LONAFARNIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII IOW153004F
EPA CompTox DTXSID90172927

Structure

InChI Key DHMTURDWPRKSOA-RUZDIDTESA-N
Smiles NC(=O)N1CCC(CC(=O)N2CCC([C@H]3c4ncc(Br)cc4CCc4cc(Cl)cc(Br)c43)CC2)CC1
InChI
InChI=1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H31Br2ClN4O2
Molecular Weight 638.83
AlogP 5.91
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 79.53
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 36.0

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 Transferase
100 2-1900 - - 100
Other cytosolic protein
- 70 - - -
Assay Description Organism Bioactivity Reference
Inhibiting the farnesylation of H-ras proteins in COS-7 monkey cells transiently expressing H-ras[Val12]-CVLS in the whole cell assay. Cercopithecidae 10.0 nM
Effect on Ras processing in Cos-1 monkey kidney cells expressing either H-Ras-Val 12-CVLS or H-Ras-Val12. Cercopithecidae 10.0 nM
inhibition of tumor colony formation in soft agar Cercopithecidae 75.0 nM
Inhibition of Farnesyltransferase None 2.0 nM
In vitro inhibitory activity against farnesyltransferase (FTase) Bos taurus 7.8 nM
Compound ability to inhibit the transfer of [3H]- farnesyl from Farnesyltransferase to H-Ras-CVLS, a process that is mediated by FPT None 1.9 nM
Inhibition of Farnesyl protein transferase Homo sapiens 1.9 nM
Inhibitory activity against Hras Farnesyltransferase (FPT). None 1.9 nM
Inhibitory concentration against farnesyltransferase was determined Homo sapiens 1.9 nM
Compound was measured for inhibition of H-ras NIH tumor cell line under soft agar assay. None 70.0 nM
Compound was measured for inhibition of HCT116 tumor cell line in colon under soft agar assay. Homo sapiens 70.0 nM
Compound was measured for inhibition of K-ras NIH tumor cell line under soft agar assay. None 500.0 nM
Compound was measured for inhibition of MCF-7 tumor cell line in breast under soft agar assay. Homo sapiens 50.0 nM
Compound was measured for inhibition of Mia Paca tumor cell line in pancreatic under soft agar assay. Homo sapiens 250.0 nM
Compound was measured for inhibition of NCI-HI146 tumor cell line in lung under soft agar assay. Homo sapiens 50.0 nM
Compound ability to inhibit anchorage-independent growth of NIH-H tumor cell lines in soft agar. Homo sapiens 72.0 nM
Compound ability to inhibit anchorage-independent growth of NIH-K tumor cell lines in soft agar. Homo sapiens 500.0 nM
Effective concentration against Ha-RAS processing in NIH3T3 ras-transformed cells Mus musculus 160.0 nM
Inhibition of Protein farnesyltransferase in Cos-1 monkey kidney cells expressing H-Ras-val monkey 1.9 nM
Inhibition of COS cell proliferation None 10.0 nM
Inhibition of soft agar colony formation in H-Ras transformed cells None 70.0 nM
Inhibition of [3H]FPP incorporation into H-ras CVLS by Farnesyltransferase None 2.0 nM
Inhibition of Bovine farnesyltransferase (FTase) Bos taurus 8.3 nM
Inhibition of bovine farnesyltransferase Bos taurus 8.3 nM
Inhibition of [3H]-FPP incorporation into H-ras CVLS by farnesyltransferase None 2.0 nM
Inhibition of biotinylated lamin B peptide farnesylation by Plasmodium falciparum farnesyltransferase Plasmodium falciparum 250.0 nM
Inhibition of Ras farnesylation in H-Ras transformed NIH3T3 cells Mus musculus 100.0 nM
Percent inhibition of H-ras processing in transformed NIH3T3 cells at 100 nM Mus musculus 100.0 %
Inhibition of rat farnesyl transferase after 30 mins Rattus norvegicus 100.0 nM
Inhibition of FTase in human COS7 cells Homo sapiens 10.0 nM
Inhibition of human recombinant FTase using [3H]farnesyldiphosphate Homo sapiens 1.9 nM
Inhibition of rat brain FTase assessed as decrease in transfer of [3H]farnesyl from [3H]farnesyl PPi to H-Ras-CVLS after 30 mins by liquid scintillation counting method Rattus norvegicus 1.9 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 104.38 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.968 %
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 -0.06 % 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 -0.06 %

Cross References

Resources Reference
ChEBI 47097
ChEMBL CHEMBL298734
DrugBank DB06448
FDA SRS IOW153004F
Guide to Pharmacology 8024
PDB 336
PharmGKB PA166129466
PubChem 148195
SureChEMBL SCHEMBL19032
ZINC ZINC000003950115
CONTENTS