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

Similar Structures

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

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Drug Discovery

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Associated Conditions

Contraindications & Blackbox Warnings

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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

Target	Actions	Organism
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

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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.

Drug	Interaction
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1,2-Benzodiazepine	The metabolism of Tucatinib can be decreased when combined with 1,2-Benzodiazepine.
Abaloparatide	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.
Acalabrutinib	The metabolism of Tucatinib can be decreased when combined with Acalabrutinib.
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.

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Tukysa	Tablet	50 mg	Oral	Seattle Genetics, Inc.	2020-10-08	Not applicable
Tukysa	Tablet	150 mg/1	Oral	Seagen Inc.	2020-04-17	Not applicable
Tukysa	Tablet, film coated	150 mg	Oral	Seagen B.V.	2021-03-03	Not applicable
Tukysa	Tablet	50 mg/1	Oral	Seagen Inc.	2020-04-17	Not applicable
Tukysa	Tablet	150 mg	Oral	Seattle Genetics, Inc.	2020-08-27	Not applicable
Tukysa	Tablet, film coated	50 mg	Oral	Seagen B.V.	2021-03-03	Not applicable

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. [Article]
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]
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]
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]
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]
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]
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
RxNav: 2361285
ChEMBL: CHEMBL3989868
ZINC: ZINC000068250462
Wikipedia: Tucatinib

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Recruiting	Treatment	Anatomic 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 Carcinoma	1
3	Recruiting	Treatment	HER2/Neu-positive Breast Cancer	1
2	Active Not Recruiting	Treatment	HER2/Neu-positive Breast Cancer	1
2	Active Not Recruiting	Treatment	Leptomeningeal Disease / Metastatic Breast Cancer	1
2	Not Yet Recruiting	Treatment	Breast Cancer / HER2/Neu-positive Breast Cancer	1
2	Not Yet Recruiting	Treatment	HER2/Neu-positive Breast Cancer / Tumors Metastatic to Brain	1
2	Recruiting	Treatment	Advanced Solid Tumors / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL)	1
2	Recruiting	Treatment	Advanced Unresectable or Metastatic Solid Malignancy	1
2	Recruiting	Treatment	Biliary Tract Neoplasms / Neoplasms, Breast / Non-Small Cell Lung Carcinoma (NSCLC) / Urologic Neoplasms / Uterine Cervical Neoplasms / Uterine Neoplasms	1
2	Recruiting	Treatment	Breast Cancer	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral	150 mg/1
Tablet	Oral	150 mg
Tablet	Oral	50 mg/1
Tablet	Oral	50 mg
Tablet, film coated	Oral	150 mg
Tablet, film coated	Oral	50 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US7452895	No	2004-11-16	2024-11-16
US9457093	No	2012-10-12	2032-10-12
US9693989	No	2007-05-09	2027-05-09
US8648087	No	2011-04-12	2031-04-12

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

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Details1. Receptor tyrosine-protein kinase erbB-2

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. [Article]
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]
FDA approved products: Tukysa (tucatinib) oral tablets [Link]

Details2. Receptor tyrosine-protein kinase erbB-3

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

Details1. Cytochrome P450 2C8

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]

Details2. Cytochrome P450 3A Subfamily (Protein Group)

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

FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
FDA approved products: Tukysa (tucatinib) oral tablets [Link]

Details3. Receptor tyrosine-protein kinase erbB-2

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. [Article]
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]
FDA approved products: Tukysa (tucatinib) oral tablets [Link]

Transporters

Details1. ATP-binding cassette sub-family G member 2

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]

Details2. P-glycoprotein 1

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]

Details3. Solute carrier family 22 member 2

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]

Details4. Multidrug and toxin extrusion protein 1

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]

Details5. Multidrug and toxin extrusion protein 2

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 20:37 / Updated on July 24, 2021 14:57

Tucatinib

Identification

Structure for Tucatinib (DB11652)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

Enzymes

References

Components:

References

References

Transporters

References

References

References

References

References