POMALIDOMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (2013)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L04AX06
UNII: D2UX06XLB5

Structure
InChI Key UVSMNLNDYGZFPF-UHFFFAOYSA-N
Smile Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O
InChI
InChI=1S/C13H11N3O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5,14H2,(H,15,17,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H11N3O4
Molecular Weight 273.25
AlogP -0.33
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 109.57
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 20.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR CRL4(CRBN) E3 ubiquitin ligase inhibitor PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Unclassified protein
22 1200-25800 - 10000 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Multiple Myeloma 4 D009101 ClinicalTrials
Primary Myelofibrosis 3 D055728 ClinicalTrials
Primary Myelofibrosis 3 D055728 ClinicalTrials
Leukemia, Plasma Cell 2 D007952 ClinicalTrials
Scleroderma, Systemic 2 D012595 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Polycythemia Vera 2 D011087 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Plasmacytoma 2 D010954 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Amyloidosis, Familial 2 D028226 ClinicalTrials
Lung Diseases, Interstitial 2 D017563 ClinicalTrials
Pulmonary Fibrosis 2 D011658 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Telangiectasia, Hereditary Hemorrhagic 2 D013683 ClinicalTrials
Anemia, Sickle Cell 1 D000755 ClinicalTrials
Amyloidosis 1 D000686 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 1 D016403 ClinicalTrials
Small Cell Lung Carcinoma 1 D055752 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Pancreatic Neoplasms 1 D010190 ClinicalTrials
Hodgkin Disease 1 D006689 ClinicalTrials
Castleman Disease 1 D005871 ClinicalTrials
Lymphoma, Non-Hodgkin 1 D008228 ClinicalTrials
Waldenstrom Macroglobulinemia 1 D008258 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Asthenia 62.5
General disorders and administration site conditions Fatigue 62.5
General disorders and administration site conditions Asthenia 55.1
General disorders and administration site conditions Fatigue 55.1
Blood and lymphatic system disorders Neutropenia 52.3
Blood and lymphatic system disorders Neutropenia 47.3
Blood and lymphatic system disorders Neutropenia 46.7
Blood and lymphatic system disorders Anaemia 45.7
Blood and lymphatic system disorders Neutropenia 45.3
Cardiac disorders Dyspnoea 44.6
Blood and lymphatic system disorders Neutropenia 41.7
Blood and lymphatic system disorders Anaemia 39.3
Blood and lymphatic system disorders Neutropenia 38.4
Blood and lymphatic system disorders Anaemia 38.3
Gastrointestinal disorders Constipation 35.5
Gastrointestinal disorders Nausea 35.5
Gastrointestinal disorders Constipation 34.8
Gastrointestinal disorders Diarrhoea 33.6
Cardiac disorders Dyspnoea 33.6
Gastrointestinal disorders Diarrhoea 33.0
Musculoskeletal and connective tissue disorders Back pain 31.8
Infections and infestations Upper respiratory tract infection 31.8
Musculoskeletal and connective tissue disorders Back pain 30.4
Investigations Body temperature increased 30.4
Infections and infestations Pneumonia 28.6
General disorders and administration site conditions Asthenia 28.3
General disorders and administration site conditions Fatigue 28.3
Blood and lymphatic system disorders Anaemia 27.0
Blood and lymphatic system disorders Thrombocytopenia 27.0
Blood and lymphatic system disorders Thrombocytopenia 25.2
Infections and infestations Upper respiratory tract infection 25.0
Cardiac disorders Oedema peripheral 23.4
Infections and infestations Pneumonia 23.4
Infections and infestations Pneumonia 23.2
Blood and lymphatic system disorders Thrombocytopenia 23.2
Blood and lymphatic system disorders Anaemia 22.4
Blood and lymphatic system disorders Thrombocytopenia 22.4
Gastrointestinal disorders Nausea 22.3
General disorders and administration site conditions Decreased appetite 21.5
Skin and subcutaneous tissue disorders Dermatitis 21.5
Musculoskeletal and connective tissue disorders Musculoskeletal chest pain 21.5
