Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00068)
Name
Bexarotene
Synonyms    Click to Show/Hide the Synonyms of This API
Bexarotene; 153559-49-0; Targretin; Targrexin; LGD1069; LGD 1069; LG100069; LGD-1069; 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid; UNII-A61RXM4375; Targretyn; 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid; p-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid; 166175-31-1; CHEMBL1023; LG 100069; LG-100069; Targret; CHEBI:50859; A61RXM4375; MFCD00932428; NCGC00181016-01; SR 11247; 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl]benzoic acid; DSSTox_CID_20619; DSSTox_RID_79514; DSSTox_GSID_40619; bexaroteno; bexarotenum; Bexaroten; Targretin (TN); LG 1069; CAS-153559-49-0; HSDB 7453; SR-05000001480; Bexarotene [USAN:INN:BAN]; Ro 26-4455; Bexarotene oral(targretin); SCHEMBL9025; BIDD:PXR0021; cc-197; MLS006010146; Bexarotene (JAN/USAN/INN); GTPL2807; Bexarotene, >=98% (HPLC); DTXSID1040619; AOB1247; QCR-117; HMS2089L14; HMS3655D19; HMS3747C21; HMS3884B07; 4-[1-(1,1,4,4,7-pentamethyltetralin-6-yl)vinyl]benzoic acid; ACT03911; BCP04099; ZINC1539579; Tox21_112666; Tox21_302407; BDBM50032675; DL-298; NSC747528; NSC783322; AKOS015902814; Tox21_112666_1; BCP9000396; CCG-221823; CS-0626; DB00307; MCULE-3783114634; NSC-747528; NSC-783322; SB17341; SS-4628; NCGC00181016-02; NCGC00181016-03; NCGC00181016-04; NCGC00181016-08; NCGC00181016-20; NCGC00255426-01; AC-24569; AK-64115; AT-22934; HY-14171; SMR001614557; BCP0726000106; AB0009892; FT-0657110; FT-0702645; SW203810-3; D03106; W-5228; 42161-EP2295426A1; 42161-EP2295427A1; 42161-EP2298768A1; 42161-EP2308861A1; 42161-EP2311808A1; 42161-EP2311829A1; 42161-EP2311840A1; AB01275475-01; AB01275475_02; 559B490; A809441; Q418192; J-009026; J-519847; SR-05000001480-1; SR-05000001480-2; BRD-K92441787-001-02-5; 4,6-DICHLORO-2,3-DIHYDRO-1H-INDOLEHYDROCHLORIDE; 4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic acid; 4-[1-(3,5,5,8,8-Pentamethyl-2-5,8-dihydronaphthyl)vinyl]benzoic acid; 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid; Benzoic acid,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-
Clinical Status
Approved
Disease Indication Anaplastic large cell lymphoma ICD-11: 2A90 [1]
PubChem CID
82146
Formula
C24H28O2
Canonical SMILES
CC1=CC2=C(C=C1C(=C)C3=CC=C(C=C3)C(=O)O)C(CCC2(C)C)(C)C
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=82146"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 348.5 Topological Polar Surface Area 37.3
XlogP 7.6 Complexity 551
Heavy Atom Count 26 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Bexarotene 75 mg capsule Click to Show/Hide the Full List of Formulation(s):          4 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Mannitol; Sorbitol; Butylated hydroxyanisole; Glycerin; Titanium dioxide; Water; Polyethylene glycol 400; Polysorbate 20; Povidone; 1,4-sorbitan; Gelatin
                   Dosage Form Oral Capsule
                   Company Eisai
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [3]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Mannitol; Sorbitol; Butylated hydroxyanisole; Glycerin; Titanium dioxide; Water; Polyethylene glycol 400; Polysorbate 20; 1,4-sorbitan; Gelatin; Povidones
                   Dosage Form Oral Capsule
                   Company Oceanside Pharmaceuticals; Valeant Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [3]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxyanisole; Titanium dioxide; Polyethylene glycol 400; Polysorbate 20; Povidone; Gelatin; Sorbitol special-glycerin blend
                   Dosage Form Oral Capsule
                   Company Cardinal Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [3]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sorbitol; Butylated hydroxyanisole; Glycerin; Titanium dioxide; Water; Polyethylene glycol 400; Polysorbate 20; Gelatin; Povidones
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [3]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
References
1 FDA label for approved bexarotene from the official website of the U.S. Food and Drug Administration.
2 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.