Details of the Drug

General Information of Drug (ID: DMBESUA)

Drug Name

Tucatinib

Synonyms

Irbinitinib; 937263-43-9; ONT-380; UNII-234248D0HH; 234248D0HH; 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; 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)-; ONT 380; 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]-; Tucatinib [USAN:INN]; 6-DIAMINE

Indication

Disease Entry	ICD 11	Status	REF
HER2-positive breast cancer	2C60-2C65	Approved	[1]
Gastric adenocarcinoma	2B72	Phase 2/3	[2]
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Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

480.5

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 7120 mcgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 1120 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1-4 h [3]
Clearance: The apparent clearance of drug is 148 L/h [3]
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 [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 5.38 hours [4]
Metabolism: The drug is metabolized via the CYP2C8 with some contributions from CYP3A [3]
Vd: The volume of distribution (Vd) of drug is 1670 L [3]

Chemical Identifiers

Formula: C26H24N8O2
IUPAC Name: 6-N-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-4-N-[3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)phenyl]quinazoline-4,6-diamine
Canonical SMILES: CC1=C(C=CC(=C1)NC2=NC=NC3=C2C=C(C=C3)NC4=NC(CO4)(C)C)OC5=CC6=NC=NN6C=C5
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)
InChIKey: SDEAXTCZPQIFQM-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 51039094
CAS Number: 937263-43-9
DrugBank ID: DB11652
TTD ID: D09GRX
ACDINA ID: D01510

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Erbb2 tyrosine kinase receptor (HER2)	TT6EO5L	ERBB2_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
UDP-glucuronosyltransferase 1-6	OTGTQ2C9	UD16_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A1	OTH1C8OJ	UD11_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A10	OTOTZVEY	UD110_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A3	OTUEOER3	UD13_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A7	OTY4JJ32	UD17_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A8	OTTMABBG	UD18_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A9	OTPCHAFX	UD19_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 2B15	OTABTFU2	UDB15_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 2B17	OTSVIF4E	UDB17_HUMAN	Gene/Protein Processing	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

HER2-positive breast cancer

ICD Disease Classification

2C60-2C65

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Erbb2 tyrosine kinase receptor (HER2)	DTT	ERBB2	5.67E-03	-1.26	-2.05

