UPAMOSTAT HYDROGEN SULFATE

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

Molecular Formula	C32H47N5O6S
Molecular Weight	629.81
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8297
Trypsin II 4 Target ID: CHEMBL3159 Sources: DOI: 10.1158/1535-7163.TARG-17-B055	Inhibitor 8297	75.0 nM [Ki]
Trypsin III 4 Target ID: CHEMBL4551 Sources: DOI: 10.1158/1535-7163.TARG-17-B055	Inhibitor 8297	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 8297

PubMed

Title	Date	PubMed
Protease inhibitors prevent plasminogen-mediated, but not pemphigus vulgaris-induced, acantholysis in human epidermis.	2003 Feb	12675525
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 Mar 5	23412098
Activation of the anti-cancer agent upamostat by the mARC enzyme system.	2013 Sep	23379481
DCE-MRI biomarkers for monitoring an anti-angiogenic triple combination therapy in experimental hypopharynx carcinoma xenografts with immunohistochemical validation.	2015 Mar	24609871

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:25:06 UTC 2023` Edited by `admin` on `Sat Dec 16 01:25:06 UTC 2023`
Record UNII	RW7SKM7M5Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

UPAMOSTAT HYDROGEN SULFATE

Common Name

English

WX-671 HYDROGEN SULFATE

Code

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 Sat Dec 16 01:25:06 UTC 2023 , Edited by admin on Sat Dec 16 01:25:06 UTC 2023

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FDA UNII

RW7SKM7M5Q

Created by admin on Sat Dec 16 01:25:06 UTC 2023 , Edited by admin on Sat Dec 16 01:25:06 UTC 2023

PRIMARY

PUBCHEM

163203513

Created by admin on Sat Dec 16 01:25:06 UTC 2023 , Edited by admin on Sat Dec 16 01:25:06 UTC 2023

PRIMARY

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UPAMOSTAT

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