Skin and subcutaneous tissue disorders Rash 21.5
Investigations Body temperature increased 21.0
Blood and lymphatic system disorders Thrombocytopenia 20.7
Endocrine disorders Hypercalcaemia 20.6
Blood and lymphatic system disorders Anaemia 20.5
Respiratory, thoracic and mediastinal disorders Cough 20.5
Cardiac disorders Dizziness 19.6
Musculoskeletal and connective tissue disorders Musculoskeletal chest pain 19.6
Musculoskeletal and connective tissue disorders Muscle spasms 18.8
Infections and infestations Pneumonia 18.8
Blood and lymphatic system disorders Thrombocytopenia 18.8
Investigations Body temperature increased 18.7
Musculoskeletal and connective tissue disorders Muscle spasms 18.7
General disorders and administration site conditions Decreased appetite 17.9
Blood and lymphatic system disorders Leukopenia 17.9
Cardiac disorders Dizziness 17.0
Skin and subcutaneous tissue disorders Dermatitis 16.1
General disorders and administration site conditions Hyperhidrosis 16.1
Cardiac disorders Oedema peripheral 16.1
Skin and subcutaneous tissue disorders Rash 16.1
Infections and infestations Urinary tract infection 16.1
Musculoskeletal and connective tissue disorders Arthralgia 15.9
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 15.9
Infections and infestations Pneumonia 15.9
Musculoskeletal and connective tissue disorders Arthralgia 15.2
Endocrine disorders Hyperglycaemia 15.2
Blood and lymphatic system disorders Lymphopenia 15.2
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 15.2
Musculoskeletal and connective tissue disorders Musculoskeletal pain 15.2
Investigations Blood creatinine increased 15.0
Respiratory, thoracic and mediastinal disorders Epistaxis 15.0
Skin and subcutaneous tissue disorders Pruritus 15.0
Renal and urinary disorders Renal failure 15.0
Nervous system disorders Insomnia 14.3
Musculoskeletal and connective tissue disorders Pain in extremity 14.3
Respiratory, thoracic and mediastinal disorders Cough 14.0
Infections and infestations Pneumonia 14.0
Gastrointestinal disorders Vomiting 14.0
Investigations Weight decreased 14.0
Nervous system disorders Confusional state 13.4
General disorders and administration site conditions Feeling abnormal 13.4
Gastrointestinal disorders Vomiting 13.4
Nervous system disorders Headache 13.1
Cardiac disorders Oedema peripheral 13.0
General disorders and administration site conditions Asthenia 12.5
Cardiac disorders Dyspnoea 12.5
General disorders and administration site conditions Fatigue 12.5
Metabolism and nutrition disorders Hyponatraemia 12.5
General disorders and administration site conditions Night sweats 12.5
Nervous system disorders Tremor 12.5
Musculoskeletal and connective tissue disorders Back pain 12.1
Musculoskeletal and connective tissue disorders Bone pain 12.1
Endocrine disorders Hyperglycaemia 12.1
Nervous system disorders Muscular weakness 12.1
Endocrine disorders Hypercalcaemia 11.6
Metabolism and nutrition disorders Hypocalcaemia 11.6
Nervous system disorders Muscular weakness 11.6
Psychiatric disorders Anxiety 11.2
General disorders and administration site conditions Asthenia 11.2
General disorders and administration site conditions Fatigue 11.2
Blood and lymphatic system disorders Leukopenia 11.2
Musculoskeletal and connective tissue disorders Musculoskeletal pain 11.2
Investigations Blood creatinine increased 10.7
General disorders and administration site conditions Chills 10.7
Skin and subcutaneous tissue disorders Dry skin 10.7
Respiratory, thoracic and mediastinal disorders Epistaxis 10.7
Metabolism and nutrition disorders Hypokalaemia 10.7
Infections and infestations Pneumonia 10.7
Skin and subcutaneous tissue disorders Pruritus 10.7
Investigations Weight increased 10.7
Nervous system disorders Confusional state 10.3
General disorders and administration site conditions Feeling abnormal 10.3
Metabolism and nutrition disorders Hypokalaemia 10.3
Metabolism and nutrition disorders Hyponatraemia 10.3
Nervous system disorders Neuropathy peripheral 10.3
Blood and lymphatic system disorders Leukopenia 9.82
Renal and urinary disorders Renal failure 9.82
General disorders and administration site conditions Chills 9.35
