Tirbanibulin

HCID 23635314

基本情報

CAS
897016-82-9
標準SMILES
O=C(Cc1ccc(-c2ccc(OCCN3CCOCC3)cc2)cn1)NCc1ccccc1
InChIKey
HUNGUWOZPQBXGX-UHFFFAOYSA-N
分子式
C26H29N3O3
平均分子量
431.5 g/mol
単同位体質量
431.22089179

概要

Tirbanibulin is a member of the class of pyridines that is pyridine substituted by 2-(benzylamino)-2-oxoethyl and 4-[2-(morpholin-4-yl)ethoxy]phenyl groups at positions 2 and 5, respectively. It is a dual inhibitor of Src kinase and tubulin and approved by the FDA for the topical treatment of actinic keratosis on the face or scalp. It has a role as an antineoplastic agent, a microtubule-destabilising agent, an apoptosis inducer and an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor. It is a secondary carboxamide, a member of pyridines, an aromatic ether and a member of morpholines.

名称と識別子

優先名称
Tirbanibulin
IUPAC
N-benzyl-2-[5-[4-(2-morpholin-4-ylethoxy)phenyl]-2-pyridinyl]acetamide
英語名
Tirbanibulin
分子式
C26H29N3O3
分子量
431.53

名称と別名

Tirbanibulin897016-82-9KX2-391KX-01KlisyriN-benzyl-2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetamideKX01KX-2-391tirbanibulinatirbanibulineKX-23914V9848RS5G
名称をさらに表示
チルバニブリンKX 01CS-234KX-O1)KX2-391 (KX01)KX2-391 USP/EP/BPTirbanibulin, KX2-391KX2-391(Tirbanibulin)KX2 391Tirbanibulin, 10 mM in DMSO
KX2391N-benzyl-2-(5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}pyridin-2-yl)acetamideDTXSID302378622-Pyridineacetamide, 5-(4-(2-(4-morpholinyl)ethoxy)phenyl)-n-(phenylmethyl)-tirbanibulinumN-benzyl-2-(5-(4-(2-(morpholin-4-yl)ethoxy)phenyl)pyridin-2-yl)acetamide2-(5-(4-(2-morpholin-4-ylethoxy)phenyl)pyridin-2-yl)-N-(phenylmethyl)acetamide2-[5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-yl]-N-(phenylmethyl)acetamide

データベース識別子

CAS
897016-82-9
PubChem CID
23635314
DTXSID
DTXSID30237862
ChEMBL
CHEMBL571546
ChEBI
CHEBI:231702
UNII
4V9848RS5G
EC Number
854-810-1

物性

構造計算による物性

XLogP
2.9
極性表面積
63.7 Ų
水素結合供与体数
1
水素結合受容体数
5
回転可能結合数
9
重原子数
32

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 4 件

Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Dermatologic Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

物理化学的性質

沸点
680.9 · 680.9±55.0 °C(Predicted)
比重(密度)
1.169 · 1.169
貯蔵温度
-20 °C · Store at -20°C
溶解性
2 O; · insoluble in H2O; ≥121 mg/mL in DMSO; ≥2.44 mg/mL in EtOH with gentle warming and ultrasonic
外見
Powder
酸解離定数(Pka)
14.73 · 14.73±0.46(Predicted)

安全と法規制

GHS分類

GHS ClassificationNot Classified

危険有害性情報

Hazard Classes and CategoriesNot Classified

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

注意喚起語
警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H315

化学と産業

薬理情報

ATC Code · 2 件

D - Dermatologicals

QD - Dermatologicals

Protein BindingTirbanibulin is 88% bound to plasma proteins and the extent of plasma protein binding is independent of drug concentrations in the range of 0.01 to 10 µg/mL.
Pharmacodynamics · 1 件

In clinical trials composed comprising patients with actinic keratosis of the face or scalp, tirbanibulin promoted complete clearance of actinic keratosis lesions at day 57 in treated areas in 44-54% of patients compared to 5-13% of patients who received the placebo. Actinic keratosis is a chronic, pre-malignant condition characterized by lesions and proliferation of neoplastic keratinocytes. Tirbanibulin mediates an anti-proliferative effect by inhibiting tubulin polymerization and Src kinase signalling. Tirbanibulin inhibited primary tumour growth and metastasis in many preclinical animal models of cancer. In human triple-negative breast cancer, or estrogen receptor (ER)/progesterone receptor (PR)/human epidermal growth factor receptor 2 (HER2)-negative tumour, xenografts, tirbanibulin suppressed tumour growth and metastasis. Tirbanibulin was also shown to restore functional ERα expression in ERα-negative breast tumours. Tirbanibulin promoted synergistic tumour growth inhibition of breast cancer cell lines when used in combination with tamoxifen and paclitaxel. In a clinical trial comprising patients with advanced solid tumours, dose-limiting toxicities of tirbanibulin included elevated liver transaminases, neutropenia and fatigue.

Mechanism of Action · 1 件

Src tyrosine kinases regulate normal cell growth: the expression of Src kinase is upregulated during the normal hair cycle during the proliferative anagen phase. Additionally, Src tyrosine kinases act as key modulators of cancer cell proliferation, survival, angiogenesis, migration, invasion and metastasis. Src is frequently upregulated in various epithelial tumours including colon, breast and pancreas compared with the adjacent normal tissues. The expression and activity of Src are also enhanced in human actinic keratosis, which is characterized by hyperproliferative premalignant skin lesions. The pathogenesis of actinic keratosis commonly involves skin inflammation, oxidative stress, immunosuppression, impaired apoptosis, mutagenesis, dysregulation of keratinocyte growth and proliferation, and tissue remodelling. _In vitro_ studies suggest that Src plays a predominant role in the early stages of human skin tumour development, rather than at later stages of tumour progression. The exact mechanism of tirbanibulin as a topical treatment of actinic keratosis has not been fully elucidated; however, it mainly works by inhibiting fast proliferating cells. Tirbanibulin is a non-ATP competitive Src kinase inhibitor and tubulin polymerization inhibitor. It binds to the peptide substrate binding site of Src, a primary target of tirbanibulin, and blocking its downstream signalling pathways that promote cancer cell migration, proliferation, and survival. Tublin is responsible for cell migration, protein transport, and mitosis: tibranibulin directly binds to the colchicine-binding site of beta-tubulin and causes induces tubulin depolymerization. It is also hypothesized that inhibition of Src can also contribute to the inhibitory effects on microtubule polymerization. At low nanomolar concentrations, tirbanibulin induces G2/M phase cell cycle arrest in a reversible and dose-dependent manner. By inhibiting microtubule polymerization, tirbanibulin also induces mitotic catastrophe.

Biological Half-LifeThe half-life is about 4 hours.
Metabolism/Metabolites · 1 件

_In vitro_, tirbanibulin is mainly metabolized by CYP3A4, and to a lesser extent, CYP2C8. In adult subjects with actinic keratosis, detected metabolites were KX2-5036 and KX2-5163, which were pharmacologically inactive metabolites with the highest plasma concentrations of 0.09 ng/mL and 0.12 ng/mL, respectively.

応用分野

使用KX2-391 is a Src Inhibitor with efficacy against certain hepatic and leukemia cell lines.

サプライヤー100 社

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
天津欣康佑生物科技有限公司19922659386 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

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