Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H23N3O.ClH |
| Molecular Weight | 345.866 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)CCCOC1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3
InChI
InChIKey=HNNIWKQLJSNAEQ-UHFFFAOYSA-N
InChI=1S/C19H23N3O.ClH/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;1H
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68001591
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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0002539 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4044146 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PHARIXIA Approved UsePHARIXIA (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 UsePHARIXIA (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. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
68 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
459 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
35 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
100 mg single, oral transmucosal dose: 100 mg route of administration: Oral transmucosal experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
546 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
14 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
100 mg single, topical dose: 100 mg route of administration: Topical experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
10 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
140 mg single, vaginal dose: 140 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
0.8 μg/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
541 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4907 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
494 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
100 mg single, oral transmucosal dose: 100 mg route of administration: Oral transmucosal experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4994 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
455 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
100 mg single, topical dose: 100 mg route of administration: Topical experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
162 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
140 mg single, vaginal dose: 140 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
60.996 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819/ |
6 mg single, vaginal dose: 6 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
17.284 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819/ |
6 mg single, vaginal dose: 6 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
BENZYDAMINE N-OXIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
100.264 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819/ |
6 mg 1 times / day multiple, vaginal dose: 6 mg route of administration: Vaginal experiment type: MULTIPLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
30.477 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819/ |
6 mg 1 times / day multiple, vaginal dose: 6 mg route of administration: Vaginal experiment type: MULTIPLE co-administered: |
BENZYDAMINE N-OXIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
100 mg single, oral transmucosal dose: 100 mg route of administration: Oral transmucosal experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1932611/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
13 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZYDAMINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50.4 mg 1 times / day multiple, oral Studied dose Dose: 50.4 mg, 1 times / day Route: oral Route: multiple Dose: 50.4 mg, 1 times / day Sources: |
unhealthy, ADOLESCENT|ADULT Health Status: unhealthy Age Group: ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Urticaria, Angioedema... AEs leading to discontinuation/dose reduction: Urticaria (2.2%) Sources: Angioedema (2.2%) |
1.5 mg/mL 1 times / 3 hours multiple, oromucosal Recommended Dose: 1.5 mg/mL, 1 times / 3 hours Route: oromucosal Route: multiple Dose: 1.5 mg/mL, 1 times / 3 hours Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Pain burning, Stinging... AEs leading to discontinuation/dose reduction: Pain burning Sources: Stinging |
50 mg 3 times / day multiple, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Angioedema | 2.2% Disc. AE |
50.4 mg 1 times / day multiple, oral Studied dose Dose: 50.4 mg, 1 times / day Route: oral Route: multiple Dose: 50.4 mg, 1 times / day Sources: |
unhealthy, ADOLESCENT|ADULT Health Status: unhealthy Age Group: ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Urticaria | 2.2% Disc. AE |
50.4 mg 1 times / day multiple, oral Studied dose Dose: 50.4 mg, 1 times / day Route: oral Route: multiple Dose: 50.4 mg, 1 times / day Sources: |
unhealthy, ADOLESCENT|ADULT Health Status: unhealthy Age Group: ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Pain burning | Disc. AE | 1.5 mg/mL 1 times / 3 hours multiple, oromucosal Recommended Dose: 1.5 mg/mL, 1 times / 3 hours Route: oromucosal Route: multiple Dose: 1.5 mg/mL, 1 times / 3 hours Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Stinging | Disc. AE | 1.5 mg/mL 1 times / 3 hours multiple, oromucosal Recommended Dose: 1.5 mg/mL, 1 times / 3 hours Route: oromucosal Route: multiple Dose: 1.5 mg/mL, 1 times / 3 hours Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| yes [IC50 5.0119 uM] | ||||
| yes [IC50 7.9433 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 5 | 66 |
inconclusive | |||
| major [Km 40.4 uM] | ||||
| major | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Km 23.6 uM] |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect on postoperative sore throat of spraying the endotracheal tube cuff with benzydamine hydrochloride, 10% lidocaine, and 2% lidocaine. | 2010-10 |
|
| The development and in vitro evaluation of sustained release tablet formulations of benzydamine hydrochloride and its determination. | 2010-09 |
|
| [Use abusive of benzydamine in Brazil: an overview in pharmacovigilance]. | 2010-05 |
