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Cabazitaxel

Antitumour Activity Pharmacokinetics
Cabazitaxel
Cabazitaxel structure
CAS No.
183133-96-2
Chemical Name:
Cabazitaxel
Synonyms
CS-877;TXD-258;Jevtana;XRP 6258;Cabazitaxel;RPR-116258A;Cabazitaxelum;taxoid XRP6258;Cabazitaxel, >=98%;Cabazitaxel(XRP-6258)
CBNumber:
CB42517227
Molecular Formula:
C45H57NO14
Formula Weight:
835.93
MOL File:
183133-96-2.mol

Cabazitaxel Properties

Melting point:
180 °C
Boiling point:
870.7±65.0 °C(Predicted)
Density 
1.31
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
form 
White solid.
pka
11.20±0.46(Predicted)
FDA UNII
51F690397J
NCI Dictionary of Cancer Terms
cabazitaxel; taxoid XRP6258
NCI Drug Dictionary
cabazitaxel
ATC code
L01CD04
SAFETY
  • Risk and Safety Statements
Safety Statements  24/25
HS Code  29329990

Cabazitaxel price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical C3390 Cabazitaxel 183133-96-2 25MG $88 2021-03-22 Buy
TCI Chemical C3390 Cabazitaxel 183133-96-2 100MG $260 2021-03-22 Buy
Cayman Chemical 22262 Cabazitaxel ≥98% 183133-96-2 5mg $35 2021-03-22 Buy
Cayman Chemical 22262 Cabazitaxel ≥98% 183133-96-2 10mg $53 2021-03-22 Buy
Cayman Chemical 22262 Cabazitaxel ≥98% 183133-96-2 25mg $114 2021-03-22 Buy

Cabazitaxel Chemical Properties,Uses,Production

Antitumour Activity

Cabazitaxel is a semisynthetic taxane derivative that acts as a microtubule inhibitor. It binds to tubulin, promoting the assembly of tubulin into microtubules and inhibiting their disassembly, which results in microtubule stabilization, the inhibition of cell division, cell cycle arrest and the arrest of tumour proliferation. Cabazitaxel demonstrated antitumour activity against advanced human tumours xenografted in mice. As well as being active in docetaxel-sensitive tumours, cabazitaxel showed activity in tumour models insensitive to chemotherapy, including docetaxel. Cabazitaxel also penetrates the blood-brain barrier to a greater extent than docetaxel.

Pharmacokinetics

The pharmacokinetic data for cabazitaxel demonstrated dose proportionality, with a high plasma clearance and a long terminal half-life. The very large volume of distribution at steady state suggests extensive penetration into tissues. Of interest, cabazitaxel is able to cross the blood-brain barrier in preclinical models. Cabazitaxel is mainly metabolized by the cytochrome P450 (CYP) enzyme 3A4/5 and to a lesser extent by CYP2C8, suggesting that it has the potential to inhibit CYP3A enzymes.

Description

In June 2010, the U.S. FDA approved cabazitaxel (also referred to as XRP6258 and RPR 116258A) in combination with the steroid prednisone for the treatment of metastatic Castration-Resistant Prostate Cancer (mCRPC) for patients who were previously treated with a docetaxelcontaining regimen for late-stage disease.
Cabazitaxel is a semisynthetic analog of the natural product taxol, which is isolated from the bark of the yew tree. Cabazitaxel is a microtubule inhibitor that binds to the taxol-binding site of tubulin. Similar to other tubulin inhibitors of the taxol class, cabazitaxel inhibits microtubule disassembly resulting in mitotic blockade and cell death. Docetaxel, also a semisynthetic taxol analog, was approved by the FDA for the treatment of mCRPC in 2004. However, docetaxel is a substrate for P-gp, which is thought to contribute to the constitutive and acquired resistance of cancer cells to taxanes. Cabazitaxel has poor affinity for P-gp and showed antitumor activity in preclinical in vitro studies and in vivo tumor models that overexpress this protein. Cabazitaxel is synthesized on a commercial scale from 10-deacetylbaccatin .

