VEMURAFENIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2011)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01EC01
UNII: 207SMY3FQT

Structure
InChI Key GPXBXXGIAQBQNI-UHFFFAOYSA-N
Smile CCCS(=O)(=O)Nc1ccc(F)c(C(=O)c2c[nH]c3ncc(-c4ccc(Cl)cc4)cc23)c1F
InChI
InChI=1S/C23H18ClF2N3O3S/c1-2-9-33(31,32)29-19-8-7-18(25)20(21(19)26)22(30)17-12-28-23-16(17)10-14(11-27-23)13-3-5-15(24)6-4-13/h3-8,10-12,29H,2,9H2,1H3,(H,27,28)

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H18ClF2N3O3S
Molecular Weight 489.93
AlogP 5.54
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 7.0
Polar Surface Area 91.92
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 33.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Serine/threonine-protein kinase B-raf inhibitor FDA
Primary Target
B-Raf proto-oncogene, serine/threonine kinase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 16600 - - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE7 family
- 1500 - - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase MLK family TKL protein kinase MLK subfamily
- 23-31 - - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase RAF family
794-2290 3-1140 51-58 - 72-95
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 360 - - -
Enzyme Lyase
5012 - - - -
Enzyme Oxidoreductase
- 10500-16900 - - 81

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Melanoma 4 D008545 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Melanoma 4 D008545 ClinicalTrials
Melanoma 4 D008545 ClinicalTrials
Craniopharyngioma 2 D003397 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Histiocytosis 2 D015614 ClinicalTrials
Leukemia, Hairy Cell 2 D007943 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Lymphoma 1 D008223 ClinicalTrials
Skin Neoplasms 1 D012878 ClinicalTrials
Skin Neoplasms 1 D012878 ClinicalTrials
Glioma 0 D005910 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Musculoskeletal and connective tissue disorders Arthralgia 67.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 67.0
General disorders and administration site conditions Asthenia 54.0
General disorders and administration site conditions Fatigue 54.0
Musculoskeletal and connective tissue disorders Arthralgia 53.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 53.0
Skin and subcutaneous tissue disorders Dermatitis 52.0
Skin and subcutaneous tissue disorders Rash 52.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 49.0
Skin and subcutaneous tissue disorders Alopecia 45.0
Gastrointestinal disorders Nausea 43.0
General disorders and administration site conditions Asthenia 38.0
General disorders and administration site conditions Fatigue 38.0
Skin and subcutaneous tissue disorders Dermatitis 37.0
Gastrointestinal disorders Nausea 37.0
Skin and subcutaneous tissue disorders Rash 37.0
Skin and subcutaneous tissue disorders Alopecia 36.0
Gastrointestinal disorders Nausea 35.0
General disorders and administration site conditions Asthenia 33.0
General disorders and administration site conditions Fatigue 33.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 33.0
Skin and subcutaneous tissue disorders Pruritus 30.0
Infections and infestations Skin papilloma 30.0
Gastrointestinal disorders Diarrhoea 29.0
Gastrointestinal disorders Diarrhoea 28.0
Skin and subcutaneous tissue disorders Hyperkeratosis 28.0
Nervous system disorders Headache 27.0
Gastrointestinal disorders Vomiting 26.0
Gastrointestinal disorders Constipation 24.0
Skin and subcutaneous tissue disorders Hyperkeratosis 24.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 24.0
Musculoskeletal and connective tissue disorders Myalgia 24.0
Nervous system disorders Headache 23.0
Cardiac disorders Oedema peripheral 23.0
Skin and subcutaneous tissue disorders Pruritus 23.0
General disorders and administration site conditions Decreased appetite 21.0
Skin and subcutaneous tissue disorders Rash maculo-papular 21.0
Infections and infestations Skin papilloma 21.0
Investigations Body temperature increased 19.0
Skin and subcutaneous tissue disorders Dry skin 19.0
General disorders and administration site conditions Decreased appetite 18.0
Musculoskeletal and connective tissue disorders Pain in extremity 18.0
Gastrointestinal disorders Vomiting 18.0
Skin and subcutaneous tissue disorders Actinic keratosis 17.0
Investigations Body temperature increased 17.0
Cardiac disorders Oedema peripheral 17.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Seborrhoeic keratosis 17.0
Gastrointestinal disorders Constipation 16.0
Skin and subcutaneous tissue disorders Dry skin 16.0
Investigations Gamma-glutamyltransferase increased 15.0
Gastrointestinal disorders Dysgeusia 14.0
Skin and subcutaneous tissue disorders Erythema 14.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 14.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Seborrhoeic keratosis 14.0
Injury, poisoning and procedural complications Sunburn 14.0
Gastrointestinal disorders Diarrhoea 13.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 13.0
Musculoskeletal and connective tissue disorders Myalgia 13.0
Skin and subcutaneous tissue disorders Rash papular 13.0
Gastrointestinal disorders Constipation 12.0
Respiratory, thoracic and mediastinal disorders Cough 12.0
