Amsilarotene

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

MedKoo CAT#: 200720

CAS#: 125973-56-0

Description: 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

img
Amsilarotene
CAS# 125973-56-0

Theoretical Analysis

MedKoo Cat#: 200720
Name: Amsilarotene
CAS#: 125973-56-0
Chemical Formula: C20H27NO3Si2
Exact Mass: 385.15295
Molecular Weight: 385.6
Elemental Analysis: C, 62.30; H, 7.06; N, 3.63; O, 12.45; Si, 14.57

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2021-03-08. Prices are subject to change without notice.

Amsilarotene, purity > 98%, is not in stock, 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.

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 385.6 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.

Select a batch to recalculate based on the batch molecular weight:
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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.



Additional Information