Larotaxel

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

MedKoo CAT#: 201710

CAS#: 156294-36-9

Description: Larotaxel is a semi-synthetic derivative of the taxane 10-deacetylbaccatin III with potential antineoplastic activities. Larotaxel binds to tubulin, promoting microtubule assembly and stabilization and preventing microtubule depolymerization, thereby inhibiting cell proliferation. As it represents poor substrate for P-glycoprotein-related drug resistance mechanisms, this agent may be useful for treating multi-drug resistant tumors. Larotaxel penetrates the blood brain barrier.


Chemical Structure

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Larotaxel
CAS# 156294-36-9

Theoretical Analysis

MedKoo Cat#: 201710
Name: Larotaxel
CAS#: 156294-36-9
Chemical Formula: C45H53NO14
Exact Mass: 831.34661
Molecular Weight: 831.9
Elemental Analysis: C, 64.97; H, 6.42; N, 1.68; O, 26.93

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2021-03-06. Prices are subject to change without notice.

Larotaxel is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: XRP9881; XRP 9881 XRP-9881; RPR109881; RPR-109881; RPR 109881; RPR109881A; RPR 109881; RPR-109881A; PNU100940; PNU-100940; PNU 100940; Larotaxel.

IUPAC/Chemical Name: (1S,2S,4S,7R,8aR,9aS,10aR,12aS,12bR)-1-(benzoyloxy)-4-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-2-hydroxy-5,13,13-trimethyl-8-oxo-1,3,4,7,8,9,9a,10,10a,12b-decahydro-2H-2,6-methanocyclodeca[3,4]cyclopropa[4,5]benzo[1,2-b]oxete-7,12a(12H)-diyl diacetate

InChi Key: DXOJIXGRFSHVKA-BZVZGCBYSA-N

InChi Code: InChI=1S/C45H53NO14/c1-23-29(57-39(52)33(49)32(26-15-11-9-12-16-26)46-40(53)60-41(4,5)6)21-45(54)37(58-38(51)27-17-13-10-14-18-27)35-43(36(50)34(56-24(2)47)31(23)42(45,7)8)20-28(43)19-30-44(35,22-55-30)59-25(3)48/h9-18,28-30,32-35,37,49,54H,19-22H2,1-8H3,(H,46,53)/t28-,29+,30-,32+,33-,34-,35+,37+,43-,44+,45-/m1/s1

SMILES Code: CC1=C2[C@H](C(=O)[C@]34C[C@H]3C[C@@H]5[C@]([C@H]4[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C6=CC=CC=C6)NC(=O)OC(C)(C)C)O)O)OC(=O)C7=CC=CC=C7)(CO5)OC(=O)C)OC(=O)C

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 soluble 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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 831.9 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.

Select a batch to recalculate based on the batch molecular weight:
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. Chauchereau, Anne; Al Nakouzi, Nader. Gene expression markers for prediction of the response of a tumor to taxane therapy. Eur. Pat. Appl. (2010), 59pp. CODEN: EPXXDW EP 2177630 A1 20100421 CAN 152:493436 AN 2010:498376

2. Chauchereau, Anne; Al Nakouzi, Nader. Resistance expression signature-based methods for predicting or monitoring whether a patient affected by a cancer is responsive to a treatment with a molecule of the taxoid family. PCT Int. Appl. (2010), 73pp. CODEN: PIXXD2 WO 2010037859 A2 20100408 CAN 152:446754 AN 2010:437266

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4. Robert, Francisco; Harper, Karen; Ackerman, Judie; Gupta, Sunil. A phase I study of larotaxel (XRP9881) administered in combination with carboplatin in chemotherapy-naive patients with stage IIIB or stage IV non-small cell lung cancer. Cancer Chemotherapy and Pharmacology (2010), 65(2), 227-234. CODEN: CCPHDZ ISSN:0344-5704. CAN 152:421757 AN 2009:1464218

5. Moreno-Aspitia, Alvaro; Perez, Edith A. Anthracycline- and/or taxane-resistant breast cancer: results of a literature review to determine the clinical challenges and current treatment trends. Clinical Therapeutics (2009), 31(8), 1619-1640. CODEN: CLTHDG ISSN:0149-2918. CAN 152:491588 AN 2009:1293108

6. Burger, Angelika; Hendriks, Hans; Rademaker, Bernardus. Method and compositions for treatment of cancer. U.S. Pat. Appl. Publ. (2009), 11 pp. CODEN: USXXCO US 2009246291 A1 20091001 CAN 151:411468 AN 2009:1202677

7. Yamamoto, Nobuyuki; Boku, Narikazu; Minami, Hironobu. Phase I study of larotaxel administered as a 1-h intravenous infusion every 3 weeks to Japanese patients with advanced solid tumours. Cancer Chemotherapy and Pharmacology (2009), 65(1), 129-136. CODEN: CCPHDZ ISSN:0344-5704. CAN 152:469239 AN 2009:1133913

8. Bascomb, Newell; Maki, John; Young, Fredric S. Compositions and methods for mucositis and oncology therapies. PCT Int. Appl. (2009), 183pp. CODEN: PIXXD2 WO 2009111648 A1 20090911 CAN 151:350870 AN 2009:1108114

9. Metzger-Filho, Otto; Moulin, Camilo; de Azambuja, Evandro; Ahmad, Awada. Larotaxel: broadening the road with new taxanes. Expert Opinion on Investigational Drugs (2009), 18(8), 1183-1189. CODEN: EOIDER ISSN:1354-3784. CAN 151:259528 AN 2009:854569

10. Rortais, Paticia; Gachon, Carine. Novel taxoid-based compositions. PCT Int. Appl. (2009), 24pp.; Chemical Indexing Equivalent to 150:431520 (FR). CODEN: PIXXD2 WO 2009083664 A1 20090709 CAN 151:132219 AN 2009:824984

11. Qiao, Hua. Advances of clinical treatment of drug-resistant advanced breast cancer. Guoji Zhongliuxue Zazhi (2009), 36(2), 133-135. CODEN: GZZUAK ISSN:1673-422X. CAN 152:67 AN 2009:552093



Additional Information

 
Chemical structure:  The chemical structure of larotaxel is similar to that of docetaxel except there is a cyclopropane ring in the molecule of larotaxel: