Details of the Drug

General Information of Drug (ID: DMJNV4O)

Drug Name

Tirbanibulin

Synonyms

KX2-391; 897016-82-9; KX-01; UNII-4V9848RS5G; N-benzyl-2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetamide; KX-2-391; CHEMBL571546; 4V9848RS5G; KX2391; KX 01; KX-2391; MLS006011272; SCHEMBL153779; KX01; GTPL7957; DTXSID30237862; MolPort-023-293-512; HUNGUWOZPQBXGX-UHFFFAOYSA-N; HMS3656J15; EX-A2434; BCP02845; ZINC43152787; s2700; BDBM50303801; AKOS027276392; KX2-391; KX-01; SB16619; CS-0248; KX2-391 (KX01); BCP9000828; 2-Pyridineacetamide, 5-(4-(2-(4-morpholinyl)ethoxy)phenyl)-n-(phenylmethyl)-; NCGC00346644-05; NCGC00346644-01; KX 2

Indication

Disease Entry	ICD 11	Status	REF
Actinic keratosis	EK90.0	Approved	[1]
Prostate cancer	2C82.0	Phase 2	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

431.5

Logarithm of the Partition Coefficient (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 5.0 +/- 3.9 mcgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 0.34 +/- 0.30 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 7 h [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 4 hours [4]
Metabolism: The drug is metabolized via the CYP3A4, and to a lesser extent, CYP2C8 [5]

Chemical Identifiers

Formula: C26H29N3O3
IUPAC Name: N-benzyl-2-[5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-yl]acetamide
Canonical SMILES: C1COCCN1CCOC2=CC=C(C=C2)C3=CN=C(C=C3)CC(=O)NCC4=CC=CC=C4
InChI: InChI=1S/C26H29N3O3/c30-26(28-19-21-4-2-1-3-5-21)18-24-9-6-23(20-27-24)22-7-10-25(11-8-22)32-17-14-29-12-15-31-16-13-29/h1-11,20H,12-19H2,(H,28,30)
InChIKey: HUNGUWOZPQBXGX-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 23635314
CAS Number: 897016-82-9
DrugBank ID: DB06137
TTD ID: D02LJW
ACDINA ID: D01489

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Tubulin polymerization (TubP)	TTHVQ4N	NOUNIPROTAC	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Serine protease HTRA1 (HTRA1)	OTR8ACBF	HTRA1_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tirbanibulin 1% ointment	1%	Ointment	Topical

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7957).
3	Niu L, Yang J, Yan W, Yu Y, Zheng Y, Ye H, Chen Q, Chen L: Reversible binding of the anticancer drug KXO1 (tirbanibulin) to the colchicine-binding site of beta-tubulin explains KXO1's low clinical toxicity. J Biol Chem. 2019 Nov 29;294(48):18099-18108. doi: 10.1074/jbc.RA119.010732. Epub 2019 Oct 18.
4	A phase 2 study of KX2-391, an oral inhibitor of Src kinase and tubulin polymerization, in men with bone-metastatic castration-resistant prostate cancer. Cancer Chemother Pharmacol. 2013 Apr;71(4):883-92. doi: 10.1007/s00280-013-2079-z. Epub 2013 Jan 13.
5	FDA Approved Drug Products: KLISYRI (tirbanibulin) ointment, for topical use
6	Inorganic arsenic exposure promotes malignant progression by HDAC6-mediated down-regulation of HTRA1. J Appl Toxicol. 2023 Aug;43(8):1214-1224. doi: 10.1002/jat.4457. Epub 2023 Mar 11.