Bexarotene
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MedKoo CAT#: 100080

CAS#: 153559-49-0

Description: Bexarotene, also known as LGD-1069, is a synthetic retinoic acid agent with potential antineoplastic, chemopreventive, teratogenic and embryotoxic properties. Bexarotene selectively binds to and activates retinoid X receptors (RXRs), thereby inducing changes in gene expression that lead to cell differentiation, decreased cell proliferation, apoptosis of some cancer cell types, and tumor regression.


Price and Availability

Size
Price

100mg
USD 90
1g
USD 350
10g
USD 1250
Size
Price

250mg
USD 150
2g
USD 450
20g
USD 2250
Size
Price

500mg
USD 250
5g
USD 750
100g
Ask price

Bexarotene,purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100080
Name: Bexarotene
CAS#: 153559-49-0
Chemical Formula: C24H28O2
Exact Mass: 348.20893
Molecular Weight: 348.48
Elemental Analysis: C, 82.72; H, 8.10; O, 9.18


Synonym: LGD1069; LGD 1069; LGD-1069; 3-methyl TTNEB. US brand name: Targretin.

IUPAC/Chemical Name: 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid

InChi Key: NAVMQTYZDKMPEU-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)

SMILES Code: O=C(O)C1=CC=C(C(C2=C(C)C=C3C(C)(C)CCC(C)(C)C3=C2)=C)C=C1


Technical Data

Appearance:
Off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

Bexarotene (Targretin) is an oral antineoplastic agent indicated by the FDA (in 2000) for cutaneous T cell lymphoma. It has been used off-label for lung cancer,  breast cancer, and Kaposi's sarcoma. Bexarotene is indicated for the treatment of cutaneous manifestations of cutaneous T-cell lymphoma in patients who are refractory to at least one prior systemic therapy (oral) and for the topical treatment of cutaneous lesions in patients with CTCL (Stage IA and IB) who have refractory or persistent disease after other therapies or who have not tolerated other therapies (topical).
 
Bexarotene is an off-white to white powder with a molecular weight of 348.48 and a molecular formula of C24H28O2. It is insoluble in water and slightly soluble in vegetable oils and ethanol, USP. Each Targretin® (bexarotene) capsule also contains the following inactive ingredients: polyethylene glycol 400, NF, polysorbate 20, NF, povidone, USP, and butylated hydroxyanisole, NF. The capsule shell contains gelatin, NF, sorbitol special-glycerin blend, and titanium dioxide, USP.
 
 
Mechanism of Action: Bexarotene selectively binds and activates retinoid X receptor subtypes (RXRα, RXRβ, RXRγ). RXRs can form heterodimers with various receptor partners such as retinoic acid receptors (RARs), vitamin D receptor, thyroid receptor, and peroxisome proliferator activator receptors (PPARs). Once activated, these receptors function as transcription factors that regulate the expression of genes that control cellular differentiation and proliferation. Bexarotene inhibits the growth in vitro of some tumor cell lines of hematopoietic and squamous cell origin. It also induces tumor regression in vivo in some animal models. The exact mechanism of action of bexarotene in the treatment of cutaneous T-cell lymphoma (CTCL) is unknown.
Mechanism of Action: Bexarotene selectively binds and activates retinoid X receptor subtypes (RXRα, RXRβ, RXRγ). RXRs can form heterodimers with various receptor partners such as retinoic acid receptors (RARs), vitamin D receptor, thyroid receptor, and peroxisome proliferator activator receptors (PPARs). Once activated, these receptors function as transcription factors that regulate the expression of genes that control cellular differentiation and proliferation. Bexarotene inhibits the growth in vitro of some tumor cell lines of hematopoietic and squamous cell origin. It also induces tumor regression in vivo in some animal models. The exact mechanism of action of bexarotene in the treatment of cutaneous T-cell lymphoma (CTCL) is unknown.


References

1: Scarisbrick JJ, Morris S, Azurdia R, Illidge T, Parry E, Graham-Brown R, Cowan R, Gallop-Evans E, Wachsmuth R, Eagle M, Wierzbicki AS, Soran H, Whittaker S, Wain EM. U.K. consensus statement on safe clinical prescribing of bexarotene for patients with cutaneous T-cell lymphoma. Br J Dermatol. 2013 Jan;168(1):192-200. doi: 10.1111/bjd.12042. Epub 2012 Dec 3. PubMed PMID: 22963233.

2: Qu L, Tang X. Bexarotene: a promising anticancer agent. Cancer Chemother Pharmacol. 2010 Jan;65(2):201-5. doi: 10.1007/s00280-009-1140-4. Epub 2009 Sep 24. Review. PubMed PMID: 19777233.

3: Gopaluni S, Perzova R, Abbott L, Farah R, Shrimpton A, Hutchison R, Poiesz BJ. CD8+ cutaneous T-cell lymphoma successfully treated with bexarotene: a case report and review of the literature. Am J Hematol. 2008 Sep;83(9):744-6. doi: 10.1002/ajh.21231. Review. PubMed PMID: 18615708.

4: Gniadecki R, Assaf C, Bagot M, Dummer R, Duvic M, Knobler R, Ranki A, Schwandt P, Whittaker S. The optimal use of bexarotene in cutaneous T-cell lymphoma. Br J Dermatol. 2007 Sep;157(3):433-40. Epub 2007 Jun 6. Review. PubMed PMID: 17553039.

5: Assaf C, Bagot M, Dummer R, Duvic M, Gniadecki R, Knobler R, Ranki A, Schwandt P, Whittaker S. Minimizing adverse side-effects of oral bexarotene in cutaneous T-cell lymphoma: an expert opinion. Br J Dermatol. 2006 Aug;155(2):261-6. Review. PubMed PMID: 16882161.

6: Querfeld C, Nagelli LV, Rosen ST, Kuzel TM, Guitart J. Bexarotene in the treatment of cutaneous T-cell lymphoma. Expert Opin Pharmacother. 2006 May;7(7):907-15. Review. PubMed PMID: 16634713.

7: Coors EA, Von den Driesch P. Treatment of mycosis fungoides with bexarotene and psoralen plus ultraviolet A. Br J Dermatol. 2005 Jun;152(6):1379-81. Review. PubMed PMID: 15949024.

8: Rigas JR, Dragnev KH. Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33. Review. PubMed PMID: 15632250.

9: Farol LT, Hymes KB. Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. Review. PubMed PMID: 15056048.

10: Martin AG. Bexarotene gel: a new skin-directed treatment option for cutaneous T-cell lymphomas. J Drugs Dermatol. 2003 Apr;2(2):155-67. Review. PubMed PMID: 12852367.