U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H20N4O4S.CH4O3S
Molecular Weight 508.568
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PATAMOSTAT MESILATE

SMILES

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

InChI

InChIKey=HTSFLDCSCNSKJW-UHFFFAOYSA-N
InChI=1S/C20H20N4O4S.CH4O3S/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;1-5(2,3)4/h1-8H,9-12H2,(H4,21,22,23);1H3,(H,2,3,4)

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
Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.39 nM [IC50]
Inhibitor
8504
 95.0 µM [IC50]
Inhibitor
8504
 1.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Protective effects of prophylaxis with a protease inhibitor and a free radical scavenger against a temporary ischemia model of pancreatitis.
1995-06
[Effects of E3123 on pancreatic injury in the isolated, perfused rat pancreas and in a pancreatic slice].
1994-10
Intracellular action of an exogenous low-molecular-weight synthetic protease inhibitor, E3123, in cerulein-induced acute pancreatitis in rats.
1994-04
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
The therapeutic effect of a new synthetic protease inhibitor (E-3123) on hemodynamic changes during experimental acute pancreatitis in dogs.
1993-02
Patents

Patents

US6469036
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: additional regimens: 1.5 mg/kg subcutaneously (rats): https://www.ncbi.nlm.nih.gov/pubmed/7514553
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 21:34:04 GMT 2025
Edited
by admin
on Mon Mar 31 21:34:04 GMT 2025
Record UNII
4697U796PV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PATOMOSTAT MESILATE
JAN  
Preferred Name English
PATAMOSTAT MESILATE
Common Name English
PATOMOSTAT MESILATE [JAN]
Common Name English
E-3123
Code English
BENZOIC ACID, 4-((AMINOIMINOMETHYL)AMINO)-, 4-((2-(2,5-DIOXO-1-PYRROLIDINYL)ETHYL)THIO)PHENYL ESTER, METHANESULFONATE (1:1)
Common Name English
BENZOIC ACID, 4-((AMINOIMINOMETHYL)AMINO)-, 4-((2-(2,5-DIOXO-1-PYRROLIDINYL)ETHYL)THIO)PHENYL ESTER, MONOMETHANESULFONATE
Common Name English
E 3123
Code English
PATOMOSTAT MESYLATE
Common Name English
Code System Code Type Description
PUBCHEM
6918009
Created by admin on Mon Mar 31 21:34:04 GMT 2025 , Edited by admin on Mon Mar 31 21:34:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID50150786
Created by admin on Mon Mar 31 21:34:04 GMT 2025 , Edited by admin on Mon Mar 31 21:34:04 GMT 2025
PRIMARY
CAS
114568-32-0
Created by admin on Mon Mar 31 21:34:04 GMT 2025 , Edited by admin on Mon Mar 31 21:34:04 GMT 2025
PRIMARY
FDA UNII
4697U796PV
Created by admin on Mon Mar 31 21:34:04 GMT 2025 , Edited by admin on Mon Mar 31 21:34:04 GMT 2025
PRIMARY
Related Record Type Details
Structure of PATAMOSTAT
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PATAMOSTAT
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966