NAV

Tirabrutinib

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Tirabrutinib
DrugBank Accession Number
DB15227
Background

Tirabrutinib is under investigation in clinical trial NCT02626026 (Safety and Pharmacokinetics of GS-4059 in Healthy Volunteers and Subjects With Rheumatoid Arthritis (RA)).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 454.49
Monoisotopic: 454.175338592
Chemical Formula
C25H22N6O3
Synonyms
  • 6-amino-9-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-7-(4-phenoxyphenyl)purin-8-one
  • ONO-4059 (free base)
  • Tirabrutinib
External IDs
  • GS-4059
  • ONO-4059
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTyrosine-protein kinase BTK
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tirabrutinib hydrochlorideU374135N481439901-97-9Not applicable

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
LXG44NDL2T
CAS number
1351636-18-4
InChI Key
SEJLPXCPMNSRAM-GOSISDBHSA-N
InChI
InChI=1S/C25H22N6O3/c1-2-6-21(32)29-14-13-18(15-29)31-24-22(23(26)27-16-28-24)30(25(31)33)17-9-11-20(12-10-17)34-19-7-4-3-5-8-19/h3-5,7-12,16,18H,13-15H2,1H3,(H2,26,27,28)/t18-/m1/s1
IUPAC Name
6-amino-9-[(3R)-1-(but-2-ynoyl)pyrrolidin-3-yl]-7-(4-phenoxyphenyl)-8,9-dihydro-7H-purin-8-one
SMILES
CC#CC(=O)N1CC[C@H](C1)N1C(=O)N(C2=C(N)N=CN=C12)C1=CC=C(OC2=CC=CC=C2)C=C1

References

General References
Not Available
ChemSpider
58171734
BindingDB
194087
ChEMBL
CHEMBL4071161
ZINC
ZINC000072318699
Wikipedia
Tirabrutinib

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Lymphocytic Leukemia2
2CompletedTreatmentSjögren's Syndrome (SS)1
2RecruitingTreatmentPrimary Central Nervous System Lymphoma / Refractory Primary Central Nervous System Lymphoma1
2WithdrawnTreatmentChronic Spontaneous Urticaria1
1Active Not RecruitingTreatmentB-cell Malignancy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0267 mg/mLALOGPS
logP1.92ALOGPS
logP3.27Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.57Chemaxon
pKa (Strongest Basic)3.33Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area104.89 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity127.73 m3·mol-1Chemaxon
Polarizability48.25 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
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/MSsplash10-0a4i-0002900000-78d9f4c048b4bacaaa3f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-24f44af9414675a67a92
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0003900000-29305dd2d40f6bffa155
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0023900000-406eca460139a4cba9a6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009200000-cb08176afbd4fa9686ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f7o-8669600000-45260274e73d1fafdc11
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Tyrosine-protein kinase BTK
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein tyrosine kinase activity
Specific Function
Non-receptor tyrosine kinase indispensable for B lymphocyte development, differentiation and signaling. Binding of antigen to the B-cell antigen receptor (BCR) triggers signaling that ultimately le...
Gene Name
BTK
Uniprot ID
Q06187
Uniprot Name
Tyrosine-protein kinase BTK
Molecular Weight
76280.71 Da
References
  1. Castillo JJ, Treon SP: Management of Waldenstrom macroglobulinemia in 2020. Hematology Am Soc Hematol Educ Program. 2020 Dec 4;2020(1):372-379. doi: 10.1182/hematology.2020000121. [Article]
  2. Zheng TJ, Lofurno ER, Melrose AR, Lakshmanan HHS, Pang J, Phillips KG, Fallon ME, Kohs TCL, Ngo ATP, Shatzel JJ, Hinds MT, McCarty OJT, Aslan JE: Assessment of the effects of Syk and BTK inhibitors on GPVI-mediated platelet signaling and function. Am J Physiol Cell Physiol. 2021 May 1;320(5):C902-C915. doi: 10.1152/ajpcell.00296.2020. Epub 2021 Mar 10. [Article]

Drug created at May 20, 2019 15:01 / Updated at December 13, 2022 10:46