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Merck
CN

SML2487

Sigma-Aldrich

Cabazitaxel

≥95% (HPLC), taxane microtubule inhibitor, powder

Synonym(s):

1-hydroxy-7β,10β-dimethoxy-9-oxo-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-[[(tert-butoxy)carbonyl]amino]-2-hydroxy-3-phenylpropanoate], DEP cabazitaxel, Jevtana, TXD 258, XRP 6258, XRP-6258, dimethoxydocetaxel

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About This Item

Empirical Formula (Hill Notation):
C45H57NO14
CAS Number:
183133-96-2
Molecular Weight:
835.93
MDL number:
MFCD18827611
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Cabazitaxel, ≥95% (HPLC)

Assay

≥95% (HPLC)

form

powder

optical activity

[α]/D -36 to -44°, c = 0.5 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

N([C@H]([C@@H](O)C(=O)O[C@H]2C[C@]3([C@H]([C@@H]5[C@]6([C@H](OC6)C[C@@H]([C@]5(C(=O)[C@@H](C(=C2C)C3(C)C)OC)C)OC)OC(=O)C)OC(=O)c4ccccc4)O)c1ccccc1)C(=O)OC(C)(C)C

InChI

1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1

InChI key

BMQGVNUXMIRLCK-OAGWZNDDSA-N

Related Categories

Biochem/physiol Actions

Cabazitaxel is a synthetic taxane microtubule inhibitor and anticancer agent. It acts by stabilization of microtubules, promoting tubulin assembly into microtubules but inhibiting disassembly, resulting in the inhibition of mitotic and interphase cellular functions.
Synthetic taxane microtubule inhibitor

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Muta. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000334126
0000334126
0000279142
0000279142
0000279143

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Patricia Vrignaud et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 19(11), 2973-2983 (2013-04-17)
Taxanes are important chemotherapeutic agents with proven efficacy in human cancers, but their use is limited by resistance development. We report here the preclinical characteristics of cabazitaxel (XRP6258), a semisynthetic taxane developed to overcome taxane resistance. Cabazitaxel effects on purified
Sheel A Patel et al.
OncoTargets and therapy, 10, 4089-4098 (2017-09-02)
Cabazitaxel is an effective chemotherapeutic agent used in the treatment of metastatic castration-resistant prostate cancer (mCRPC) refractory to docetaxel. With the advent of new antiandrogen therapies, immune-based treatments, and radioactive-targeted therapy, there are now multiple effective and approved agents for
Takeo Kosaka et al.
Cancer chemotherapy and pharmacology, 82(6), 1061-1066 (2018-10-05)
The correlation of the oncological outcomes of docetaxel and cabazitaxel in Japanese metastatic castration-resistant prostate cancer (mCRPC) patients has not been unclear. This study included a total of 47 consecutive Japanese mCRPC patients treated with cabazitaxel and assessed the prognostic
Maria J Martinez et al.
iScience, 26(9), 107681-107681 (2023-09-14)
Men with incurable castration resistant prostate cancer (CRPC) are typically treated with taxanes; however, drug resistance rapidly develops. We previously identified a clinically relevant seven gene network in aggressive CRPC, which includes the spindle assembly checkpoint (SAC) kinase BUB1. Since
Buse Cevatemre et al.
Cell death & disease, 15(2), 132-132 (2024-02-13)
The development of taxane resistance remains a major challenge for castration resistant prostate cancer (CR-PCa), despite the effectiveness of taxanes in prolonging patient survival. To uncover novel targets, we performed an epigenetic drug screen on taxane (docetaxel and cabazitaxel) resistant

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