BEXAROTENE

Search structure
Trade Names:
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01XF03
UNII: A61RXM4375

Structure
InChI Key NAVMQTYZDKMPEU-UHFFFAOYSA-N
Smile C=C(c1ccc(C(=O)O)cc1)c1cc2c(cc1C)C(C)(C)CCC2(C)C
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H28O2
Molecular Weight 348.49
AlogP 6.1
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Retinoid X receptor agonist FDA
Primary Target
Retinoid X receptor-α
Retinoid X receptor-β
Retinoid X receptor-γ
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 26 Cytochrome P450 family 26A Cytochrome P450 26A1
- 13500 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 26
- 13500 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 1
6 - - 180-5453 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 2
282 - - 50-5353 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3
648 - - 130-3206 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group H Nuclear hormone receptor subfamily 1 group H member 3
196 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 1
3-149 632 14-1890 14-379 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 2
24-112 - 21-21 6-21 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 3
20-122 - 29-29 8-75 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 4 Nuclear hormone receptor subfamily 4 group A Nuclear hormone receptor subfamily 4 group A member 2
10 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Mycosis Fungoides 3 D009182 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 3 D017728 ClinicalTrials
Psychotic Disorders 3 D011618 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 2 D054437 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Alopecia Areata 2 D000506 ClinicalTrials
Psoriasis 2 D011565 ClinicalTrials
Parapsoriasis 2 D010267 ClinicalTrials
Sezary Syndrome 2 D012751 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Carcinoma, Intraductal, Noninfiltrating 1 D002285 ClinicalTrials
Pituitary ACTH Hypersecretion 1 D047748 ClinicalTrials
Thyroid Neoplasms 0 D013964 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Metabolism and nutrition disorders Hyperlipidaemia 79.2
Metabolism and nutrition disorders Malnutrition 79.2
Metabolism and nutrition disorders Hyperlipidaemia 78.6
Metabolism and nutrition disorders Malnutrition 78.6
Skin and subcutaneous tissue disorders Dermatitis 78.0
Skin and subcutaneous tissue disorders Rash 78.0
Skin and subcutaneous tissue disorders Dermatitis 72.0
Skin and subcutaneous tissue disorders Rash 72.0
Metabolism and nutrition disorders Hypercholesterolaemia 62.3
Skin and subcutaneous tissue disorders Dermatitis 56.0
Skin and subcutaneous tissue disorders Rash 56.0
Endocrine disorders Hypothyroidism 52.8
Blood and lymphatic system disorders Leukopenia 47.2
General disorders and administration site conditions Asthenia 45.3
Gastrointestinal disorders Diarrhoea 41.5
Nervous system disorders Headache 41.5
General disorders and administration site conditions Pain 40.0
Skin and subcutaneous tissue disorders Pruritus 40.0
Skin and subcutaneous tissue disorders Pruritus 36.0
Metabolism and nutrition disorders Hypercholesterolaemia 32.1
Metabolism and nutrition disorders Hyperlipidaemia 32.1
General disorders and administration site conditions Pain 30.0
Nervous system disorders Headache 29.8
Endocrine disorders Hypothyroidism 29.0
Endocrine disorders Hypothyroidism 28.6
Immune system disorders Dermatitis exfoliative 28.3
Metabolism and nutrition disorders Hypercholesterolaemia 28.0
Nervous system disorders Headache 27.0
Skin and subcutaneous tissue disorders Skin disorder 26.0
Blood and lymphatic system disorders Anaemia 24.5
General disorders and administration site conditions Decreased appetite 22.6
Skin and subcutaneous tissue disorders Dermatitis 22.6
Infections and infestations Infection 22.6
Skin and subcutaneous tissue disorders Rash 22.6
General disorders and administration site conditions Asthenia 20.2
Blood and lymphatic system disorders Leukopenia 20.0
Skin and subcutaneous tissue disorders Pruritus 20.0
General disorders and administration site conditions Asthenia 19.0
Eye disorders Cataract 19.0
Infections and infestations Infection 18.0
General disorders and administration site conditions Pain 18.0
Skin and subcutaneous tissue disorders Pruritus 18.0
Skin and subcutaneous tissue disorders Skin disorder 18.0
Investigations Body temperature increased 17.0
Skin and subcutaneous tissue disorders Dermatitis 16.7
Blood and lymphatic system disorders Leukopenia 16.7
Skin and subcutaneous tissue disorders Rash 16.7
