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MedKoo Cat#: 200720 | Name: Amsilarotene

Description:

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

Amsilarotene ( TAC-101) is a retinobenzoic acid with potential antineoplastic activity. TAC-101 inhibits retinoblastoma-gene product (RB) phosphorylation and increases the presence of 2 cyclin-dependent kinase (CDK) inhibitors, resulting in cell cycle arrest. This agent also causes a cytotoxic decline in cyclin A and thymidylate synthase expression.

Chemical Structure

Amsilarotene
Amsilarotene
CAS#125973-56-0

Theoretical Analysis

MedKoo Cat#: 200720

Name: Amsilarotene

CAS#: 125973-56-0

Chemical Formula: C20H27NO3Si2

Exact Mass: 385.1530

Molecular Weight: 385.60

Elemental Analysis: C, 62.30; H, 7.06; N, 3.63; O, 12.45; Si, 14.57

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
TAC101; TAC-101; TAC 101.
IUPAC/Chemical Name
4-[3,5-Bis(trimethylsilyl) benzamido] benzoic acid
InChi Key
VVTNSTLJOVCBDL-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H27NO3Si2/c1-25(2,3)17-11-15(12-18(13-17)26(4,5)6)19(22)21-16-9-7-14(8-10-16)20(23)24/h7-13H,1-6H3,(H,21,22)(H,23,24)
SMILES Code
O=C(O)C1=CC=C(NC(C2=CC([Si](C)(C)C)=CC([Si](C)(C)C)=C2)=O)C=C1
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
>2 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
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Preparing Stock Solutions

The following data is based on the product molecular weight 385.60 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: Okusaka T, Ueno H, Ikeda M, Takezako Y, Morizane C. Phase I study of TAC-101, an oral synthetic retinoid, in Japanese patients with advanced hepatocellular carcinoma. Cancer Sci. 2012 Aug;103(8):1524-30. doi: 10.1111/j.1349-7006.2012.02334.x. Epub 2012 Jun 18. PubMed PMID: 22587457. 2: Nakayama Y, Inoue Y, Minagawa N, Onitsuka K, Nagata J, Shibao K, Hirata K, Sako T, Nagata N, Yamaguchi K. Chemopreventive effect of 4-[3,5-Bis(trimethylsilyl) benzamido] benzoic acid (TAC-101) on MNU-induced colon carcinogenesis in a rat model. Anticancer Res. 2009 Jun;29(6):2059-65. PubMed PMID: 19528465. 3: Eshima K, Fukaya S, Sugimoto A, Mori T, Yokoi H, Yamamoto Y, Sugiura S, Honda S, Masuko N, Murakami K, Yamasaki Y, Kagechika H. Contribution of AP-1 interference induced by TAC-101 to tumor growth suppression in a hepatocellular carcinoma model. Tumour Biol. 2009;30(1):1-7. doi: 10.1159/000189712. Epub 2009 Jan 12. PubMed PMID: 19142034. 4: Higginbotham KB, Lozano R, Brown T, Patt YZ, Arima T, Abbruzzese JL, Thomas MB. A phase I/II trial of TAC-101, an oral synthetic retinoid, in patients with advanced hepatocellular carcinoma. J Cancer Res Clin Oncol. 2008 Dec;134(12):1325-35. doi: 10.1007/s00432-008-0406-2. Epub 2008 May 27. PubMed PMID: 18504614. 5: Ezawa S, Suzuki N, Ohie S, Higashiguchi A, Hosoi F, Kitazato K, Susumu N, Aoki D. A synthetic retinoid, TAC-101 (4-[3,5-bis (trimethylsilyl) benzamido] benzoic acid), plus cisplatin: potential new therapy for ovarian clear cell adenocarcinoma. Gynecol Oncol. 2008 Mar;108(3):627-31. Epub 2007 Nov 28. PubMed PMID: 18048092. 6: Inoue Y, Nakayama Y, Sako T, Minagawa N, Abe Y, Nagato M, Kadowaki K, Katsuki T, Matsumoto K, Tsurudome Y, Shibao K, Hirata K, Nagata N. 4- [3,5-bis(trimethylsilyl)benzamido] benzoic acid (TAC-101) induced fas expression and activated caspase-3 and -8 in a DLD-1 colon cancer cell line. In Vivo. 2007 Mar-Apr;21(2):381-7. PubMed PMID: 17436592. 7: Sako T, Nakayama Y, Minagawa N, Inoue Y, Onitsuka K, Katsuki T, Tsurudome Y, Shibao K, Hirata K, Nagata N, Ohie S, Kohno K, Itoh H. 4-[3,5-Bis(trimethylsilyl)benzamido] benzoic acid (TAC-101) induces apoptosis in colon cancer partially through the induction of Fas expression. In Vivo. 2005 Jan-Feb;19(1):125-32. PubMed PMID: 15796164. 8: Suzuki N, Aoki D, Oie S, Horiuchi M, Hasegawa Y, Ezawa S, Suzuki A, Susumu N, Hosoi F, Kitazato K, Nozawa S. A novel retinoid, 4-[3,5-bis (trimethylsilyl) benzamido] benzoic acid (TAC-101), induces apoptosis of human ovarian carcinoma cells and shows potential as a new antitumor agent for clear cell adenocarcinoma. Gynecol Oncol. 2004 Sep;94(3):643-9. PubMed PMID: 15350353. 9: Lee SJ, Ohashi Y, Sakurai H, Saiki I. TAC-101 inhibits intrahepatic metastasis of orthotopically implanted murine hepatocellular carcinoma. Cancer Lett. 2003 Aug 20;198(2):169-77. PubMed PMID: 12957355. 10: Miyagawa N, Homma T, Kagechika H, Shudo K, Nagai H. Effect of synthetic retinoid, TAC-101, on experimental autoimmune disease. Pharmacology. 2003 Jan;67(1):21-31. PubMed PMID: 12444300.

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