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MedKoo Cat#: 201710 | Name: Larotaxel

Description:

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

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

Larotaxel
Larotaxel
CAS#156294-36-9

Theoretical Analysis

MedKoo Cat#: 201710

Name: Larotaxel

CAS#: 156294-36-9

Chemical Formula: C45H53NO14

Exact Mass: 831.3466

Molecular Weight: 831.90

Elemental Analysis: C, 64.97; H, 6.42; N, 1.68; O, 26.93

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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
More Info
  Chemical structure:  The chemical structure of larotaxel is similar to that of docetaxel except there is a cyclopropane ring in the molecule of larotaxel:       

Preparing Stock Solutions

The following data is based on the product molecular weight 831.90 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
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 3. Coffey, Matthew C.; Thompson, Bradley G.; Pandha, Hardev. Modulating interstitial pressure and oncolytic viral delivery and distribution. PCT Int. Appl. (2009), 43pp. CODEN: PIXXD2 WO 2009143610 A1 20091203 CAN 152:1822 AN 2009:1501162 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

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GSK 525768A

GSK 525768A

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