Milataxel

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

MedKoo CAT#: 201880

CAS#: 393101-41-2

Description: Milataxel is an orally bioavailable taxane with potential antineoplastic activity. Upon oral administration, milataxel and its major active metabolite M-10 bind to and stabilize 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, milataxel appears to be a poor substrate for the multidrug resistance (MDR) membrane-associated P-glycoprotein (P-gp) efflux pump and may be useful for treating multidrug-resistant tumors. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

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10mg
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100mg
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1g
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10g
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25mg
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200mg
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2g
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50mg
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500mg
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5g
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Milataxel 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.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 201880
Name: Milataxel
CAS#: 393101-41-2
Chemical Formula: C44H55NO16
Exact Mass: 853.35208
Molecular Weight: 853.9
Elemental Analysis: C, 61.89; H, 6.49; N, 1.64; O, 29.98


Synonym: MAC-321; MAC 321; MAC321; TL-139; TL-139; TL-139; Milataxel

IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12bS)-12b-acetoxy-9-(((2R,3R)-3-((tert-butoxycarbonyl)amino)-3-(furan-2-yl)-2-hydroxypropanoyl)oxy)-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-(propionyloxy)-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

SMILES Code: O=C(O[C@@H]1C(C)=C(C2(C)C)[C@@H](O)C([C@@]([C@@H](OC(CC)=O)C3)(C)C([C@@]4(OC(C)=O)[C@]3([H])OC4)[C@H](OC(C5=CC=CC=C5)=O)[C@]2(O)C1)=O)[C@H](O)[C@@H](NC(OC(C)(C)C)=O)C6=CC=CO6


Technical Data

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).

Harmonized System Code:
293490


Additional Information

Milataxel is an orally bioavailable taxane with potential antineoplastic activity. Upon oral administration, milataxel and its major active metabolite M-10 bind to and stabilize 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, milataxel appears to be a poor substrate for the multidrug resistance (MDR) membrane-associated P-glycoprotein (P-gp) efflux pump and may be useful for treating multidrug-resistant tumors. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
 
Current developer:   
 
 


References

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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. Mann, David Marshall. Gene expression profiling in the pulmonary artery in the selection of therapies for vascular-related diseases. PCT Int. Appl. (2009), 115pp. CODEN: PIXXD2 WO 2009121031 A1 20091001 CAN 151:418165 AN 2009:1194632

4. Barry, John J.; Heck, Robert K. Local delivery of chemotherapeutic agents to skeletal metastases. PCT Int. Appl. (2009), 20pp. CODEN: PIXXD2 WO 2009114462 A2 20090917 CAN 151:344848 AN 2009:1139011

5. Safarpour, Hudan; Connolly, Paul; Tong, Xiaojie; Bielawski, Mike; Wilcox, Everett. Overcoming extractability hurdles of a 14C labeled taxane analogue milataxel and its metabolite from xenograft mouse tumor and brain tissues. Journal of Pharmaceutical and Biomedical Analysis (2009), 49(3), 774-779. CODEN: JPBADA ISSN:0731-7085. CAN 150:506136 AN 2009:285070

6. Brown, Jeffery Lester; Huszar, Dennis; McCoon, Patricia Elizabeth. Therapeutic methods using a pharmaceutical combination of an Eg5 protein inhibitor and a microtubule interfering agent to treat cancer. PCT Int. Appl. (2008), 25pp. CODEN: PIXXD2 WO 2008122798 A2 20081016 CAN 149:440348 AN 2008:1248885

7. Ramanathan, Ramesh K.; Picus, Joel; Raftopoulos, Haralambos; Bernard, Stephen; Lockhar, A. Craig; Frenette, Gary; Macdonald, John; Melin, Susan; Berg, Daniel; Brescia, Frank; Hochster, Howard; Cohn, Allen. A phase II study of milataxel: a novel taxane analogue in previously treated patients with advanced colorectal cancer. Cancer Chemotherapy and Pharmacology (2008), 61(3), 453-458. CODEN: CCPHDZ ISSN:0344-5704. CAN 148:417505 AN 2008:279708

8. Singh, Chandra Ulagaraj. Solid nanoparticle formulation of water insoluble pharmaceuticals with reduced Ostwald ripening. PCT Int. Appl. (2008), 134pp. CODEN: PIXXD2 WO 2008013785 A2 20080131 CAN 148:198644 AN 2008:124314

