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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23N3O
Molecular Weight 309.4054
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZYDAMINE

SMILES

CN(C)CCCOC1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3

InChI

InChIKey=CNBGNNVCVSKAQZ-UHFFFAOYSA-N
InChI=1S/C19H23N3O/c1-21(2)13-8-14-23-19-17-11-6-7-12-18(17)22(20-19)15-16-9-4-3-5-10-16/h3-7,9-12H,8,13-15H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C19H23N3O
Molecular Weight 309.4054
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/mesh/68001591

Benzydamine (benzydamine hydrochloride, PHARIXIA®) is a benzyl-indazole having analgesic, antipyretic, and anti-inflammatory effects. It is indicated for the relief of pain in acute sore throat and for the symptomatic relief of oro-pharyngeal mucositis caused by radiation therapy.

Originator

Curator's Comment: Fr. Patent No. 1,382,855; 21.02.1964; Assigned to Aziende Chimiche Riunite Angeloni Francesco, residant en Italie.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHARIXIA

Approved Use

PHARIXIA (benzydamine hydrochloride) is indicated for the relief of pain in acute sore throat and for the symptomatic relief of oro-pharyngeal mucositis caused by radiation therapy.
Primary
PHARIXIA

Approved Use

PHARIXIA (benzydamine hydrochloride) is indicated for the relief of pain in acute sore throat and for the symptomatic relief of oro-pharyngeal mucositis caused by radiation therapy.
PubMed

PubMed

TitleDatePubMed
Several therapies may prevent or reduce the severity of oral mucositis associated with cancer treatment.
2006
Benzydamine N-oxygenation as a measure of flavin-containing monooxygenase activity.
2006
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2006 Apr 19
Local irritant effects of topical oral sprays on oral mucosa in mice.
2006 Jan-Feb
Oral mucositis.
2006 May
An evaluation of the efficacy of aspirin and benzydamine hydrochloride gargle for attenuating postoperative sore throat: a prospective, randomized, single-blind study.
2006 Oct
Cancer treatment-induced mucositis pain: strategies for assessment and management.
2006 Sep
A pilot study of chlorhexidine and benzydamine oral rinses for the prevention and treatment of irradiation mucositis in patients with head and neck cancer.
2006 Sep-Oct
[Clinical experience with tantum rosa (benzydamine hydrochloride) in prophylaxis and treatment of vaginitis and proctitis, following radiotherapy of patients with cancer of the vagina and uterus].
2007
Recreational abuse with benzydamine hydrochloride (tantum rosa).
2007
Cytotoxicity of mouthrinses on epithelial cells by micronucleus test.
2007 Apr
Digital analysis of mouthrinses' staining characteristics on provisional acrylic resins.
2007 Apr
Interventions for treating oral mucositis for patients with cancer receiving treatment.
2007 Apr 18
Mucocutaneous lesions of Behcet's disease.
2007 Aug 31
Effect of leukocyte inhibitors benzydamine and cyclophosphamide, on lung injury caused by Tityus discrepans scorpion venom.
2007 Dec 15
Dexpanthenol pastille and benzydamine hydrochloride spray for the prevention of post-operative sore throat.
2007 Feb
Combined photocontact dermatitis to benzydamine hydrochloride and the emulsifiers, Span 60 and Tween 60 contained in Tantum cream.
2007 Jul
Reduction of mouth malodour and volatile sulphur compounds in intensive care patients using an essential oil mouthwash.
2007 Jul
Novel hydrogels via click chemistry: synthesis and potential biomedical applications.
2007 Jun
Effect of genetic variants of the human flavin-containing monooxygenase 3 on N- and S-oxygenation activities.
2007 Mar
Cancer treatment-induced oral mucositis.
2007 Mar-Apr
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2007 Oct 17
New pathways for alimentary mucositis.
2008
Antifungal effect of mouth rinses on oral Candida counts and salivary flow in treatment-naïve HIV-infected patients.
2008 Aug
Altered metabolism of growth hormone receptor mutant mice: a combined NMR metabonomics and microarray study.
2008 Jul 23
Effect of different mouth rinses on third molar surgery-related oral malodor.
2008 Mar
Spectrophotometric determination of benzydamine HCl, levamisole HCl and mebeverine HCl through ion-pair complex formation with methyl orange.
2008 Mar
Burning mouth syndrome.
2008 Mar 14
[Medicine consumption and the internet: critical evaluation of a virtual community].
2008 May-Jun
Evaluation of sutures after immersion in nonalcoholic benzydamine hydrochloride mouthrinse by scanning electron microscopy.
2008 Sep
Benzydamine hydrochloride buccal bioadhesive gels designed for oral ulcers: preparation, rheological, textural, mucoadhesive and release properties.
2009
[Misuse of substances theoretically without abuse potential--case series].
2009
Inter-individual variation in flavin-containing monooxygenase 3 in livers from Japanese: correlation with hepatic transcription factors.
2009
Stevens-Johnson Syndrome triggered by chemical hair relaxer: a case report.
2009 Aug 5
Ingestions of benzydamine-containing vaginal preparations.
2009 Feb
Relief of radiation-induced oral mucositis in head and neck cancer.
2009 Jan-Feb
Formulation studies of benzydamine mucoadhesive formulations for vaginal administration.
2009 Jul
Photopatch testing with an extended series of photoallergens: a 5-year study.
2009 Jun
Benzydamine for prophylaxis of radiation-induced oral mucositis in head and neck cancers: a double-blind placebo-controlled randomized clinical trial.
2009 Mar
Expression and characterization of functional dog flavin-containing monooxygenase 3.
2009 Oct
Recreational use of benzydamine as a hallucinogen among street youth in Brazil.
2009 Sep
Lymphomatoid photocontact dermatitis to benzydamine hydrochloride.
2010 Feb
Thermally sensitive gels based on chitosan derivatives for the treatment of oral mucositis.
2010 Feb
Respiratory symptoms and inflammatory responses to Difflam throat-spray intervention in half-marathon runners: a randomised controlled trial.
2010 Feb
Oral rinses, mouthwashes and sprays for improving recovery following tonsillectomy.
2010 Jan 20
Direct electrochemistry of drug metabolizing human flavin-containing monooxygenase: electrochemical turnover of benzydamine and tamoxifen.
2010 Jan 20
Hippocampal and caudate volume reductions in antipsychotic-naive first-episode schizophrenia.
2010 Mar
[Use abusive of benzydamine in Brazil: an overview in pharmacovigilance].
2010 May
Effect on postoperative sore throat of spraying the endotracheal tube cuff with benzydamine hydrochloride, 10% lidocaine, and 2% lidocaine.
2010 Oct
The development and in vitro evaluation of sustained release tablet formulations of benzydamine hydrochloride and its determination.
2010 Sep
Patents

