growth in a cell viability assay. Homo sapiens 216.69 nM
SANGER: Inhibition of human KYSE-450 cell growth in a cell viability assay. Homo sapiens 728.85 nM
SANGER: Inhibition of human KYSE-510 cell growth in a cell viability assay. Homo sapiens 977.1 nM
SANGER: Inhibition of human LCLC-103H cell growth in a cell viability assay. Homo sapiens 129.02 nM
SANGER: Inhibition of human LoVo cell growth in a cell viability assay. Homo sapiens 240.91 nM
SANGER: Inhibition of human MCF7 cell growth in a cell viability assay. Homo sapiens 166.3 nM
SANGER: Inhibition of human MEL-JUSO cell growth in a cell viability assay. Homo sapiens 23.44 nM
SANGER: Inhibition of human MFH-ino cell growth in a cell viability assay. Homo sapiens 814.5 nM
SANGER: Inhibition of human MIA-PaCa-2 cell growth in a cell viability assay. Homo sapiens 320.4 nM
SANGER: Inhibition of human ML-2 cell growth in a cell viability assay. Homo sapiens 13.64 nM
SANGER: Inhibition of human MOLT-16 cell growth in a cell viability assay. Homo sapiens 258.23 nM
SANGER: Inhibition of human MV-4-11 cell growth in a cell viability assay. Homo sapiens 732.79 nM
SANGER: Inhibition of human MZ7-mel cell growth in a cell viability assay. Homo sapiens 722.0 nM
SANGER: Inhibition of human NALM-6 cell growth in a cell viability assay. Homo sapiens 36.21 nM
SANGER: Inhibition of human NCI-H1299 cell growth in a cell viability assay. Homo sapiens 693.08 nM
SANGER: Inhibition of human NCI-H1355 cell growth in a cell viability assay. Homo sapiens 973.77 nM
Inhibition of human FTase using farnesyl pyrophosphate as substrate by fluorescent assay Homo sapiens 3.0 nM
Inhibition of human recombinant FTase using [3H]farnesyldiphosphate Homo sapiens 0.9 nM
Inhibition of FTase isolated from Kirsten virus-transformed human osteosarcoma cells using K-rasB peptide as substrate in presence of [3H]farnesyl PPi by scintillation proximity assay Homo sapiens 7.9 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 20.28 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 18.57 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -3.427 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 2.29 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.57 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.57 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 2.29 %
Inhibition of C-terminal His6-tagged human recombinat FTase expressed in Escherichia coli BL21 RIL (DE3) cells using Dansyl-GCVLS peptide and farnesyl pyrophosphate as substrate measured for 15 mins by fluorimetric analysis Homo sapiens 7.9 nM

Related Entries

Cross References

Resources Reference
ChEBI 141969
ChEMBL CHEMBL289228
DrugBank DB04960
FDA SRS MAT637500A
Guide to Pharmacology 8025
PDB JAN
PubChem 159324
SureChEMBL SCHEMBL21544535
ZINC ZINC000024809155
CONTENTS