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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22N4O5
Molecular Weight 398.4125
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAMOSTAT

SMILES

CN(C)C(=O)COC(=O)CC1=CC=C(OC(=O)C2=CC=C(NC(N)=N)C=C2)C=C1

InChI

InChIKey=XASIMHXSUQUHLV-UHFFFAOYSA-N
InChI=1S/C20H22N4O5/c1-24(2)17(25)12-28-18(26)11-13-3-9-16(10-4-13)29-19(27)14-5-7-15(8-6-14)23-20(21)22/h3-10H,11-12H2,1-2H3,(H4,21,22,23)

HIDE SMILES / InChI

Description

Camostat mesilate (FOY-305) is a synthetic f low-molecular weight protease inhibitor. It is able to inhibit trypsin, prostasin, matriptase and plasma kallikrein. In addition camostat attenuates airway epithelial sodium channel function and enhances mucociliary clearance. Camostat mesilate tablets (FOIPAN®) are approved in Japan and used for the treatment of remission of acute symptoms of chronic pancreatitis and postoperative reflux esophagitis.

CNS Activity

CNS Active
4,002

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
Trypsin
7
Inhibitor
8,504
 1.0 nM [Ki]
Matriptase
2
Inhibitor
8,504
 4.0 nM [Ki]
Prostasin
2
Inhibitor
8,504
 0.576 µM [Ki]
Amiloride-sensitive sodium channel, ENaC
4
Inhibitor
8,504
 50.0 nM [IC50]
Plasma kallikrein
9
Inhibitor
8,504

Conditions

ConditionModalityTargetsHighest PhaseProduct
Multiple sclerosis
107
 Primary
Preclinical
Unknown
Chronic pancreatitis
3
 Primary
Approved
8,583
FOIPAN
Postoperative reflux esophagitis
2
 Primary
Approved
8,583
FOIPAN
Hepatic fibrosis
3
 Primary
Preclinical
Unknown
Hypertension
575
 Primary
Preclinical
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
371 ng/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
95.8 ng/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
93.5 ng/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
177 ng/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
218 ng/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
367 ng/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
87.1 ng/mL
200 mg single, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
683 ng × h/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
206 ng × h/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
194 ng × h/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
227 ng × h/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
366 ng × h/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
556 ng × h/mL
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
10400 ng × h/mL
200 mg single, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.58 h
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
1.33 h
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
1.16 h
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
1.35 h
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
1.05 h
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
0.962 h
600 mg 4 times / day multiple, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens
100 min
200 mg single, oral
 4-(4-GUANIDINOBENZOYLOXY)PHENYLACETIC ACID plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
71.8%
CAMOSTAT serum
Homo sapiens

Doses

PubMed

Patents

JP2002114755A
2
JP2006213728A
2
WO2008142397A1
2

Sample Use Guides

In Vivo Use Guide
1. Remission of acute symptoms of chronic pancreatitis. The usual dosage for oral use is 600 mg of camostat mesilate daily in three divided doses. The dosage may be adjusted according to the patient’s symptoms. 2. Postoperative reflux esophagitis. The usual dosage for oral use is 300 mg of camostat mesilate daily in three divided doses after each meal.
Route of Administration: Oral
In Vitro Use Guide
Camostat mesilate (500 uM) inhibited generation of TGF-beta by suppressing plasmin activity and reduced the activity of TGF-beta, which blocked in vitro activation of the rat hepatic stellate cells.
ACTIVE MOIETY
Structure of CAMOSTAT
METABOLITE ACTIVE (PARENT)
Structure of FOY-251
SALT/SOLVATE (PARENT)
Structure of CAMOSTAT MESYLATE
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