PATAMOSTAT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H20N4O4S
Molecular Weight	412.462
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NC1=CC=C(C=C1)C(=O)OC2=CC=C(SCCN3C(=O)CCC3=O)C=C2

InChI

InChIKey=ILRQPCQIFIURTG-UHFFFAOYSA-N

InChI=1S/C20H20N4O4S/c21-20(22)23-14-3-1-13(2-4-14)19(27)28-15-5-7-16(8-6-15)29-12-11-24-17(25)9-10-18(24)26/h1-8H,9-12H2,(H4,21,22,23)

HIDE SMILES / InChI

Molecular Formula	C20H20N4O4S
Molecular Weight	412.462
Charge	0
Count

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

Description
Sources: http://adisinsight.springer.com/drugs/800003114
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2611946 https://www.ncbi.nlm.nih.gov/pubmed/8071570 https://www.ncbi.nlm.nih.gov/pubmed/3410375

Patamostat (E-3123) is a protease inhibitor in vivo and in vitro. Inhibitory activity was shown toward trypsin, thrombin, plasmin, cathepsin-B and kallikrein. Patamostat is effective toward experimental pancreatitis and disseminated intravascular coagulation (animal models).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
CHEBI:9765 - Trypsin 2 Target ID: CHEBI:9765 - Trypsin Sources: https://www.ncbi.nlm.nih.gov/pubmed/3410375 \| https://www.ncbi.nlm.nih.gov/pubmed/8071570 \| https://www.ncbi.nlm.nih.gov/pubmed/2611946	Inhibitor 8504	0.39 nM [IC50]
HINO_0005745 Plasmin 2 Target ID: HINO_0005745 Plasmin Sources: https://www.ncbi.nlm.nih.gov/pubmed/3410375	Inhibitor 8504	95.0 µM [IC50]
CHEBI:9574 - Thrombin 2 Target ID: CHEBI:9574 - Thrombin Sources: https://www.ncbi.nlm.nih.gov/pubmed/3410375 \| https://www.ncbi.nlm.nih.gov/pubmed/2611946	Inhibitor 8504	1.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Disseminated intravascular coagulation 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1644370	Primary		Basic research	Unknown Approved Use Unknown
Pancreatitis 16 Sources: http://adisinsight.springer.com/drugs/800003114	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Protective effects of prophylaxis with a protease inhibitor and a free radical scavenger against a temporary ischemia model of pancreatitis.	1995-06	7540502
[Effects of E3123 on pancreatic injury in the isolated, perfused rat pancreas and in a pancreatic slice].	1994-10	7959424
Intracellular action of an exogenous low-molecular-weight synthetic protease inhibitor, E3123, in cerulein-induced acute pancreatitis in rats.	1994-04	8071570
Effect of short-term pancreatico-biliary duct obstruction with intraductal hypertension on subcellular organelle fragility and pancreatic adenylate energy metabolism in rats: protective effect of a new protease inhibitor, E-3123.	1994-03-01	7517090
The therapeutic effect of a new synthetic protease inhibitor (E-3123) on hemodynamic changes during experimental acute pancreatitis in dogs.	1993-02	8440425

Patents

Sample Use Guides

In Vivo Use Guide

0.4 mg/kg (bolus), 3-5 mg/kg/hr (infusion) (dogs)

Route of Administration: Intravenous

In Vitro Use Guide

Patamostat (E-3123) potently inhibited trypsin, plasmin and thrombin with IC50 values of 3.9 x 10(-8) M, 9.5 x 10(-7) M and 1.9 x 10(-6) M

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:31 GMT 2025`
Record UNII	2T7W4EA51W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PATAMOSTAT

Official Name

English

P-((2-SUCCINIMIDOETHYL)THIO)PHENYL P-GUANIDINOBENZOATE

Preferred Name

English

patamostat [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783