AXITINIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2012)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01EK01
UNII: C9LVQ0YUXG

Structure
InChI Key RITAVMQDGBJQJZ-FMIVXFBMSA-N
Smile CNC(=O)c1ccccc1Sc1ccc2c(/C=C/c3ccccn3)n[nH]c2c1
InChI
InChI=1S/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H18N4OS
Molecular Weight 386.48
AlogP 4.64
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 70.67
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Vascular endothelial growth factor receptor inhibitor DailyMed
Primary Target
kinase insert domain receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase DMPK family AGC protein kinase GEK subfamily
- - 4800 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase GRK family AGC protein kinase GRK subfamily
- - 2300 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKN family
- - 2700 - -
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase RIO family Atypical protein kinase RIO1 subfamily
- - 1200 - -
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase RIO family Atypical protein kinase RIO3 subfamily
- - 1000 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family CAMK protein kinase NuaK subfamily
- - 1300 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family CAMK protein kinase QIK subfamily
- - 2100 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase MLCK family
- - 1300 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group
- - 1300 - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase TAIRE subfamily
- - 5300 - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDKL family
- - 530 - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase JNK subfamily
- - 1100 - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase SRPK family
- - 1800 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase AUR family
- - 1 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase CAMKK family Other protein kinase Meta subfamily
- - 1400 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase CK2 family
- - 2800 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase NAK family
- - 1000 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase PEK family Other protein kinase PKR
- - 7400 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase PLK family
- 43-46 16 4-4 -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase TTK family
- - 3900 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase ULK family
- - 670 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE11 family STE protein kinase MEKK2
- - 2800 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE11 family
- - 270 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase KHS subfamily
- - 1200 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase MSN subfamily
- - 180 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase MST subfamily
- - 1400 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase NinaC subfamily
- - 1900 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase PAKB subfamily
- - 4500 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase SLK subfamily
- - 1000 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE7 family
- - 140 - -
Enzyme Kinase Protein Kinase STE protein kinase group
- - 1000 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase IRAK family
- - 3100 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase LISK family TKL protein kinase TESK subfamily
- - 4300 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase LRRK family
- - 920-990 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase MLK family TKL protein kinase MLK subfamily
- - 2600 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase RIPK family
- - 1400 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase STKR family TKL protein kinase STKR Type 1 subfamily
- - 2900 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase STKR family TKL protein kinase STKR Type 2 subfamily
- - 5200 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- 0-170 2-2600 - 57
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ack family
- - 160 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Axl family
- - 3200 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Csk family
- - 1100 - 11
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase DDR family
- - 340 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- - 2300-6200 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase FGFR family
- - 210-210 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
- - 3100 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- - 3100 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Met family
- - 820-1100 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- - 1-4200 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ret family
- - 100-1600 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Sev family
- - 3200 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- - 1800 - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tec family
- - 1200 - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tie family
- - 310 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Trk family
- - 1800 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 0-39 170 - -
Membrane receptor
- - 360 - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Carcinoma, Renal Cell 4 D002292 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Carcinoma, Renal Cell 4 D002292 ClinicalTrials
Carcinoma, Renal Cell 4 D002292 ClinicalTrials
Carcinoma, Pancreatic Ductal 3 D021441 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Sarcoma, Alveolar Soft Part 2 D018234 ClinicalTrials
Adrenal Cortex Neoplasms 2 D000306 ClinicalTrials
Skin Neoplasms 2 D012878 ClinicalTrials
Carcinoma, Adenoid Cystic 2 D003528 ClinicalTrials
Carcinoid Tumor 2 D002276 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Carcinoma, Hepatocellular 2 D006528 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Biliary Tract Neoplasms 2 D001661 ClinicalTrials
Salivary Gland Neoplasms 2 D012468 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Solitary Fibrous Tumors 2 D054364 ClinicalTrials
Gastrointestinal Stromal Tumors 2 D046152 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Gliosarcoma 1 D018316 ClinicalTrials
Stomach Neoplasms 1 D013274 ClinicalTrials
Breast Neoplasms 1 D001943 ClinicalTrials
Carcinoma 1 D002277 ClinicalTrials
Endometriosis 1 D004715 ClinicalTrials
Mesothelioma 1 D008654 ClinicalTrials
Blast Crisis 1 D001752 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Metabolism and nutrition disorders Hypocalcaemia 59.0
Investigations Blood creatinine increased 55.0
Gastrointestinal disorders Diarrhoea 55.0
Gastrointestinal disorders Diarrhoea 53.0
Investigations Haemoglobin decreased 52.0
Metabolism and nutrition disorders Hypophosphataemia 49.0
Investigations Lipase increased 46.0
Investigations Blood creatinine increased 41.0
Vascular disorders Hypertension 40.0
General disorders and administration site conditions Asthenia 39.0
General disorders and administration site conditions Fatigue 39.0
Metabolism and nutrition disorders Hypocalcaemia 39.0
Investigations Haemoglobin decreased 35.0
Investigations Blood alkaline phosphatase increased 34.0
General disorders and administration site conditions Decreased appetite 34.0
Investigations Amylase increased 33.0
Skin and subcutaneous tissue disorders Alopecia 32.0
General disorders and administration site conditions Asthenia 32.0
Skin and subcutaneous tissue disorders Dermatitis 32.0
General disorders and administration site conditions Fatigue 32.0
Gastrointestinal disorders Nausea 32.0
Skin and subcutaneous tissue disorders Rash 32.0
Nervous system disorders Dysphonia 31.0
Investigations Blood alkaline phosphatase increased 30.0
General disorders and administration site conditions Decreased appetite 29.0
Vascular disorders Hypertension 29.0
Endocrine disorders Hyperglycaemia 28.0
Investigations Lipase increased 27.0
Investigations Amylase increased 25.0
Investigations Aspartate aminotransferase increased 25.0
Investigations Weight decreased 25.0
Gastrointestinal disorders Vomiting 24.0
Endocrine disorders Hyperglycaemia 23.0
Investigations Alanine aminotransferase increased 22.0
Gastrointestinal disorders Nausea 22.0
General disorders and administration site conditions Asthenia 21.0
Investigations Weight decreased 21.0
Investigations Aspartate aminotransferase increased 20.0
Gastrointestinal disorders Constipation 20.0
Endocrine disorders Hypothyroidism 19.0
Hepatobiliary disorders Hypoalbuminaemia 18.0
Respiratory, thoracic and mediastinal disorders Cough 17.0
Metabolism and nutrition disorders Hypernatraemia 17.0
Gastrointestinal disorders Vomiting 17.0
Vascular disorders Hypertension 16.0
Metabolism and nutrition disorders Hypophosphataemia 16.0
Investigations White blood cell count decreased 16.0
Musculoskeletal and connective tissue disorders Arthralgia 15.0
Respiratory, thoracic and mediastinal disorders Cough 15.0
Cardiac disorders Dyspnoea 15.0
Metabolism and nutrition disorders Hyperkalaemia 15.0
Hepatobiliary disorders Hypoalbuminaemia 15.0
Investigations Lipase increased 15.0
General disorders and administration site conditions Mucosal inflammation 15.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 15.0
Investigations Platelet count decreased 15.0
Gastrointestinal disorders Stomatitis 15.0
Gastrointestinal disorders Abdominal pain 14.0
General disorders and administration site conditions Asthenia 14.0
Nervous system disorders Dysphonia 14.0
Gastrointestinal disorders Gastrointestinal pain 14.0
Nervous system disorders Headache 14.0
Musculoskeletal and connective tissue disorders Pain in extremity 14.0
Investigations Platelet count decreased 14.0
Skin and subcutaneous tissue disorders Dermatitis 13.0
Metabolism and nutrition disorders Hypernatraemia 13.0
Metabolism and nutrition disorders Hyponatraemia 13.0
Metabolism and nutrition disorders Hypophosphataemia 13.0
Musculoskeletal and connective tissue disorders Pain in extremity 13.0
Skin and subcutaneous tissue disorders Rash 13.0
Cardiac disorders Dyspnoea 12.0
General disorders and administration site conditions Mucosal inflammation 12.0
Skin and subcutaneous tissue disorders Pruritus 12.0
Gastrointestinal disorders Stomatitis 12.0
Gastrointestinal disorders Abdominal pain 11.0
Musculoskeletal and connective tissue disorders Arthralgia 11.0
General disorders and administration site conditions Asthenia 11.0
Gastrointestinal disorders Diarrhoea 11.0
Skin and subcutaneous tissue disorders Dry skin 11.0
Gastrointestinal disorders Dysgeusia 11.0
General disorders and administration site conditions Fatigue 11.0
Gastrointestinal disorders Gastrointestinal pain 11.0
Nervous system disorders Headache 11.0
Vascular disorders Hypertension 11.0
Endocrine disorders Hypoglycaemia 11.0
Metabolism and nutrition disorders Hyponatraemia 11.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 11.0
Renal and urinary disorders Proteinuria 11.0
Investigations Protein urine present 11.0
Investigations White blood cell count decreased 11.0
Skin and subcutaneous tissue disorders Dry skin 10.0
Gastrointestinal disorders Dyspepsia 10.0
Skin and subcutaneous tissue disorders Erythema 10.0
Metabolism and nutrition disorders Hyperkalaemia 10.0
Cardiac disorders Dizziness 9.0
Gastrointestinal disorders Abdominal pain upper 8.0
Gastrointestinal disorders Dysgeusia 8.0
Endocrine disorders Hypoglycaemia 8.0
Endocrine disorders Hypothyroidism 8.0
Respiratory, thoracic and mediastinal disorders Epistaxis 7.8
Gastrointestinal disorders Diarrhoea 7.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 7.0
Musculoskeletal and connective tissue disorders Myalgia 7.0
Renal and urinary disorders Proteinuria 7.0
Investigations Protein urine present 7.0
Skin and subcutaneous tissue disorders Pruritus 7.0
Metabolism and nutrition disorders Dehydration 6.0
Respiratory, thoracic and mediastinal disorders Epistaxis 6.0
General disorders and administration site conditions Asthenia 5.0
General disorders and administration site conditions Decreased appetite 5.0
General disorders and administration site conditions Fatigue 5.0
Investigations Lipase increased 5.0
Skin and subcutaneous tissue disorders Alopecia 4.0
Blood and lymphatic system disorders Anaemia 4.0
General disorders and administration site conditions Decreased appetite 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Investigations Haemoglobin decreased 4.0
Gastrointestinal disorders Haemorrhoids 4.0
Metabolism and nutrition disorders Hyponatraemia 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Renal and urinary disorders Haematuria 3.6
General disorders and administration site conditions Asthenia 3.0
Cardiac disorders Dyspnoea 3.0
Gastrointestinal disorders Glossodynia 3.0
Renal and urinary disorders Haematuria 3.0
Metabolism and nutrition disorders Hyperkalaemia 3.0
Investigations Lipase increased 3.0
Gastrointestinal disorders Nausea 3.0
