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Identification
- Name
- Tucatinib
- Accession Number
- DB11652
- Description
Tucatinbib is a kinase inhibitor drug used with trastuzumab and capecitabine in the treatment of unresectable or metastatic HER-2 positive breast cancer. It was developed by Seattle Genetics and approved by the FDA on April 17, 2020.8 Tucatinib is a promising new treatment for patients with metastatic breast cancer who have not responded adequately to other chemotherapy regimens.7
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Tucatinib (DB11652)
- Weight
- Average: 480.532
Monoisotopic: 480.202222045 - Chemical Formula
- C26H24N8O2
- Synonyms
- Tucatinib
- External IDs
- ARRY 380
- ARRY-380
- ONT 380
- ONT-380
Pharmacology
- Indication
Tucatinib is indicated with trastuzumab and capecitabine for treatment of adults diagnosed with advanced unresectable or metastatic HER2-positive breast cancer. This includes patients with brain metastases and those who have received one or more prior anti-HER2-based regimens in the metastatic setting.7
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
By inhibiting tyrosine kinase, tucatinib exerts anti-tumor activity, reducing the size of HER-2 positive breast cancer tumors. In clinical trials, the regimen of tucatinib and trastuzumab showed enhanced activity both in vitro and in vivo when compared to either drug administered by itself.7
- Mechanism of action
Mutations in the HER-2 gene are observed in some types of breast carcinoma. Tucatinib inhibits the tyrosine kinase enzyme of the HER-2 gene.1 Mutations of tyrosine kinase in the HER-2 gene lead to cascade effects of increased cell signaling and proliferation, resulting in malignancy.6 Results of in vitro studies show that tucatinib inhibits the phosphorylation of both HER-2 and HER-3, leading to downstream changes in MAPK and AKT signaling and cell proliferation. Anti-tumor activity occured in the cells that expressed HER-2. In vivo, tucatinib has been shown to inhibit HER-2 expressing tumors, likely by the same mechanism.1,7
Target Actions Organism AReceptor tyrosine-protein kinase erbB-2 inhibitorHumans UReceptor tyrosine-protein kinase erbB-3 inhibitorHumans - Absorption
The Tmax for tucatinib ranges from 1 to 4 hours.7 One pharmacokinetic study revealed a Cmax of 1120 ng/mL after a dose of 350 mg twice daily with a Tmax ranging from 1 to 3 hours. The AUCtau was reported to be about 7120 hours×ng/mL.2
- Volume of distribution
The volume of distribution of tucatinib is about 1670 L.7 This drug penetrates the blood-brain barrier.5
- Protein binding
Tucatinib is about 97% bound to plasma proteins.7
- Metabolism
Tucatinib is metabolized by CYP2C8 with some contributions from CYP3A.7
- Route of elimination
In a study of radiolabled tucatinib, about 86% of the total dose was excreted in the feces and 4.1% was found in the urine. About 16% of the tucatinib dose recovered in the feces was identified as unchanged tucatinib.7
- Half-life
A pharmacokinetic study revealed a half-life of approximately 5.38 hours.4 Prescribing information mentions a geometric mean half-life of about 8.21 hours.7
- Clearance
The apparent clearance is 148 L/h.7
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50 information and overdose information for tucatinib are not readily available in the literature. In the case of an overdose with this drug, increased adverse effects, such as diarrhea, nausea, abdominal pain, vomiting fatigue, hepatotoxicity, vomiting, decreased appetite, anemia, headache, and rash are expected.3,7
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbaloparatide The therapeutic efficacy of Abaloparatide can be decreased when used in combination with Tucatinib. Abatacept The metabolism of Tucatinib can be increased when combined with Abatacept. Abemaciclib The metabolism of Tucatinib can be decreased when combined with Abemaciclib. Abiraterone The metabolism of Tucatinib can be decreased when combined with Abiraterone. Acenocoumarol The metabolism of Tucatinib can be decreased when combined with Acenocoumarol. Acetaminophen The metabolism of Tucatinib can be decreased when combined with Acetaminophen. Acyclovir The excretion of Acyclovir can be decreased when combined with Tucatinib. Adalimumab The metabolism of Tucatinib can be increased when combined with Adalimumab. Afatinib Afatinib may decrease the excretion rate of Tucatinib which could result in a higher serum level. Albendazole The metabolism of Tucatinib can be decreased when combined with Albendazole. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food. There is no meaningful clinical effect of food on this drug.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataTukysa Tablet 150 mg/1 Oral Seattle Genetics, Inc. 2020-04-17 Not applicable US 
Tukysa Tablet 150 mg Oral Seattle Genetics, Inc. Not applicable Not applicable Canada 
Tukysa Tablet 50 mg/1 Oral Seattle Genetics, Inc. 2020-04-17 Not applicable US Tukysa Tablet 50 mg Oral Seattle Genetics, Inc. Not applicable Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Benzodiazines
- Direct Parent
- Quinazolinamines
- Alternative Parents
- Diarylethers / Triazolopyridines / Aniline and substituted anilines / Phenoxy compounds / Phenol ethers / Aminopyrimidines and derivatives / Toluenes / Pyridines and derivatives / Imidolactams / Triazoles show 8 more
- Substituents
- 1,2,4-triazole / Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Diaryl ether / Ether show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 234248D0HH
- CAS number
- 937263-43-9
- InChI Key
- SDEAXTCZPQIFQM-UHFFFAOYSA-N
- InChI
- InChI=1S/C26H24N8O2/c1-16-10-17(5-7-22(16)36-19-8-9-34-23(12-19)28-15-30-34)31-24-20-11-18(4-6-21(20)27-14-29-24)32-25-33-26(2,3)13-35-25/h4-12,14-15H,13H2,1-3H3,(H,32,33)(H,27,29,31)
- IUPAC Name
- N6-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-N4-(3-methyl-4-{[1,2,4]triazolo[1,5-a]pyridin-7-yloxy}phenyl)quinazoline-4,6-diamine
- SMILES
- CC1=CC(NC2=NC=NC3=CC=C(NC4=NC(C)(C)CO4)C=C23)=CC=C1OC1=CC2=NC=NN2C=C1
References
- Synthesis Reference
Philip Kocienski. Synthesis of Tucatinib.Synthesis of Natural Products and Potential Drugs 2019. Georg Thieme Verlag Stuttgart DOI 10.1055/s-0039-1690496
- General References
- Kulukian A, Lee P, Taylor J, Rosler R, de Vries P, Watson D, Forero-Torres A, Peterson S: Preclinical Activity of HER2-Selective Tyrosine Kinase Inhibitor Tucatinib as a Single Agent or in Combination with Trastuzumab or Docetaxel in Solid Tumor Models. Mol Cancer Ther. 2020 Apr;19(4):976-987. doi: 10.1158/1535-7163.MCT-19-0873. [PubMed:32241871]
- Borges VF, Ferrario C, Aucoin N, Falkson C, Khan Q, Krop I, Welch S, Conlin A, Chaves J, Bedard PL, Chamberlain M, Gray T, Vo A, Hamilton E: Tucatinib Combined With Ado-Trastuzumab Emtansine in Advanced ERBB2/HER2-Positive Metastatic Breast Cancer: A Phase 1b Clinical Trial. JAMA Oncol. 2018 Sep 1;4(9):1214-1220. doi: 10.1001/jamaoncol.2018.1812. [PubMed:29955792]
- Murthy R, Borges VF, Conlin A, Chaves J, Chamberlain M, Gray T, Vo A, Hamilton E: Tucatinib with capecitabine and trastuzumab in advanced HER2-positive metastatic breast cancer with and without brain metastases: a non-randomised, open-label, phase 1b study. Lancet Oncol. 2018 Jul;19(7):880-888. doi: 10.1016/S1470-2045(18)30256-0. Epub 2018 May 24. [PubMed:29804905]
- Moulder SL, Borges VF, Baetz T, Mcspadden T, Fernetich G, Murthy RK, Chavira R, Guthrie K, Barrett E, Chia SK: Phase I Study of ONT-380, a HER2 Inhibitor, in Patients with HER2(+)-Advanced Solid Tumors, with an Expansion Cohort in HER2(+) Metastatic Breast Cancer (MBC). Clin Cancer Res. 2017 Jul 15;23(14):3529-3536. doi: 10.1158/1078-0432.CCR-16-1496. Epub 2017 Jan 4. [PubMed:28053022]
- Duchnowska R, Loibl S, Jassem J: Tyrosine kinase inhibitors for brain metastases in HER2-positive breast cancer. Cancer Treat Rev. 2018 Jun;67:71-77. doi: 10.1016/j.ctrv.2018.05.004. Epub 2018 May 9. [PubMed:29772459]
- Paul MK, Mukhopadhyay AK: Tyrosine kinase - Role and significance in Cancer. Int J Med Sci. 2004;1(2):101-115. doi: 10.7150/ijms.1.101. Epub 2004 Jun 1. [PubMed:15912202]
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- FDA News Release: FDA Approves First New Drug Under International Collaboration, A Treatment Option for Patients with HER2-Positive Metastatic Breast Cancer [Link]
- External Links
- PubChem Compound
- 51039094
- PubChem Substance
- 347828023
- ChemSpider
- 34995558
- 2361285
- ChEMBL
- CHEMBL3989868
- ZINC
- ZINC000068250462
- Wikipedia
- Tucatinib
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 150 mg Tablet Oral 150 mg/1 Tablet Oral 50 mg Tablet Oral 50 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7452895 No 2004-11-16 2024-11-16 US US9457093 No 2012-10-12 2032-10-12 US US9693989 No 2007-05-09 2027-05-09 US US8648087 No 2011-04-12 2031-04-12 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 230 https://sss.hovione.com/SDSSearch/SSS.aspx?Id=1893 logP 3.62 https://www.chemsrc.com/en/cas/937263-43-9_731232.html - Predicted Properties
Property Value Source Water Solubility 0.004 mg/mL ALOGPS logP 3.87 ALOGPS logP 5.25 ChemAxon logS -5.1 ALOGPS pKa (Strongest Acidic) 17.08 ChemAxon pKa (Strongest Basic) 4.57 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 110.85 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 148.37 m3·mol-1 ChemAxon Polarizability 50.76 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Protein tyrosine kinase that is part of several cell surface receptor complexes, but that apparently needs a coreceptor for ligand binding. Essential component of a neuregulin-receptor complex, alt...
