Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
WX-UK1
Accession Number
DB05476
Type
Small Molecule
Groups
Investigational
Description

WX-UK1 is a 3-amidinophenylalanine-based non-cytotoxic small molecule that belongs to a new class of drugs. In animal models, WX-UK1 blocks tumor cell invasion, metastasis and primary tumor growth by inhibiting serine proteases and the urokinase Plasminogen Activator (uPA) system, which have been shown to play a key role in metastasis and primary tumor growth of breast, gastric, colon cancer, and various other solid tumors. Independent studies show that administration of Wx-UK1 resulted in a decrease of tumor cell invasion, suggesting its efficacy as a an adjuvant antimetastatic therapy of carcinomas.

Structure
Thumb
Synonyms
Not Available
External IDs
WX UK1 / WX-UK1
Categories
UNII
UJ925Q0P3B
CAS number
Not Available
Weight
Average: 650.28
Monoisotopic: 649.3064685
Chemical Formula
C32H48ClN5O5S
InChI Key
FMHIVIJVVYYSRN-JCOPYZAKSA-N
InChI
InChI=1S/C32H47N5O5S.ClH/c1-8-42-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34)35-43(40,41)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7;/h9-11,16,18-22,28,35H,8,12-15,17H2,1-7H3,(H3,33,34);1H/t28-;/m0./s1
IUPAC Name
ethyl 4-[(2S)-3-(3-carbamimidoylphenyl)-2-[2,4,6-tris(propan-2-yl)benzenesulfonamido]propanoyl]piperazine-1-carboxylate hydrochloride
SMILES
Cl.CCOC(=O)N1CCN(CC1)C(=O)[C@H](CC1=CC=CC(=C1)C(N)=N)NS(=O)(=O)C1=C(C=C(C=C1C(C)C)C(C)C)C(C)C

Pharmacology

Indication

Investigated for use/treatment in solid tumors.

Pharmacodynamics

WX-UK1 is a 3-amidinophenylalanine-based non-cytotoxic small molecule that belongs to a new class of drugs. In animal models, WX-UK1 blocks tumor cell invasion, metastasis and primary tumor growth by inhibiting serine proteases and the urokinase Plasminogen Activator (uPA) system, which have been shown to play a key role in metastasis and primary tumor growth of breast, gastric, colon cancer, and various other solid tumors.

Mechanism of action

Activity at urokinase plasminogen activator receptors (uPAR) results in inhibition of uPA system.

TargetActionsOrganism
UUrokinase plasminogen activator surface receptorNot AvailableHumans
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
Toxicity
Not Available
Affected organisms
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

References

General References
  1. Setyono-Han B, Sturzebecher J, Schmalix WA, Muehlenweg B, Sieuwerts AM, Timmermans M, Magdolen V, Schmitt M, Klijn JG, Foekens JA: Suppression of rat breast cancer metastasis and reduction of primary tumour growth by the small synthetic urokinase inhibitor WX-UK1. Thromb Haemost. 2005 Apr;93(4):779-86. [PubMed:15841327]
  2. Ertongur S, Lang S, Mack B, Wosikowski K, Muehlenweg B, Gires O: Inhibition of the invasion capacity of carcinoma cells by WX-UK1, a novel synthetic inhibitor of the urokinase-type plasminogen activator system. Int J Cancer. 2004 Jul 20;110(6):815-24. [PubMed:15170662]
  3. Schuh T, Besch R, Braungart E, Flaig MJ, Douwes K, Sander CA, Magdolen V, Probst C, Wosikowski K, Degitz K: Protease inhibitors prevent plasminogen-mediated, but not pemphigus vulgaris-induced, acantholysis in human epidermis. Biol Chem. 2003 Feb;384(2):311-5. [PubMed:12675525]
External Links
PubChem Compound
9939426
PubChem Substance
347827733
ChemSpider
8115047

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAdvanced Malignancies1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00462 mg/mLALOGPS
logP3.02ALOGPS
logP4.44ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)11.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area145.89 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity180.86 m3·mol-1ChemAxon
Polarizability67.55 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Amphetamines and derivatives / Benzenesulfonamides / Piperazine carboxylic acids / Phenylpropanes / Cumenes / Benzenesulfonyl compounds / Organosulfonamides / Tertiary carboxylic acid amides / Aminosulfonyl compounds / Carbamate esters
show 7 more
Substituents
Alpha-amino acid amide / Amphetamine or derivatives / Benzenesulfonamide / Benzenesulfonyl group / Cumene / Phenylpropane / Piperazine-1-carboxylic acid / Monocyclic benzene moiety / 1,4-diazinane / Benzenoid
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Urokinase plasminogen activator receptor activity
Specific Function
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-...
Gene Name
PLAUR
Uniprot ID
Q03405
Uniprot Name
Urokinase plasminogen activator surface receptor
Molecular Weight
36977.62 Da

Drug created on November 18, 2007 11:25 / Updated on September 02, 2019 18:13