General disorders and administration site conditions Asthenia 11.0
Musculoskeletal and connective tissue disorders Back pain 11.0
Gastrointestinal disorders Dysgeusia 11.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 11.0
Nervous system disorders Headache 10.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 10.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Seborrhoeic keratosis 10.0
Injury, poisoning and procedural complications Sunburn 10.0
General disorders and administration site conditions Asthenia 9.0
Investigations Body temperature increased 9.0
Musculoskeletal and connective tissue disorders Pain in extremity 9.0
Skin and subcutaneous tissue disorders Rash maculo-papular 9.0
Skin and subcutaneous tissue disorders Actinic keratosis 8.0
Musculoskeletal and connective tissue disorders Arthralgia 8.0
Musculoskeletal and connective tissue disorders Back pain 8.0
Respiratory, thoracic and mediastinal disorders Cough 8.0
General disorders and administration site conditions Decreased appetite 8.0
Skin and subcutaneous tissue disorders Dermatitis 8.0
Skin and subcutaneous tissue disorders Erythema 8.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 8.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 8.0
Skin and subcutaneous tissue disorders Rash 8.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Seborrhoeic keratosis 8.0
Respiratory, thoracic and mediastinal disorders Cough 7.0
Skin and subcutaneous tissue disorders Dermatitis 7.0
Skin and subcutaneous tissue disorders Rash 7.0
Investigations Gamma-glutamyltransferase increased 6.0
Musculoskeletal and connective tissue disorders Pain in extremity 6.0
Skin and subcutaneous tissue disorders Rash maculo-papular 6.0
Musculoskeletal and connective tissue disorders Back pain 5.0
Investigations Gamma-glutamyltransferase increased 5.0
Cardiac disorders Oedema peripheral 5.0
Skin and subcutaneous tissue disorders Rash papular 5.0
Musculoskeletal and connective tissue disorders Arthralgia 4.0
General disorders and administration site conditions Asthenia 4.0
General disorders and administration site conditions Fatigue 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 4.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 4.0
Skin and subcutaneous tissue disorders Actinic keratosis 3.0
Musculoskeletal and connective tissue disorders Arthralgia 3.0
Gastrointestinal disorders Dysgeusia 3.0
Investigations Gamma-glutamyltransferase increased 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 3.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Seborrhoeic keratosis 3.0
Skin and subcutaneous tissue disorders Alopecia 2.0
General disorders and administration site conditions Asthenia 2.0
Investigations Body temperature increased 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Skin and subcutaneous tissue disorders Erythema 2.0
General disorders and administration site conditions Fatigue 2.0
Gastrointestinal disorders Nausea 2.0
Musculoskeletal and connective tissue disorders Pain in extremity 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Skin and subcutaneous tissue disorders Rash maculo-papular 2.0
Gastrointestinal disorders Vomiting 2.0
Skin and subcutaneous tissue disorders Alopecia 1.0
Musculoskeletal and connective tissue disorders Arthralgia 1.0
General disorders and administration site conditions Asthenia 1.0
Musculoskeletal and connective tissue disorders Back pain 1.0
Investigations Body temperature increased 1.0
Gastrointestinal disorders Constipation 1.0
General disorders and administration site conditions Decreased appetite 1.0
Gastrointestinal disorders Diarrhoea 1.0
Skin and subcutaneous tissue disorders Dry skin 1.0
Investigations Gamma-glutamyltransferase increased 1.0
Nervous system disorders Headache 1.0
Skin and subcutaneous tissue disorders Hyperkeratosis 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 1.0
Musculoskeletal and connective tissue disorders Myalgia 1.0
Cardiac disorders Oedema peripheral 1.0
Musculoskeletal and connective tissue disorders Pain in extremity 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Rash maculo-papular 1.0
Skin and subcutaneous tissue disorders Rash papular 1.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Seborrhoeic keratosis 1.0
Infections and infestations Skin papilloma 1.0
Gastrointestinal disorders Vomiting 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
18.98
General disorders and administration site conditions
14.2
Gastrointestinal disorders
8.73
Nervous system disorders
7.2
Musculoskeletal and connective tissue disorders
6.14
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
4.84
Investigations
4.73
Injury, poisoning and procedural complications
4.19
Infections and infestations
3.65
Respiratory, thoracic and mediastinal disorders
3.42
Metabolism and nutrition disorders
3.37
Immune system disorders
3.25
Cardiac disorders
3.14
Vascular disorders
3.01
Eye disorders
2.86

Cross References

Resources Reference
CAS NUMBER 918504-65-1
ChEBI 63637
ChEMBL CHEMBL1229517
DrugBank DB08881
DrugCentral 4185
EPA CompTox DTXSID50238710
FDA SRS 207SMY3FQT
Guide to Pharmacology 5893
KEGG D09996
PDB 032
PharmGKB PA165946873
PubChem 42611257
SureChEMBL SCHEMBL298931
ZINC ZINC000052509366
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