bexarotene 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 4.015 High 0.86
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.069 High 0.86
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 19.275 10^-6 cm/s High 0.86
dh-clint Dog hepatocyte intrinsic clearance 26.915 uL/min/10^6 cells High 0.86
dppb Dog plasma protein binding (% unbound) 0.150 % High 0.86
fcs-ppb Fetal calf serum protein binding (% unbound) 0.840 % High 0.86
herg hERG pIC50 4.993 pIC50 High 0.86
hh-clint Human hepatocyte intrinsic clearance 57.810 uL/min/10^6 cells High 0.86
hlm-clint Human liver microsomal intrinsic clearance 32.961 uL/min/mg protein High 0.86
hppb Human plasma protein binding (% unbound) 0.380 % High 0.86
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DYRK1B,EIF2AK3,ERBB2,GRK2,GSK3B,IKBKB,ITK,JAK2,MAP2K6,MAP3K7,MAPK10,MAPK7,MAPKAPK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CG,PIM2,PRKDC,STK33,SYK,TEK,TGFBR1,TTK 35
kinase-selectivity-class AXL,BRAF,EIF2AK3,EPHB4,GRK2,PDK4 6
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.259 High 0.86
mh-clint Mouse hepatocyte intrinsic clearance 24.660 High 0.86
mppb Mouse plasma protein binding (% unbound) 0.370 High 0.86
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 8.128 High 0.86
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.220 % High 0.86
rh-clint Rat hepatocyte intrinsic clearance 27.733 uL/min/10^6 cells High 0.86
rh-fuinc Rat hepatocyte fraction unbound in incubation 1.950 % High 0.86
rppb Rat plasma protein binding (% unbound) 0.180 % High 0.86
solubility-dd Solubility at pH 7.4 in DMSO 191.426 uM High 0.86

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
Hypertriglyceridaemia 100.78 39.02 20 539 7869 90620019
Cutaneous T-cell lymphoma 59.19 39.02 10 549 1610 90626278
Hypothyroidism 54.72 39.02 18 541 53109 90574779

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 140.50 32.12 47 1154 32037 42588097
Hypertriglyceridaemia 119.74 32.12 32 1169 10094 42610040
Cutaneous T-cell lymphoma 74.56 32.12 16 1185 1982 42618152
Cutaneous T-cell lymphoma stage I 61.80 32.12 9 1192 114 42620020
Thyroid stimulating hormone deficiency 45.20 32.12 6 1195 36 42620098
Dyslipidaemia 37.92 32.12 13 1188 9405 42610729
Cutaneous T-cell lymphoma refractory 37.53 32.12 5 1196 31 42620103
Disease progression 34.42 32.12 30 1171 143626 42476508

FDA Adverse Event Reporting System (Geriatric)

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
Hypertriglyceridaemia 193.80 27.31 46 1701 16108 110571444
Hypothyroidism 179.35 27.31 60 1687 72839 110514713
Cutaneous T-cell lymphoma 128.93 27.31 25 1722 3359 110584193
Cutaneous T-cell lymphoma stage I 65.15 27.31 9 1738 142 110587410
Disease progression 60.19 27.31 41 1706 243993 110343559
Dyslipidaemia 59.17 27.31 18 1729 15947 110571605
Blood triglycerides increased 48.16 27.31 17 1730 23909 110563643
Thyroid stimulating hormone deficiency 47.75 27.31 6 1741 43 110587509
Cutaneous T-cell lymphoma recurrent 43.23 27.31 6 1741 98 110587454
Diffuse large B-cell lymphoma 42.60 27.31 14 1733 15884 110571668
Malignant neoplasm progression 39.84 27.31 28 1719 174539 110413013
Drug ineffective 29.51 27.31 70 1677 1520470 109067082
Application site pain 28.29 27.31 8 1739 5491 110582061

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01XF03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Retinoids for cancer treatment
FDA CS M0018962 Retinoids
MeSH PA D000970 Antineoplastic Agents
FDA EPC N0000175607 Retinoid
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50748 antipsoriatic

Related Drugs by ATC class:

L01XF Retinoids for cancer treatment 2 drugs
alitretinointretinoin

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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-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 RXR-alpha Nuclear hormone receptor AGONIST Kd 7.85 CHEMBL CHEMBL
Retinoic acid receptor gamma Nuclear hormone receptor Ki 6.89 CHEMBL
Cytochrome P450 26A1 Enzyme IC50 4.87 CHEMBL
Cytochrome P450 26B1 Enzyme IC50 5.23 CHEMBL
Oxysterols receptor LXR-beta Nuclear other EC50 6.36 CHEMBL
Retinoic acid receptor alpha Nuclear hormone receptor Ki 6.74 CHEMBL
Oxysterols receptor LXR-alpha Nuclear other EC50 6.71 CHEMBL
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor ANTAGONIST IC50 5.52 IUPHAR
Retinoic acid receptor beta Nuclear hormone receptor Ki 7.30 CHEMBL
Retinoic acid receptor RXR-beta Transcription factor Kd 7.68 CHEMBL
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 Nuclear hormone receptor EC50 7.40 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 0591-2832 CAPSULE, LIQUID FILLED 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 0832-0285 CAPSULE 75 mg ORAL ANDA 28 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 31722-380 CAPSULE 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 42291-072 CAPSULE 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 42291-072 CAPSULE 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 43602-176 CAPSULE 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 43975-315 CAPSULE, LIQUID FILLED 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 69238-1250 CAPSULE 75 mg ORAL ANDA 27 sections
Bexarotene HUMAN PRESCRIPTION DRUG LABEL 1 69238-2088 GEL 10 mg TOPICAL ANDA 21 sections