Sample Use Guides

Not less than 15 mL of the liquid should be used for each gargle or rinse and repeated three or four times a day, depending on the severity of the treated condition. The liquid should be kept in contact with the inflamed mucosa for at least 30 seconds and then expelled from the mouth. Administration should begin the day prior to commencement of radiation therapy and continue daily during the treatment period as well as after cessation of radiation applications until desired improvement is obtained. In acute sore throat, gargle with 15 mL every 1.5 to 3 hours. The solution should be expelled from the mouth after use.
Route of Administration: Other
Benzydamine significantly reduced the basal production of both prostaglandin E2 (PGE2) and 6-keto-PGF1 alpha, the stable breakdown product of prostaglandin I2 (PGI2), in unstimulated human gingival fibroblasts. When the cells were treated simultaneously with benzydamine and the cytokines IL-1beta or TNF-alpha, the agent benzydamine reduced (P < 0.05) the stimulatory effect of IL-1beta and TNF-alpha respectively, on PGE2 and PGI2 production in human gingival fibroblasts. Furthermore, benzydamine reduced (P < 0.05) both the basal level and the cytokine-induced 3H-arachidonic acid release in gingival fibroblasts. The addition of exogenous arachidonic acid to the cells resulted in enhanced PGE2 production, which was reduced (P < 0.05) in the presence of benzydamine.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:41 UTC 2023
Edited
by admin
on Fri Dec 15 15:13:41 UTC 2023
Record UNII
4O21U048EF
Record Status Validated (UNII)
Record Version
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Name Type Language
BENZYDAMINE
INN   MI   WHO-DD  
INN  
Official Name English
Benzydamine [WHO-DD]
Common Name English
1-BENZYL-3-(3-(DIMETHYLAMINO)PROPOXY)-1H-INDAZOLE
Systematic Name English
1-PROPANAMINE, N,N-DIMETHYL-3-((1-(PHENYLMETHYL)-1H-INDAZOL-3-YL)OXY)-
Systematic Name English
BENZINDAMINE
Common Name English
benzydamine [INN]
Common Name English
N,N-DIMETHYL-3-((1-(PHENYLMETHYL)-1H-INDAZOL-3-YL)OXY)-1-PROPANAMINE
Systematic Name English
APO-BENZYDAMINE
Brand Name English
1-BENZYL-1H-INDAZOL-3-YL 3-(DIMETHYLAMINO)PROPYL ETHER
Systematic Name English
BENZYDAMINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QG02CC03
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-VATC QM02AA05
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-ATC M02AA05
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-ATC R02AX03
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-VATC QM01AX07
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-ATC G02CC03
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-ATC A01AD02
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-VATC QA01AD02
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
WHO-ATC M01AX07
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
Code System Code Type Description
INN
1927
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
SMS_ID
100000086414
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID7047859
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
DRUG CENTRAL
3881
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
MERCK INDEX
m2395
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY Merck Index
RXCUI
1425
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY RxNorm
MESH
D001591
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
FDA UNII
4O21U048EF
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
DRUG BANK
DB09084
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
WIKIPEDIA
Benzydamine
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
ECHA (EC/EINECS)
211-388-8
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL12610
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
PUBCHEM
12555
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
EVMPD
SUB05770MIG
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
CAS
642-72-8
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
CHEBI
134500
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
CHEBI
94563
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
NCI_THESAURUS
C83548
Created by admin on Fri Dec 15 15:13:41 UTC 2023 , Edited by admin on Fri Dec 15 15:13:41 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY