LAPATINIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2007)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01EH01
UNII: 0VUA21238F

Structure
InChI Key BCFGMOOMADDAQU-UHFFFAOYSA-N
Smile CS(=O)(=O)CCNCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1
InChI
InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H26ClFN4O4S
Molecular Weight 581.07
AlogP 6.14
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 11.0
Polar Surface Area 106.35
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 40.0

Pharmacology

Primary Target
epidermal growth factor receptor
erb-b2 receptor tyrosine kinase 2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 1700 45-45
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- - - 37600 22-45
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase CDC2 subfamily
- 11000 - - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase NAK family
- - - - 0
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase SLK subfamily
- - 2600-4400 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE7 family
- - 1100 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase RIPK family
- - 3600-3600 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- 23000 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 0-61060 1-860 3 -99-100
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase InsR family
- 17000 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 8500 - - -
Enzyme Transferase
- - 670 - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 1000 - - -
Structural protein
- - 54 - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 6500-6500 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Head and Neck Neoplasms 3 D006258 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Brain Diseases 3 D001927 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Head and Neck Neoplasms 3 D006258 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Adenocarcinoma 2 D000230 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Pituitary Neoplasms 2 D010911 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Carcinoma, Ductal 2 D044584 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Renal Insufficiency, Chronic 1 D051436 ClinicalTrials
Endometrial Neoplasms 1 D016889 ClinicalTrials
Thyroid Neoplasms 1 D013964 ClinicalTrials
Urinary Bladder Neoplasms 0 D001749 ClinicalTrials

Related Entries

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Blood and lymphatic system disorders Neutropenia 47.0
Gastrointestinal disorders Nausea 43.0
Gastrointestinal disorders Diarrhoea 40.0
Gastrointestinal disorders Nausea 39.0
Gastrointestinal disorders Diarrhoea 37.0
Blood and lymphatic system disorders Leukopenia 33.0
Gastrointestinal disorders Diarrhoea 29.0
Skin and subcutaneous tissue disorders Dermatitis 24.0
Skin and subcutaneous tissue disorders Rash 24.0
General disorders and administration site conditions Asthenia 21.0
General disorders and administration site conditions Fatigue 21.0
Gastrointestinal disorders Nausea 21.0
Gastrointestinal disorders Vomiting 21.0
Gastrointestinal disorders Diarrhoea 20.0
General disorders and administration site conditions Decreased appetite 19.0
Gastrointestinal disorders Nausea 19.0
General disorders and administration site conditions Decreased appetite 18.0
General disorders and administration site conditions Asthenia 17.0
General disorders and administration site conditions Fatigue 17.0
Gastrointestinal disorders Vomiting 17.0
General disorders and administration site conditions Asthenia 16.0
General disorders and administration site conditions Fatigue 16.0
Blood and lymphatic system disorders Neutropenia 15.0
Skin and subcutaneous tissue disorders Dermatitis 14.0
Skin and subcutaneous tissue disorders Rash 14.0
Skin and subcutaneous tissue disorders Dermatitis 13.0
Nervous system disorders Headache 13.0
Skin and subcutaneous tissue disorders Rash 13.0
Gastrointestinal disorders Abdominal pain 12.0
Skin and subcutaneous tissue disorders Dermatitis 12.0
Gastrointestinal disorders Gastrointestinal pain 12.0
General disorders and administration site conditions Mucosal inflammation 12.0
Skin and subcutaneous tissue disorders Rash 12.0
Gastrointestinal disorders Vomiting 12.0
General disorders and administration site conditions Asthenia 11.0
General disorders and administration site conditions Mucosal inflammation 11.0
Gastrointestinal disorders Stomatitis 11.0
Gastrointestinal disorders Vomiting 11.0
Blood and lymphatic system disorders Anaemia 10.0
Gastrointestinal disorders Diarrhoea 10.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 10.0
Musculoskeletal and connective tissue disorders Myalgia 10.0
General disorders and administration site conditions Asthenia 9.0
Respiratory, thoracic and mediastinal disorders Cough 9.0
General disorders and administration site conditions Decreased appetite 9.0
Skin and subcutaneous tissue disorders Pruritus 9.0
Gastrointestinal disorders Stomatitis 9.0
Investigations Alanine aminotransferase increased 8.0
Cardiac disorders Dyspnoea 8.0
Blood and lymphatic system disorders Leukopenia 8.0
Skin and subcutaneous tissue disorders Alopecia 7.0
Musculoskeletal and connective tissue disorders Pain in extremity 7.0
Musculoskeletal and connective tissue disorders Back pain 6.0
Skin and subcutaneous tissue disorders Dry skin 6.0
Nervous system disorders Insomnia 6.0
Blood and lymphatic system disorders Neutropenia 6.0
Blood and lymphatic system disorders Anaemia 5.0
Nervous system disorders Headache 5.0
Blood and lymphatic system disorders Neutropenia 5.0
Musculoskeletal and connective tissue disorders Pain in extremity 5.0
Nervous system disorders Peripheral sensory neuropathy 5.0
Gastrointestinal disorders Diarrhoea 4.0
Skin and subcutaneous tissue disorders Dry skin 4.0
Gastrointestinal disorders Dyspepsia 3.0
Gastrointestinal disorders Dyspepsia 2.0
Cardiac disorders Dyspnoea 2.0
Respiratory, thoracic and mediastinal disorders Epistaxis 2.0
Investigations Haemoglobin decreased 2.0
General disorders and administration site conditions Mucosal inflammation 2.0
Skin and subcutaneous tissue disorders Nail disorder 2.0
Gastrointestinal disorders Nausea 2.0
Gastrointestinal disorders Vomiting 2.0
Investigations Alanine aminotransferase increased 1.0
Blood and lymphatic system disorders Anaemia 1.0
General disorders and administration site conditions Asthenia 1.0
Musculoskeletal and connective tissue disorders Back pain 1.0
Respiratory, thoracic and mediastinal disorders Cough 1.0
General disorders and administration site conditions Decreased appetite 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
Gastrointestinal disorders Diarrhoea 1.0
Respiratory, thoracic and mediastinal disorders Epistaxis 1.0
General disorders and administration site conditions Fatigue 1.0
Investigations Haemoglobin decreased 1.0
Nervous system disorders Headache 1.0
Blood and lymphatic system disorders Leukopenia 1.0
Skin and subcutaneous tissue disorders Nail disorder 1.0
Gastrointestinal disorders Nausea 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 1.0
Gastrointestinal disorders Stomatitis 1.0
Gastrointestinal disorders Vomiting 1.0

Cross References

Resources Reference
CAS NUMBER 231277-92-2
ChEBI 49603
ChEMBL CHEMBL554
DrugBank DB01259
DrugCentral 1548
EPA CompTox DTXSID7046675
FDA SRS 0VUA21238F
Human Metabolome Database HMDB0015388
Guide to Pharmacology 5692
PDB FMM
PharmGKB PA152241907
PubChem 208908
SureChEMBL SCHEMBL8100
ZINC ZINC000001550477
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