|
| Hippocampal and caudate volume reductions in antipsychotic-naive first-episode schizophrenia. | 2010-03 |
|
| Lymphomatoid photocontact dermatitis to benzydamine hydrochloride. | 2010-02 |
|
| Thermally sensitive gels based on chitosan derivatives for the treatment of oral mucositis. | 2010-02 |
|
| Respiratory symptoms and inflammatory responses to Difflam throat-spray intervention in half-marathon runners: a randomised controlled trial. | 2010-02 |
|
| Oral rinses, mouthwashes and sprays for improving recovery following tonsillectomy. | 2010-01-20 |
|
| Direct electrochemistry of drug metabolizing human flavin-containing monooxygenase: electrochemical turnover of benzydamine and tamoxifen. | 2010-01-20 |
|
| Expression and characterization of functional dog flavin-containing monooxygenase 3. | 2009-10 |
|
| Recreational use of benzydamine as a hallucinogen among street youth in Brazil. | 2009-09 |
|
| Stevens-Johnson Syndrome triggered by chemical hair relaxer: a case report. | 2009-08-05 |
|
| Formulation studies of benzydamine mucoadhesive formulations for vaginal administration. | 2009-07 |
|
| Photopatch testing with an extended series of photoallergens: a 5-year study. | 2009-06 |
|
| Benzydamine for prophylaxis of radiation-induced oral mucositis in head and neck cancers: a double-blind placebo-controlled randomized clinical trial. | 2009-03 |
|
| Ingestions of benzydamine-containing vaginal preparations. | 2009-02 |
|
| 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 |
|
| Relief of radiation-induced oral mucositis in head and neck cancer. | 2008-12-24 |
|
| Evaluation of sutures after immersion in nonalcoholic benzydamine hydrochloride mouthrinse by scanning electron microscopy. | 2008-09 |
|
| Antifungal effect of mouth rinses on oral Candida counts and salivary flow in treatment-naïve HIV-infected patients. | 2008-08 |
|
| Altered metabolism of growth hormone receptor mutant mice: a combined NMR metabonomics and microarray study. | 2008-07-23 |
|
| Burning mouth syndrome. | 2008-03-14 |
|
| Effect of different mouth rinses on third molar surgery-related oral malodor. | 2008-03 |
|
| Spectrophotometric determination of benzydamine HCl, levamisole HCl and mebeverine HCl through ion-pair complex formation with methyl orange. | 2008-03 |
|
| New pathways for alimentary mucositis. | 2008 |
|
| Effect of leukocyte inhibitors benzydamine and cyclophosphamide, on lung injury caused by Tityus discrepans scorpion venom. | 2007-12-15 |
|
| Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2007-10-17 |
|
| Mucocutaneous lesions of Behcet's disease. | 2007-08-31 |
|
| Combined photocontact dermatitis to benzydamine hydrochloride and the emulsifiers, Span 60 and Tween 60 contained in Tantum cream. | 2007-07 |
|
| Reduction of mouth malodour and volatile sulphur compounds in intensive care patients using an essential oil mouthwash. | 2007-07 |
|
| Novel hydrogels via click chemistry: synthesis and potential biomedical applications. | 2007-06 |
|
| Cancer treatment-induced oral mucositis. | 2007-05-01 |
|
| Interventions for treating oral mucositis for patients with cancer receiving treatment. | 2007-04-18 |
|
| [Medicine consumption and the internet: critical evaluation of a virtual community]. | 2007-04-05 |
|
| Cytotoxicity of mouthrinses on epithelial cells by micronucleus test. | 2007-04 |
|
| Digital analysis of mouthrinses' staining characteristics on provisional acrylic resins. | 2007-04 |
|
| Effect of genetic variants of the human flavin-containing monooxygenase 3 on N- and S-oxygenation activities. | 2007-03 |
|
| Dexpanthenol pastille and benzydamine hydrochloride spray for the prevention of post-operative sore throat. | 2007-02 |
|
| [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 |
|
| An evaluation of the efficacy of aspirin and benzydamine hydrochloride gargle for attenuating postoperative sore throat: a prospective, randomized, single-blind study. | 2006-10 |
|
| A pilot study of chlorhexidine and benzydamine oral rinses for the prevention and treatment of irradiation mucositis in patients with head and neck cancer. | 2006-09-29 |
|
| Cancer treatment-induced mucositis pain: strategies for assessment and management. | 2006-09 |
|
| Oral mucositis. | 2006-05 |
|
| Local irritant effects of topical oral sprays on oral mucosa in mice. | 2006-04-29 |
|
| Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2006-04-19 |
|
| 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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10207535
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
Edited
Mon Mar 31 17:52:52 GMT 2025
by
admin
on
Mon Mar 31 17:52:52 GMT 2025
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| Record UNII |
K2GI407R4Q
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| Record Status |
Validated (UNII)
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| Record Version |
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FDA ORPHAN DRUG |
111898
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NCI_THESAURUS |
C257
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C1581
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132-69-4
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m2395
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81963
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CHEMBL12610
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759276
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205-076-0
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DTXSID1045293
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SUB00737MIG
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100000091695
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K2GI407R4Q
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DBSALT001124
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65464
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