9. Lockhart, A. C.; Bukowski, R.; Rothenberg, M. L.; Wang, K. K.; Cooper, W.; Grover, J.; Appleman, L.; Mayer, P. R.; Shapiro, M.; Zhu, A. X. Phase I trial of oral MAC-321 in subjects with advanced malignant solid tumors. Cancer Chemotherapy and Pharmacology (2007), 60(2), 203-209. CODEN: CCPHDZ ISSN:0344-5704. CAN 147:268548 AN 2007:510766

10. Bradke, Frank; Witte, Harald; Ertuerk, Ali. Use of microtubule-stabilizing compounds to induce axonal growth. PCT Int. Appl. (2006), 97pp. CODEN: PIXXD2 WO 2006094811 A2 20060914 CAN 145:306846 AN 2006:949233

11. Liversidge, Gary; Jenkins, Scott; Liversidge, Elaine. Nanoparticulate formulations of docetaxel and analogues. U.S. Pat. Appl. Publ. (2006), 47pp. CODEN: USXXCO US 2006188566 A1 20060824 CAN 145:278275 AN 2006:847774

12. Hari, Malathi; Loganzo, Frank; Annable, Tami; Tan, Xingzhi; Musto, Sylvia; Morilla, Daniel B.; Nettles, James H.; Snyder, James P.; Greenberger, Lee M. Paclitaxel-resistant cells have a mutation in the paclitaxel-binding region of  -tubulin (Asp26Glu) and less stable microtubules. Molecular Cancer Therapeutics (2006), 5(2), 270-278. CODEN: MCTOCF ISSN:1535-7163. CAN 144:304722 AN 2006:183614

13. Rose, William C. Anticancer synergistic combinations of taxanes and EGF receptor binding compounds. PCT Int. Appl. (2005), 27 pp. CODEN: PIXXD2 WO 2005089372 A2 20050929 CAN 143:319125 AN 2005:1049808

14. Lacasse, Eric; McManus, Daniel. Human protein IAP (inhibitor of apoptosis protein) nucleobase oligomers, including dsRNA, shRNA, and siRNA, and their use for enhancing apoptosis in cancer therapy. PCT Int. Appl. (2005), 112 pp. CODEN: PIXXD2 WO 2005042558 A1 20050512 CAN 142:457053 AN 2005:409543

15. Lacasse, Eric; McManus, Daniel; Durkin, Jon P. Sequences of antisense IAP (inhibitor of apoptosis protein) oligomers and their use for treatment of proliferative diseases with a chemotherapeutic agent. PCT Int. Appl. (2005), 285 pp. CODEN: PIXXD2 WO 2005042030 A1 20050512 CAN 142:457052 AN 2005:409357

16. Dang, Long; Bettegowda, Chetan; Kinzler, Kenneth W.; Vogelstein, Bert. Improved combination bacteriolytic therapy for the treatment of tumors using spores of anaerobic bacteria and microtubule agents. PCT Int. Appl. (2005), 48 pp. CODEN: PIXXD2 WO 2005039492 A2 20050506 CAN 142:423824 AN 2005:395031

17. Dang, Long H.; Bettegowda, Chetan; Agrawal, Nishant; Cheong, Ian; Huso, David; Frost, Philip; Loganzo, Frank; Greenberger, Lee; Barkoczy, Jozsef; Pettit, George R.; Smith, Amos B., III; Gurulingappa, Hallur; Khan, Saeed; Kinzler, Kenneth W.; Zhou, Shibin; Vogelstein, Bert. Targeting vascular and avascular compartments of tumors with C. novyi-NT and anti-microtubule agents. Cancer Biology & Therapy (2004), 3(3), 326-337. CODEN: CBTAAO ISSN:1538-4047. CAN 142:106673 AN 2004:624546

18. Sampath, Deepak; Discafani, Carolyn M.; Loganzo, Frank; Beyer, Carl; Liu, Hao; Tan, Xingzhi; Musto, Sylvia; Annable, Tami; Gallagher, Patricia; Rios, Carol; Greenberger, Lee M. MAC-321, a novel taxane with greater efficacy than paclitaxel and docetaxel in vitro and in vivo. Molecular Cancer Therapeutics (2003), 2(9), 873-884. CODEN: MCTOCF ISSN:1535-7163. CAN 140:138892 AN 2003:800267

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