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Compound Detail

CHEMBL571546

TIRBANIBULIN
💊 Approved Drug
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💊 Approved Drug
O=C(Cc1ccc(-c2ccc(OCCN3CCOCC3)cc2)cn1)NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL571546
Name TIRBANIBULIN
Phase Approved
Structure Type MOL
InChI Key HUNGUWOZPQBXGX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Klisyri KX-01 KX-2-391 KX-2391 KX01 Kx2-391 KX2391 Tirbanibulin Tirbanibulina Tirbanibuline
11
Targets
16
Activities
2
Assay Types
19
PK Parameters
20
Publications
10
Known Names
6
Indications
1
Mechanisms

Molecular Properties

431.5
MW (Da)
3.32
ALogP
5
HBA
1
HBD
63.7
PSA (Ų)
0.56
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2020
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product First in Class
USAN Stem -bulin
USAN Year 2019

Extended Properties

Molecular Formula C26H29N3O3
MW 431.54
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.49

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tyrosine-protein kinase SRC inhibitor INHIBITOR Proto-oncogene tyrosine-protein kinase Src ✓ ✓

Indications

Keratosis, Actinic Carcinoma, Basal Cell Prostatic Neoplasms, Castration-Resistant Leukemia, Myeloid, Acute Lymphoma Neoplasms

ATC Classification

D06BX03
tirbanibulin
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

Activity Summary

IC50 15 meas. best 8.3
Kd 1 meas. best 5.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HT-29
CHEMBL384
 IC50 8.3 7.97 5.0 2
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
 IC50 8.19 6.47 6.5 5
SK-OV-3
CHEMBL614925
 IC50 8.17 8.17 6.8 1
Ramos
CHEMBL614629
 IC50 7.8 7.8 15.7 1
K562
CHEMBL385
 IC50 7.74 7.74 18.2 1
MCF7
CHEMBL387
 IC50 7.55 7.55 28.0 1
HCT-116
CHEMBL394
 IC50 7.54 7.54 29.0 1
A549
CHEMBL392
 IC50 7.12 7.12 75.0 1
Bcr/Abl fusion protein
CHEMBL2096618
 IC50 7.0 7.0 100.0 1
Tyrosine-protein kinase Lyn
CHEMBL3905
 IC50 7.0 7.0 100.0 1
Tubulin
CHEMBL2095182
 Kd 5.96 5.96 1110.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 839.57 ng.hr.mL-1 Rattus norvegicus
CL 88.5 mL.min-1.kg-1 Rattus norvegicus
Cmax 141.35 nM Homo sapiens
Cmax 505.17 nM Homo sapiens
Cmax 535.29 nM Homo sapiens
Cmax 632.62 nM Homo sapiens
Cmax 185.38 nM Homo sapiens
Cmax 999.68 nM Rattus norvegicus
F 49.0 % Mus musculus
F 34.92 % Rattus norvegicus
T1/2 2.2 hr Homo sapiens
T1/2 4.0 hr Homo sapiens
T1/2 8.0 hr Canis lupus familiaris
T1/2 2.0 hr Rattus norvegicus
T1/2 1.0 hr Mus musculus
T1/2 0.735 hr Homo sapiens
T1/2 12.33 hr Rattus norvegicus
Tmax 1.0 hr Homo sapiens
Tmax 0.25 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HT-29 IC50 = 5.0 nM 8.3 Antiproliferative activity against human HT-29 cells in presence of 0.5% FCS 29617135
Proto-oncogene tyrosine-protein kinase Src IC50 = 6.5 nM 8.19 Inhibition of human c-SRC expressed in mouse NIH/3T3 cells assessed as inhibitio... 29617135
SK-OV-3 IC50 = 6.8 nM 8.17 Antiproliferative activity against human SK-OV-3 cells assessed as inhibition of... 34081857
Proto-oncogene tyrosine-protein kinase Src IC50 = 13.0 nM 7.89 Inhibition of human c-SRC expressed in mouse NIH/3T3 cells assessed as inhibitio... 29617135
Ramos IC50 = 15.7 nM 7.8 Antiproliferative activity against human Ramos cells assessed as inhibition of c... 34081857
K562 IC50 = 18.2 nM 7.74 Antiproliferative activity against human K562 cells assessed as inhibition of ce... 34081857
Proto-oncogene tyrosine-protein kinase Src IC50 = 20.0 nM 7.7 Inhibition of c-SRC 21459579
HT-29 IC50 = 23.0 nM 7.64 Antiproliferative activity against human HT-29 cells in presence of 1.5% FCS by ... 29617135
MCF7 IC50 = 28.0 nM 7.55 Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT ... 38703557
HCT-116 IC50 = 29.0 nM 7.54 Antiproliferative activity against human HCT-116 cells incubated for 72 hrs by M... 38703557
A549 IC50 = 75.0 nM 7.12 Antiproliferative activity against human A549 cells incubated for 72 hrs by MTT ... 38703557
Bcr/Abl fusion protein IC50 = 100.0 nM 7.0 Inhibition of BCR/ABL (unknown origin) 29617135
Tyrosine-protein kinase Lyn IC50 = 100.0 nM 7.0 Inhibition of LYN (unknown origin) 29617135
Tubulin Kd = 1110.0 nM 5.96 Binding affinity to tubulin (unknown origin) assessed as dissociation constant b... 34081857
Proto-oncogene tyrosine-protein kinase Src IC50 = 40000.0 nM 4.4 Inhibition of src kinase by cell based functional assay 20038108
Proto-oncogene tyrosine-protein kinase Src IC50 = 67000.0 nM 4.17 Inhibition of Src (unknown origin) 29617135

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 U2OS 345
- 10.6019/CHEMBL4689842 HEK-293T 344
- 10.6019/CHEMBL4689842 Fibroblast 344
29617135 10.1021/acs.jmedchem.8b00164 ADMET 18
34081857 10.1021/acs.jmedchem.0c01961 SK-OV-3 10
34081857 10.1021/acs.jmedchem.0c01961 ADMET 9
29191878 10.1126/science.aan4368 Unchecked 5
29617135 10.1021/acs.jmedchem.8b00164 Unchecked 4
29617135 10.1021/acs.jmedchem.8b00164 Proto-oncogene tyrosine-protein kinase Src 4
20038108 10.1021/jm901525b Proto-oncogene tyrosine-protein kinase Src 4
29617135 10.1021/acs.jmedchem.8b00164 Bcr/Abl fusion protein 3
29617135 10.1021/acs.jmedchem.8b00164 HT-29 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
34081857 10.1021/acs.jmedchem.0c01961 Unchecked 2
21852023 10.1016/j.ejmech.2011.07.050 Unchecked 2
29617135 10.1021/acs.jmedchem.8b00164 SW-620 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
20038108 10.1021/jm901525b Tyrosine-protein kinase Lck 2
29617135 10.1021/acs.jmedchem.8b00164 HCT-116 2
18979199 10.1007/s10620-008-0519-0 HepG2 2

Data from ChEMBL 36 via Core Engine