Tesetaxel

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202881

CAS#: 333754-36-2

Description: Tesetaxel is a semi-synthetic, orally bioavailable taxane derivative with potential antineoplastic and antiangiogenic properties. Tesetaxel binds to and stabilizes tubulin, promoting microtubule assembly and thereby preventing microtubule depolymerization. This may lead to cell cycle arrest and an inhibition of cell proliferation. This agent may also inhibit pro-angiogenic factors such as vascular endothelial growth factor (VEGF). As it represents poor substrate for P-glycoprotein-related drug resistance mechanisms, this agent may be useful for treating multi-drug resistant tumors.


Chemical Structure

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Tesetaxel
CAS# 333754-36-2

Theoretical Analysis

MedKoo Cat#: 202881
Name: Tesetaxel
CAS#: 333754-36-2
Chemical Formula: C46H60FN3O13
Exact Mass: 881.41102
Molecular Weight: 881.98
Elemental Analysis: C, 62.64; H, 6.86; F, 2.15; N, 4.76; O, 23.58

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: DJ927; DJ-927; DJ 927; Tesetaxel

IUPAC/Chemical Name: (2aS,3S,4S,6S,8aR,10R,11bR,13aR)-2a-acetoxy-6-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-3-(3-fluoropyridin-2-yl)-2-hydroxypropanoyl)oxy)-10-((dimethylamino)methyl)-4-hydroxy-7,11b,14,14-tetramethyl-2a,2b,3,4,5,6,8a,11a,11b,12,13,13a-dodecahydro-2H-4,8-methanooxeto[3'',2'':3',4']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxol-3-yl benzoate

InChi Key: MODVSQKJJIBWPZ-MILZTGCVSA-N

InChi Code: InChI=1S/C46H60FN3O13/c1-24-28(58-40(54)34(52)33(32-27(47)17-14-20-48-32)49-41(55)63-42(3,4)5)21-46(56)38(61-39(53)26-15-12-11-13-16-26)36-44(8,19-18-29-45(36,23-57-29)62-25(2)51)37-35(31(24)43(46,6)7)59-30(60-37)22-50(9)10/h11-17,20,28-30,33-38,52,56H,18-19,21-23H2,1-10H3,(H,49,55)/t28-,29+,30+,33-,34+,35+,36?,37?,38-,44+,45-,46+/m0/s1

SMILES Code: O=C(O[C@H]([C@]1(O)C[C@H](OC([C@H](O)[C@@H](NC(OC(C)(C)C)=O)C2=NC=CC=C2F)=O)C(C)=C3C1(C)C)C4[C@@](C5[C@]3([H])O[C@@H](CN(C)C)O5)(C)CC[C@]6([H])[C@@]4(OC(C)=O)CO6)C7=CC=CC=C7

Appearance: 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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 881.98 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

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 1: Baas P, Szczesna A, Albert I, Milanowski J, Juhász E, Sztancsik Z, von Pawel J, Oyama R, Burgers S. Phase I/II study of a 3 weekly oral taxane (DJ-927) in patients with recurrent, advanced non-small cell lung cancer. J Thorac Oncol. 2008 Jul;3(7):745-50. PubMed PMID: 18594320.

2: Potential new drug targets against hormone-dependent breast cancer identified. Expert Rev Anticancer Ther. 2008 Apr;8(4):507. PubMed PMID: 18402517.

3: Roche M, Kyriakou H, Seiden M. Drug evaluation: tesetaxel--an oral semisynthetic taxane derivative. Curr Opin Investig Drugs. 2006 Dec;7(12):1092-9. Review. PubMed PMID: 17209527.

4: Attard G, Greystoke A, Kaye S, De Bono J. Update on tubulin-binding agents. Pathol Biol (Paris). 2006 Mar;54(2):72-84. Review. PubMed PMID: 16545633.

5: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Oct;26(8):639-63. PubMed PMID: 15605126.

6: Ono C, Takao A, Atsumi R. Absorption, distribution, and excretion of DJ-927, a novel orally effective taxane, in mice, dogs, and monkeys. Biol Pharm Bull. 2004 Mar;27(3):345-51. PubMed PMID: 14993800.

7: Shionoya M, Jimbo T, Kitagawa M, Soga T, Tohgo A. DJ-927, a novel oral taxane, overcomes P-glycoprotein-mediated multidrug resistance in vitro and in vivo. Cancer Sci. 2003 May;94(5):459-66. PubMed PMID: 12824894. 



Additional Information

 
Tesetaxel is a novel, orally absorbed, semi-synthetic taxane that is in the same class of drugs as paclitaxel and docetaxel. However, both prototype agents suffer from serious safety issues, particularly hypersensitivity reactions related to intravenous infusions that are occasionally fatal and that require careful premedication and observation. Other prominent side-effects of this drug class include myelosuppression (low blood counts) and peripheral neuropathy (disabling nerve damage). With administration as an oral capsule, tesetaxel was developed to maintain the high antitumor activity of the taxane drug class while eliminating infusion reactions, reducing neuropathy, and increasing patient convenience. The oral route also enables development of novel schedules that may expand dosing options when tesetaxel is used alone or in combination with other anticancer drugs. Preclinically, tesetaxel has demonstrated substantially higher activity against cell lines that were resistant to paclitaxel and docetaxel, since acquired resistance is not mediated by the multidrug-resistant p-glycoprotein. As a late Phase 2 oncology product, tesetaxel has demonstrated anticancer activity in its initial clinical trials, and the drug has not been associated with the severe infusion reactions that are linked with other taxanes. Moreover, unlike other oral taxanes, nerve damage has not been a prominent side effect of tesetaxel. Thus, the drug offers substantial opportunities to improve patient convenience, safety, and anticancer activity. More than 250 patients worldwide have been treated with oral tesetaxel in Phase 1 and Phase 2 clinical trials. For more information, please visit http://www.medicalnewstoday.com/articles/132058.php.