Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  API >  Digestive system drugs >  Other digestive system drugs >  Gabexate mesylate

Gabexate mesylate

Basic information Safety Supplier Related

Gabexate mesylate Basic information

Product Name:
Gabexate mesylate
Synonyms:
  • 4-[[6-[(Amino-iminomethyl)amino]-1-oxohexyl]oxy]benzoic acid ethyl ester monomethanesulfonate
  • Gapexate Mesylate
  • Megacert
  • Agalit
  • Arodate
  • FOY-007
  • FOY-S 983
  • Mesyl Gabexate
CAS:
56974-61-9
MF:
C17H27N3O7S
MW:
417.48
EINECS:
611-438-2
Product Categories:
  • Aromatics
  • Inhibitors
  • Benzoic acid
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Other APIs
  • Active Pharmaceutical Ingredients
Mol File:
56974-61-9.mol
More
Less

Gabexate mesylate Chemical Properties

Melting point:
89.0 to 93.0 °C
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
form 
solid
Merck 
14,4320
InChIKey
DNTNDFLIKUKKOC-UHFFFAOYSA-N
CAS DataBase Reference
56974-61-9(CAS DataBase Reference)
More
Less

Safety Information

Hazard Codes 
Xn
RIDADR 
3077
WGK Germany 
2
RTECS 
DG2800800
HS Code 
29252900
Toxicity
LD50 in mice (mg/kg): 8000 orally; 4700 s.c.; 25 i.v. (Fujita)

MSDS

More
Less

Gabexate mesylate Usage And Synthesis

Chemical Properties

Gabexate mesylate is supplied as a crystalline solid. A stock solution may be made by dissolving the gabexate (mesylate) in the solvent of choice. Gabexate (mesylate) is soluble in organic solvents such as DMSO and dimethyl formamide, which should be purged with an inert gas. The solubility of gabexate (mesylate) in these solvents is approximately 25 mg/ml.
Gabexate is a competitive inhibitor of serine proteases that inhibits human thrombin, urokinase, plasmin, and Factor Xa (Kis = 0.97, 1.3, 1.6, and 8.5 μM, respectively). It also inhibits bovine thrombin, Factor Xa, and trypsin, and porcine plasma kallikrein (Kis = 1.4, 2.1, 2.6, and 0.2 μM, respectively). In vitro, gabexate inhibits clotting activity of thrombin (IC50 = 10 μM).In vivo, it inhibits fibrin formation in rats when administered at a continuous infusion of 120 μmol/kg per hour. Gabexate inhibits LPS-stimulated TNF-α production from monocytes by inhibiting binding of NF-κB and activator protein 1 (AP-1) to target sites and inducing degradation of IκBα.

Originator

Gabexate Mesylate,Shangai Lansheng

Uses

Gabexate Mesylate is a serine protease inhibitor. Gabexate Mesylate inhibits trypsin, plasmin, plasma kallikrein and thrombin. Gabexate Mesylate inhibits lipopolysaccharide-induced tumor necrosis factor-α (TNF-α) production through nuclear factor-κB and activator protein-1 activation.

Uses

Pancreatitis;Serine protease inhibitor.
Gabexate Mesylate is a serine protease inhibitor with IC50 of 0.19 μM which is used therapeutically in the treatment of pancreatitis and disseminated intravascular coagulation.

Preparation

Guanidinocaproic acid p-tosyl salt and thionyl chloride were mixed together toreact at the room temperature. An endothermic reaction occurred and thecaproic acid gradually dissolved. Then the reaction mixture was left standingfor 1 to 2 h and was extracted with ether. The lower oily layer and the etherlayer were separated from each other and the lower layer was repeatedlywashed with ether. Then the oily substance (caproic acid chloride) was addedwith benzoic acid ethyl ester in tetrahydrofuran, and the mixture was stirred.After the mixture became a uniform solution, of pyridine were graduallyadded. An exothermic reaction occurred and an oily substance came to beseparated in the lower layer. After the completion of the reaction, the oilysubstance was washed with water and then recrystallized from hot water onceor twice. Thus 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester salt wasobtained as white crystals.
To obtained the base 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl esterthe 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester salt must be treatedby, for example, sodium hydroxide.
In practice it is usually used as gabexate Mesylate.

Manufacturing Process

Guanidinocaproic acid p-tosyl salt and thionyl chloride were mixed together to react at the room temperature. An endothermic reaction occurred and the caproic acid gradually dissolved. Then the reaction mixture was left standing for 1 to 2 h and was extracted with ether. The lower oily layer and the ether layer were separated from each other and the lower layer was repeatedly washed with ether. Then the oily substance (caproic acid chloride) was added with benzoic acid ethyl ester in tetrahydrofuran, and the mixture was stirred. After the mixture became a uniform solution, of pyridine were gradually added. An exothermic reaction occurred and an oily substance came to be separated in the lower layer. After the completion of the reaction, the oily substance was washed with water and then recrystallized from hot water once or twice. Thus 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester salt was obtained as white crystals.
To obtained the base 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester the 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester salt must be treated by, for example, sodium hydroxide.
In practice it is usually used as mesylate.

Therapeutic Function

Enzyme inhibitor

Mechanism of action

Gabexate mesilate (FOY-007) is a protease inhibitor with a broad spectrum inhibiting not only trypsin and kallikrein, but also plasmin, thrombin,factor Xa, elastase, complement 1 (C1), esterase and phospholipase A2. Prophylactic application of FOY-007 or Camostat mesilate (FOY-305) showed some beneficial effect in CDEinduced pancreatitis, cerulein-induced panceratitis and sodium taurocholate-induced panceratitis. The therapeutic effect of FOY-007 in acute panceratitis has been ascribed to its inhibition of pancreatic enzyme activity, like trypsin, thus preventing autodigestion.

Clinical Use

Gabexate mesylate inhibits proteases and suppresses endothelial cell injury and may be used to treat DIC ascribed to various kinds of diseases.
Therapeutic Function: Enzyme inhibitor

Gabexate mesylate Preparation Products And Raw materials

Raw materials

Gabexate mesylateSupplier

Shanghai Hongbang Pharmaceutical Co., Ltd. Gold
Tel
021-24280809-
Email
1377976036@qq.com;
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Email
jkinfo@jkchemical.com;market6@jkchemical.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Email
3bsc@sina.com
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Email
Sales-CN@TCIchemicals.com
Capot Chemical Co., Ltd
Tel
+86 (0) 571 85 58 67 18
Email
sales@capotchem.com