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Details

Stereochemistry ACHIRAL
Molecular Formula C15H20N2O2
Molecular Weight 260.3315
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENSPIRIDE

SMILES

O=C1NCC2(CCN(CCC3=CC=CC=C3)CC2)O1

InChI

InChIKey=FVNFBBAOMBJTST-UHFFFAOYSA-N
InChI=1S/C15H20N2O2/c18-14-16-12-15(19-14)7-10-17(11-8-15)9-6-13-4-2-1-3-5-13/h1-5H,6-12H2,(H,16,18)

HIDE SMILES / InChI

Molecular Formula C15H20N2O2
Molecular Weight 260.3315
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fenspiride is an oxazolidinone spiro compound used as a drug in the treatment of certain respiratory diseases. It is approved for use in Russia for the treatment of acute and chronic inflammatory diseases of ENT organs and the respiratory tract (like rhinopharyngitis, laryngitis, tracheobronchitis, otitis and sinusitis), as well as for maintenance treatment of asthma. Fenspiride is marketed under the brand names Eurespal, Pneumorel, SYRESP, Oxofen and others. Erespal (fenspiride) is a drug with a bronchodilator and spasmolytic effect, which is often used in the complex therapy of bronchial asthma. Fenspiride has a clinically proven ability to increase the activity of the cilia of the bronchial ciliated epithelium, normalize the secretion of the bronchi and reduce its viscosity. Effectively removes bronchial obstruction, restores pulmonary gas exchange. Inhibits the metabolism of arachidonic acid, in parallel blocking histamine H1-receptors, since it is histamine that stimulates the chemical reactions of the transformation of arachidonic acid into the final metabolites-factors of inflammation. Reduces the production of other mediators of inflammation - serotonin and bradykinin. It blocks α-adrenergic receptors, the activation of which increases the secretion of bronchial glands. The complex effect of fenspiride reduces the pathological effect of a number of factors that promote hypersecretion of anti-inflammatory substances and cause obstruction of the bronchial tree. Has a pronounced antispasmodic and myotropic effect.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Detection of fenspiride and identification of in vivo metabolites in horse body fluids by capillary gas chromatography-mass spectrometry: administration, biotransformation and urinary excretion after a single oral dose.
2002 Feb 5
[Erespal effectiveness in exudative otitis media].
2003
[Potential of antiinflammatory therapy in patients with chronic obstructive lung disease].
2005
[The effect of fenspiride on the number of exacerbations and the time of first exacerbation in patients with chronic bronchitis].
2005 Aug
[Anti-inflammatory therapy of paranasal sinuses diseases].
2006
Comparison of fenspiride with beclomethasone as adjunctive anti-inflammatory treatment in patients with chronic obstructive pulmonary disease.
2006
[Erespal in combined therapy of acute rhinosinusitis].
2006
[New pharmaceuticals in treatment of chronic dust bronchitis].
2007
Patents

Sample Use Guides

In Vivo Use Guide
Tablets: One tablet (80 mg) twice-thrice a day. The maximum dose for a daily intake is 240 mg (3 tablets). Syrup: For 45-90 milliliters (3-6 tablespoons, respectively) per day.
Route of Administration: Oral
In Vitro Use Guide
Fenspiride (10(-6) to 10(-4) M) inhibited the nonadrenergic, noncholinergic (NANC) component of the contraction of the guinea-pig isolated main bronchus induced by EFS. Fenspiride significantly affected contractions induced by exogenously added substance P or [Nle10]-NKA(4-10) only at concentrations higher than 10(-3) M. In the guinea-pig perfused lung, fenspiride inhibited low pH- but not capsaicin-evoked release of CGRP. At higher concentrations (10(-4) M to 3x10(-4) M) fenspiride exhibited a significant inhibitory effect both on the cholinergic component of contractile response induced by EFS in the guinea-pig isolated main bronchus and on exogenously added acetylcholine.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:33:03 UTC 2019
Edited
by admin
on Tue Oct 22 00:33:03 UTC 2019
Record UNII
S983QC7HKM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENSPIRIDE
INN   MI   WHO-DD  
INN  
Official Name English
FENSPIRIDE [WHO-DD]
Common Name English
1-OXA-3,8-DIAZASPIRO(4,5)DECAN-2-ONE, 8-(2-PHENYLETHYL)-
Systematic Name English
FENSPIRIDE [INN]
Common Name English
8-PHENETHYL-1-OXA-3,8-DIAZASPIRO(4.5)DECAN-2-ONE
Systematic Name English
EURESPAL
Brand Name English
FENSPIRIDE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR03BX01
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
NCI_THESAURUS C29707
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
WHO-ATC R03BX01
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
WHO-VATC QR03DX03
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
WHO-ATC R03DX03
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL576127
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
EPA CompTox
5053-06-5
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
CAS
5053-06-5
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
PUBCHEM
3344
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
EVMPD
SUB07596MIG
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
WIKIPEDIA
FENSPIRIDE
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
DRUG BANK
DB08979
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
INN
2577
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
MERCK INDEX
M5296
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C80880
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
RXCUI
4335
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY RxNorm
MESH
C084775
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
ECHA (EC/EINECS)
225-751-3
Created by admin on Tue Oct 22 00:33:03 UTC 2019 , Edited by admin on Tue Oct 22 00:33:03 UTC 2019
PRIMARY
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SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY