Tucatinib

Identification

Summary

Tucatinib is a kinase inhibitor used to treat certain types of unresectable/metastatic HER-2 positive breast cancer.

Brand Names
Tukysa
Generic Name
Tucatinib
DrugBank Accession Number
DB11652
Background

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
Thumb
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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

TargetActionsOrganism
AReceptor tyrosine-protein kinase erbB-2
inhibitor
Humans
UReceptor tyrosine-protein kinase erbB-3
inhibitor
Humans
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
Adverseeffects
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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

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.
DrugInteraction
1,2-BenzodiazepineThe metabolism of Tucatinib can be decreased when combined with 1,2-Benzodiazepine.
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Tucatinib.
AbataceptThe metabolism of Tucatinib can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Tucatinib can be decreased when combined with Abemaciclib.
AbirateroneThe metabolism of Tucatinib can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Tucatinib can be decreased when combined with Acalabrutinib.
AcenocoumarolThe metabolism of Tucatinib can be decreased when combined with Acenocoumarol.
AcetaminophenThe metabolism of Tucatinib can be decreased when combined with Acetaminophen.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Tucatinib.
AdalimumabThe metabolism of Tucatinib can be increased when combined with Adalimumab.
Interactions
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Food Interactions
  • Take with or without food. There is no meaningful clinical effect of food on this drug.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TukysaTablet150 mg/1OralSeagen Inc.2020-04-17Not applicableUS flag
TukysaTablet, film coated150 mgOralSeagen B.V.2021-03-03Not applicableEU flag
TukysaTablet50 mg/1OralSeagen Inc.2020-04-17Not applicableUS flag
TukysaTablet150 mgOralSeagen Inc.2020-08-27Not applicableCanada flag
TukysaTablet, film coated50 mgOralSeagen B.V.2021-03-03Not applicableEU flag
TukysaTablet50 mgOralSeagen Inc.2020-10-08Not applicableCanada flag

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
Affected organisms
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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
  6. 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. [Article]
  7. FDA approved products: Tukysa (tucatinib) oral tablets [Link]
  8. FDA News Release: FDA Approves First New Drug Under International Collaboration, A Treatment Option for Patients with HER2-Positive Metastatic Breast Cancer [Link]
PubChem Compound
51039094
PubChem Substance
347828023
ChemSpider
34995558
RxNav
2361285
ChEMBL
CHEMBL3989868
ZINC
ZINC000068250462
Wikipedia
Tucatinib

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentAnatomic Stage IA Breast Cancer AJCC v8 / Anatomic Stage II Breast Cancer AJCC v8 / Anatomic Stage IIA Breast Cancer AJCC v8 / Anatomic Stage IIB Breast Cancer AJCC v8 / Anatomic Stage III Breast Cancer AJCC v8 / Anatomic Stage IIIA Breast Cancer AJCC v8 / Anatomic Stage IIIB Breast Cancer AJCC v8 / Anatomic Stage IIIC Breast Cancer AJCC v8 / HER2 Positive Carcinoma of Breast / Invasive Breast Carcinoma / Multifocal Breast Carcinoma / Prognostic Stage 1 Breast Cancer AJCC v8 / Prognostic Stage 2 Breast Cancer AJCC v8 / Prognostic Stage IA Breast Cancer AJCC v8 / Prognostic Stage IB Breast Cancer AJCC v8 / Prognostic Stage IIA Breast Cancer AJCC v8 / Prognostic Stage IIB Breast Cancer AJCC v8 / Prognostic Stage III Breast Cancer AJCC v8 / Prognostic Stage IIIA Breast Cancer AJCC v8 / Prognostic Stage IIIB Breast Cancer AJCC v8 / Prognostic Stage IIIC Breast Cancer AJCC v8 / Synchronous Bilateral Breast Carcinoma1
3RecruitingTreatmentHER2/Neu-positive Breast Cancer1
2Active Not RecruitingTreatmentHER2/Neu-positive Breast Cancer1
2Active Not RecruitingTreatmentLeptomeningeal Disease (LMD) / Metastatic Breast Cancer1
2Active Not RecruitingTreatmentMetastatic Colorectal Adenocarcinoma1
2Not Yet RecruitingTreatmentBreast Cancer / HER2/Neu-positive Breast Cancer1
2Not Yet RecruitingTreatmentHER2/Neu-positive Breast Cancer / Tumors Metastatic to Brain1
2Not Yet RecruitingTreatmentMetastatic Breast Cancer With a Isolated Brain Progression1
2RecruitingTreatmentAdvanced Unresectable or Metastatic Solid Malignancy1
2RecruitingTreatmentBiliary Tract Neoplasms / Neoplasms, Breast / Non-Small Cell Lung Carcinoma (NSCLC) / Urologic Neoplasms / Uterine Cervical Neoplasms / Uterine Neoplasms1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral150 mg/1
TabletOral150 mg
TabletOral50 mg/1
TabletOral50 mg
Tablet, film coatedOral150 MG
Tablet, film coatedOral50 MG
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7452895No2008-11-182024-11-16US flag
US9457093No2016-10-042032-10-12US flag
US9693989No2017-07-042027-05-09US flag
US8648087No2014-02-112031-04-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230https://sss.hovione.com/SDSSearch/SSS.aspx?Id=1893
logP3.62https://www.chemsrc.com/en/cas/937263-43-9_731232.html
Predicted Properties
PropertyValueSource
Water Solubility0.004 mg/mLALOGPS
logP3.87ALOGPS
logP5.25ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)17.08ChemAxon
pKa (Strongest Basic)4.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.85 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity148.37 m3·mol-1ChemAxon
Polarizability50.76 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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insights and accelerate drug research.
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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
  1. 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. [Article]
  2. 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. [Article]
  3. 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
  1. 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
  1. 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:
References
  1. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  2. FDA approved products: Tukysa (tucatinib) oral tablets [Link]
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
  1. 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. [Article]
  2. 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. [Article]
  3. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. FDA approved products: Tukysa (tucatinib) oral tablets [Link]

Drug created on October 20, 2016 20:37 / Updated on October 19, 2021 07:39