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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H36O16
Molecular Weight 652.5972
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HIDROSMIN

SMILES

COC1=CC=C(C=C1O)C2=CC(=O)C3=C(OCCO)C=C(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2

InChI

InChIKey=XYFLWVOTXWXNAM-WTNNCJBMSA-N
InChI=1S/C30H36O16/c1-12-23(34)25(36)27(38)29(43-12)42-11-21-24(35)26(37)28(39)30(46-21)44-14-8-19(41-6-5-31)22-16(33)10-18(45-20(22)9-14)13-3-4-17(40-2)15(32)7-13/h3-4,7-10,12,21,23-32,34-39H,5-6,11H2,1-2H3/t12-,21+,23-,24+,25+,26-,27+,28+,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H36O16
Molecular Weight 652.5972
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Hidrosmin, a synthetic bioflavonoid, is a phlebotonic (capillary stabilising agent). It is marketed under the brand name Venosmil among others. Venosmil is a medicinal product indicated for: short-term (2-3 months) relief from oedema and symptoms related to chronic venous insufficiency in adults. Although the mechanism of action of hidrosmin has not been fully elucidated, it could be related toinhibition of the degradation of catecholamines, specifically inhibition of catechol-O-methyltransferase. Although the exact mechanism of action is unknown, hidrosmin has four main pharmacological actions: 1.It reduces the capillary permeability induced by various agents such as histamine, bradykinin, etc. and reduces the capillary fragility induced by a deficiency diet. 2.It increases the deformability of red blood cells and the viscosity of the blood. 3.It induces the contraction of smooth muscle in the vein wall in a gradual and sustained manner. 4.It produces dilation of the lymphatic collectors and increases the rate of lymphatic conduction, thereby improving lymphatic flow. The efficacy of Venosmil was evaluated in two clinical trials in a total of 70 patients with acute and chronic venous disease, who were treated with 200 mg hidrosmin orally three times per day and/or 2 g hidrosmin topically (gel) two or three times per day for one and two months Hidrosmin was effective at reducing oedema, ulcers and varicose eczema. Venosmil therefore possesses intrinsic activity against the consequences of venous stasis secondary to varicose dilation of the veins in the lower limbs, producing an improvement in the clinical symptoms of peripheral venous insufficiency (pain, heaviness, oedema, etc.) that is significantly different to that produced by placebo.

Originator

Curator's Comment: 1978 was the year of one of the events that spurred the growth and development of Laboratorios Faes Farma: the synthesis of hidrosmin, which would be subsequently marketed under the brand-name Venosmil in 1987.

Approval Year

PubMed

PubMed

TitleDatePubMed
[A double-blind study comparing the clinical efficacy of the preparation F-117 (hidrosmin) versus diosmin in the treatment of patients with peripheral venous disorders].
1990 Apr-Jun
Therapeutic effects of hidrosmin on chronic venous insufficiency of the lower limbs.
1992

Sample Use Guides

In Vivo Use Guide
Curator's Comment: After oral, intraperitoneal and intravenous administration in rat and mouse, the acute LD50 for hidrosmin is very high (>5000 mg/kg) with respect to the clinical dose (10 mg/kg/day).
Adults: VENOSMIL capsules: One 200 mg capsule three times a day. VENOSMIL gel: Three applications per day Method of administration VENOSMIL capsules Oral route. Once removed from the blister, the capsule must be taken immediately. It can be taken with water or another drink to aid swallowing. VENOSMIL gel: Cutaneous use. For external use only on intact skin. 1.Unscrew the cap of the tube and perforate the metal opening of the tube sufficiently using the back of the cap. 2.Apply approximately 3-4 cm of product to the skin. 3.Spread over the affected region by gently rubbing to form a thin layer of gel.
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:39 UTC 2023
Edited
by admin
on Sat Dec 16 01:37:39 UTC 2023
Record UNII
4I5K8199OQ
Record Status Validated (UNII)
Record Version
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Name Type Language
HIDROSMIN
WHO-DD  
Common Name English
O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-(2-HYDROXYETHOXY)-2-(3-HYDROXY-4-METHOXYPHENYL)-
Common Name English
Hidrosmin [WHO-DD]
Common Name English
5-O-(.BETA.-HYDROXYETHYL)DIOSMIN
Common Name English
Classification Tree Code System Code
WHO-ATC C05CA05
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
WHO-VATC QC05CA05
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
Code System Code Type Description
PUBCHEM
3087722
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
MESH
C071047
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
DRUG BANK
DB13490
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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DRUG CENTRAL
3956
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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CAS
115960-14-0
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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EPA CompTox
DTXSID90151237
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
FDA UNII
4I5K8199OQ
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
WIKIPEDIA
Hidrosmin
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL3707286
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
SMS_ID
100000077943
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY
EVMPD
SUB14104MIG
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY