LEFLUNOMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1998)
Entry Type: Small molecule
Molecule Category: UNKNOWN Prodrug
ATC: L04AA13
UNII: G162GK9U4W

Structure
InChI Key VHOGYURTWQBHIL-UHFFFAOYSA-N
Smile Cc1oncc1C(=O)Nc1ccc(C(F)(F)F)cc1
InChI
InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H9F3N2O2
Molecular Weight 270.21
AlogP 3.25
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 55.13
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 19.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Dihydroorotate dehydrogenase inhibitor DailyMed
Primary Target
dihydroorotate dehydrogenase (quinone)
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - -
Enzyme Oxidoreductase
- 10000-13000 - - 12
Epigenetic regulator Writer Protein methyltransferase SET domain
- - - - 4

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Myasthenia Gravis 3 D009157 ClinicalTrials
Lupus Nephritis 3 D008181 ClinicalTrials
Central Nervous System Neoplasms 3 D016543 ClinicalTrials
Polymyalgia Rheumatica 3 D011111 ClinicalTrials
Arthritis, Psoriatic 3 D015535 ClinicalTrials
Smoldering Multiple Myeloma 2 D000075122 ClinicalTrials
Lymphoproliferative Disorders 2 D008232 ClinicalTrials
Lupus Erythematosus, Systemic 2 D008180 ClinicalTrials
Pemphigoid, Bullous 2 D010391 ClinicalTrials
Purpura, Schoenlein-Henoch 2 D011695 ClinicalTrials
Uveitis 2 D014605 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Graft vs Host Disease 1 D006086 ClinicalTrials
Severe Acute Respiratory Syndrome 1 D045169 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Breast Neoplasms 1 D001943 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Respiratory tract infection
Infections and infestations Respiratory tract infection 32.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 27.0
Infections and infestations Respiratory tract infection 27.0
Infections and infestations Respiratory tract infection 25.0
Gastrointestinal disorders Diarrhoea 22.0
Nervous system disorders Headache
Nervous system disorders Headache 21.0
Infections and infestations Respiratory tract infection
Infections and infestations Respiratory tract infection 21.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 20.0
Infections and infestations Respiratory tract infection
Infections and infestations Respiratory tract infection 20.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 19.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 18.0
Skin and subcutaneous tissue disorders Alopecia 17.0
Gastrointestinal disorders Diarrhoea 17.0
Investigations Hepatic enzyme abnormal 17.0
Investigations Liver function test abnormal 17.0
Infections and infestations Respiratory tract infection 15.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 13.0
Nervous system disorders Headache
Nervous system disorders Headache 13.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 13.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 12.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 12.0
Nervous system disorders Headache
Nervous system disorders Headache 12.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 12.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 11.0
Nervous system disorders Headache
Nervous system disorders Headache 11.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 11.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 11.0
Skin and subcutaneous tissue disorders Alopecia 10.0
Skin and subcutaneous tissue disorders Dermatitis 10.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 10.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 10.0
Nervous system disorders Headache 10.0
Investigations Hepatic enzyme abnormal
Investigations Hepatic enzyme abnormal 10.0
Vascular disorders Hypertension 10.0
Investigations Liver function test abnormal
Gastrointestinal disorders Mouth ulceration
Gastrointestinal disorders Mouth ulceration 10.0
Skin and subcutaneous tissue disorders Rash 10.0
Infections and infestations Sinusitis
Infections and infestations Sinusitis 10.0
Gastrointestinal disorders Stomatitis
Gastrointestinal disorders Stomatitis 10.0
Skin and subcutaneous tissue disorders Alopecia
Skin and subcutaneous tissue disorders Alopecia 9.0
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Arthralgia 9.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 9.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 9.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 9.0
Vascular disorders Hypertension
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 9.0
Gastrointestinal disorders Nausea 9.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 9.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 8.0
Musculoskeletal and connective tissue disorders Arthropathy 8.0
Musculoskeletal and connective tissue disorders Back pain 8.0
Infections and infestations Bronchitis 8.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 8.0
Nervous system disorders Headache 8.0
Musculoskeletal and connective tissue disorders Osteoarthritis 8.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 7.0
Musculoskeletal and connective tissue disorders Back pain 7.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 7.0
