UPAMOSTAT

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H47N5O6S
Molecular Weight	629.81
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

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=HUASEDVYRABWCV-NDEPHWFRSA-N

InChI=1S/C32H47N5O6S/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/h9-11,16,18-22,28,35,40H,8,12-15,17H2,1-7H3,(H2,33,34)/t28-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C32H47N5O6S
Molecular Weight	629.81
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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

Targets

Primary Target	Pharmacology	Potency
Urokinase-type plasminogen activator 4	Inhibitor 8,504
Trypsin II 4	Inhibitor 8,504	75.0 nM [Ki]
Trypsin III 4	Inhibitor 8,504	19.0 nM [Ki]
Urokinase-type plasminogen activator 4	Inhibitor 8,504

PubMed

PubMed

Show entries

Title	Date	PubMed
Protease inhibitors prevent plasminogen-mediated, but not pemphigus vulgaris-induced, acantholysis in human epidermis.	2003 Feb	12675525
Inhibition of the invasion capacity of carcinoma cells by WX-UK1, a novel synthetic inhibitor of the urokinase-type plasminogen activator system.	2004 Jul 20	15170662
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

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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
Record UNII	S5M7KW6U17
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

UPAMOSTAT

Official Name

English

MESUPRON

Preferred Name

English

Upamostat [WHO-DD]

Common Name

English

upamostat [INN]

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

Common Name

English

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