Bexarotene
Bexarotene
CAS: 153559-49-0
Molecular Formula: C24H28O2
Bexarotene - Names and Identifiers
| Name | Bexarotene |
| Synonyms | LG 69 LGD1069 Targret SR 11247 Targretin Bexarotene RO 26-4455 Bexzarotene 1-Bexarotene Bexarotene, Free 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid Bexarotene(4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentaMethyl-2-naphthalenyl)ethenyl]benzoic acid 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid, SR-11247, LGD-1069, Targretin |
| CAS | 153559-49-0 |
| InChI | InChI=1/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 |
Bexarotene - Physico-chemical Properties
| Molecular Formula | C24H28O2 |
| Molar Mass | 348.48 |
| Density | 1.042 |
| Melting Point | 230-231°C |
| Boling Point | 489.7±44.0 °C(Predicted) |
| Solubility | DMSO 8 mg/mL Water <1 mg/mL Ethanol <1 mg/mL |
| Appearance | White solid |
| Color | white to beige |
| Maximum wavelength(λmax) | ['264nm(MeOH)(lit.)'] |
| Merck | 14,1194 |
| pKa | 4.08±0.10(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 week. |
| MDL | MFCD00932428 |
| Use | A selective agonist of retinoid X receptors |
| In vitro study | In CTCL cell lines (MJ,HUT78, and 11h), Bexarotene(1 mM and 10 mM) treatment for 96 H increased cellular subg1 population and annexin V binding in a dose-dependent manner. In CTCL cell lines (MJ,HUT78 and 11h), Bexarotene treatment inhibited the expression of retinoid X receptor α and retinoic acid receptor α proteins. Bexarotene treatment reduces survival protein levels, activates caspase-3 and cleaves poly (ADP-ribose) polymerase, however, there was no significant effect on the expression of Fas/ Fas ligand and bcl-2 protein in these three cells. In CTCL cell lines (MJ,HUT78, and 11h), Bexarotene(1 mM and 10 mM) treatment for 96 H increased cellular subg1 population and annexin V binding in a dose-dependent manner. In CTCL cell lines (MJ,HUT78 and 11h), Bexarotene treatment inhibited the expression of retinoid X receptor α and retinoic acid receptor α proteins. Bexarotene treatment reduces survival protein levels, activates caspase-3 and cleaves poly (ADP-ribose) polymerase, however, there was no significant effect on the expression of Fas/ Fas ligand and bcl-2 protein in these three cells. |
| In vivo study | In animal models, Bexarotene significantly prevents ER-negative breast tumor formation with lower toxicity than naturally occurring retinoids. In MMTV-erbB2 mice, Bexarotene inhibits the development of pre-invasive breast lesions such as hyperplasia and carcinoma. |
Bexarotene - Risk and Safety
| WGK Germany | 3 |
| RTECS | DH6834830 |
| HS Code | 29163990 |
Bexarotene - Nature
Open Data Verified Data
a white crystalline solid having a melting point of 230 to 231 ° C., and mp234 ° C. Is also reported. UV absorption maximum (methanol): 16400 nm(e).
Last Update：2024-01-02 23:10:35
Bexarotene - Preparation Method
Open Data Verified Data
aluminum trichloride was suspended in 1,2-= ethyl chloride, and 1.2,3,4-tetrahydro-1 was added at room temperature under protection of ammonia gas. 1,4,4,6-pentamethylnaphthalene and 1,2-= chloroethyl ether containing 4-methoxycarbonyl benzoyl chloride, stirred. Ice water was added and extracted with ethyl acetate in hexane. The extract was washed with saturated sodium bicarbonate and brine, dried, filtered and concentrated, and the obtained compound was obtained by column chromatography [4-(5,6,7, 8-tetrahydro-3, 5,5,8,8-pentamethyl-2-aryl) carbonyl] benzoic acid methyl ester. To a suspension of methyltriphenylphosphine bromide in benzene was added a solution of potassium hexamethyldisilazide in toluene at room temperature and under protection with ammonia, and the mixture was stirred. Add a benzene solution containing methyl [4-(5,6,7, 8-tetrahydro-3, 5,5,8, 8-pentamethyl-2-naphthyl) carbonyl] benzoate, stir at room temperature. It was then filtered through silica gel and washed with ethyl acetate in hexane. The filtrate was concentrated and the obtained substance was subjected to column chromatography to obtain 4-[1-(5,6,7.8-tetrahydro-3, 5,5,8,8-pentamethyl-2-naphthyl)-1-vinyl] benzoic acid methyl ester. This compound was suspended in aqueous methanol, potassium hydroxide was added, cooled to room temperature, acidified with hydrochloric acid, and extracted with ethyl acetate in hexane. The extract was dried, concentrated and recrystallized from dichloromethane-hexane to obtain beasarodine.
Last Update：2022-01-01 09:09:19
Bexarotene - Introduction
Bexarotene
Last Update：2022-10-16 17:14:08
Bexarotene - Use
Open Data Verified Data
It was developed by Ligand Pharmaceutical Company of the United States and was first listed in the United States on January 15, 2000. Retinoid agonists. The product can selectively bind to and activate retinoic acid class X receptor subtypes (RXRa, RBP, RXR7). RXR can form a heterodimer with a variety of receptors, such as vitamin A receptor (RAR), vitamin D receptor, thyroxine receptor. It is used as a topical treatment for skin lesions in patients with refractory early stage cutaneous T-cell lymphoma (CTCL), or in patients with lymphoma who have failed other treatments.
Last Update：2022-01-01 09:09:19
Bexarotene - Reference Information
| Pharmacological effects | Besarodin has an inhibitory effect on lung and breast tumors. The side effects are hypertriglyceridemia and hypercholesterolemia. The researchers optimized the formulation of sprayed bezarotin using a clinically relevant solvent system. The optimized preparation has good chemoprevention effect on lung squamous cell carcinoma and lung adenocarcinoma mouse models, and does not cause obvious toxic symptoms, nor does it increase plasma triglyceride or cholesterol concentration. Nebulized bezarodin can be evenly distributed in the lung parenchyma of mice and regulate the microenvironment in vivo by increasing the number of tumor infiltrating T cells. RNA sequencing of lung cancer cell lines shows that bezarotin can regulate various pathways of cancer. |
| biological activity | Bexarotene (Targretin, LGD1069) is a retinoic acid, which specifically selectively acts on retinoic acid X receptor and is used as an oral anti-tumor drug to treat cutaneous T-cell lymphoma. |
| Target | Value |
| use | retinoid agonist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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View History
Bexarotene
P3E-5CF3
2-甲基硫醚-7H-吡咯并[2,3-D]嘧啶-4-醇
6-Hydroxykaempferol 3,6-diglucoside
(4Z,7Z)-癸二烯醇
(2-(二氟甲氧基)乙基)氨基甲酸苄酯
2-[(3-氟苯基)氨基]乙腈
2-甲基异硫氰酸苯甲酰酯
CIS-2-(2-METHYLBENZOYL)CYCLOPENTANE-1-CARBOXYLIC ACID
8-(4-硫代氯苯基)鸟苷 3',5'-环状单磷酸钠盐
P3E-5CF3
2-甲基硫醚-7H-吡咯并[2,3-D]嘧啶-4-醇
6-Hydroxykaempferol 3,6-diglucoside
(4Z,7Z)-癸二烯醇
(2-(二氟甲氧基)乙基)氨基甲酸苄酯
2-[(3-氟苯基)氨基]乙腈
2-甲基异硫氰酸苯甲酰酯
CIS-2-(2-METHYLBENZOYL)CYCLOPENTANE-1-CARBOXYLIC ACID
8-(4-硫代氯苯基)鸟苷 3',5'-环状单磷酸钠盐