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153559-49-0 molecular structure
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4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid

ChemBase ID: 192
Molecular Formular: C24H28O2
Molecular Mass: 348.47792
Monoisotopic Mass: 348.20893014
SMILES and InChIs

SMILES:
OC(=O)c1ccc(C(=C)c2cc3C(CCC(c3cc2C)(C)C)(C)C)cc1
Canonical SMILES:
Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C(C)(C)CCC2(C)C
InChI:
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)
InChIKey:
NAVMQTYZDKMPEU-UHFFFAOYSA-N

Cite this record

CBID:192 http://www.chembase.cn/molecule-192.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
IUPAC Traditional name
bexarotene
targretin
Brand Name
Targret
Targretin
Targretyn
Targrexin
Targretin-gel
Synonyms
4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid
LG 100069
LG 1069
LG 69
LGD 1069
RO 26-4455
SR 11247
Targret
Targretin
Targretyn
Targrexin
bexarotene
Bexarotene
CAS Number
153559-49-0
PubChem SID
46509119
160963655
PubChem CID
82146

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.0707927  H Acceptors
H Donor LogD (pH = 5.5) 5.4988923 
LogD (pH = 7.4) 3.8234684  Log P 6.9405375 
Molar Refractivity 117.124 cm3 Polarizability 41.398285 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 6.86  LOG S -6.37 
Solubility (Water) 1.49e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
230-231°C expand Show data source
Hydrophobicity(logP)
6.9 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Target
Others expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00307 external link
Item Information
Drug Groups approved; investigational
Description Bexarotene (Targretin) is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi's sarcoma. [Wikipedia]
Indication Used orally for the treatment of skin manifestations of cutaneous T-cell lymphoma (CTCL) in patients who are refractory to at least one prior systemic therapy. Also used topically for the treatment of skin lesions in early (stage IA and IB) CTCL in patients who experience refractory or persistent disease with the use of other therapies or are intolerant of other therapies.
Pharmacology Bexarotene is a member of a subclass of retinoids that selectively activate retinoid X receptors (RXRs). These retinoid receptors have biologic activity distinct from that of retinoic acid receptors (RARs). 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. 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.
Affected Organisms
Humans and other mammals
Half Life 7 hours
Protein Binding >99%
Elimination Urinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).
References
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. [Pubmed]
Dragnev KH, Petty WJ, Shah SJ, Lewis LD, Black CC, Memoli V, Nugent WC, Hermann T, Negro-Vilar A, Rigas JR, Dmitrovsky E: A proof-of-principle clinical trial of bexarotene in patients with non-small cell lung cancer. Clin Cancer Res. 2007 Mar 15;13(6):1794-800. [Pubmed]
Smit JW, Stokkel MP, Pereira AM, Romijn JA, Visser TJ: Bexarotene-induced hypothyroidism: bexarotene stimulates the peripheral metabolism of thyroid hormones. J Clin Endocrinol Metab. 2007 Jul;92(7):2496-9. Epub 2007 Apr 17. [Pubmed]
Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [Pubmed]
Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [Pubmed]
Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - B336750 external link
Used as an antineoplastic. A selective retinoid X receptor (RXR) agonist.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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. Pubmed
  • • Dragnev KH, Petty WJ, Shah SJ, Lewis LD, Black CC, Memoli V, Nugent WC, Hermann T, Negro-Vilar A, Rigas JR, Dmitrovsky E: A proof-of-principle clinical trial of bexarotene in patients with non-small cell lung cancer. Clin Cancer Res. 2007 Mar 15;13(6):1794-800. Pubmed
  • • Smit JW, Stokkel MP, Pereira AM, Romijn JA, Visser TJ: Bexarotene-induced hypothyroidism: bexarotene stimulates the peripheral metabolism of thyroid hormones. J Clin Endocrinol Metab. 2007 Jul;92(7):2496-9. Epub 2007 Apr 17. Pubmed
  • • Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. Pubmed
  • • Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. Pubmed
  • • Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. Pubmed
  • • Boehm, M.F., et al.: J. Med. Che., 37,2930 (1994)
  • • Gottardis, M.M., et al.: Cancer Res., 56, 5566 (1994)
  • • Mukherjee, R., et al.: Nature, 386, 407 (1994)
  • • Miller, V.A., et al.: J. Clin. Oncol., 15, 790 (1997)
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PATENTS

PATENTS

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INTERNET

INTERNET

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