UPAMOSTAT HYDROGEN SULFATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H47N5O6S.H2O4S
Molecular Weight	727.889
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CCOC(=O)N1CCN(CC1)C(=O)[C@H](CC2=CC(=CC=C2)C(\N)=N/O)NS(=O)(=O)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C

InChI

InChIKey=KLXJMUHOAZJDAS-JCOPYZAKSA-N

InChI=1S/C32H47N5O6S.H2O4S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34-40)35-44(41,42)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7;1-5(2,3)4/h9-11,16,18-22,28,35,40H,8,12-15,17H2,1-7H3,(H2,33,34);(H2,1,2,3,4)/t28-;/m0./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23379481 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C73985DOI: 10.1158/1535-7163.TARG-17-B055 | https://clinicaltrials.gov/ct2/show/NCT00083525 | https://adisinsight.springer.com/drugs/800012176

Wilex developed WX-UK1 as a specific inhibitor of human trypsin-2, human trypsin-3 and urokinase-plasminogen activator. WX-UK1 participated in phase I clinical trial in combination with capecitabine in advanced malignancies to determine the safety, tolerability, maximum tolerated dose, pharmacokinetics, and pharmacodynamics. However, in April 2014, the clinical development of this drug was discontinued, as part of a company restructure.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Urokinase-type plasminogen activator 4 Target ID: CHEMBL3286 Sources: https://adisinsight.springer.com/drugs/800021537\|https://www.ncbi.nlm.nih.gov/pubmed/23379481\|http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=6497	Inhibitor 8504
Trypsin II 4 Target ID: CHEMBL3159 Sources: DOI: 10.1158/1535-7163.TARG-17-B055	Inhibitor 8504	75.0 nM [Ki]
Trypsin III 4 Target ID: CHEMBL4551 Sources: DOI: 10.1158/1535-7163.TARG-17-B055	Inhibitor 8504	19.0 nM [Ki]
Urokinase-type plasminogen activator 4 Target ID: P00749 Gene ID: 5328.0 Gene Symbol: PLAU Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15170662	Inhibitor 8504

PubMed

Title	Date	PubMed
DCE-MRI biomarkers for monitoring an anti-angiogenic triple combination therapy in experimental hypopharynx carcinoma xenografts with immunohistochemical validation.	2015-03	24609871
Activation of the anti-cancer agent upamostat by the mARC enzyme system.	2013-09	23379481
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.	2013-03-05	23412098
Inhibition of the invasion capacity of carcinoma cells by WX-UK1, a novel synthetic inhibitor of the urokinase-type plasminogen activator system.	2004-07-20	15170662
Protease inhibitors prevent plasminogen-mediated, but not pemphigus vulgaris-induced, acantholysis in human epidermis.	2003-02	12675525

Sample Use Guides

In Vivo Use Guide

Advanced pancreatic adenocarcinoma: 1000 mg m(-2) of gemcitabine IV weekly either alone (arm A) or in combination with 200 mg (arm B) or 400 mg (arm C) oral upamostat daily.

Route of Administration: Oral

Name

Type

Language

WX-671 HYDROGEN SULFATE

Preferred Name

English

UPAMOSTAT HYDROGEN SULFATE

Common Name

English

1-PIPERAZINECARBOXYLIC ACID, 4-((2S)-3-(3-((E)-AMINO(HYDROXYIMINO)METHYL)PHENYL)-1-OXO-2-(((2,4,6-TRIS(1-METHYLETHYL)PHENYL)SULFONYL)AMINO)PROPYL)-, ETHYL ESTER, SULFATE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

1191101-19-5

Created by admin on Mon Mar 31 20:49:42 GMT 2025 , Edited by admin on Mon Mar 31 20:49:42 GMT 2025

PRIMARY

FDA UNII

RW7SKM7M5Q

Created by admin on Mon Mar 31 20:49:42 GMT 2025 , Edited by admin on Mon Mar 31 20:49:42 GMT 2025

PRIMARY

PUBCHEM