Skin and subcutaneous tissue disorders Dermatitis 16.0
Gastrointestinal disorders Nausea 16.0
Skin and subcutaneous tissue disorders Rash 16.0
Gastrointestinal disorders Nausea 15.5
Immune system disorders Dermatitis exfoliative 15.0
Immune system disorders Dermatitis contact 14.0
Nervous system disorders Headache 14.0
Infections and infestations Bacterial infection 13.2
Investigations Blood lactate dehydrogenase increased 13.2
General disorders and administration site conditions Chills 13.2
Blood and lymphatic system disorders Hypochromic anaemia 13.2
Infections and infestations Influenza 13.2
Gastrointestinal disorders Vomiting 13.2
Infections and infestations Infection 13.1
Cardiac disorders Oedema peripheral 13.1
General disorders and administration site conditions Pain 12.0
Skin and subcutaneous tissue disorders Alopecia 11.3
Musculoskeletal and connective tissue disorders Back pain 11.3
Nervous system disorders Insomnia 11.3
Blood and lymphatic system disorders Leukopenia 11.3
Cardiac disorders Oedema peripheral 11.3
Gastrointestinal disorders Abdominal pain 11.0
Skin and subcutaneous tissue disorders Dry skin 11.0
Gastrointestinal disorders Gastrointestinal pain 11.0
Gastrointestinal disorders Abdominal pain 10.7
Skin and subcutaneous tissue disorders Dry skin 10.7
Gastrointestinal disorders Gastrointestinal pain 10.7
Nervous system disorders Agitation 10.0
Renal and urinary disorders Albuminuria 10.0
Cardiac disorders Angina pectoris 10.0
Musculoskeletal and connective tissue disorders Arthralgia 10.0
Musculoskeletal and connective tissue disorders Arthropathy 10.0
Nervous system disorders Ataxia 10.0
Eye disorders Blepharitis 10.0
Musculoskeletal and connective tissue disorders Bone pain 10.0
Reproductive system and breast disorders Breast pain 10.0
Infections and infestations Bronchitis 10.0
Infections and infestations Cellulitis 10.0
Nervous system disorders Cerebrovascular accident 10.0
Gastrointestinal disorders Cheilitis 10.0
Cardiac disorders Chest pain 10.0
General disorders and administration site conditions Chills 10.0
Investigations Coagulation time prolonged 10.0
Gastrointestinal disorders Colitis 10.0
Nervous system disorders Confusional state 10.0
Eye disorders Conjunctivitis 10.0
Gastrointestinal disorders Constipation 10.0
Eye disorders Corneal lesion 10.0
Respiratory, thoracic and mediastinal disorders Cough 10.0
Cardiac disorders Dizziness 10.0
Eye disorders Dry eye 10.0
Gastrointestinal disorders Dry mouth 10.0
Gastrointestinal disorders Dyspepsia 10.0
Cardiac disorders Dyspnoea 10.0
Renal and urinary disorders Dysuria 10.0
Ear and labyrinth disorders Ear pain 10.0
Blood and lymphatic system disorders Eosinophilia 10.0
General disorders and administration site conditions Feeling abnormal 10.0
Gastrointestinal disorders Flatulence 10.0
Gastrointestinal disorders Gastroenteritis 10.0
Gastrointestinal disorders Gingivitis 10.0
Renal and urinary disorders Haematuria 10.0
Cardiac disorders Haemoptysis 10.0
Skin and subcutaneous tissue disorders Hyperaesthesia 10.0
Endocrine disorders Hyperglycaemia 10.0
Metabolism and nutrition disorders Hyperlipidaemia 10.0
Vascular disorders Hypertension 10.0
Nervous system disorders Hypoaesthesia 10.0
Hepatobiliary disorders Hypoproteinaemia 10.0
Eye disorders Keratitis 10.0
Nervous system disorders Loss of consciousness 10.0
Blood and lymphatic system disorders Lymphocytosis 10.0
Gastrointestinal disorders Melaena 10.0
Renal and urinary disorders Micturition urgency 10.0
Nervous system disorders Muscular weakness 10.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 10.0
Musculoskeletal and connective tissue disorders Myalgia 10.0
Nervous system disorders Neuropathy peripheral 10.0
General disorders and administration site conditions Oedema 10.0
Musculoskeletal and connective tissue disorders Osteoarthritis 10.0
Ear and labyrinth disorders Otitis externa 10.0
Gastrointestinal disorders Pharyngitis 10.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 10.0
Renal and urinary disorders Pollakiuria 10.0
Cardiac disorders Pulmonary oedema 10.0
Infections and infestations Rhinitis 10.0
Cardiac disorders Right ventricular failure 10.0
Scotoma 10.0
Infections and infestations Sepsis 10.0
Vascular disorders Shock 10.0
Skin and subcutaneous tissue disorders Skin mass 10.0
Skin and subcutaneous tissue disorders Skin ulcer 10.0
Cardiac disorders Syncope 10.0
Cardiac disorders Tachycardia 10.0
Blood and lymphatic system disorders Thrombocytopenia 10.0
Blood and lymphatic system disorders Thrombocytosis 10.0
Nervous system disorders Urinary incontinence 10.0