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Tucatinib

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Talazoparib	DM1KS78	Moderate	Decreased clearance of Tucatinib due to the transporter inhibition by Talazoparib.	Breast cancer [2C60-2C6Y]	[6]
HKI-272	DM6QOVN	Major	Decreased metabolism of Tucatinib caused by HKI-272 mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[7]
LY2835219	DM93VBZ	Major	Decreased metabolism of Tucatinib caused by LY2835219 mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[8]
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Coadministration of a Drug Treating the Disease Different from Tucatinib (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Tucatinib and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[9]
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Tucatinib caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[10]
Gilteritinib	DMTI0ZO	Major	Decreased metabolism of Tucatinib caused by Gilteritinib mediated inhibition of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[11]
Oliceridine	DM6MDCF	Major	Decreased metabolism of Tucatinib caused by Oliceridine mediated inhibition of CYP450 enzyme.	Acute pain [MG31]	[12]
ABT-492	DMJFD2I	Moderate	Decreased clearance of Tucatinib due to the transporter inhibition by ABT-492.	Bacterial infection [1A00-1C4Z]	[13]
Pexidartinib	DMS2J0Z	Major	Decreased metabolism of Tucatinib caused by Pexidartinib mediated inhibition of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[14]
PF-04449913	DMSB068	Major	Decreased metabolism of Tucatinib caused by PF-04449913 mediated inhibition of CYP450 enzyme.	Chronic myelomonocytic leukaemia [2A40]	[15]
Osilodrostat	DMIJC9X	Major	Decreased metabolism of Tucatinib caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[16]
Polatuzumab vedotin	DMF6Y0L	Major	Decreased metabolism of Tucatinib caused by Polatuzumab vedotin mediated inhibition of CYP450 enzyme.	Diffuse large B-cell lymphoma [2A81]	[17]
Ingrezza	DMVPLNC	Major	Additive CNS depression effects by the combination of Tucatinib and Ingrezza.	Dystonic disorder [8A02]	[18]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Tucatinib caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[13]
Bay 80-6946	DMLOS5R	Major	Decreased clearance of Tucatinib due to the transporter inhibition by Bay 80-6946.	Follicular lymphoma [2A80]	[19]
Tazemetostat	DMWP1BH	Major	Decreased metabolism of Tucatinib caused by Tazemetostat mediated inhibition of CYP450 enzyme.	Follicular lymphoma [2A80]	[20]
Ripretinib	DM958QB	Major	Decreased metabolism of Tucatinib caused by Ripretinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[9]
Avapritinib	DMK2GZX	Major	Decreased metabolism of Tucatinib caused by Avapritinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[21]
MK-1439	DM215WE	Moderate	Increased metabolism of Tucatinib caused by MK-1439 mediated induction of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
TP-434	DM5A31S	Minor	Decreased metabolism of Tucatinib caused by TP-434 mediated inhibition of CYP450 enzyme.	Infectious gastroenteritis/colitis [1A40]	[22]
Berotralstat	DMWA2DZ	Major	Decreased clearance of Tucatinib due to the transporter inhibition by Berotralstat.	Innate/adaptive immunodeficiency [4A00]	[23]
Pemigatinib	DM819JF	Major	Decreased metabolism of Tucatinib caused by Pemigatinib mediated inhibition of CYP450 enzyme.	Liver cancer [2C12]	[24]
Brigatinib	DM7W94S	Major	Decreased metabolism of Tucatinib caused by Brigatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[25]
Lurbinectedin	DMEFRTZ	Major	Decreased metabolism of Tucatinib caused by Lurbinectedin mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[26]
PF-06463922	DMKM7EW	Major	Decreased metabolism of Tucatinib caused by PF-06463922 mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[27]
Pralsetinib	DMWU0I2	Major	Decreased metabolism of Tucatinib caused by Pralsetinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[28]
Capmatinib	DMYCXKL	Major	Decreased metabolism of Tucatinib caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[29]
Selpercatinib	DMZR15V	Major	Decreased metabolism of Tucatinib caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[12]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Tucatinib and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[30]
IPI-145	DMWA24P	Major	Decreased metabolism of Tucatinib caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[31]
Acalabrutinib	DM7GCVW	Major	Decreased metabolism of Tucatinib caused by Acalabrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[32]
Selumetinib	DMC7W6R	Major	Decreased metabolism of Tucatinib caused by Selumetinib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[33]
LGX818	DMNQXV8	Major	Decreased metabolism of Tucatinib caused by LGX818 mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[34]
Ubrogepant	DM749I3	Major	Decreased metabolism of Tucatinib caused by Ubrogepant mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[35]
Rimegepant	DMHOAUG	Moderate	Decreased metabolism of Tucatinib caused by Rimegepant mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[36]
Siponimod	DM2R86O	Major	Decreased metabolism of Tucatinib caused by Siponimod mediated inhibition of CYP450 enzyme.	Multiple sclerosis [8A40]	[9]
Deflazacort	DMV0RNS	Major	Decreased metabolism of Tucatinib caused by Deflazacort mediated inhibition of CYP450 enzyme.	Muscular dystrophy [8C70]	[21]
Fedratinib	DM4ZBK6	Major	Decreased metabolism of Tucatinib caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[21]
Entrectinib	DMMPTLH	Major	Decreased metabolism of Tucatinib caused by Entrectinib mediated inhibition of CYP450 enzyme.	Non-small cell lung cancer [2C25]	[21]
S-297995	DM26IH8	Moderate	Decreased metabolism of Tucatinib caused by S-297995 mediated inhibition of CYP450 enzyme.	Opioid use disorder [6C43]	[21]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Tucatinib caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[37]
MK-4827	DMLYGH4	Moderate	Decreased clearance of Tucatinib due to the transporter inhibition by MK-4827.	Ovarian cancer [2C73]	[13]
Istradefylline	DM20VSK	Major	Decreased metabolism of Tucatinib caused by Istradefylline mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[38]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Tucatinib caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[39]
Lefamulin	DME6G97	Major	Decreased clearance of Tucatinib due to the transporter inhibition by Lefamulin.	Pneumonia [CA40]	[40]
Relugolix	DMK7IWL	Major	Decreased clearance of Tucatinib due to the transporter inhibition by Relugolix.	Prostate cancer [2C82]	[41]
Darolutamide	DMV7YFT	Moderate	Decreased metabolism of Tucatinib caused by Darolutamide mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[42]
Upadacitinib	DM32B5U	Major	Decreased metabolism of Tucatinib caused by Upadacitinib mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[43]
Voxelotor	DMCS6M5	Major	Decreased metabolism of Tucatinib caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[44]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Tucatinib caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[10]
Larotrectinib	DM26CQR	Major	Decreased metabolism of Tucatinib caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[9]
LEE011	DMMX75K	Major	Decreased metabolism of Tucatinib caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[21]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Tucatinib caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[45]
Lusutrombopag	DMH6IKO	Moderate	Decreased clearance of Tucatinib due to the transporter inhibition by Lusutrombopag.	Thrombocytopenia [3B64]	[13]
As-1670542	DMV05SW	Moderate	Decreased metabolism of Tucatinib caused by As-1670542 mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[13]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Tucatinib caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[10]
Fluticasone	DMGCSVF	Major	Decreased metabolism of Tucatinib caused by Fluticasone mediated inhibition of CYP450 enzyme.	Vasomotor/allergic rhinitis [CA08]	[46]
Betrixaban	DM2C4RF	Moderate	Decreased clearance of Tucatinib due to the transporter inhibition by Betrixaban.	Venous thromboembolism [BD72]	[47]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Potassium chloride	E00074	4873	Tonicity agent
Crospovidone	E00626	Not Available	Disintegrant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 4000	E00654	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Sodium bicarbonate	E00424	516892	Alkalizing agent; Diluent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
Copovidone	E00693	Not Available	Film/membrane-forming agent; Modified-release agent; Binding agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tucatinib 50 mg tablet	50 mg	Tablet	Oral
Tucatinib 150 mg tablet	150 mg	Tablet	Oral

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
2	ClinicalTrials.gov (NCT04499924) Tucatinib, Trastuzumab, Ramucirumab, and Paclitaxel Versus Paclitaxel and Ramucirumab in Previously Treated HER2+ Gastroesophageal Cancer (MOUNTAINEER-02). U.S. National Institutes of Health.
3	FDA approved products: Tukysa (tucatinib) oral tablets
4	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.
5	Drug-drug interaction potentials of tucatinib inhibition of human UDP-glucuronosyltransferases. Chem Biol Interact. 2023 Aug 25;381:110574. doi: 10.1016/j.cbi.2023.110574. Epub 2023 May 30.
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26	Product Information. Zepzelca (lurbinectedin). Jazz Pharmaceuticals, Palo Alto, CA.
27	Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
28	Product Information. Gavreto (pralsetinib). Blueprint Medicines Corporation, Cambridge, MA.
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40	Product Information. VFEND (voriconazole). Pfizer U.S. Pharmaceuticals, New York, NY.
41	Product Information. Orgovyx (relugolix). Myovant Sciences, Inc., Brisbane, CA.
42	Product Information. Nubeqa (darolutamide). Bayer HealthCare Pharmaceuticals Inc., Whippany, NJ.
43	Product Information. Rinvoq (upadacitinib). AbbVie US LLC, North Chicago, IL.
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