ETHAMSYLATE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6O5S.C4H11N
Molecular Weight	263.311
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNCC.OC1=CC(=C(O)C=C1)S(O)(=O)=O

InChI

InChIKey=HBGOLJKPSFNJSD-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C4H11N
Molecular Weight	73.1368
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C6H6O5S
Molecular Weight	190.174
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15230646 | https://www.ncbi.nlm.nih.gov/pubmed/2847355https://www.ncbi.nlm.nih.gov/pubmed/16772766
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7319004 | https://www.ncbi.nlm.nih.gov/pubmed/15312148

Ethamsylate (2,5-dihydroxy-benzene-sulfonate diethylammonium salt) is a synthetic hemostatic drug indicated in cases of capillary bleeding. Ethamsylate acts on the first step of hemostasis by improving platelet adhesiveness and restoring capillary resistance. In addition it inhibits prostaglandin biosynthesis. Well-controlled clinical trials clearly showed the therapeutic efficacy of ethamsylate in dysfunctional uterine bleeding, with the magnitude of blood-loss reduction being directly proportional to the severity of the menorrhagia. Other well-controlled clinical trials showed therapeutic efficacy of ethamsylate in periventricular hemorrhage in very low birth weight babies and surgical or postsurgical capillary bleeding.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
prostaglandin biosynthetic process 23 Target ID: GO:0001516 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7319004	Inhibitor 8504
platelet activation 9 Target ID: GO:0030168 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7193361 \| https://www.ncbi.nlm.nih.gov/pubmed/6819650 \| https://www.ncbi.nlm.nih.gov/pubmed/15312148 \| https://www.ncbi.nlm.nih.gov/pubmed/12565720	Activator 1447
cAMP signaling pathway 8 Target ID: map04024 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2847355	Activator 1447
Adenylate cyclase 13 Target ID: CHEMBL2097167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2847355	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Chronic venous insufficiency 12 Sources: http://www.farmaciasahumada.cl/fasa/MFT/PRODUCTO/P229.HTM	Primary	Approved 8583	Doxium Approved Use Unknown
Diabetic microangiopathy 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15230646	Primary	Approved 8583	Doxium Approved Use Unknown
Venous ulcers 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12709007	Primary	Phase III 665	Doxium Approved Use Unknown
Hemorrhage 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16772766	Primary	Approved 8583	DICYNONE Approved Use ETHAMSYLATE is a haemostatic agent. It reduces bleeding from capillaries. Oral form prescribed for the management of blood loss in menorrhagia. Parenteral form used in surgery: prevention and treatment of pre-, per-, or postsurgical capillary haemorrhages in all delicate operations and in those affecting highly vascularised tissues: E.N.T., gynaecology, obstetrics, urology, odontostomatology, ophthalmology, plastic and reconstructive surgery. It also is used in paediatrics for the prevention of periventricular haemorrhages in premature babies.

C_max

Value	Dose	Co-administered	Analyte	Population
8.05 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24227961/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMSYLATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
15 μg/mL DRUG LABEL https://webcache.googleusercontent.com/search?q=cache:_8wbgGwkacYJ:https://mri.cts-mrp.eu/Human/Downloads/PL_H_0390_001_FinalSPC.pdf+&cd=11&hl=ru&ct=clnk&gl=ru&lr=lang_en%7Clang_ru	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMSYLATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
84.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24227961/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMSYLATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24227961/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMSYLATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.7 h DRUG LABEL https://webcache.googleusercontent.com/search?q=cache:_8wbgGwkacYJ:https://mri.cts-mrp.eu/Human/Downloads/PL_H_0390_001_FinalSPC.pdf+&cd=11&hl=ru&ct=clnk&gl=ru&lr=lang_en%7Clang_ru	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMSYLATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% DRUG LABEL https://webcache.googleusercontent.com/search?q=cache:_8wbgGwkacYJ:https://mri.cts-mrp.eu/Human/Downloads/PL_H_0390_001_FinalSPC.pdf+&cd=11&hl=ru&ct=clnk&gl=ru&lr=lang_en%7Clang_ru	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMSYLATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
500 mg 4 times / day multiple, oral Recommended Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1883797/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1883797/	Sources: https://pubmed.ncbi.nlm.nih.gov/1883797/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252 activator 150	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1MTQ3MTUifX0=	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1MTQ3MTUifX0=	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1MTQ3MTUifX0=	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTUxNDcxNSJ9fQ==	no [IC50 >10 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/17506#section=BioAssay-Results Page: 59.0	no
CYP3A4 2633	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/17506#section=BioAssay-Results Page: 10.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/17506#section=BioAssay-Results Page: 65.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/17506#section=BioAssay-Results Page: 3.0	yes [IC50 18.9991 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/17506#section=BioAssay-Results Page: 62 \| 65	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/17506#section=BioAssay-Results Page: 44.0

