Cabazitaxel-d6
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MedKoo CAT#: 600585

CAS#: 1383561-29-2 (d6-labeled)

Description: Cabazitaxel-d6 is a deuterium labeled cabazitaxel. Cabazitaxel is a semi-synthetic derivative of the natural taxoid 10-deacetylbaccatin III with potential antineoplastic activity. Cabazitaxel binds to and stabilizes tubulin, resulting in the inhibition of microtubule depolymerization and cell division, cell cycle arrest in the G2/M phase, and the inhibition of tumor cell proliferation. Unlike other taxane compounds, this agent is a poor substrate for the membrane-associated, multidrug resistance (MDR), P-glycoprotein (P-gp) efflux pump and may be useful for treating multidrug-resistant tumors. In addition, cabazitaxel penetrates the blood-brain barrier (BBB).


Chemical Structure

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Cabazitaxel-d6
CAS# 1383561-29-2 (d6-labeled)

Theoretical Analysis

MedKoo Cat#: 600585
Name: Cabazitaxel-d6
CAS#: 1383561-29-2 (d6-labeled)
Chemical Formula: C45H51D6NO14
Exact Mass: 841.42
Molecular Weight: 841.970
Elemental Analysis: C, 64.19; H, 7.54; N, 1.66; O, 26.60

Price and Availability

Size Price Availability Quantity
1mg USD 150 Ready to ship
5mg USD 450 Ready to ship
10mg USD 750 Ready to ship
25mg USD 1350 Ready to ship
50mg USD 2250 Ready to ship
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Related CAS #: 183133-96-2   1383561-29-2 (d6-labeled)   1383572-18-6 (d3-labeled)   1383572-17-5 (d3-labeled)    

Synonym: dimethoxydocetaxeld-6; deuteriumlabeled cabazitaxel.

IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-11-hydroxy-4,6-bis(methoxy-d3)-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

InChi Key: BMQGVNUXMIRLCK-YHVGWTKXSA-N

InChi Code: 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/i9D3,10D3

SMILES Code: O=C(O[C@@H]([C@@]1([H])[C@@]2(C)[C@@H](OC([2H])([2H])[2H])C[C@H]3OC[C@]31OC(C)=O)[C@]4(O)C[C@H](OC([C@H](O)[C@@H](NC(OC(C)(C)C)=O)C5=CC=CC=C5)=O)C(C)=C(C4(C)C)[C@@H](OC([2H])([2H])[2H])C2=O)C6=CC=CC=C6

