Adarotene
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MedKoo CAT#: 402120

CAS#: 496868-77-0

Description: Adarotene, also known as ST1926, is an atypical retinoid and a promising anti-tumour agent with selective apoptotic activity on the leukaemic blast. The anti-tumour activity of the compound has been associated with its capacity to induce DNA double stranded breaks. (source: Eur J Cancer. 2012 Dec 11. pii: S0959-8049(12)00909-4.).


Chemical Structure

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Adarotene
CAS# 496868-77-0

Theoretical Analysis

MedKoo Cat#: 402120
Name: Adarotene
CAS#: 496868-77-0
Chemical Formula: C25H26O3
Exact Mass: 374.18819
Molecular Weight: 374.47214
Elemental Analysis: C, 80.18; H, 7.00; O, 12.82

Price and Availability

Size Price Availability Quantity
1.0g USD 3850.0 2 Weeks
2.0g USD 5450.0 2 Weeks
5.0g USD 7950.0 2 Weeks
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Synonym: ST1926; ST 1926; ST-1926; Adarotene.

IUPAC/Chemical Name: (E)-3-(3'-((3r,5r,7r)-adamantan-1-yl)-4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylic acid

InChi Key: QAWBIEIZDDIEMW-RXJOCBMKSA-N

InChi Code: InChI=1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+/t17-,18+,19-,25?

SMILES Code: O=C(O)/C=C/C1=CC=C(C2=CC=C(O)C(C34C[C@H]5C[C@@H](C4)C[C@H](C5)C3)=C2)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

Preparing Stock Solutions

The following data is based on the product molecular weight 374.47214 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

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1: Fratelli M, Fisher JN, Paroni G, Di Francesco AM, Pierri F, Pisano C, Godl K, Marx S, Tebbe A, Valli C, Gianni M, Stravalaci M, Gobbi M, Terao M, Garattini E. New insights into the molecular mechanisms underlying sensitivity/resistance to the atypical retinoid ST1926 in acute myeloid leukaemia cells: The role of histone H2A.Z, cAMP-dependent protein kinase A and the proteasome. Eur J Cancer. 2012 Dec 11. doi:pii: S0959-8049(12)00909-4. 10.1016/j.ejca.2012.11.013. [Epub ahead of print] PubMed PMID: 23245330.

2: Di Francesco AM, Ubezio P, Torella AR, Meco D, Pierri F, Barone G, Cusano G, Pisano C, D'Incalci M, Riccardi R. Enhanced cell cycle perturbation and apoptosis mediate the synergistic effects of ST1926 and ATRA in neuroblastoma preclinical models. Invest New Drugs. 2012 Aug;30(4):1319-30. doi: 10.1007/s10637-011-9689-2. Epub 2011 Jun 3. PubMed PMID: 21633925.

3: Sala F, Zucchetti M, Bagnati R, D'Incalci M, Pace S, Capocasa F, Marangon E. Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ST1926, a novel oral antitumor agent, adamantyl retinoid derivative, in plasma of patients in a Phase I study. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Oct 1;877(27):3118-26. doi: 10.1016/j.jchromb.2009.08.001. Epub 2009 Aug 7. PubMed PMID: 19695967.

4: Zuco V, Benedetti V, De Cesare M, Zunino F. Sensitization of ovarian carcinoma cells to the atypical retinoid ST1926 by the histone deacetylase inhibitor, RC307: enhanced DNA damage response. Int J Cancer. 2010 Mar 1;126(5):1246-55. doi: 10.1002/ijc.24819. PubMed PMID: 19676051.

5: Valli C, Paroni G, Di Francesco AM, Riccardi R, Tavecchio M, Erba E, Boldetti A, Gianni' M, Fratelli M, Pisano C, Merlini L, Antoccia A, Cenciarelli C, Terao M, Garattini E. Atypical retinoids ST1926 and CD437 are S-phase-specific agents causing DNA double-strand breaks: significance for the cytotoxic and antiproliferative activity. Mol Cancer Ther. 2008 Sep;7(9):2941-54. doi: 10.1158/1535-7163.MCT-08-0419. PubMed PMID: 18790775.

6: Pisano C, Vesci L, Foderà R, Ferrara FF, Rossi C, De Cesare M, Zuco V, Pratesi G, Supino R, Zunino F. Antitumor activity of the combination of synthetic retinoid ST1926 and cisplatin in ovarian carcinoma models. Ann Oncol. 2007 Sep;18(9):1500-5. Epub 2007 Aug 13. PubMed PMID: 17698835.

7: Di Francesco AM, Meco D, Torella AR, Barone G, D'Incalci M, Pisano C, Carminati P, Riccardi R. The novel atypical retinoid ST1926 is active in ATRA resistant neuroblastoma cells acting by a different mechanism. Biochem Pharmacol. 2007 Mar 1;73(5):643-55. Epub 2006 Nov 7. PubMed PMID: 17150196.

8: Parrella E, Giannì M, Fratelli M, Barzago MM, Raska I Jr, Diomede L, Kurosaki M, Pisano C, Carminati P, Merlini L, Dallavalle S, Tavecchio M, Rochette-Egly C, Terao M, Garattini E. Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways. Mol Pharmacol. 2006 Sep;70(3):909-24. Epub 2006 Jun 20. PubMed PMID: 16788091.

9: Zuco V, Zanchi C, Lanzi C, Beretta GL, Supino R, Pisano C, Barbarino M, Zanier R, Bucci F, Aulicino C, Carminati P, Zunino F. Development of resistance to the atypical retinoid, ST1926, in the lung carcinoma cell line H460 is associated with reduced formation of DNA strand breaks and a defective DNA damage response. Neoplasia. 2005 Jul;7(7):667-77. PubMed PMID: 16026646; PubMed Central PMCID: PMC1501428.

10: Zanchi C, Zuco V, Lanzi C, Supino R, Zunino F. Modulation of survival signaling pathways and persistence of the genotoxic stress as a basis for the synergistic interaction between the atypical retinoid ST1926 and the epidermal growth factor receptor inhibitor ZD1839. Cancer Res. 2005 Mar 15;65(6):2364-72. PubMed PMID: 15781651.



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