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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O5S.C4H11N
Molecular Weight 263.3122
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHAMSYLATE

SMILES

c1cc(c(cc1O)S(=O)(=O)O)O.CCNCC

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 C6H6O5S
Molecular Weight 190.1752
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H11N
Molecular Weight 73.137
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Calcium dobesilate (brand name Doxium) is a veno-tonic drug, which is widely prescribed in more than 60 countries from Europe, Latin America, Asia and the Middle East for three main indications: chronic venous disease, diabetic retinopathy and the symptoms of haemorrhoidal attack. This drugs also in the phase III of clinical trial is an effective adjuvant therapy, with an absence of significant side-effects, in patients with venous ulcers and stasis dermatitis. It was suggested, that the inhibitory effect of calcium dobesilate on platelet function is mediated through the cyclic AMP pathway, and probably through activation of adenyl cyclase.

Originator

Sources: Esteve A, Canal J, Laporte J. Ensayo clinico de la accion del 141-E sobre los tiempos de coagulacion y sangria. Medicina Clinica 1959; 33: 249
Curator's Comment:: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/16772766

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Doxium

Approved Use

Unknown
Primary
Doxium

Approved Use

Unknown
Primary
Doxium

Approved Use

Unknown
Primary
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.
PubMed

PubMed

TitleDatePubMed
Clinical and experimental studies on the action of ethamsylate on haemostasis and on platelet functions.
1980 Sep 15
Etamsylate as inhibitor of prostaglandin biosynthesis in pregnant human myometrium in vitro.
1981 Nov 15
Effects of etamsylate on platelet functions and arachidonic acid metabolism.
1982 Dec 27
The hemostatic agent ethamsylate enhances P-selectin membrane expression in human platelets and cultured endothelial cells.
2002 Sep 15
The hemostatic agent ethamsylate promotes platelet/leukocyte aggregate formation in a model of vascular injury.
2004 Aug
Calcium dobesilate for chronic venous insufficiency: a systematic review.
2004 Mar-Apr
Therapeutic efficacy and mechanism of action of ethamsylate, a long-standing hemostatic agent.
2006 May-Jun
Calcium dobesilate inhibits the alterations in tight junction proteins and leukocyte adhesion to retinal endothelial cells induced by diabetes.
2010 Oct
Calcium dobesilate in patients suffering from chronic venous insufficiency: a double-blind, placebo-controlled, clinical trial.
2011 Jun
Strong Negative Interference by Calcium Dobesilate in Sarcosine Oxidase Assays for Serum Creatinine Involving the Trinder Reaction.
2015 Jun
Patents

Sample Use Guides

Oral. Menorrhagia - The recommended dose is 500 mg 4 times/day during menstruation. Control of hemorrhage after surgery - The recommended dose is 250-500 mg 4-6 hourly as needed. Adults. Presurgical: 1-2 ampoules i.v. or i.m. (250-500mg) 1 hour before surgery. Persurgical: 1-2 ampoules i.v. Repeat the dosage if necessary. Postsurgical: 1-2 ampoules (250-500mg) every 4-6 hours as long as the risk of bleeding persists. Emergency cases, according to the severity of the case: 1-2 ampoules i.v. or i.m. every 4-6 hours as long as the bleeding risk persists. Local treatment: soak a swab with the contents of one ampoule and apply to haemorrhagic area, or in the tooth socket after dental extraction. The application may be repeated if necessary; it may be associated with oral or parenteral administration. Children. Half the adult dose. Neonatology: 10mg per kg body weight (0,1ml=12,5mg) injected intramuscularly within 2 hours of birth then every 6 hours for 4 days.
Route of Administration: Other
Under basal conditions, ethamsylate was unable to modify whole-blood platelet-leukocyte aggregation, but following whole-blood perfusion through a damaged vessel, ethamsylate produced a modest, but significant increase in platelet-leukocyte aggregates at concentrations 20-40 uM
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:17:19 UTC 2021
Edited
by admin
on Fri Jun 25 21:17:19 UTC 2021
Record UNII
24YL531VOH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHAMSYLATE
MI   USAN  
USAN  
Official Name English
BENZENESULFONIC ACID, 2,5-DIHYDROXY-, COMPD. WITH N-ETHYLETHANAMINE (1:1)
Common Name English
ETAMSYLATE [INN]
Common Name English
ETAMSILATE [WHO-DD]
Common Name English
ETAMSYLATE
EP   INN   JAN   MART.  
INN  
Official Name English
ETAMSYLATE [EP MONOGRAPH]
Common Name English
ETAMSYLATE [MART.]
Common Name English
DIETHYLAMINE DOBESILATE
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
WHO-DD  
Common Name English
ETAMSYLATE [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC B02BX01
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
WHO-VATC QB02BX01
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
EU-Orphan Drug EU/3/18/2087
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
Code System Code Type Description
FDA UNII
24YL531VOH
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
MERCK INDEX
M5047
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
Etamsylate
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
MESH
D004979
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL1232131
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
NCI_THESAURUS
C171814
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
EPA CompTox
2624-44-4
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
EVMPD
SUB11943MIG
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
RXCUI
4112
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY RxNorm
INN
1903
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
DRUG CENTRAL
1075
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
PUBCHEM
17506
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
220-090-7
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
DRUG BANK
DB13483
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
CAS
2624-44-4
Created by admin on Fri Jun 25 21:17:19 UTC 2021 , Edited by admin on Fri Jun 25 21:17:19 UTC 2021
PRIMARY
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ACTIVE MOIETY