Respiratory, thoracic and mediastinal disorders Cough 7.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 7.0
Cardiac disorders Dizziness 7.0
Gastrointestinal disorders Dyspepsia 7.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 7.0
Nervous system disorders Headache 7.0
Infections and infestations Influenza
Infections and infestations Influenza 7.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 7.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 7.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 6.0
Skin and subcutaneous tissue disorders Alopecia
Skin and subcutaneous tissue disorders Alopecia 6.0
Musculoskeletal and connective tissue disorders Arthropathy 6.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 6.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 6.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 6.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 6.0
Gastrointestinal disorders Dyspepsia 6.0
Gastrointestinal disorders Gastroenteritis
Gastrointestinal disorders Gastroenteritis 6.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 6.0
Investigations Hepatic enzyme abnormal 6.0
Immune system disorders Hypersensitivity
Immune system disorders Hypersensitivity 6.0
Investigations Liver function test abnormal 6.0
Gastrointestinal disorders Mouth ulceration 6.0
Musculoskeletal and connective tissue disorders Muscle spasms
Musculoskeletal and connective tissue disorders Muscle spasms 6.0
Musculoskeletal and connective tissue disorders Osteoarthritis 6.0
Skin and subcutaneous tissue disorders Pruritus 6.0
Gastrointestinal disorders Stomatitis 6.0
Infections and infestations Urinary tract infection 6.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 5.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 5.0
Musculoskeletal and connective tissue disorders Back pain 5.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 5.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 5.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 5.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 5.0
Gastrointestinal disorders Dyspepsia 5.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 5.0
Investigations Hepatic enzyme abnormal 5.0
Immune system disorders Hypersensitivity
Immune system disorders Hypersensitivity 5.0
Investigations Liver function test abnormal 5.0
Gastrointestinal disorders Mouth ulceration
Gastrointestinal disorders Mouth ulceration 5.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 5.0
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Pruritus 5.0
Infections and infestations Rhinitis
Infections and infestations Rhinitis 5.0
Infections and infestations Sinusitis
Infections and infestations Sinusitis 5.0
Gastrointestinal disorders Stomatitis
Gastrointestinal disorders Stomatitis 5.0
Musculoskeletal and connective tissue disorders Tenosynovitis 5.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 5.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 5.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 4.0
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Arthralgia 4.0
Musculoskeletal and connective tissue disorders Arthropathy 4.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 4.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 4.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 4.0
Cardiac disorders Chest pain
Cardiac disorders Chest pain 4.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 4.0
Cardiac disorders Dizziness 4.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 4.0
Investigations Hepatic enzyme abnormal
Investigations Hepatic enzyme abnormal 4.0
Vascular disorders Hypertension
Vascular disorders Hypertension 4.0
Infections and infestations Infection 4.0
Infections and infestations Influenza
Infections and infestations Influenza 4.0
Investigations Liver function test abnormal
Gastrointestinal disorders Mouth ulceration
Gastrointestinal disorders Mouth ulceration 4.0
Musculoskeletal and connective tissue disorders Muscle spasms
Musculoskeletal and connective tissue disorders Muscle spasms 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.0
Musculoskeletal and connective tissue disorders Osteoarthritis 4.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 4.0
Nervous system disorders Paraesthesia 4.0
Skin and subcutaneous tissue disorders Pruritus 4.0
Infections and infestations Rhinitis
Infections and infestations Rhinitis 4.0
Gastrointestinal disorders Stomatitis
Gastrointestinal disorders Stomatitis 4.0
Musculoskeletal and connective tissue disorders Synovitis 4.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 4.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 4.0
Investigations Weight decreased 4.0
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Arthralgia 3.0
General disorders and administration site conditions Asthenia 3.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 3.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 3.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 3.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 3.0