PubMed

Title	Date	PubMed
Strong Negative Interference by Calcium Dobesilate in Sarcosine Oxidase Assays for Serum Creatinine Involving the Trinder Reaction.	2015-06	26061311
Calcium dobesilate in patients suffering from chronic venous insufficiency: a double-blind, placebo-controlled, clinical trial.	2011-06	21478142
Calcium dobesilate inhibits the alterations in tight junction proteins and leukocyte adhesion to retinal endothelial cells induced by diabetes.	2010-10	20627932
Therapeutic efficacy and mechanism of action of ethamsylate, a long-standing hemostatic agent.	2006-06-15	16772766
The hemostatic agent ethamsylate promotes platelet/leukocyte aggregate formation in a model of vascular injury.	2004-08	15312148
Calcium dobesilate for chronic venous insufficiency: a systematic review.	2004-03-18	15026869
The hemostatic agent ethamsylate enhances P-selectin membrane expression in human platelets and cultured endothelial cells.	2002-09-15	12565720
Effects of etamsylate on platelet functions and arachidonic acid metabolism.	1982-12-27	6819650
Etamsylate as inhibitor of prostaglandin biosynthesis in pregnant human myometrium in vitro.	1981-11-15	7319004
Clinical and experimental studies on the action of ethamsylate on haemostasis and on platelet functions.	1980-09-15	7193361

Patents

Sample Use Guides

In Vivo Use Guide

2 capsules per day. In chronic venous insufficiency a treatment of 3 weeks allows, in most cases, to obtain a lasting improvement. Repeat treatment 3 times a year. In severe cases the initial dose can be increased to 3 or 4 capsules daily. In diabetic microangiopathy: 2 to 3 capsules per day

Route of Administration: Oral

In Vitro Use Guide

Calcium dobesilate was tested in vitro for its protective action against oxidative/inflammatory stress in human varicose veins. Varicose greater saphenous veins were obtained from 14 patients. Calcium dobesilate significantly prevented oxidative disturbances in the micromolar range. PMS/NADH-dependent total antioxidant status (TAS) decrease was fully prevented with IC(50) = 11.4 ± 2.3 µmol/L (n = 6 veins), whereas malondialdehyde (MDA) increase was fully prevented with IC(50) = (102 ± -3) µmol/L (n = 6 veins). Calcium dobesilate acted quali- and quantitatively like rutin, the reference compound. Comparison with pharmacokinetic data suggests that calcium dobesilate can act at therapeutic concentrations.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:39:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:39:28 GMT 2025`
Record UNII	24YL531VOH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ETAMSYLATE

Preferred Name

English

ETHAMSYLATE

Official Name

English

BENZENESULFONIC ACID, 2,5-DIHYDROXY-, COMPD. WITH N-ETHYLETHANAMINE (1:1)

Common Name

English

etamsylate [INN]

Common Name

English

ETAMSYLATE [EP MONOGRAPH]

Common Name

English

ETAMSYLATE [MART.]

Common Name

English

DIETHYLAMINE DOBESILATE

Common Name

English

Etamsilate [WHO-DD]

Common Name

English

MD-141

Code

English

E 141

Code

English

MD 141

Code

English

E-141

Code

English

ETHAMSYLATE [MI]

Common Name

English

ETHAMSYLATE [USAN]

Common Name

English

2,5-Dihydroxybenzenesulfonic acid compound with diethylamine (1:1)

Systematic Name

English

ETAMSILATE

Common Name

English

ETAMSYLATE [JAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

B02BX01