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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 540
実験および物理化学的性質
Human Drugs
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)
- 色
- White to off-white
- 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
- SMILES
- C1(CC(NCC2=CC=CC=C2)=O)=NC=C(C2=CC=C(OCCN3CCOCC3)C=C2)C=C1
安全と法規制
GHS分類
危険有害性情報
毒性情報
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
D - Dermatologicals
QD - Dermatologicals
Pharmacodynamics
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
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.
Metabolism/Metabolites
_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.
FDA Pharmacological Classification
4V9848RS5G
TIRBANIBULIN
Physiologic Effects [PE] - Microtubule Inhibition
Established Pharmacologic Class [EPC] - Microtubule Inhibitor
Tirbanibulin is a Microtubule Inhibitor. The physiologic effect of tirbanibulin is by means of Microtubule Inhibition.
TIRBANIBULIN
Absorption, Distribution and Excretion
Tirbanibulin demonstrates good oral bioavailability. Following topical administration of doses ranging from 54 to 295 mg on the face or scalp, the steady-state concentration of tirbanibulin was achieved by 72 hours. At five days following initial administration, the mean Cmax was 0.34±0.30 ng/mL in subjects who received topical treatment on the face and 0.18±0.10 ng/mL in subjects who received topical treatment on the scalp. The mean AUC24 was 5.0±3.9 h x ng/mL in subjects who received topical treatment on the face and 3.2±1.9 h x ng/mL in subjects who received topical treatment on the scalp. The median Tmax was about seven hours.
There is limited information on the route of elimination of tirbanibulin.
There is limited information on the volume of distribution of tirbanibulin. In mouse HT29 xenograft studies, the tissue to plasma ration of tirbanibulin was 1.52.
There is limited information on the clearance rate of tirbanibulin.
応用分野
使用KX2-391 is a Src Inhibitor with efficacy against certain hepatic and leukemia cell lines.
上流・下流製品情報
上流原料
サプライヤー100 社
関連反応
化合物ノート
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