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:   Chemical structure of cabazitaxel Comparing to the chemical structure of docetaxel, cabazitaxel has two more methyl groups. For this reason, cabazitaxel is also called dimethoxydocetaxel (see the following chemical structures).   Scheme 1: chemical structures of cabazitaxel and docetaxel   Cabazitaxel: Drug Description JEVTANA (cabazitaxel) is an antineoplastic agent belonging to the taxane class. It is prepared by semi-synthesis with a precursor extracted from yew needles. The chemical name of cabazitaxel is (2α,5β;,7β;,10β;,13α)-4-acetoxy-13-({(2R,3S)-3[(tertbutoxycarbonyl) amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1-hydroxy-7,10-dimethoxy-9oxo-5,20-epoxytax-11-en-2-yl benzoate – propan-2-one(1:1). Cabazitaxel is a white to off-white powder with a molecular formula of C45H57NO14•C3H6O and a molecular weight of 894.01 (for the acetone solvate) / 835.93 (for the solvent free). It is lipophilic, practically insoluble in water and soluble in alcohol.  JEVTANA (cabazitaxel) Injection 60 mg/1.5 mL is a sterile, non-pyrogenic, clear yellow to brownish-yellow viscous solution and is available in single-use vials containing 60 mg cabazitaxel (anhydrous and solvent free) and 1.56 g polysorbate 80. Each mL contains 40 mg cabazitaxel (anhydrous) and 1.04 g polysorbate 80. DILUENT for JEVTANA is a clear, colorless, sterile, and non-pyrogenic solution containing 13% (w/w) ethanol in water for injection, approximately 5.7 mL.  JEVTANA requires two dilutions prior to intravenous infusion. JEVTANA injection should be diluted only with the supplied DILUENT for JEVTANA, followed by dilution in either 0.9% sodium chloride solution or 5% dextrose solution.   Cabazitaxel: Mechanism of Action The taxanes act by binding to microtubules, cytoskeletal polymers composed of α-tubulin and β-tubulin heterodimers. The binding of taxanes to tubulin promotes the stabilization of GDP-bound tubulin in the microtubule resulting in inhibition of disassembly and prevention of subsequent mitosis and cell division.  Derived from the bark of yew trees, in 1992, paclitaxel was the first taxane approved by the Food and Drug Administration (FDA) as an anti-neoplastic agent. Docetaxel, a semisynthetic analog with increased potency, was approved by the FDA in 1996 for the treatment advanced breast cancer and later in 2004 for the treatment of metastatic CRPC. These earlier generation taxanes have high substrate affinity for the ATP-dependent drug efflux pump P-glycoprotein 1 (P-gp1). Therefore, P-gp1 is thought to account for, at least in part, both inherent and acquired resistance to these agents.   Cabazitaxel, also known as XRP6258, is a semi-synthetic taxane from a single diastereoisomer of 10-deacetyl baccatin III, and derived from the needles of various Taxus species. By binding to tubulin, cabazitaxel inhibits microtubule depolymerization and cell division, resulting in cell cycle arrest. This compound was selected for clinical testing due to its poor affinity for ATP-dependent drug efflux pump P-gp1, and its greater blood-brain barrier penetration compared to paclitaxel and docetaxel. Cabazitaxel has also demonstrated superior in vitro cytotoxicity compared to docetaxel in several murine and human cancer cell lines. ( source: Clinical Development of Cabazitaxel for the Treatment of Castration-Resistant Prostate Cancer . Che-Kai Tsao, Sonia Seng, William K. Oh, and Matthew D. Galsky Division of Hematology and Medical Oncology, Tisch Cancer Institute, Mount Sinai School of Medicine, New York, NY 10029, USA, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3117627/ ).     

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 841.97 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hofman MS, Emmett L, Sandhu S, Iravani A, Joshua AM, Goh JC, Pattison DA, Tan TH, Kirkwood ID, Ng S, Francis RJ, Gedye C, Rutherford NK, Weickhardt A, Scott AM, Lee ST, Kwan EM, Azad AA, Ramdave S, Redfern AD, Macdonald W, Guminski A, Hsiao E, Chua W, Lin P, Zhang AY, McJannett MM, Stockler MR, Violet JA, Williams SG, Martin AJ, Davis ID; TheraP Trial Investigators and the Australian and New Zealand Urogenital and Prostate Cancer Trials Group. [177Lu]Lu- PSMA-617 versus cabazitaxel in patients with metastatic castration-resistant prostate cancer (TheraP): a randomised, open-label, phase 2 trial. Lancet. 2021 Feb 27;397(10276):797-804. doi: 10.1016/S0140-6736(21)00237-3. Epub 2021 Feb 11. PMID: 33581798.


2: de Wit R, de Bono J, Sternberg CN, Fizazi K, Tombal B, Wülfing C, Kramer G, Eymard JC, Bamias A, Carles J, Iacovelli R, Melichar B, Sverrisdóttir Á, Theodore C, Feyerabend S, Helissey C, Ozatilgan A, Geffriaud-Ricouard C, Castellano D; CARD Investigators. Cabazitaxel versus Abiraterone or Enzalutamide in Metastatic Prostate Cancer. N Engl J Med. 2019 Dec 26;381(26):2506-2518. doi: 10.1056/NEJMoa1911206. Epub 2019 Sep 30. PMID: 31566937.


