WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202964
Description: TPI 287 is a synthetic, third generation taxane with potential antineoplastic activity. TPI 287 binds to tubulin and stabilizes microtubules, resulting in inhibition of microtubule assembly/disassembly dynamics, cell cycle arrest at the G2/M phase, and apoptosis.
MedKoo Cat#: 202964
Chemical Formula: C46H63NO15
Exact Mass: 869.41977
Molecular Weight: 869.99
Elemental Analysis: C, 63.51; H, 7.30; N, 1.61; O, 27.59
This product is not in stock, which may be available by custom synthesis.
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Synonym: TPI287; TPI-287; TPI 287; ARC100; ARC-100; ARC 100; NBT-287; NBT287; NBT 287
IUPAC/Chemical Name: (1S,2S,4S,7S,7aR,7a1S,10aS,11aR,13aS,13bR)-1-(benzoyloxy)-4-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-5-methylhexanoyl)oxy)-2-hydroxy-5,7a1,14,14-tetramethyl-9-vinyl-2,3,4,7,7a,7a1,10a,11,11a,13,13a,13b-dodecahydro-1H-8,10,12-trioxa-2,6-methanocyclobuta[b]cyclodeca[de]naphthalene-7,13a-diyl diacetate
InChi Key: FDTAUJJRHBRHIJ-FDJAAIFISA-N
InChi Code: InChI=1S/C46H63NO15/c1-13-32-58-30-20-31-45(22-55-31,61-26(6)49)36-38(60-39(51)27-17-15-14-16-18-27)46(54)21-29(57-40(52)34(50)28(19-23(2)3)47-41(53)62-42(7,8)9)24(4)33(43(46,10)11)35(56-25(5)48)37(59-32)44(30,36)12/h13-18,23,28-32,34-38,50,54H,1,19-22H2,2-12H3,(H,47,53)/t28-,29-,30-,31+,32?,34+,35-,36-,37-,38-,44+,45-,46+/m0/s1
SMILES Code: C=CC1O[C@]([C@@H](OC(C)=O)C2=C(C)[C@@H](OC([C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)C)=O)C[C@@](C2(C)C)(O)[C@H]3OC(C4=CC=CC=C4)=O)([H])[C@@]5(C)[C@@]3([H])[C@@](CO6)(OC(C)=O)[C@@]6([H])C[C@]5([H])O1
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
The following data is based on the product molecular weight 869.99 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.
|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. 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 CAPLUS
2. McChesney, James D.; Henri, John T.; Venkataraman, Sylesh K.; Lamb, Rodger L.; Foster, Jonathan E.; Sumner, Christian M.; Ye, Shangping; Yiannkouros, George Petros; Stemphoski, Aaron Michael; Walker, Donald G. Processes for the preparation of taxane derivatives and intermediates useful therein. PCT Int. Appl. (2007), 58 pp. CODEN: PIXXD2 WO 2007075870 A2 20070705 CAN 147:143571 AN 2007:728689 CAPLUS
3. Tomillero A; Moral M A Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology (2008), 30(8), 643-72. Journal code: 7909595. ISSN:0379-0355. PubMed ID 19088949 AN 2009036942 MEDLINE
TPI 287, a proprietary next-generation taxane, is Tapestry's lead clinical compound. This compound was designed to overcome multiple drug resistance in solid tumors that are innately resistant to taxane therapy or have become resistant to taxanes following exposure to chemotherapy drugs. In preclinical testing, TPI 287 demonstrated the ability to inhibit tumor cell growth in a number of in vitro cell lines and has shown inhibition of human tumor growth in certain animal xenograft models when tested against standard comparative agents. The in vitro activity was seen across multiple cell lines including cell lines known to be sensitive to taxanes as well as cell lines known to be resistant to taxanes. Taxane sensitive cell lines in which TPI 287 has shown activity include cell lines derived from breast cancer, uterine cancer and non-small cell lung cancer. Taxane resistant cell lines in which TPI 287 has shown activity include cell lines derived from breast cancer, colon cancer and prostate cancer. See http://www.tapestrypharma.com.