Skin and subcutaneous tissue disorders Dry skin 9.35
Endocrine disorders Hypercalcaemia 9.35
Renal and urinary disorders Renal failure 9.35
Nervous system disorders Tremor 9.35
Infections and infestations Pneumonia 9.3
Infections and infestations Pneumonia 9.0
Musculoskeletal and connective tissue disorders Back pain 8.93
Renal and urinary disorders Renal failure 8.41
Nervous system disorders Headache 8.04
Infections and infestations Urinary tract infection 8.04
Investigations Weight decreased 8.04
Infections and infestations Urinary tract infection 7.48
Psychiatric disorders Anxiety 7.14
Blood and lymphatic system disorders Lymphopenia 7.14
Nervous system disorders Neuropathy peripheral 7.14
Cardiac disorders Dyspnoea 6.54
Nervous system disorders Insomnia 6.54
Cardiac disorders Dyspnoea 6.25
Renal and urinary disorders Renal failure 6.25
Investigations Blood creatinine increased 5.61
General disorders and administration site conditions Hyperhidrosis 5.61
Metabolism and nutrition disorders Hypocalcaemia 5.61
Blood and lymphatic system disorders Leukopenia 5.61
Nervous system disorders Muscular weakness 5.61
General disorders and administration site conditions Pain 5.61
Infections and infestations Sepsis 5.61
Infections and infestations Urinary tract infection 5.36
General disorders and administration site conditions Asthenia 4.7
General disorders and administration site conditions Fatigue 4.7
Metabolism and nutrition disorders Dehydration 4.67
Cardiac disorders Dyspnoea 4.67
Blood and lymphatic system disorders Febrile neutropenia 4.67
Endocrine disorders Hypercalcaemia 4.67
General disorders and administration site conditions Night sweats 4.67
Musculoskeletal and connective tissue disorders Pain in extremity 4.67
Investigations Body temperature increased 4.46
Musculoskeletal and connective tissue disorders Bone pain 4.46
General disorders and administration site conditions Pain 4.46
Blood and lymphatic system disorders Febrile neutropenia 4.0
Musculoskeletal and connective tissue disorders Back pain 3.74
Blood and lymphatic system disorders Lymphopenia 3.74
Nervous system disorders Muscular weakness 3.57
Investigations Body temperature increased 3.0
Investigations Body temperature increased 2.8
Cardiac disorders Atrial fibrillation 2.68
Investigations Blood creatinine increased 2.68
Cardiac disorders Cardiac failure congestive 2.68
Gastrointestinal disorders Constipation 2.68
Metabolism and nutrition disorders Dehydration 2.68
Infections and infestations Sepsis 2.68
Blood and lymphatic system disorders Neutropenia 2.0
Cardiac disorders Atrial fibrillation 1.87
Blood and lymphatic system disorders Lymphopenia 1.87
Infections and infestations Urinary tract infection 1.87
Musculoskeletal and connective tissue disorders Back pain 1.79
General disorders and administration site conditions General physical health deterioration 1.79
Endocrine disorders Hypercalcaemia 1.79
Blood and lymphatic system disorders Thrombocytopenia 1.7
Cardiac disorders Oedema peripheral 1.3
Gastrointestinal disorders Constipation 0.935
Investigations Weight increased 0.935
Blood and lymphatic system disorders Febrile neutropenia 0.893
Endocrine disorders Hypercalcaemia 0.893

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
13.9
Respiratory, thoracic and mediastinal disorders
9.93
Infections and infestations
9.52
Investigations
9.24
Nervous system disorders
7.3
Blood and lymphatic system disorders
7.03
Gastrointestinal disorders
6.1
Cardiac disorders
4.99
Vascular disorders
4.74
Musculoskeletal and connective tissue disorders
4.72
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
4.27
Skin and subcutaneous tissue disorders
4.07
Injury, poisoning and procedural complications
2.98
Psychiatric disorders
2.58
Metabolism and nutrition disorders
2.43
Renal and urinary disorders
2.14

Cross References

Resources Reference
CAS NUMBER 19171-19-8
ChEBI 72690
ChEMBL CHEMBL43452
DrugBank DB08910
DrugCentral 4746
EPA CompTox DTXSID40893458
FDA SRS D2UX06XLB5
Guide to Pharmacology 7348
PubChem 134780
SureChEMBL SCHEMBL19250920
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