3: Cao X, Li B, Chen J, Dang J, Chen S, Gunes EG, Xu B, Tian L, Muend S, Raoof M, Querfeld C, Yu J, Rosen ST, Wang Y, Feng M. Effect of cabazitaxel on macrophages improves CD47-targeted immunotherapy for triple-negative breast cancer. J Immunother Cancer. 2021 Mar;9(3):e002022. doi: 10.1136/jitc-2020-002022. PMID: 33753567; PMCID: PMC7986678.


4: de Bono JS, Oudard S, Ozguroglu M, Hansen S, Machiels JP, Kocak I, Gravis G, Bodrogi I, Mackenzie MJ, Shen L, Roessner M, Gupta S, Sartor AO; TROPIC Investigators. Prednisone plus cabazitaxel or mitoxantrone for metastatic castration-resistant prostate cancer progressing after docetaxel treatment: a randomised open-label trial. Lancet. 2010 Oct 2;376(9747):1147-54. doi: 10.1016/S0140-6736(10)61389-X. PMID: 20888992.


5: Corn PG, Heath EI, Zurita A, Ramesh N, Xiao L, Sei E, Li-Ning-Tapia E, Tu SM, Subudhi SK, Wang J, Wang X, Efstathiou E, Thompson TC, Troncoso P, Navin N, Logothetis CJ, Aparicio AM. Cabazitaxel plus carboplatin for the treatment of men with metastatic castration-resistant prostate cancers: a randomised, open- label, phase 1-2 trial. Lancet Oncol. 2019 Oct;20(10):1432-1443. doi: 10.1016/S1470-2045(19)30408-5. Epub 2019 Sep 9. Erratum in: Lancet Oncol. 2020 Jan;21(1):e14. PMID: 31515154; PMCID: PMC6858999.


6: Pobel C, Auclin E, Procureur A, Clément-Zhao A, Simonaggio A, Delanoy N, Vano YA, Thibault C, Oudard S. Cabazitaxel schedules in metastatic castration- resistant prostate cancer: a review. Future Oncol. 2021 Jan;17(1):91-102. doi: 10.2217/fon-2020-0672. Epub 2020 Dec 2. PMID: 33463373.


7: Buteau JP, Martin AJ, Emmett L, Iravani A, Sandhu S, Joshua AM, Francis RJ, Zhang AY, Scott AM, Lee ST, Azad AA, McJannett MM, Stockler MR, Williams SG, Davis ID, Hofman MS; TheraP Trial Investigators and the Australian and New Zealand Urogenital and Prostate Cancer Trials Group. PSMA and FDG-PET as predictive and prognostic biomarkers in patients given [177Lu]Lu- PSMA-617 versus cabazitaxel for metastatic castration-resistant prostate cancer (TheraP): a biomarker analysis from a randomised, open-label, phase 2 trial. Lancet Oncol. 2022 Nov;23(11):1389-1397. doi: 10.1016/S1470-2045(22)00605-2. Epub 2022 Oct 16. PMID: 36261050.


8: Sun B, Lovell JF, Zhang Y. Current development of cabazitaxel drug delivery systems. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2023 Mar;15(2):e1854. doi: 10.1002/wnan.1854. Epub 2022 Sep 25. PMID: 36161272.


9: Oudard S, Fizazi K, Sengeløv L, Daugaard G, Saad F, Hansen S, Hjälm-Eriksson M, Jassem J, Thiery-Vuillemin A, Caffo O, Castellano D, Mainwaring PN, Bernard J, Shen L, Chadjaa M, Sartor O. Cabazitaxel Versus Docetaxel As First-Line Therapy for Patients With Metastatic Castration-Resistant Prostate Cancer: A Randomized Phase III Trial-FIRSTANA. J Clin Oncol. 2017 Oct 1;35(28):3189-3197. doi: 10.1200/JCO.2016.72.1068. Epub 2017 Jul 28. PMID: 28753384.


10: Galsky MD, Dritselis A, Kirkpatrick P, Oh WK. Cabazitaxel. Nat Rev Drug Discov. 2010 Sep;9(9):677-8. doi: 10.1038/nrd3254. PMID: 20811375.


