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Details

Stereochemistry ACHIRAL
Molecular Formula C26H24N8O2
Molecular Weight 480.5221
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TUCATINIB

SMILES

Cc1cc(ccc1Oc2ccn3c(c2)ncn3)Nc4c5cc(ccc5ncn4)N=C6NC(C)(C)CO6

InChI

InChIKey=SDEAXTCZPQIFQM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C26H24N8O2
Molecular Weight 480.5221
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

TUCATINIB (ONT-380 or ARRY-380) is an orally active, reversible and selective small-molecule HER2 inhibitor invented by Array and licensed to Cascadian Therapeutics (previously named Oncothyreon) for development, manufacturing and commercialization. HER2, a growth factor receptor that is over-expressed in multiple cancers, including breast, ovarian, and stomach cancer. HER2 mediates cell growth, differentiation and survival, and tumors that overexpress HER2 are more aggressive and historically have been associated with poorer overall survival compared with HER2-negative cancers. ONT-380 is highly active as a single agent and in combination with both chemotherapy and Herceptin® (trastuzumab) in xenograft models of HER2+ breast cancer, including models of CNS metastases that were refractory to Tykerb® (lapatinib) or neratinib treatment. In a Phase 1 single agent clinical study, ONT-380 administered orally twice a day was well tolerated and demonstrated anti-tumor activity in heavily pre-treated HER2+ breast cancer patients with metastatic disease. Based on the strength of these preclinical and clinical trials, ONT-380 is advancing in one Phase 2 and three Phase 1b combination trials in patients with metastatic breast cancer. A second study reported the CNS activity of ONT-380 in combination with either T-DM1 or trastuzumab or capecitabine. Patients with brain metastases assessable for response were included in the combined analysis. Responses and clinical benefit in the CNS were reported with the three combinations tested, supporting future development of the drug for this particular indication.

CNS Activity

Originator

Approval Year

2020
91
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7701
Breast cancer
Colorectal cancer
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Receptor protein-tyrosine kinase erbB-2
Phase II
Primary
Receptor protein-tyrosine kinase erbB-2
Phase II
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
790 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29955792
300 mg 2 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TUCATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2920 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29955792
300 mg 2 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TUCATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.5 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29955792
300 mg 2 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TUCATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.9%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
TUCATINIB plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
300 mg 2 times / day steady, oral
Recommended
Dose: 300 mg, 2 times / day
Route: oral
Route: steady
Dose: 300 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
unhealthy, 54 years (range: 22 - 82 years)
Health Status: unhealthy
Age Group: 54 years (range: 22 - 82 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
Disc. AE: Hepatotoxicity, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (1.5%)
Diarrhea (1%)
Hepatotoxicity (8%)
Diarrhea (6%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
800 mg 2 times / day steady, oral
Highest studied dose
Dose: 800 mg, 2 times / day
Route: oral
Route: steady
Dose: 800 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
DLT: Alanine aminotransferase increased, Aspartate aminotransferase increased...
Dose limiting toxicities:
Alanine aminotransferase increased (grade 3, 2 patients)
Aspartate aminotransferase increased (grade 3, 2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Other AEs: Diarrhea, Nausea...
Other AEs:
Diarrhea (grade 1-2, 26%)
Nausea (grade 1-2, 33%)
Fatigue (grade 1-2, 19%)
Vomiting (grade 1-2, 3%)
Acne (grade 3, 4%)
Dermatitis acneiform (grade 3, 4%)
Skin exfoliation (grade 3, 4%)
Alanine aminotransferase increased (grade 3, 4%)
Aspartate aminotransferase increased (grade 2, 11%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
AEs

AEs

AESignificanceDosePopulation
Diarrhea 1%
Disc. AE
300 mg 2 times / day steady, oral
Recommended
Dose: 300 mg, 2 times / day
Route: oral
Route: steady
Dose: 300 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
unhealthy, 54 years (range: 22 - 82 years)
Health Status: unhealthy
Age Group: 54 years (range: 22 - 82 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
Hepatotoxicity 1.5%
Disc. AE
300 mg 2 times / day steady, oral
Recommended
Dose: 300 mg, 2 times / day
Route: oral
Route: steady
Dose: 300 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
unhealthy, 54 years (range: 22 - 82 years)
Health Status: unhealthy
Age Group: 54 years (range: 22 - 82 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
Diarrhea 6%
Disc. AE
300 mg 2 times / day steady, oral
Recommended
Dose: 300 mg, 2 times / day
Route: oral
Route: steady
Dose: 300 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
unhealthy, 54 years (range: 22 - 82 years)
Health Status: unhealthy
Age Group: 54 years (range: 22 - 82 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
Hepatotoxicity 8%
Disc. AE
300 mg 2 times / day steady, oral
Recommended
Dose: 300 mg, 2 times / day
Route: oral
Route: steady
Dose: 300 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
unhealthy, 54 years (range: 22 - 82 years)
Health Status: unhealthy
Age Group: 54 years (range: 22 - 82 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213411s000lbl.pdf
Alanine aminotransferase increased grade 3, 2 patients
DLT, Disc. AE
800 mg 2 times / day steady, oral
Highest studied dose
Dose: 800 mg, 2 times / day
Route: oral
Route: steady
Dose: 800 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
Aspartate aminotransferase increased grade 3, 2 patients
DLT, Disc. AE
800 mg 2 times / day steady, oral
Highest studied dose
Dose: 800 mg, 2 times / day
Route: oral
Route: steady
Dose: 800 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053023
Fatigue grade 1-2, 19%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Diarrhea grade 1-2, 26%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Vomiting grade 1-2, 3%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Nausea grade 1-2, 33%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Aspartate aminotransferase increased grade 2, 11%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Acne grade 3, 4%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Alanine aminotransferase increased grade 3, 4%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Dermatitis acneiform grade 3, 4%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Skin exfoliation grade 3, 4%
600 mg 2 times / day steady, oral
MTD
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
unhealthy, 58 years (range: 31–77 years)
Health Status: unhealthy
Age Group: 58 years (range: 31–77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28053022
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1318
inhibitor
1360

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
175

CYP2C8
761

OCT2
582

MATE1
290

MATE2
258

P-gp
1089
CYP2C8
586

CYP3A
154

P-gp
1223

BCRP
461
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1255
 yes [IC50 20 uM]
yes (co-administration study)
Comment: Digoxin Cmax increased by 2.4-fold
Page: 81, 83
MATE2
258
 yes [Ki 0.135 uM]
yes (co-administration study)
Comment: Metformin Cmax increased by 1.1-fold
Page: 81, 83
CYP2C8
810
 yes [Ki 0.17 uM]
yes (co-administration study)
Comment: Repaglinide Cmax increased by 1.7-fold
Page: 80, 83
MATE1
291
 yes [Ki 0.34 uM]
yes (co-administration study)
Comment: Metformin Cmax increased by 1.1-fold
Page: 81, 83
CYP3A
244
 yes [Ki 0.805 uM]
yes (co-administration study)
Comment: Midazolam Cmax increased by 3-fold
Page: 80, 83
OCT2
583
 yes [Ki 14.7 uM]
CYP2C9
1362
 yes [Ki 4.57 uM]
no (co-administration study)
Comment: No effect on tolbutamide Cmax or AUC
Page: 80, 83
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
461
 yes
P-gp
1223
 yes
CYP3A
154
 yes
weak (co-administration study)
Comment: Itraconazole increased tucatinib Cmax by 1.3-fold; Rifampin decreased tucatinib Cmax by 37%
Page: 80, 83
CYP2C8
586
 yes
yes (co-administration study)
Comment: Gemfibrozil increased tucatinib Cmax by 1.6-fold; Rifampin decreased tucatinib Cmax by 37%
Page: 80, 83
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1392
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00GUGJ
AChemBlock
M22591
AbovChem LLC
HY-16069
Ambeed
A100992
AstaTech
40195
BLDpharm
BD631037
BOC Sciences
937263-43-9
Chem Scene
CS-3906
Excenen
EX-A1031
Hangzhou Yuhao Chemical Technology
RT10803
KeyOrganics
AS-56109
Lan Pharmatech
LQT-B27924
MedChem Express
HY-16069
MolPort
MolPort-042-676-278
Molnova
M17675
MuseChem
I005570
Nanjing Pope Bio-tech
NSTH-D45464
Norris Pharm
NSTH-D45464
Selleck Chemicals
S8362
ShangHai Biochempartner
BCP15983
TargetMol
T2364
Toronto Research Chemicals
D449790
Toronto Research Chemicals
N900290
ZINC
ZINC000068250462
http://zinc15.docking.org/substances/ZINC000068250462
eMolecules
46100601
mcule
MCULE-4848624315
PubMed

PubMed

TitleDatePubMed
Emerging Therapeutic Options for HER2-Positive Breast Cancer.
2016
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).
2017 Jul 15
Patents

Patents

WO2013056183
1
WO2013142875
1

Sample Use Guides

In Vivo Use Guide
Phase 2 Study of tucatinib in combination with capecitabine & trastuzumab in patients with advanced HER2+ breast cancer: Tucatinib 300 mg or placebo will be given orally twice daily (PO BID).
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:36:01 UTC 2021
Edited
by admin
on Sat Jun 26 03:36:01 UTC 2021
Record UNII
234248D0HH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TUCATINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
TUKYSA
Brand Name English
TUCATINIB [USAN]
Common Name English
TUCATINIB [WHO-DD]
Common Name English
IRBINITINIB
Common Name English
ONT-380
Code English
4,6-QUINAZOLINEDIAMINE, N6-(4,5-DIHYDRO-4,4-DIMETHYL-2-OXAZOLYL)-N4-(3-METHYL-4-((1,2,4)TRIAZOLO(1,5-A)PYRIDIN-7-YLOXY)PHENYL)-
Systematic Name English
TUCATINIB [INN]
Common Name English
ARRY-380
Code English
N6-(4,4-DIMETHYL-4,5-DIHYDROOXAZOL-2-YL)-N4-(3-METHYL-4-((1,2,4)TRIAZOLO(1,5-A)PYRIDIN-7-YLOXY)PHENYL)QUINAZOLINE-4,6-DIAMINE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 570716
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
NCI_THESAURUS C2167
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
FDA ORPHAN DRUG 571216
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
FDA ORPHAN DRUG 603217
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL3545380
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
INN
9997
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
CAS
937263-43-9
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
NCI_THESAURUS
C77896
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
DRUG CENTRAL
5389
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
EVMPD
SUB177913
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
RXCUI
2361285
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
FDA UNII
234248D0HH
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
PUBCHEM
51039094
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
DRUG BANK
DB11652
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
LACTMED
Tucatinib
Created by admin on Sat Jun 26 03:36:02 UTC 2021 , Edited by admin on Sat Jun 26 03:36:02 UTC 2021
PRIMARY
Related Record Type Details
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
CYTOCHROME P450 2C8
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
Structure of TUCATINIB
EXCRETED UNCHANGED
FECAL
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
MAJOR
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2
TARGET -> INHIBITOR
SELECTIVE
Ki
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of TUCATINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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