Renal and urinary disorders Proteinuria 3.0
Investigations Protein urine present 3.0
Ear and labyrinth disorders Tinnitus 3.0
Gastrointestinal disorders Vomiting 3.0
Cardiac disorders Haemoptysis 2.5
Respiratory, thoracic and mediastinal disorders Pulmonary embolism 2.2
Gastrointestinal disorders Rectal haemorrhage 2.2
Gastrointestinal disorders Abdominal pain 2.0
Investigations Alanine aminotransferase increased 2.0
Investigations Amylase increased 2.0
Musculoskeletal and connective tissue disorders Arthralgia 2.0
Gastrointestinal disorders Dyspepsia 2.0
Skin and subcutaneous tissue disorders Erythema 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Cardiac disorders Haemoptysis 2.0
Endocrine disorders Hyperglycaemia 2.0
Metabolism and nutrition disorders Hypocalcaemia 2.0
Metabolism and nutrition disorders Hyponatraemia 2.0
Metabolism and nutrition disorders Hypophosphataemia 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Renal and urinary disorders Proteinuria 2.0
Investigations Protein urine present 2.0
Respiratory, thoracic and mediastinal disorders Pulmonary embolism 2.0
Gastrointestinal disorders Rectal haemorrhage 2.0
Investigations Weight decreased 2.0
Cardiac disorders Acute coronary syndrome 1.4
Cardiac disorders Myocardial infarction 1.4
Gastrointestinal disorders Gingival bleeding 1.1
Gastrointestinal disorders Abdominal pain 1.0
Investigations Alanine aminotransferase increased 1.0
Musculoskeletal and connective tissue disorders Arthralgia 1.0
Investigations Aspartate aminotransferase increased 1.0
Investigations Blood alkaline phosphatase increased 1.0
Investigations Blood creatinine increased 1.0
Gastrointestinal disorders Constipation 1.0
Respiratory, thoracic and mediastinal disorders Cough 1.0
Vascular disorders Deep vein thrombosis 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
Skin and subcutaneous tissue disorders Erythema 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Investigations Haemoglobin decreased 1.0
Nervous system disorders Headache 1.0
Metabolism and nutrition disorders Hypernatraemia 1.0
Hepatobiliary disorders Hypoalbuminaemia 1.0
Metabolism and nutrition disorders Hypocalcaemia 1.0
Endocrine disorders Hypoglycaemia 1.0
Endocrine disorders Hypothyroidism 1.0
General disorders and administration site conditions Mucosal inflammation 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Gastrointestinal disorders Nausea 1.0
Musculoskeletal and connective tissue disorders Pain in extremity 1.0
Investigations Platelet count decreased 1.0
Blood and lymphatic system disorders Polycythaemia 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Gastrointestinal disorders Stomatitis 1.0
Vascular disorders Thrombosis 1.0
Nervous system disorders Transient ischaemic attack 1.0
Gastrointestinal disorders Vomiting 1.0
Investigations Weight decreased 1.0
Investigations White blood cell count decreased 1.0
Nervous system disorders Transient ischaemic attack 0.8
Gastrointestinal disorders Anal fistula 0.6
Nervous system disorders Cerebrovascular accident 0.6
Vascular disorders Deep vein thrombosis 0.6
Gastrointestinal disorders Gastric haemorrhage 0.6
Vascular disorders Thrombosis 0.6
Nervous system disorders Cerebral haemorrhage 0.3
Musculoskeletal and connective tissue disorders Fistula 0.3
Gastrointestinal disorders Gastrointestinal perforation 0.3
Gastrointestinal disorders Lower gastrointestinal haemorrhage 0.3

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.49
Gastrointestinal disorders
13.67
Nervous system disorders
9.62
Respiratory, thoracic and mediastinal disorders
6.57
Vascular disorders
6.18
Investigations
5.43
Renal and urinary disorders
5.37
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
4.98
Metabolism and nutrition disorders
4.56
Musculoskeletal and connective tissue disorders
4.39
Skin and subcutaneous tissue disorders
4.31
Psychiatric disorders
3.99
Cardiac disorders
3.89
Injury, poisoning and procedural complications
2.75
Infections and infestations
2.52

Cross References

Resources Reference
CAS NUMBER 319460-85-0
ChEBI 66910
ChEMBL CHEMBL1289926
DrugBank DB06626
DrugCentral 4225
EPA CompTox DTXSID3049049
FDA SRS C9LVQ0YUXG
Guide to Pharmacology 5659
KEGG D03218
PDB AXI
PubChem 6450551
SureChEMBL SCHEMBL172918
ZINC ZINC000003816287
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