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TAS-108

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TAS-108

Clinical data

Other names

17β-[2-[4-[(diethylamino)methyl]-2-methoxyphenoxy]ethyl]-7α-methylestra-1,3,5(10)-trien-3-ol; 17β-[2-[4-[(diethylamino)methyl]-2-methoxyphenoxy]ethyl]-7α-methylestradiol

Routes of
administration

By mouth^[1]

ATC code

L02BA (WHO)

Identifiers

IUPAC name

(1S,9R,10S,11S,14R,15R)-14-(2-{4-[(diethylamino)methyl]-2-methoxyphenoxy}ethyl)-9,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-2(7),3,5-trien-5-ol

CAS Number

229634-97-3

Citrate: 229634-98-4

PubChem CID

9874875

Citrate: 9874874

ChemSpider

8050564^Y

Citrate: 8050563

UNII

42U0C8VOLO

Citrate: 9B29N23K7E

CompTox Dashboard (EPA)

DTXSID601117925

Chemical and physical data

Formula

C₃₃H₄₇NO₃

Molar mass

505.743 g·mol⁻¹

3D model (JSmol)

Interactive image

Citrate: Interactive image

SMILES

CCN(CC)CC1=CC(=C(C=C1)OCC[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3[C@@H](CC5=C4C=CC(=C5)O)C)C)OC

Citrate: CCN(CC)CC1=CC(=C(C=C1)OCC[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3[C@@H](CC5=C4C=CC(=C5)O)C)C)OC.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChI=1S/C33H47NO3/c1-6-34(7-2)21-23-8-13-30(31(19-23)36-5)37-17-15-25-9-12-29-32-22(3)18-24-20-26(35)10-11-27(24)28(32)14-16-33(25,29)4/h8,10-11,13,19-20,22,25,28-29,32,35H,6-7,9,12,14-18,21H2,1-5H3/t22-,25-,28-,29+,32-,33-/m1/s1^Y

Key:OHCPNHFLPCVWRG-MWSJHZLTSA-N^Y

Citrate: InChI=1S/C33H47NO3.C6H8O7/c1-6-34(7-2)21-23-8-13-30(31(19-23)36-5)37-17-15-25-9-12-29-32-22(3)18-24-20-26(35)10-11-27(24)28(32)14-16-33(25,29)4;7-3(8)1-6(13,5(11)12)2-4(9)10/h8,10-11,13,19-20,22,25,28-29,32,35H,6-7,9,12,14-18,21H2,1-5H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t22-,25-,28-,29+,32-,33-;/m1./s1

Key:VOHOCSJONOJOSD-SCIDSJFVSA-N

TAS-108, also known as SR-16234, is a drug discovered by Masato Tanabe and under development by SRI International and Taiho Pharmaceutical. It is a steroid hormone that has shown signs of treating and preventing breast cancer, even in patients where tamoxifen has failed.^[2]^[3]

Development[edit]

Masato Tanabe's team at SRI has focused on the development of steroid hormones. A compound discovered in a previous SRI contract from the National Institutes of Health showed potential – it acted like "anti-estrogen" in the breasts and uterus but like normal estrogen elsewhere in the body, and was more "tissue-selective".^[4] A contract was proposed to Taiho Pharmaceutical in July 1996, and within six years and slightly under $3 million (an unusually short amount of time), two new drugs were discovered and tested on people (particularly people for which tamoxifen has failed): SR-16234 and SR-16287.^[4]

The first of those, SR-16234, also inhibited the growth of blood vessels angiogenesis and accelerated the death of cancer cells apoptosis and thus was particularly well suited to be an anti-cancer drug.^[4] As of August 2010, the drug had been through five Phase I and two Phase II studies,^[5] and Phase III studies are being planned.^[6]

References[edit]

^ Yamamoto Y, Shibata J, Yonekura K, Sato K, Hashimoto A, Aoyagi Y, et al. (January 2005). "TAS-108, a novel oral steroidal antiestrogenic agent, is a pure antagonist on estrogen receptor alpha and a partial agonist on estrogen receptor beta with low uterotrophic effect". Clinical Cancer Research. 11 (1): 315–322. doi:10.1158/1078-0432.315.11.1. PMID 15671561.

^ Yamamoto Y, Wada O, Takada I, Yogiashi Y, Shibata J, Yanagisawa J, et al. (December 2003). "Both N- and C-terminal transactivation functions of DNA-bound ERalpha are blocked by a novel synthetic estrogen ligand". Biochemical and Biophysical Research Communications. 312 (3): 656–662. doi:10.1016/j.bbrc.2003.10.178. PMID 14680815.

^ "Alumni Hall of Fame 2004: Masato Tanabe". SRI International. Retrieved 2013-02-10.

^ ^a ^b ^c Nielson D (2006). A Heritage of Innovation: SRI's First Half Century. Menlo Park, California: SRI International. pp. 10–15. ISBN 978-0-9745208-1-0.

^ "SRI International to Advance Clinical Development of TAS-108, a Late-Stage Breast Cancer Drug" (Press release). SRI International. Retrieved 2013-02-24.