bexarotene Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
arotinoid derivatives 361 153559-49-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • LGD 1069
  • bexarotene
  • targretin
  • targretyn
  • targrexin
A tetrahydronaphthalene derivative and RETINOID X RECEPTOR antagonist that is used in the treatment of CUTANEOUS T-CELL LYMPHOMA.
  • Molecular weight: 348.49
  • Formula: C24H28O2
  • CLOGP: 8.19
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 1
  • TPSA: 37.30
  • ALOGS: -6.37
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.01 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 28.70 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
March 29, 2001 EMA
Dec. 29, 1999 FDA VALEANT LUXEMBOURG

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Cutaneous T-cell lymphoma 78.03 35.67 13 399 1350 46684300
Hypertriglyceridaemia 76.55 35.67 16 396 5688 46679962
Diffuse large B-cell lymphoma 37.47 35.67 9 403 5929 46679721

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypothyroidism 118.50 28.91 34 759 14929 29936756
Hypertriglyceridaemia 104.24 28.91 27 766 8071 29943614
Cutaneous T-cell lymphoma 88.21 28.91 17 776 1318 29950367
Dyslipidaemia 40.70 28.91 12 781 5715 29945970
Thyroid stimulating hormone deficiency 31.94 28.91 4 789 15 29951670

Pharmacologic Action:

SourceCodeDescription
ATC L01XF03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Retinoids for cancer treatment
FDA CS M0018962 Retinoids
FDA EPC N0000175607 Retinoid
MeSH PA D000970 Antineoplastic Agents
CHEBI has role CHEBI:35610 cytostatic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Primary cutaneous T-cell lymphoma indication 400122007
Alcoholism contraindication 7200002
Hypothyroidism contraindication 40930008 DOID:1459
Hepatic failure contraindication 59927004
Diabetes mellitus contraindication 73211009 DOID:9351
Leukopenia contraindication 84828003 DOID:615
Bilateral cataracts contraindication 95722004
Disorder of biliary tract contraindication 105997008 DOID:9741
Acute pancreatitis contraindication 197456007 DOID:2913
Chronic pancreatitis contraindication 235494005
Disease of liver contraindication 235856003 DOID:409
Diabetic - poor control contraindication 268519009
Pregnancy, function contraindication 289908002
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.23 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Retinoic acid receptor RXR-alpha Nuclear hormone receptor AGONIST Kd 7.85 CHEMBL CHEMBL
Retinoic acid receptor RXR-beta Nuclear hormone receptor AGONIST Ki 8.23 CHEMBL CHEMBL
Retinoic acid receptor RXR-gamma Nuclear hormone receptor AGONIST Ki 8.08 CHEMBL CHEMBL
Retinoic acid receptor beta Nuclear hormone receptor Ki 7.30 CHEMBL
Retinoic acid receptor alpha Nuclear hormone receptor Ki 6.74 CHEMBL
Retinoic acid receptor gamma Nuclear hormone receptor Ki 6.89 CHEMBL
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor ANTAGONIST IC50 5.52 IUPHAR
Retinoic acid receptor RXR-gamma Transcription factor Kd 7.54 CHEMBL
Retinoic acid receptor RXR-alpha Transcription factor EC50 7.40 CHEMBL
Retinoic acid receptor RXR-alpha Unclassified EC50 7.40 CHEMBL
Retinoic acid receptor RXR-beta Transcription factor Kd 7.68 CHEMBL

External reference:

IDSource
A61RXM4375 UNII
4021197 VUID
N0000148643 NUI
D03106 KEGG_DRUG
4021197 VANDF
C0765273 UMLSCUI
CHEBI:50859 CHEBI
9RA PDB_CHEM_ID
CHEMBL1023 ChEMBL_ID
DB00307 DRUGBANK_ID
D000077610 MESH_DESCRIPTOR_UI
7782 INN_ID
82146 PUBCHEM_CID
2807 IUPHAR_LIGAND_ID
233272 RXNORM
234760 MMSL
31640 MMSL
8604 MMSL
d04507 MMSL
008004 NDDF
116346006 SNOMEDCT_US
387023000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 0054-0399 CAPSULE, LIQUID FILLED 75 mg ORAL ANDA 25 sections
Targretin HUMAN PRESCRIPTION DRUG LABEL 1 0187-5525 GEL 1 g TOPICAL NDA 20 sections
Targretin HUMAN PRESCRIPTION DRUG LABEL 1 0187-5526 CAPSULE, LIQUID FILLED 75 mg ORAL NDA 25 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 0378-6955 CAPSULE, LIQUID FILLED 75 mg ORAL ANDA 28 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 0832-0285 CAPSULE 75 mg ORAL ANDA 28 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 43975-315 CAPSULE, LIQUID FILLED 75 mg ORAL ANDA 27 sections
bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 68682-003 CAPSULE, LIQUID FILLED 75 mg ORAL NDA authorized generic 25 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 69238-1250 CAPSULE 75 mg ORAL ANDA 27 sections