Etamsylate Chemical Properties

Melting point:

125°

Density 

1.3441 (rough estimate)

refractive index 

1.5060 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Very soluble in water, freely soluble in methanol, soluble in anhydrous ethanol, practically insoluble in methylene chloride.

form 

Solid

color 

White to Pale Red

Merck 

14,3722

Stability:

Hygroscopic

InChI

InChI=1S/C6H6O5S.C4H11N/c7-4-1-2-5(8)6(3-4)12(9,10)11;1-3-5-4-2/h1-3,7-8H,(H,9,10,11);5H,3-4H2,1-2H3

InChIKey

HBGOLJKPSFNJSD-UHFFFAOYSA-N

SMILES

C1(S(=O)(=O)O)=CC(=CC=C1O)O.N(CC)CC

CAS DataBase Reference

2624-44-4(CAS DataBase Reference)

EPA Substance Registry System

Ethamsylate (2624-44-4)

Safety Information

WGK Germany 

WGK 3

RTECS 

DB6145000

TSCA 

TSCA listed

HS Code 

2921.19.6190

HazardClass 

IRRITANT

Storage Class

11 - Combustible Solids

Toxicity

LD50 i.v. in mice, rats: 800, 1350 mg/kg (Esteve)

MSDS

• Language:English Provider:Etamsylate

Etamsylate Usage And Synthesis

Chemical Properties

White Solid

Uses

Haemostatic / Anti Coagulant

Uses

Hemostatic;prostaglandin synthesis inhibitor

Definition

ChEBI: Etamsylate is a sulfonic acid derivative and an organosulfur compound.

Biological Activity

Etamsylate is a haemostatic agent th at is used for the management of blood loss. Apparently etamsylate increases capillary wall resistance and platelet adhesives by inhibition of the biosynthesis of prostaglandins causing platelet disaggregation in a presence of vascular wound. Recent studies suggest th at etamsylate antagonizes anti-coagulant activity of heparin.

Mechanism of action

Etamsylate is an antihaemorrhagic and vasoprotective agent. It increases platelet adhesiveness and capillary vascular wall resistance, thereby reducing capillary exudation and blood loss.

Clinical Use

Short-term treatment of blood loss in menorrhagia
Prophylaxis of surgical bleeding (unlicensed)

Side effects

Significant: Hypotension (parenteral). Rarely, severe hypersensitivity reaction, including anaphylaxis.
Blood and lymphatic system disorders: Parenteral: Rarely, neutropenia, agranulocytosis, thrombocytopenia.
Gastrointestinal disorders: Nausea, vomiting, diarrhoea, abdominal pain or discomfort.
General disorders and administration site conditions: Asthenia (parenteral). Rarely, fever.
Musculoskeletal and connective tissue disorders: Rarely, arthralgia.
Nervous system disorders: Headache.
Skin and subcutaneous tissue disorders: Rash.
Vascular disorders: Rarely, thromboembolism (parenteral).

Synthesis

Nowadays, the production methods of etamsylate in the market are benzoquinone method, in which benzoquinone method is to pass sulfur dioxide in the solution of diethylamine, ethanol and water, and then make diethylamine sulfite salt, then add p-benzoquinone into diethylamine sulfite salt solution under low temperature, and then distill and recycle the ethanol under reduced pressure after the reaction is finished and precipitate out the crude product after cooling, and then add sodium bisulfite and activated carbon to decolorize it in the water or diluted ethanol and then refine it to obtain the product, the The disadvantages of the process are: due to the incomplete reaction of p-benzoquinone, coupled with the solubility of phenolsulfonyl ethylamine in water and ethanol, so that the product yield is low, generally not more than 40%, and p-benzoquinone is more expensive, the use of sulfur dioxide, there are problems such as absorption of the tail gas.
Also on the market is the use of chlorosulfonic acid as a sulfonation agent, before sulfonation so that p-benzoquinone and organic solvents azeotropic dehydration to anhydrous, but this method uses organic solvents, pollution of the environment, which in the process of sulfonation reaction of hydrogen chloride gas, pollution of the environment.

Metabolism

Etamsylate is excreted unchanged, mainly in the urine.

Etamsylate(2624-44-4)Related Product Information

• Calcium dobesilate
• Amlodipine Besylate
• Sulfanilic acid
• Ethylamine
• Glycine
• Benzenesulfonic acid
• Dodecylbenzenesulphonic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Diethylamine hydrochloride
• ETAMSYLATE FOR INJECTION
• Diethylamine
• PHENOLSULFONIC ACID
• Etamsylate
• ETAMSYLATE EPE(CRM STANDARD)
• phosphoric acid