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bexarotene 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| arotinoid derivatives | 361 | 153559-49-0 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
A tetrahydronaphthalene derivative and RETINOID X RECEPTOR antagonist that is used in the treatment of CUTANEOUS T-CELL LYMPHOMA.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
None
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| 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:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| March 29, 2001 | EMA | ||
| Dec. 29, 1999 | FDA | VALEANT LUXEMBOURG |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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:
| Source | Code | Description |
|---|---|---|
| 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
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 4.23 | acidic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 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:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 |