WX-UK1
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Identification
- Generic Name
- WX-UK1
- DrugBank Accession Number
- DB05476
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 650.28
Monoisotopic: 649.3064685 - Chemical Formula
- C32H48ClN5O5S
- Synonyms
- Not Available
- External IDs
- WX UK1
- WX-UK1
Pharmacology
- Indication
Investigated for use/treatment in solid tumors.
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- 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.
Target Actions Organism UUrokinase plasminogen activator surface receptor Not Available 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- 1,4-diazinane / Alpha-amino acid amide / Amidine / Aminosulfonyl compound / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid show 24 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- UJ925Q0P3B
- CAS number
- 255374-84-6
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 0.00462 mg/mL ALOGPS logP 3.02 ALOGPS logP 4.44 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 10.55 Chemaxon pKa (Strongest Basic) 11.51 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 145.89 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 180.86 m3·mol-1 Chemaxon Polarizability 68.31 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 247.50577 predictedDeepCCS 1.0 (2019) [M+H]+ 249.33067 predictedDeepCCS 1.0 (2019) [M+Na]+ 254.93648 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Acts as a receptor for urokinase plasminogen activator (PubMed:15677461). Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form
- Specific Function
- enzyme binding
- Gene Name
- PLAUR
- Uniprot ID
- Q03405
- Uniprot Name
- Urokinase plasminogen activator surface receptor
- Molecular Weight
- 36977.62 Da
Drug created at November 18, 2007 18:25 / Updated at June 12, 2020 16:52