REGORAFENIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2012)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01EX05
UNII: 24T2A1DOYB

Structure
InChI Key FNHKPVJBJVTLMP-UHFFFAOYSA-N
Smile CNC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(C(F)(F)F)c3)c(F)c2)ccn1
InChI
InChI=1S/C21H15ClF4N4O3/c1-27-19(31)18-10-13(6-7-28-18)33-12-3-5-17(16(23)9-12)30-20(32)29-11-2-4-15(22)14(8-11)21(24,25)26/h2-10H,1H3,(H,27,31)(H2,29,30,32)

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H15ClF4N4O3
Molecular Weight 482.82
AlogP 5.69
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 92.35
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 33.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Discoidin domain-containing receptor 2 inhibitor Expert
Primary Target
B-Raf proto-oncogene, serine/threonine kinase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase RAF family
- 2-40 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase FGFR family
- 2 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 6-2153 - - 0-88
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tie family
- 2 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 4-5 - - -
Enzyme Protease Serine protease Serine protease SC clan Serine protease S33 family
- 1 - - -
Enzyme Transferase
- - - - 89-96
Ion channel Ligand-gated ion channel Glycine receptor
1800 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Colorectal Neoplasms 4 D015179 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Colorectal Neoplasms 4 D015179 ClinicalTrials
Colorectal Neoplasms 4 D015179 ClinicalTrials
Esophageal Neoplasms 3 D004938 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Gastrointestinal Stromal Tumors 3 D046152 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Osteosarcoma 2 D012516 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Hemangiosarcoma 2 D006394 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Macular Degeneration 2 D008268 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Liposarcoma 2 D008080 ClinicalTrials
Carcinoma, Adenoid Cystic 2 D003528 ClinicalTrials
Bile Duct Neoplasms 2 D001650 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Carcinoma 2 D002277 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Biliary Tract Neoplasms 1 D001661 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Small Cell Lung Carcinoma 1 D055752 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Blood and lymphatic system disorders Anaemia 79.0
Blood and lymphatic system disorders Anaemia
Investigations Aspartate aminotransferase increased 65.0
Renal and urinary disorders Proteinuria 60.0
Investigations Protein urine present 60.0
Metabolism and nutrition disorders Hypocalcaemia 59.0
Metabolism and nutrition disorders Hypophosphataemia 57.0
Blood and lymphatic system disorders Lymphopenia 54.0
General disorders and administration site conditions Decreased appetite 47.0
Metabolism and nutrition disorders Malnutrition 47.0
Investigations Aspartate aminotransferase increased
Investigations Lipase increased 46.0
Investigations Alanine aminotransferase increased 45.0
Blood and lymphatic system disorders Hyperbilirubinaemia 45.0
Blood and lymphatic system disorders Thrombocytopenia 41.0
Nervous system disorders Dysphonia 39.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 39.0
Blood and lymphatic system disorders Lymphopenia
Renal and urinary disorders Proteinuria
Investigations Protein urine present
Renal and urinary disorders Proteinuria 33.0
Investigations Protein urine present 33.0
Renal and urinary disorders Urethral disorder 33.0
Renal and urinary disorders Urinary tract disorder 33.0
Infections and infestations Infection 32.0
Infections and infestations Infestation 32.0
Investigations Weight decreased 32.0
Infections and infestations Infection 31.0
Infections and infestations Infestation 31.0
Investigations Alanine aminotransferase increased
Nervous system disorders Dysphonia 30.0
Metabolism and nutrition disorders Hyponatraemia 30.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 30.0
Renal and urinary disorders Proteinuria
Investigations Protein urine present
Renal and urinary disorders Urethral disorder
Renal and urinary disorders Urinary tract disorder
General disorders and administration site conditions Decreased appetite
Metabolism and nutrition disorders Malnutrition
Investigations Amylase increased 26.0
Metabolism and nutrition disorders Hypokalaemia 26.0
Investigations International normalised ratio increased 24.0
Metabolism and nutrition disorders Hyponatraemia
Investigations Lipase increased
Metabolism and nutrition disorders Hypocalcaemia
Investigations Amylase increased
Blood and lymphatic system disorders Hyperbilirubinaemia
Infections and infestations Infection
Infections and infestations Infestation
Investigations International normalised ratio increased
Blood and lymphatic system disorders Thrombocytopenia
Nervous system disorders Headache 16.0
Nervous system disorders Nervous system disorder 16.0
Musculoskeletal and connective tissue disorders Connective tissue disorder 14.0
Investigations Lipase increased 14.0
Musculoskeletal and connective tissue disorders Musculoskeletal stiffness 14.0
Investigations Weight decreased 14.0
Metabolism and nutrition disorders Hypophosphataemia
Nervous system disorders Headache 10.0
Nervous system disorders Nervous system disorder 10.0
Investigations Weight decreased
Nervous system disorders Dysphonia
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Nervous system disorders Nervous system disorder
Metabolism and nutrition disorders Hypokalaemia
Investigations Weight decreased
Nervous system disorders Headache
Nervous system disorders Nervous system disorder
Nervous system disorders Dysphonia
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Infections and infestations Infection
Infections and infestations Infestation
Investigations Lipase increased
Musculoskeletal and connective tissue disorders Connective tissue disorder
Musculoskeletal and connective tissue disorders Musculoskeletal stiffness
Blood and lymphatic system disorders Neutropenia 3.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
14.07
Gastrointestinal disorders
13.4
Nervous system disorders
10.16
Skin and subcutaneous tissue disorders
9.38
Investigations
6.46
Respiratory, thoracic and mediastinal disorders
5.9
Musculoskeletal and connective tissue disorders
4.79
Metabolism and nutrition disorders
4.45
Vascular disorders
4.27
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
4.01
Psychiatric disorders
3.93
Injury, poisoning and procedural complications
3.91
Cardiac disorders
3.45
Hepatobiliary disorders
3.02
Infections and infestations
2.18

Cross References

Resources Reference
CAS NUMBER 755037-03-7
ChEBI 68647
ChEMBL CHEMBL1946170
DrugBank DB08896
DrugCentral 4654
EPA CompTox DTXSID60226441
FDA SRS 24T2A1DOYB
Guide to Pharmacology 5891
KEGG D10138
PubChem 11167602
SureChEMBL SCHEMBL432230
ZINC ZINC000006745272
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