Ortataxel

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

Description:Ortataxel, also known as IDN5109, is novel seimsynthetic taxane with potential anticancer activity. Ortataxel is characterized by its high tolerability, antitumor efficacy, ability to overcome multidrug resistance, and oral bioavailabilty. In in vitro experiments, IDN5109 showed antiproliferative effects against HNSCC cell lines. After treatment with IDN5109, Bcl-2 and Bcl-XL were down-regulated, Bax was up-regulated, and caspase-3 was activated. After treatment with IDN5109, concentrations of both VEGF and IL-8 in the culture supernatant of HNSCC cells decreased. In in vivo experiments, the oral administration of IDN5109 showed antitumor effects against HNSCC tumor xenografts. Immunohistochemistry showed that IDN5109 inhibited tumor angiogenesis and induced apoptosis in HNSCC cells, producing a decreased blood vessel density and increased apoptosis index. On the basis of these results, IDN5109 is useful as a chemotherapeutic agent against HNSCC.

Price and Availability

Ortataxel 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

Theoretical Analysis

MedKoo Cat#: 202090Name: OrtataxelCAS#: 186348-23-2Chemical Formula: C44H57NO17Exact Mass: 871.36265Molecular Weight: 871.92Elemental Analysis:C, 60.61; H, 6.59; N, 1.61; O, 31.19

Synonym:Ortataxel Bay598862 IDN5109 SBT101131

IUPAC/Chemical Name:(3aS,4R,7R,8aS,9S,10aR,12aS,13S,13aS)-13-(benzoyloxy)-4-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-5-methylhexanoyl)oxy)-9-hydroxy-5,8a,14,14-tetramethyl-2,8-dioxo-3a,4,7,8,8a,9,10,10a,12,12a,12b,13-dodecahydro-6,13a-methanooxeto[2'',3'':5',6']benzo[1',2':4,5]cyclodeca[1,2-d][1,3]dioxole-7,12a-diyl diacetate

InChi Key:BWKDAMBGCPRVPI-FMWKWGOESA-N

InChi Code:InChI=1S/C44H57NO17/c1-20(2)17-25(45-38(53)61-40(6,7)8)29(49)37(52)57-30-21(3)28-31(56-22(4)46)33(50)42(11)26(48)18-27-43(19-55-27,60-23(5)47)32(42)35(58-36(51)24-15-13-12-14-16-24)44(41(28,9)10)34(30)59-39(54)62-44/h12-16,20,25-27,29-32,34-35,48-49H,17-19H2,1-11H3,(H,45,53)/t25-,26-,27+,29+,30+,31+,32?,34-,35-,42+,43-,44+/m0/s1

SMILES Code:O=C([C@H](OC(C)=O)C(C1(C)C)=C(C)[C@H]2OC([C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)C)=O)[C@@]([C@@H](O)C[C@]3([H])[C@@]4(OC(C)=O)CO3)(C)C4[C@H](OC(C5=CC=CC=C5)=O)[C@@]61[C@@]2([H])OC(O6)=O

Technical Data

Additional Information

References

 1: Xiang F, Yu J, Yin R, Ma Y, Yu L.Structure-activity relationship of taxol inferring from docking taxolanalogues to microtubule binding site. Z Naturforsch C. 2009Jul-Aug;64(7-8):551-6. PubMed PMID: 19791508.

2: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find ExpClin Pharmacol. 2008 Oct;30(8):643-72. PubMed PMID: 19088949.

3: Geney R, Chen J, Ojima I. Recent advances in the new generationtaxane anticancer agents. Med Chem. 2005 Mar;1(2):125-39. Review. PubMedPMID: 16787308.

4: Sano D, Matsuda H, Ishiguro Y, Nishimura G, Kawakami M, Tsukuda M.Antitumor effects of IDN5109 on head and neck squamous cell carcinoma.Oncol Rep. 2006 Feb;15(2):329-34. PubMed PMID: 16391850.

5: Song L, Prey JD, Xue J, Kanter P, Manzotti C, Bombardelli E,Morazzoni P, Pendyala L. Pharmacokinetic measurements of IDN 5390 usingelectrospray ionization tandem mass spectrometry: structurecharacterization and quantification in dog plasma. Rapid Commun MassSpectrom. 2005;19(24):3617-25. PubMed PMID: 16299696.

6: Barboni L, Ballini R, Giarlo G, Appendino G, Fontana G, BombardelliE. Synthesis and biological evaluation of methoxylated analogs of thenewer generation taxoids IDN5109 and IDN5390. Bioorg Med Chem Lett. 2005Dec 1;15(23):5182-6. Epub 2005 Sep 23. PubMed PMID: 16183281.

7: Lavelle F. American Association for Cancer Research 1999: 10-14April, Philadelphia, Pennsylvania. Expert Opin Investig Drugs. 1999Jun;8(6):903-9. PubMed PMID: 15992139.

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

9: Eckstein JW. Drug evaluation: Bay-59-8862. IDrugs. 2004Jun;7(6):575-81. Review. PubMed PMID: 15197663.

10: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. MethodsFind Exp Clin Pharmacol. 2004 Apr;26(3):211-44. PubMed PMID: 15148527.