11: Hofman MS, Emmett L, Violet J, Y Zhang A, Lawrence NJ, Stockler M, Francis RJ, Iravani A, Williams S, Azad A, Martin A, McJannett M; ANZUP TheraP team; Davis ID. TheraP: a randomized phase 2 trial of 177 Lu-PSMA-617 theranostic treatment vs cabazitaxel in progressive metastatic castration- resistant prostate cancer (Clinical Trial Protocol ANZUP 1603). BJU Int. 2019 Nov;124 Suppl 1:5-13. doi: 10.1111/bju.14876. Epub 2019 Oct 22. PMID: 31638341.


12: Yap TA, Pezaro CJ, de Bono JS. Cabazitaxel in metastatic castration- resistant prostate cancer. Expert Rev Anticancer Ther. 2012 Sep;12(9):1129-36. doi: 10.1586/era.12.88. PMID: 23098113.


13: Watson AS, Gagnon R, Batuyong E, Alimohamed N, Lee-Ying R. Real-World Cabazitaxel Use and Outcomes in Metastatic Castrate-Resistant Prostate Cancer: The Impact of Response to First ARPI. Clin Genitourin Cancer. 2022 Oct;20(5):496.e1-496.e9. doi: 10.1016/j.clgc.2022.04.009. Epub 2022 Apr 26. PMID: 35599196.


14: Villanueva C, Bazan F, Kim S, Demarchi M, Chaigneau L, Thiery-Vuillemin A, Nguyen T, Cals L, Dobi E, Pivot X. Cabazitaxel: a novel microtubule inhibitor. Drugs. 2011 Jul 9;71(10):1251-8. doi: 10.2165/11591390-000000000-00000. Erratum in: Drugs. 2011 Sep 10;71(13):1720. PMID: 21770474.


15: Sternberg CN, Castellano D, de Bono J, Fizazi K, Tombal B, Wülfing C, Kramer G, Eymard JC, Bamias A, Carles J, Iacovelli R, Melichar B, Sverrisdóttir Á, Theodore C, Feyerabend S, Helissey C, Poole EM, Ozatilgan A, Geffriaud-Ricouard C, de Wit R. Efficacy and Safety of Cabazitaxel Versus Abiraterone or Enzalutamide in Older Patients with Metastatic Castration-resistant Prostate Cancer in the CARD Study. Eur Urol. 2021 Oct;80(4):497-506. doi: 10.1016/j.eururo.2021.06.021. Epub 2021 Jul 15. PMID: 34274136.


16: Oudard S. TROPIC: Phase III trial of cabazitaxel for the treatment of metastatic castration-resistant prostate cancer. Future Oncol. 2011 Apr;7(4):497-506. doi: 10.2217/fon.11.23. PMID: 21463139.


17: Bouchet BP, Galmarini CM. Cabazitaxel, a new taxane with favorable properties. Drugs Today (Barc). 2010 Oct;46(10):735-42. doi: 10.1358/dot.2010.46.10.1519019. PMID: 21076710.


18: Vrignaud P, Semiond D, Benning V, Beys E, Bouchard H, Gupta S. Preclinical profile of cabazitaxel. Drug Des Devel Ther. 2014 Oct 13;8:1851-67. doi: 10.2147/DDDT.S64940. PMID: 25378905; PMCID: PMC4207555.


19: Paller CJ, Antonarakis ES. Cabazitaxel: a novel second-line treatment for metastatic castration-resistant prostate cancer. Drug Des Devel Ther. 2011 Mar 10;5:117-24. doi: 10.2147/DDDT.S13029. Erratum in: Drug Des Devel Ther. 2011;5:183. PMID: 21448449; PMCID: PMC3063116.


20: Al-Mansouri L, Gurney H. Clinical concepts for cabazitaxel in the management of metastatic castration-resistant prostate cancer. Asia Pac J Clin Oncol. 2019 Dec;15(6):288-295. doi: 10.1111/ajco.13193. Epub 2019 Jul 16. PMID: 31313526.