upamostat   Click here for help

GtoPdb Ligand ID: 6497

Synonyms: WX-671
Compound class: Synthetic organic
Comment: Upamostat (WX-671) is an oral serine protease inhibitor prodrug. Its principal molecular target is plasminogen activator, urokinase (uPA; PLAU) [2]. The uPA system plays an important role in tumour invasion and metastasis. The active substance is WX-UK1.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 15
Topological polar surface area 149.02
Molecular weight 629.32
XLogP 6.24
No. Lipinski's rules broken 2
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Canonical SMILES CCOC(=O)N1CCN(CC1)C(=O)C(NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)C=NNO
Isomeric SMILES CCOC(=O)N1CCN(CC1)C(=O)[C@@H](NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)/C=N/NO
InChI InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)29(17-24-10-9-11-25(16-24)20-33-35-40)34-44(41,42)30-27(22(4)5)18-26(21(2)3)19-28(30)23(6)7/h9-11,16,18-23,29,34-35,40H,8,12-15,17H2,1-7H3/b33-20+/t29-/m0/s1
1. Ertongur S, Lang S, Mack B, Wosikowski K, Muehlenweg B, Gires O. (2004)
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, 110 (6): 815-24. [PMID:15170662]
2. Froriep D, Clement B, Bittner F, Mendel RR, Reichmann D, Schmalix W, Havemeyer A. (2013)
Activation of the anti-cancer agent upamostat by the mARC enzyme system.
Xenobiotica, 43 (9): 780-4. [PMID:23379481]
3. Heinemann V, Ebert MP, Laubender RP, Bevan P, Mala C, Boeck S. (2013)
Phase II randomised proof-of-concept study of the urokinase inhibitor upamostat (WX-671) in combination with gemcitabine compared with gemcitabine alone in patients with non-resectable, locally advanced pancreatic cancer.
Br J Cancer, 108 (4): 766-70. [PMID:23412098]
4. Meyer JE, Brocks C, Graefe H, Mala C, Thäns N, Bürgle M, Rempel A, Rotter N, Wollenberg B, Lang S. (2008)
The Oral Serine Protease Inhibitor WX-671 - First Experience in Patients with Advanced Head and Neck Carcinoma.
Breast Care (Basel), 3 (s2): 20-24. [PMID:20824010]
5. Setyono-Han B, Stürzebecher J, Schmalix WA, Muehlenweg B, Sieuwerts AM, Timmermans M, Magdolen V, Schmitt M, Klijn JG, Foekens JA. (2005)
Suppression of rat breast cancer metastasis and reduction of primary tumour growth by the small synthetic urokinase inhibitor WX-UK1.
Thromb Haemost, 93 (4): 779-86. [PMID:15841327]