- Gene Name
- ERBB2
- Uniprot ID
- P04626
- Uniprot Name
- Receptor tyrosine-protein kinase erbB-2
- Molecular Weight
- 137909.27 Da
References
- Kulukian A, Lee P, Taylor J, Rosler R, de Vries P, Watson D, Forero-Torres A, Peterson S: Preclinical Activity of HER2-Selective Tyrosine Kinase Inhibitor Tucatinib as a Single Agent or in Combination with Trastuzumab or Docetaxel in Solid Tumor Models. Mol Cancer Ther. 2020 Apr;19(4):976-987. doi: 10.1158/1535-7163.MCT-19-0873. [PubMed:32241871]
- Borges VF, Ferrario C, Aucoin N, Falkson C, Khan Q, Krop I, Welch S, Conlin A, Chaves J, Bedard PL, Chamberlain M, Gray T, Vo A, Hamilton E: Tucatinib Combined With Ado-Trastuzumab Emtansine in Advanced ERBB2/HER2-Positive Metastatic Breast Cancer: A Phase 1b Clinical Trial. JAMA Oncol. 2018 Sep 1;4(9):1214-1220. doi: 10.1001/jamaoncol.2018.1812. [PubMed:29955792]
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Tyrosine-protein kinase that plays an essential role as cell surface receptor for neuregulins. Binds to neuregulin-1 (NRG1) and is activated by it; ligand-binding increases phosphorylation on tyrosine residues and promotes its association with the p85 subunit of phosphatidylinositol 3-kinase (PubMed:20682778). May also be activated by CSPG5 (PubMed:15358134). Involved in the regulation of myeloid cell differentiation (PubMed:27416908).
- Specific Function
- Atp binding
- Gene Name
- ERBB3
- Uniprot ID
- P21860
- Uniprot Name
- Receptor tyrosine-protein kinase erbB-3
- Molecular Weight
- 148097.055 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Components:
| Name | UniProt ID |
|---|---|
| Cytochrome P450 3A4 | P08684 |
| Cytochrome P450 3A43 | Q9HB55 |
| Cytochrome P450 3A5 | P20815 |
| Cytochrome P450 3A7 | P24462 |
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Protein tyrosine kinase that is part of several cell surface receptor complexes, but that apparently needs a coreceptor for ligand binding. Essential component of a neuregulin-receptor complex, alt...
- Gene Name
- ERBB2
- Uniprot ID
- P04626
- Uniprot Name
- Receptor tyrosine-protein kinase erbB-2
- Molecular Weight
- 137909.27 Da
References
- Moulder SL, Borges VF, Baetz T, Mcspadden T, Fernetich G, Murthy RK, Chavira R, Guthrie K, Barrett E, Chia SK: Phase I Study of ONT-380, a HER2 Inhibitor, in Patients with HER2(+)-Advanced Solid Tumors, with an Expansion Cohort in HER2(+) Metastatic Breast Cancer (MBC). Clin Cancer Res. 2017 Jul 15;23(14):3529-3536. doi: 10.1158/1078-0432.CCR-16-1496. Epub 2017 Jan 4. [PubMed:28053022]
- Borges VF, Ferrario C, Aucoin N, Falkson C, Khan Q, Krop I, Welch S, Conlin A, Chaves J, Bedard PL, Chamberlain M, Gray T, Vo A, Hamilton E: Tucatinib Combined With Ado-Trastuzumab Emtansine in Advanced ERBB2/HER2-Positive Metastatic Breast Cancer: A Phase 1b Clinical Trial. JAMA Oncol. 2018 Sep 1;4(9):1214-1220. doi: 10.1001/jamaoncol.2018.1812. [PubMed:29955792]
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Drug transmembrane transporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- FDA approved products: Tukysa (tucatinib) oral tablets [Link]
Drug created on October 20, 2016 14:37 / Updated on June 12, 2020 10:53
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