U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H20N2O2
Molecular Weight 260.3315
Optical Activity NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P16599
Gene ID: 103694380|||24835
Gene Symbol: Tnf
Target Organism: Rattus norvegicus (Rat)
4.16 null [pIC50]
3.44 null [pIC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Erespal

Approved Use

The drug is indicated in the complex therapy of respiratory diseases (upper and lower divisions): pharyngitis; Rhinopharyngitis; laryngitis; tracheitis; Tracheobronchitis; Bronchitis (with or without chronic respiratory failure); bronchial asthma; Respiratory symptoms with influenza, measles and whooping cough; sinusitis; otitis; Infection of the respiratory system, in the symptomatic complex of which there is a cough.
Primary
Erespal

Approved Use

The drug is indicated in the complex therapy of respiratory diseases (upper and lower divisions): pharyngitis; Rhinopharyngitis; laryngitis; tracheitis; Tracheobronchitis; Bronchitis (with or without chronic respiratory failure); bronchial asthma; Respiratory symptoms with influenza, measles and whooping cough; sinusitis; otitis; Infection of the respiratory system, in the symptomatic complex of which there is a cough.
Primary
Erespal

Approved Use

The drug is indicated in the complex therapy of respiratory diseases (upper and lower divisions): pharyngitis; Rhinopharyngitis; laryngitis; tracheitis; Tracheobronchitis; Bronchitis (with or without chronic respiratory failure); bronchial asthma; Respiratory symptoms with influenza, measles and whooping cough; sinusitis; otitis; Infection of the respiratory system, in the symptomatic complex of which there is a cough.
Primary
Erespal

Approved Use

The drug is indicated in the complex therapy of respiratory diseases (upper and lower divisions): pharyngitis; Rhinopharyngitis; laryngitis; tracheitis; Tracheobronchitis; Bronchitis (with or without chronic respiratory failure); bronchial asthma; Respiratory symptoms with influenza, measles and whooping cough; sinusitis; otitis; Infection of the respiratory system, in the symptomatic complex of which there is a cough.
Primary
Eurespal

Approved Use

Indications: Rinofaringitis, laryngitis — otitis, sinusitis — rinotraheobronhit — bronchitis — bronchial asthma (maintenance therapy) respiratory effects in measles, pertussis and influenza (syrup).
Primary
Eurespal

Approved Use

Indications: Rinofaringitis, laryngitis — otitis, sinusitis — rinotraheobronhit — bronchitis — bronchial asthma (maintenance therapy) respiratory effects in measles, pertussis and influenza (syrup).
PubMed

PubMed

TitleDatePubMed
[Effectiveness of fenspiride in patients with chronic obstructive bronchitis].
2001
[Experience in treating patients with chronic obstructive bronchitis with fenspirid].
2002
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
[ENT inflammation and importance of fenspiride].
2002 Sep
[Erespal effectiveness in exudative otitis media].
2003
[Fenspiride-a new alternative on the therapy of obstructive lung disease].
2003 Apr-Jun
[Acute intoxication with fenspiride].
2004
[Potential of antiinflammatory therapy in patients with chronic obstructive lung disease].
2005
[Effectiveness and tolerance of fenspiride treatment in chronic sinusitis. Results of the Polish multicenter study].
2005
[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
[Hearing rehabilitation in patients with acute otitis media treated with fenspiride].
2008
[Clinicofunctional condition and quality of life in patients with chronic obstructive pulmonary disease before and after outpatient treatment with fenspiride].
2008
[Experience with fenspiride in a rhinosurgeon's practice].
2009
[Efficiency of combination therapy for acute otitis media].
2010
[Pathogenetic correction of postoperative inflammation in modern rhinosurgery].
2010
[Experience in using erespal in the treatment of acute respiratory diseases in children in outpatient practice].
2010
Patents

Sample Use Guides

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
Curator's Comment: Fenspiride (10(-7)-10(-5) M) inhibited the histamine H1 receptor-induced Ca2+ increase in a lung epithelial cell line. Fenspiride (10(-5) M) abolished both phases of histamine-induced arachidonic acid release. https://www.ncbi.nlm.nih.gov/pubmed/9652346
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 Fri Dec 15 15:51:39 UTC 2023
Edited
by admin
on Fri Dec 15 15:51:39 UTC 2023
Record UNII
S983QC7HKM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENSPIRIDE
INN   MI   WHO-DD  
INN  
Official 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
Fenspiride [WHO-DD]
Common Name English
EURESPAL
Brand Name English
FENSPIRIDE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR03BX01
Created by admin on Fri Dec 15 15:51:39 UTC 2023 , Edited by admin on Fri Dec 15 15:51:39 UTC 2023
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:51:39 UTC 2023 , Edited by admin on Fri Dec 15 15:51:39 UTC 2023
WHO-ATC R03BX01
Created by admin on Fri Dec 15 15:51:39 UTC 2023 , Edited by admin on Fri Dec 15 15:51:39 UTC 2023
WHO-VATC QR03DX03
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WHO-ATC R03DX03
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Code System Code Type Description
ChEMBL
CHEMBL576127
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PRIMARY
EPA CompTox
DTXSID4023048
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PRIMARY
SMS_ID
100000081488
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PRIMARY
CAS
5053-06-5
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PRIMARY
PUBCHEM
3344
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PRIMARY
EVMPD
SUB07596MIG
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PRIMARY
DRUG CENTRAL
1163
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PRIMARY
WIKIPEDIA
FENSPIRIDE
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PRIMARY
DRUG BANK
DB08979
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PRIMARY
INN
2577
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PRIMARY
MERCK INDEX
m5296
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PRIMARY Merck Index
NCI_THESAURUS
C80880
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PRIMARY
RXCUI
4335
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PRIMARY RxNorm
MESH
C084775
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PRIMARY
ECHA (EC/EINECS)
225-751-3
Created by admin on Fri Dec 15 15:51:39 UTC 2023 , Edited by admin on Fri Dec 15 15:51:39 UTC 2023
PRIMARY
FDA UNII
S983QC7HKM
Created by admin on Fri Dec 15 15:51:39 UTC 2023 , Edited by admin on Fri Dec 15 15:51:39 UTC 2023
PRIMARY
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