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Also known as: 153559-49-0, Targretin, Targrexin, Lgd1069, Lgd 1069, Lgd-1069
Molecular Formula
C24H28O2
Molecular Weight
348.5  g/mol
InChI Key
NAVMQTYZDKMPEU-UHFFFAOYSA-N
FDA UNII
A61RXM4375

Bexarotene
A rexinoid (an RXR-binding ligand), tetrahydronaphthalene derivative and RETINOID X RECEPTOR antagonist that is used in the treatment of CUTANEOUS T-CELL LYMPHOMA.
Bexarotene is a Retinoid.
1 2D Structure

Bexarotene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
2.1.2 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)
2.1.3 InChI Key
NAVMQTYZDKMPEU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC2=C(C=C1C(=C)C3=CC=C(C=C3)C(=O)O)C(CCC2(C)C)(C)C
2.2 Other Identifiers
2.2.1 UNII
A61RXM4375
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-methyl-ttneb

2. 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl)benzoic Acid

3. Lg69 Compound

4. Lgd 1069

5. Lgd-1069

6. Lgd1069

7. Targretin

2.3.2 Depositor-Supplied Synonyms

1. 153559-49-0

2. Targretin

3. Targrexin

4. Lgd1069

5. Lgd 1069

6. Lgd-1069

7. Lg100069

8. 166175-31-1

9. 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic Acid

10. 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic Acid

11. P-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic Acid

12. Targretyn

13. Lg 100069

14. Lg-100069

15. 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic Acid

16. 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic Acid

17. Nsc-747528

18. Chembl1023

19. 4-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid

20. Targret

21. Chebi:50859

22. A61rxm4375

23. 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic Acid

24. Bexarotene [usan]

25. Ncgc00181016-01

26. Ro 26-4455

27. Sr 11247

28. 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl]benzoic Acid

29. Dsstox_cid_20619

30. Dsstox_rid_79514

31. Dsstox_gsid_40619

32. Bexaroteno

33. Bexarotenum

34. Bexaroten

35. Lg 1069

36. 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]benzoic Acid

37. Targretin (tn)

38. Cas-153559-49-0

39. Hsdb 7453

40. Sr-05000001480

41. Bexarotene [usan:inn:ban]

42. Unii-a61rxm4375

43. Dtxsid1040619

44. 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid

45. Lg 69

46. Bexarotene- Bio-x

47. 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl)benzoic Acid

48. Mfcd00932428

49. Bexarotene-[13c4]

50. 4k6i

51. Bexarotene [mi]

52. Bexarotene [inn]

53. Bexarotene [jan]

54. Bexarotene [hsdb]

55. Bexarotene Oral(targretin)

56. Bexarotene [vandf]

57. Bexarotene [mart.]

58. Schembl9025

59. Bexarotene [who-dd]

60. Bidd:pxr0021

61. Mls006010146

62. Bexarotene (jan/usan/inn)

63. Bexarotene [ema Epar]

64. Gtpl2807

65. Bexarotene [orange Book]

66. Bexarotene, >=98% (hplc)

67. Hms2089l14

68. Hms3655d19

69. Hms3747c21

70. Hms3884b07

71. 4-[1-(1,1,4,4,7-pentamethyltetralin-6-yl)vinyl]benzoic Acid

72. Act03911

73. Amy24869

74. Bcp04099

75. Zinc1539579

76. Tox21_112666

77. Tox21_302407

78. Bdbm50032675

79. Dl-298

80. Nsc747528

81. Nsc783322

82. S2098

83. Akos015902814

84. Tox21_112666_1

85. Bcp9000396

86. Ccg-221823

87. Cs-0626

88. Db00307

89. Nsc 741061

90. Nsc 747528

91. Nsc-783322

92. Sb17341

93. Ss-4628

94. Benzoic Acid, 4-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)-

95. Ncgc00181016-02

96. Ncgc00181016-03

97. Ncgc00181016-04

98. Ncgc00181016-08

99. Ncgc00181016-20

100. Ncgc00255426-01

101. Ac-24569

102. Bb164246

103. Hy-14171

104. Smr001614557

105. Bcp0726000106

106. Ft-0657110

107. Ft-0702645

108. Sw203810-3

109. D03106

110. Ab01275475-01

111. Ab01275475_02

112. 559b490

113. A809441

114. Q418192

115. J-009026

116. J-519847

117. Sr-05000001480-1

118. Sr-05000001480-2

119. Brd-k92441787-001-02-5

120. 4,6-dichloro-2,3-dihydro-1h-indolehydrochloride

121. 4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic Acid

122. 4-[1-(3,5,5,8,8-pentamethyl-2-5,8-dihydronaphthyl)vinyl]benzoic Acid

123. 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic Acid

124. 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-vinyl]benzoic Acid

125. 4-[1-(5,6,7,8,-tetrahydro-3,5,5,8,8-pentamethyl-2-naphtalenyl)ethenyl]benzoic Acid

126. 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-1-ethenyl]benzoic Acid

127. Benzoic Acid,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 348.5 g/mol
Molecular Formula C24H28O2
XLogP37.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass348.208930132 g/mol
Monoisotopic Mass348.208930132 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count26
Formal Charge0
Complexity551
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameTargretin
PubMed HealthBexarotene
Drug ClassesAntineoplastic Agent, Antineoplastic, Dermatological, Dermatological Agent
Drug LabelTargretin (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). Each soft gelatin capsule for o...
Active IngredientBexarotene
Dosage FormCapsule; Gel
RouteOral; Topical
Strength1%; 75mg
Market StatusPrescription
CompanyValeant Luxembourg

2 of 2  
Drug NameTargretin
PubMed HealthBexarotene
Drug ClassesAntineoplastic Agent, Antineoplastic, Dermatological, Dermatological Agent
Drug LabelTargretin (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). Each soft gelatin capsule for o...
Active IngredientBexarotene
Dosage FormCapsule; Gel
RouteOral; Topical
Strength1%; 75mg
Market StatusPrescription
CompanyValeant Luxembourg

4.2 Therapeutic Uses

THERAP CAT: Antineoplastic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 203


Bexarotene is indicated for the treatment of cutaneous manifestations of cutaneous T-cell lyphoma in patients who are refractory to at least one other prior systemic therapy. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 615


4.3 Drug Warning

May cause fetal harm; teratogenicity and embryolethality demonstrated in animals. No adequate and well-controlled studies to date in humans. Pregnancy should be avoided during therapy. If used during pregnancy, apprise of potential fetal hazard. ... Male patients receiving the drug should use condoms during sexual intercourse with women who are or may become pregnant.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 939


Effective contraception must be used for one month prior to the initiation of therapy, during therapy and for at least one month following discontinuation of therapy; it is recommended that two reliable forms of contraception be used simultaneously unless abstinence is the chosen method. Bexarotene can potentially induce metabolic enzymes and thereby theoretically reduce the plasma concentrations of oral or other systemic hormonal contraceptives.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 1720


Hyperlipidemia occurred in 79% of patients receiving oral bexarotene in phase II-III clinical studies. Elevations in fasting triglycerides and cholesterol and decreases in HDL-cholesterol were observed in more than half of patients receiving 300 mg/sq m or more. Lipid abnormalities usually developed within 2-4 weeks and were reversible with cessation of therapy. If fasting triglycerides are elevated or become elevated during treatment, antilipemic therapy should be instituted, and the dosage of bexarotene reduced or suspended.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 939


Acute pancreatitis has been reported in several patients treated with bexarotene and has been fatal in at least one patient. The manufacturer states that patients with cutaneous T-cell lymphoma (CTCL) who have risk factors for pancreatitis (eg, prior pancreatitis, uncontrolled hyperlipidemia, excessive alcohol consumption, uncontrolled diabetes mellitus, biliary tract disease, or drugs associated with pancreatic toxicity or known to increase triglyceride concentrations) generally should not be treated with bexarotene.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 939


For more Drug Warnings (Complete) data for BEXAROTENE (15 total), please visit the HSDB record page.


4.4 Drug 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.


FDA Label


Targretin capsules are indicated for the treatment of skin manifestations of advanced stage cutaneous T-cell lymphoma (CTCL) patients refractory to at least one systemic treatment.


5 Pharmacology and Biochemistry
5.1 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 (RXR, RXR, RXR). 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.


5.2 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
BEXAROTENE
5.3.2 FDA UNII
A61RXM4375
5.3.3 Pharmacological Classes
Retinoids [CS]; Retinoid [EPC]
5.4 ATC Code

L01XF03


L01XX25

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XF - Retinoids for cancer treatment

L01XF03 - Bexarotene


5.5 Absorption, Distribution and Excretion

Route of Elimination

Urinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).


After oral administration, bexarotene is absorbed with a Tmax of about two hours. ...Studies in patients with advanced malignancies show approximate single dose linearity within the therapeutic range and low accumulation with multiple doses. Plasma bexarotene AUC and Cmax values resulting from a 75 to 300 mg dose were 35% and 48% higher, respectively, after a fat-containing meal than after a glucose solution. Bexarotene is highly bound (>99%) to plasma proteins. The plasma proteins to which bexarotene binds have not been elucidated, and the ability of bexarotene to displace drugs bound to plasma proteins and the ability of drugs to displace bexarotene binding have not been studied.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 1719


The renal elimination of bexarotene and its metabolites was examined in patients with Type 2 diabetes mellitus. Neither bexarotene nor its metabolites were excreted in urine in appreciable amounts. Bexarotene is thought to be eliminated primarily through the hepatobiliary system.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 1719


5.6 Metabolism/Metabolites

Four bexarotene metabolites have been identified in plasma: 6- and 7-hydroxy-bexarotene and 6- and 7-oxo-bexarotene. In vitro studies suggest that cytochrome P450 3A4 is the major cytochrome P450 responsible for formation of the oxidative metabolites and that the oxidative metabolites may be glucuronidated. The oxidative metabolites are active in in vitro assays of retinoid receptor activation, but the relative contribution of the parent and any metabolites to the efficacy and safety of /bexarotene/ is unknown.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 1719


Bexarotene has known human metabolites that include 6-hydroxy-bexarotene, 7-hydroxy-bexarotene, and 7-oxo-bexarotene.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

7 hours


Terminal half-life of bexarotene is about seven hours.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 1719


5.8 Mechanism of Action

Bexarotene selectively binds with and activates retinoid X receptor subtypes. There are three subtypes in total: RXR, RXR, RXR. The exact mechanism of action of bexarotene in the treatment of CTCL is unknown but the drug has activity in all clinical stages of CTCL.


Bexarotene selectively binds and activates retinoid X receptor subtypes (RXR(alpha), RXR(beta), RXR(gamma)). 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.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 1719


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08-Mar-2021
08-Jul-2024
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CAPSULE;ORAL - 75MG

USFDA APPLICATION NUMBER - 21055

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DOSAGE - GEL;TOPICAL - 1%

USFDA APPLICATION NUMBER - 21056

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ABOUT THIS PAGE

Bexarotene Manufacturers

A Bexarotene manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Bexarotene, including repackagers and relabelers. The FDA regulates Bexarotene manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Bexarotene API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Bexarotene manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Bexarotene Suppliers

A Bexarotene supplier is an individual or a company that provides Bexarotene active pharmaceutical ingredient (API) or Bexarotene finished formulations upon request. The Bexarotene suppliers may include Bexarotene API manufacturers, exporters, distributors and traders.

click here to find a list of Bexarotene suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Bexarotene USDMF

A Bexarotene DMF (Drug Master File) is a document detailing the whole manufacturing process of Bexarotene active pharmaceutical ingredient (API) in detail. Different forms of Bexarotene DMFs exist exist since differing nations have different regulations, such as Bexarotene USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Bexarotene DMF submitted to regulatory agencies in the US is known as a USDMF. Bexarotene USDMF includes data on Bexarotene's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Bexarotene USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Bexarotene suppliers with USDMF on PharmaCompass.

Bexarotene WC

A Bexarotene written confirmation (Bexarotene WC) is an official document issued by a regulatory agency to a Bexarotene manufacturer, verifying that the manufacturing facility of a Bexarotene active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Bexarotene APIs or Bexarotene finished pharmaceutical products to another nation, regulatory agencies frequently require a Bexarotene WC (written confirmation) as part of the regulatory process.

click here to find a list of Bexarotene suppliers with Written Confirmation (WC) on PharmaCompass.

Bexarotene NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Bexarotene as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Bexarotene API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Bexarotene as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Bexarotene and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Bexarotene NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Bexarotene suppliers with NDC on PharmaCompass.

Bexarotene GMP

Bexarotene Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Bexarotene GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Bexarotene GMP manufacturer or Bexarotene GMP API supplier for your needs.

Bexarotene CoA

A Bexarotene CoA (Certificate of Analysis) is a formal document that attests to Bexarotene's compliance with Bexarotene specifications and serves as a tool for batch-level quality control.

Bexarotene CoA mostly includes findings from lab analyses of a specific batch. For each Bexarotene CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Bexarotene may be tested according to a variety of international standards, such as European Pharmacopoeia (Bexarotene EP), Bexarotene JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Bexarotene USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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