59721-28-7

Basic information

• Product Name: Camostat
• Synonyms: CAMOSTAT;4-[[4-[(Aminoiminomethyl)amino]benzoyl]oxy]benzeneaxetic acid 2-(dimethylamino)-oxoethyl ester;FOY 305;Camostat (base and/or unspecified salts);2-(Dimethylamino)-2-oxoethyl 4-(4-guanidinobenzoyloxy)phenylacetate;Camostat Monomethanesulfonate;FOY-305：Foipan;N，N-Dimethylcarbamoylmethyl-p(p-guanidinobenzoyloxy)phenylacetate
• CAS NO: 59721-28-7
• Molecular Formula: C₂₀H₂₂N₄O₅
• Molecular Weight: 398.41
• Product Categories: API
• Mol File: 59721-28-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 634.6 °C at 760 mmHg
• Flash Point: 337.6 °C
• Appearance: white crystals or crystalline powder
• Density: 1.28 g/cm³
• Vapor Pressure: 5.22E-16mmHg at 25°C
• Refractive Index: 1.596
• PKA: 10.17±0.10(Predicted)
• CAS DataBase Reference: Camostat(CAS DataBase Reference)
• NIST Chemistry Reference: Camostat(59721-28-7)
• EPA Substance Registry System: Camostat(59721-28-7)

Safety Data

• Hazardous Substances Data: 59721-28-7(Hazardous Substances Data)

Usage

General Description

Camostat is a synthetic serine protease inhibitor that is used to treat chronic pancreatitis and other pancreatic disorders. It works by inhibiting the activity of trypsin, a serine protease that can cause inflammation and tissue damage in the pancreas. Camostat has also been investigated for its potential to treat other conditions, including cancer, viral infections, and fibrotic diseases. It has been shown to have anti-inflammatory and anti-fibrotic properties, and is currently being studied for its potential therapeutic benefits in various medical fields. Overall, camostat is a promising compound with a wide range of potential applications in medicine.

InChI:InChI=1/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)

Synthetic route

4-guanidinobenzoic acid (16060-65-4) + p-hydroxyphenylacetic acid-N, N-dimethylcarbamoylmethyl ester (59721-16-3) → camostat (59721-28-7)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile for 5h; Reflux;	38.2 g

L-Tartaric acid (87-69-4) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate hydrogentartrate hemihydrate

Conditions	Yield
With water In isopropyl alcohol at 25 - 75℃;	99.1%

camostat (59721-28-7) + 1-hydroxy-2-naphthoic acid (86-48-6) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate xinafoate

Conditions	Yield
In water; isopropyl alcohol at 25 - 60℃;	99.1%

1,5-pentanedioic acid (110-94-1) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate glutarate

Conditions	Yield
In ethanol at 20 - 65℃;	98%

Adipic acid (124-04-9) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate adipate

Conditions	Yield
In ethanol at 20 - 65℃;	98%

glycolic Acid (79-14-1) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate glycolate

Conditions	Yield
In ethanol at 20 - 70℃;	96.3%

glycolic Acid (79-14-1) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate glycolate hemihydrate

Conditions	Yield
With water In isopropyl alcohol at 20 - 45℃;	95.3%

acetic acid (64-19-7) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate acetate

Conditions	Yield
In water; isopropyl alcohol at 20 - 45℃;	89.5%

succinic acid (110-15-6) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate succinate

Conditions	Yield
In ethanol; water at 20 - 75℃;	88%

succinic acid (110-15-6) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate hydrogensuccinate

Conditions	Yield
In ethanol; water at 20 - 70℃;	87.9%

Hippuric Acid (495-69-2) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate hippurate

Conditions	Yield
In ethanol; water at 25 - 65℃;	83.4%

camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate phosphate

Conditions	Yield
With phosphoric acid In ethanol; water at 20 - 75℃; Product distribution / selectivity;	75.4%
With phosphoric acid In water at 20 - 50℃; Product distribution / selectivity;	73.7%

4-guanidinobenzoic acid (16060-65-4) + camostat (59721-28-7) → C28H29N7O6

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile for 48h; Reflux;	45.5 g

Upstream product

• 16060-65-4 4-guanidinobenzoic acid 
• 59721-16-3 p-hydroxyphenylacetic acid-N, N-dimethylcarbamoylmethyl ester 

Downstream Products

• 59721-29-8 camostat mesylate 

Relevant articles and documents

Acyl guanidine compound as well as preparation method and application thereof

The invention discloses an acyl guanidine compound with a structure as shown in a formula I (See the specification) and pharmaceutically acceptable salt thereof. The invention also discloses a preparation method of the compound. The invention also discloses a pharmaceutical composition taking the compound or pharmaceutically acceptable salt thereof as an active ingredient, and their application tothe prevention or treatment of diseases (such as hypertension, chronic congestive heart failure, antidiuretic hormone secretion disorder syndrome or hyponatremia caused by chronic heart failure/livercirrhosis/antidiuretic hormone secretion disorder) related to an arginine vasopressin V1a receptor, an arginine vasopressin V1b receptor and an arginine vasopressin V2 receptor.