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Pyrotinib

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

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Data Packages
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Identification

Generic Name
Pyrotinib
DrugBank Accession Number
DB14993
Background

Pyrotinib is under investigation in clinical trial NCT03756064 (Neoadjuvant Study of Pyrotinib in Patients With HER2 Positive Breast Cancer).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 583.09
Monoisotopic: 582.2146166
Chemical Formula
C32H31ClN6O3
Synonyms
Not Available
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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
AEpidermal growth factor receptor
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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Aminoquinolines and derivatives
Direct Parent
4-aminoquinolines
Alternative Parents
Aminophenyl ethers / Aniline and substituted anilines / N-arylamides / Phenoxy compounds / Alkyl aryl ethers / Chlorobenzenes / Aminopyridines and derivatives / Aryl chlorides / N-alkylpyrrolidines / Primary aromatic amines
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Substituents
4-aminoquinoline / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminophenyl ether / Aminopyridine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
CJN36EQM0H
CAS number
1269662-73-8
InChI Key
SADXACCFNXBCFY-IYNHSRRRSA-N
InChI
InChI=1S/C32H31ClN6O3/c1-3-41-30-17-27-25(16-28(30)38-31(40)12-10-24-8-6-14-39(24)2)32(21(18-34)19-36-27)37-22-9-11-29(26(33)15-22)42-20-23-7-4-5-13-35-23/h4-5,7,9-13,15-17,19,24H,3,6,8,14,20H2,1-2H3,(H,36,37)(H,38,40)/b12-10+/t24-/m1/s1
IUPAC Name
(2E)-N-[4-({3-chloro-4-[(pyridin-2-yl)methoxy]phenyl}amino)-3-cyano-7-ethoxyquinolin-6-yl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide
SMILES
CCOC1=C(NC(=O)\C=C\[C@H]2CCCN2C)C=C2C(=C1)N=CC(C#N)=C2NC1=CC=C(OCC2=NC=CC=C2)C(Cl)=C1

References

General References
Not Available
ChemSpider
52083721
BindingDB
139991
ChEMBL
CHEMBL3647420
ZINC
ZINC000068250550

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not AvailableCompletedNot AvailableBreast Cancer1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableHER2/Neu-positive Breast Cancer1somestatusstop reasonjust information to hide
Not AvailableNot Yet RecruitingNot AvailableHER2/Neu-positive Breast Cancer1somestatusstop reasonjust information to hide
Not AvailableNot Yet RecruitingTreatmentBreast Cancer1somestatusstop reasonjust information to hide
Not AvailableNot Yet RecruitingTreatmentBreast Cancer / Pyrotinib / RWS1somestatusstop reasonjust information to hide

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 Solubility0.00589 mg/mLALOGPS
logP5.1ALOGPS
logP4.93Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)12.55Chemaxon
pKa (Strongest Basic)8.71Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area112.4 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity164.5 m3·mol-1Chemaxon
Polarizability60.8 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-001i-2000090000-8351a340d72562189b75
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0100090000-bdda660af07c6483e244
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-2100290000-02f1bb28b6ad8cd2c6ee
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0003920000-7403e79129d82f8b146c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-4901340000-3a62e89d26f163f2dae2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01si-5108940000-88b4836d0dd2b58e7c11
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Epidermal growth factor receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses (PubMed:10805725, PubMed:27153536, PubMed:2790960, PubMed:35538033). Known ligands include EGF, TGFA/TGF-alpha, AREG, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF (PubMed:12297049, PubMed:15611079, PubMed:17909029, PubMed:20837704, PubMed:27153536, PubMed:2790960, PubMed:7679104, PubMed:8144591, PubMed:9419975). Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules (PubMed:27153536). May also activate the NF-kappa-B signaling cascade (PubMed:11116146). Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling (PubMed:11602604). Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin (PubMed:11483589). Positively regulates cell migration via interaction with CCDC88A/GIV which retains EGFR at the cell membrane following ligand stimulation, promoting EGFR signaling which triggers cell migration (PubMed:20462955). Plays a role in enhancing learning and memory performance (By similarity). Plays a role in mammalian pain signaling (long-lasting hypersensitivity) (By similarity)
Specific Function
Actin filament binding
Gene Name
EGFR
Uniprot ID
P00533
Uniprot Name
Epidermal growth factor receptor
Molecular Weight
134276.185 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at May 20, 2019 14:40 / Updated at August 27, 2024 19:16