Chemical Properties

White solid

Originator

Sanofi-Aventis (France)

Uses

Cabazitaxel (Jevtana, XRP6258) is a semi-synthetic derivative of a natural taxoid.

Uses

A novel semi-synthetic taxane with antitumor activity used for the treatment of castration-resistant prostate cancer. A microtubule inhibitor.

Definition

ChEBI: A tetracyclic diterpenoid that is 10-deacetylbaccatin III having O-methyl groups attached at positions 7 and 10 as well as an O-(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hy roxy-3-phenylpropanoyl group attached at position 13. Acts as a microtubule inhibitor, binds tubulin and promotes microtubule assembly and simultaneously inhibits disassembly.

brand name

Jevtana

Clinical Use

Cabazitaxel was developed by Sanofi-Aventis as an intravenous injectable drug for the treatment of hormone-refractory metastatic prostate cancer. As a microtubule inhibitor, cabazitaxel differs from docetaxel because it exhibits a much weaker affinity for P-glycoprotein (P-gp), an adenosine triphosphate (ATP)-dependent drug efflux pump. Cancer cells that express P-gp become resistant to taxanes, and the effectiveness of docetaxel can be limited by its high substrate affinity for P-gp. Clinical studies confirmed that cabazitaxel retains activity in docetaxel-resistant tumors. Common adverse events with cabazitaxel include diarrhea and neutropenia. Cabazitaxel in combination with prednisone is an important new treatment option for men with docetaxel-refractory metastatic CRPC (castration-resistant prostate cancer).

Chemical Synthesis

The semi-synthesis of cabazitaxel started from 10- deacetylbaccatin III (15) which can be prepared from 7-xylosyl-10-deacetylbaccatin natural product mixture according to a literature process procedure (the Scheme). 10-Deacetylbaccatin III was protected with triethylsilyl chloride (TESCl) in pyridine to afford the corresponding 7,13-bis-silyl ether in 51% yield, which was methylated with MeI and NaH in DMF to give 10-methoxy-7,13-bis silyl ether 16 in 76% yield. After de-silylation of 16 with triethylamine trihydrofluoride complex at room temperature, triol 17 was obtained in 77% yield. Selective methylation of 17 with MeI and NaH in DMF at 0 oC provided 7,10-dimethyl ether 18 in 74% yield. Compound 18 was condensed with commercially available oxazolidinecarboxylic acid 19 in the presence of dicyclohexylcarbodiimide/dimethylaminopyridine (DCC/DMAP) in ethyl acetate at room temperature to generate ester 20 in 76% yield. The oxazolidine moiety of compound 20 was selectively hydrolyzed under mild acidic conditions to yield the hydroxy Boc-amino ester derivative cabazitaxel (III) in 32% yield.

Cabazitaxel Preparation Products And Raw materials

Raw materials

Preparation Products


Cabazitaxel Suppliers

Global( 338)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Jiangsu Yew Pharmaceutical Co., Ltd.
+86-510-66865338 +86-189-2133-5032 jiangwenjun@hongdou.com
+86-510-66865972 junwenjiang@live.cn ; jiangwenjun@hongdou.com CHINA 30 60
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 420 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26751 60
Lianyungang happen teng technology co., LTD
15950718863
wang666xt@163.com CHINA 296 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58

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View Lastest Price from Cabazitaxel manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-26 Cabazitaxel
183133-96-2
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-11-17 Cabazitaxel 183133-96-2
183133-96-2
US $60.00 / mg 20mg ≥98% 1000.00 kgs NanJing Spring & Autumn Biological Engineering CO., LTD.
2021-11-15 Cabazitaxel
183133-96-2
US $0.00 / KG 1KG 99% 200000pcs Hebei Yirun Sega Biological Technology Co. Ltd

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