Infections and infestations Urinary tract infection 10.0
Investigations Weight decreased 10.0
Investigations Weight increased 10.0
General disorders and administration site conditions Chills 9.52
Immune system disorders Dermatitis exfoliative 9.52
Skin and subcutaneous tissue disorders Dry skin 9.43
Nervous system disorders Headache 9.43
Metabolism and nutrition disorders Hypercholesterolaemia 9.43
Metabolism and nutrition disorders Hyperlipidaemia 9.4
Metabolism and nutrition disorders Hyponatraemia 9.4
Immune system disorders Dermatitis contact 8.0
Gastrointestinal disorders Nausea 7.55
Investigations Blood lactate dehydrogenase increased 7.14
Gastrointestinal disorders Diarrhoea 7.14
Blood and lymphatic system disorders Anaemia 6.0
General disorders and administration site conditions Asthenia 6.0
Respiratory, thoracic and mediastinal disorders Cough 6.0
Immune system disorders Dermatitis exfoliative 6.0
General disorders and administration site conditions Hyperhidrosis 6.0
Blood and lymphatic system disorders Leukopenia 6.0
Blood and lymphatic system disorders Lymphadenopathy 6.0
Cardiac disorders Oedema peripheral 6.0
Nervous system disorders Paraesthesia 6.0
Gastrointestinal disorders Pharyngitis 6.0
Skin and subcutaneous tissue disorders Rash maculo-papular 6.0
Blood and lymphatic system disorders White blood cell disorder 6.0
Blood and lymphatic system disorders Anaemia 5.95
Endocrine disorders Hyperglycaemia 5.7
General disorders and administration site conditions Decreased appetite 5.66
Immune system disorders Dermatitis exfoliative 5.66
Gastrointestinal disorders Pancreatitis 5.66
Investigations Body temperature increased 5.0
Metabolism and nutrition disorders Hyperlipidaemia 5.0
Nervous system disorders Insomnia 5.0
Investigations Body temperature increased 4.76
Nervous system disorders Insomnia 4.76
Skin and subcutaneous tissue disorders Alopecia 4.0
Infections and infestations Influenza 4.0
Infections and infestations Bacterial infection 3.8
Infections and infestations Pneumonia 3.8
Gastrointestinal disorders Abdominal pain 3.77
Investigations Alanine aminotransferase increased 3.77
Investigations Aspartate aminotransferase increased 3.77
Gastrointestinal disorders Diarrhoea 3.77
Gastrointestinal disorders Gastrointestinal pain 3.77
Blood and lymphatic system disorders Hyperbilirubinaemia 3.77
Endocrine disorders Hypothyroidism 3.77
Infections and infestations Pneumonia 3.77
Gastrointestinal disorders Vomiting 3.77
Skin and subcutaneous tissue disorders Alopecia 3.57
Blood and lymphatic system disorders Hypochromic anaemia 3.57
Infections and infestations Influenza 3.57
Gastrointestinal disorders Vomiting 3.57
Musculoskeletal and connective tissue disorders Back pain 2.38
General disorders and administration site conditions Decreased appetite 2.38
Musculoskeletal and connective tissue disorders Back pain 2.0
Infections and infestations Bacterial infection 2.0
Infections and infestations Pneumonia 2.0
Immune system disorders Dermatitis exfoliative 1.9
Gastrointestinal disorders Diarrhoea 1.9
Nervous system disorders Headache 1.9
Metabolism and nutrition disorders Hyperkalaemia 1.9
Blood and lymphatic system disorders Leukopenia 1.9
Skin and subcutaneous tissue disorders Dermatitis 1.89
Skin and subcutaneous tissue disorders Rash 1.89
Endocrine disorders Hyperglycaemia 1.2
Metabolism and nutrition disorders Hypernatraemia 1.2
Metabolism and nutrition disorders Hypocalcaemia 1.2
Metabolism and nutrition disorders Hyponatraemia 1.2
Infections and infestations Bacterial infection 1.19
Immune system disorders Dermatitis exfoliative 1.0
Gastrointestinal disorders Diarrhoea 1.0
Nervous system disorders Headache 1.0
Blood and lymphatic system disorders Leukopenia 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Metabolism and nutrition disorders
19.76
Investigations
13.25
General disorders and administration site conditions
11.96
Endocrine disorders
8.59
Skin and subcutaneous tissue disorders
7.02
Gastrointestinal disorders
4.72
Nervous system disorders
4.49
Infections and infestations
3.87
Vascular disorders
3.48
Blood and lymphatic system disorders
3.37
Injury, poisoning and procedural complications
2.92
Cardiac disorders
2.64

Cross References

Resources Reference
CAS NUMBER 153559-49-0
ChEBI 50859
ChEMBL CHEMBL1023
DrugBank DB00307
DrugCentral 361
EPA CompTox DTXSID1040619
FDA SRS A61RXM4375
Human Metabolome Database HMDB0014452
Guide to Pharmacology 2807
KEGG D03106
PDB 9RA
PharmGKB PA164752250
PubChem 82146
SureChEMBL SCHEMBL9025
ZINC ZINC000001539579
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