Skin and subcutaneous tissue disorders Dry skin
Skin and subcutaneous tissue disorders Dry skin 3.0
Skin and subcutaneous tissue disorders Eczema 3.0
Gastrointestinal disorders Gastroenteritis 3.0
Vascular disorders Hypertension
Vascular disorders Hypertension 3.0
Metabolism and nutrition disorders Hypokalaemia
Metabolism and nutrition disorders Hypokalaemia 3.0
Blood and lymphatic system disorders Leukopenia 3.0
Gastrointestinal disorders Mouth ulceration
Gastrointestinal disorders Mouth ulceration 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Nervous system disorders Paraesthesia
Nervous system disorders Paraesthesia 3.0
Gastrointestinal disorders Pharyngitis 3.0
Infections and infestations Pneumonia
Infections and infestations Pneumonia 3.0
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Pruritus 3.0
Infections and infestations Rhinitis
Infections and infestations Rhinitis 3.0
Gastrointestinal disorders Stomatitis
Gastrointestinal disorders Stomatitis 3.0
Musculoskeletal and connective tissue disorders Tenosynovitis 3.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 3.0
Musculoskeletal and connective tissue disorders Arthropathy
Musculoskeletal and connective tissue disorders Arthropathy 2.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 2.0
Cardiac disorders Chest pain
Cardiac disorders Chest pain 2.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 2.0
Skin and subcutaneous tissue disorders Dry skin
Skin and subcutaneous tissue disorders Dry skin 2.0
Skin and subcutaneous tissue disorders Eczema 2.0
Investigations Hepatic enzyme abnormal
Investigations Hepatic enzyme abnormal 2.0
Immune system disorders Hypersensitivity
Immune system disorders Hypersensitivity 2.0
Vascular disorders Hypertension
Vascular disorders Hypertension 2.0
Infections and infestations Influenza
Infections and infestations Influenza 2.0
Investigations Liver function test abnormal
Musculoskeletal and connective tissue disorders Muscle spasms
Musculoskeletal and connective tissue disorders Muscle spasms 2.0
Musculoskeletal and connective tissue disorders Osteoarthritis
Musculoskeletal and connective tissue disorders Osteoarthritis 2.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 2.0
Nervous system disorders Paraesthesia
Nervous system disorders Paraesthesia 2.0
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 2.0
Infections and infestations Pneumonia 2.0
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Pruritus 2.0
Infections and infestations Rhinitis
Infections and infestations Rhinitis 2.0
Infections and infestations Sinusitis 2.0
Musculoskeletal and connective tissue disorders Synovitis
Musculoskeletal and connective tissue disorders Synovitis 2.0
Musculoskeletal and connective tissue disorders Tenosynovitis
Musculoskeletal and connective tissue disorders Tenosynovitis 2.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 2.0
Investigations Weight decreased
Investigations Weight decreased 2.0
Skin and subcutaneous tissue disorders Alopecia
Skin and subcutaneous tissue disorders Alopecia 1.0
Musculoskeletal and connective tissue disorders Arthralgia 1.0
Cardiac disorders Chest pain 1.0
Skin and subcutaneous tissue disorders Dry skin 1.0
Skin and subcutaneous tissue disorders Eczema
Skin and subcutaneous tissue disorders Eczema 1.0
Gastrointestinal disorders Gastroenteritis
Gastrointestinal disorders Gastroenteritis 1.0
Immune system disorders Hypersensitivity 1.0
Vascular disorders Hypertension
Vascular disorders Hypertension 1.0
Metabolism and nutrition disorders Hypokalaemia
Metabolism and nutrition disorders Hypokalaemia 1.0
Musculoskeletal and connective tissue disorders Muscle spasms 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
General disorders and administration site conditions Pain 1.0
Nervous system disorders Paraesthesia
Nervous system disorders Paraesthesia 1.0
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 1.0
Infections and infestations Pneumonia
Infections and infestations Pneumonia 1.0
Infections and infestations Sinusitis 1.0
Musculoskeletal and connective tissue disorders Synovitis
Musculoskeletal and connective tissue disorders Synovitis 1.0
Musculoskeletal and connective tissue disorders Tenosynovitis
Musculoskeletal and connective tissue disorders Tenosynovitis 1.0
Investigations Weight decreased
Investigations Weight decreased 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
19.57
Musculoskeletal and connective tissue disorders
14.21
Gastrointestinal disorders
7.29
Immune system disorders
7.14
Skin and subcutaneous tissue disorders
6.19
Investigations
5.88
Nervous system disorders
5.33
Injury, poisoning and procedural complications
4.84
Respiratory, thoracic and mediastinal disorders
4.65
Infections and infestations
4.5
Vascular disorders
3.35
Cardiac disorders
2.53

Cross References

Resources Reference
CAS NUMBER 75706-12-6
ChEBI 6402
ChEMBL CHEMBL960
DrugBank DB01097
DrugCentral 1552
EPA CompTox DTXSID9023201
FDA SRS G162GK9U4W
Human Metabolome Database HMDB0015229
Guide to Pharmacology 6825
KEGG C07905
PharmGKB PA450192
PubChem 3899
SureChEMBL SCHEMBL5057
ZINC ZINC000000004840
CONTENTS