Benzydamine
Identification
- Name
- Benzydamine
- Accession Number
- DB09084
- Description
Benzydamine (also known as Tantum Verde or Difflam), available as the hydrochloride salt, is a locally-acting nonsteroidal anti-inflammatory drug (NSAID) with local anaesthetic and analgesic properties. It is used topically for pain relief and anti-inflammatory treatment of the mouth, throat, or muscoskeletal system.
Although the indazole analogue benzydamine is a non-steroidal anti-inflammatory drug (NSAID), it has various physicochemical properties and pharmacologic activities that are different from those of traditional aspirin-like NSAIDs but facilitate benzydamine's mechanism of action as an effective locally-acting NSAID with local anaesthetic and analgesic properties. Moreover, unlike aspirin-like NSAIDs which are acids or metabolised to acids, benzydamine is in fact a weak base.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Benzydamine (DB09084)
- Weight
- Average: 309.413
Monoisotopic: 309.184112373 - Chemical Formula
- C19H23N3O
- Synonyms
- Bencidamina
- Benzydamine
- Benzydaminum
Pharmacology
- Indication
Available predominantly as a liquid mouthwash, oromucosal spray, or topical cream, benzydamine is most frequently employed as a locally acting analgesic and anti-inflammatory treatment for the relief of painful inflammatory conditions.
When formulated as a mouthwash or spray, benzydamine may be used to treat traumatic conditions like pharyngitis following tonsillectomy or the use of a naso-gastric tube, inflammatory conditions like pharyngitis, aphthous ulcers and oral ulceration due to radiation therapy, dentistry operations and procedures, or more general conditions like sore throat, sore tongue, sore gums, mouth ulcers, or discomfort caused by dentures. 6
When used as a topical cream, benzydamine may be employed to relieve symptoms associated with painful inflammatory conditions of the muscolo-skeletal system including acute inflammatory disorders such as myalgia and bursitis or traumatic conditions like sprains, strains, bruises, sore muscles, stiff joints, or even the after-effects of fractures. 7
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Benzydamine is a non-steroidal anti-inflammatory drug (NSAID) designed to elicit local anesthetic and analgesic effects mainly for the mouth and throat. It specifically acts on the local mechanisms of inflammation such as pain, oedema, or granuloma. Typically applied topically, the drug demonstrates anti-inflammatory activity reducing oedema as well as exudate and granuloma formation. Moreover, benzydamine exhibits analgesic properties and local anaesthetic activity if pain is caused by an inflammatory condition. Benzydamine can be absorbed into the oral mucosa and intact skin. Once absorbed in the local area of pain or inflammation, benzydamine binds selectively to local inflamed tissues, usually allowing it to act with few adverse systemic effects. On average a period of 2 to 4 hours is necessary for the substance to reach peak plasma concentration. 5
Benzydamine can be synthesized with the reaction of the N-benzyl derivative from methyl anthranilate with nitrous acid to give N-nitoso derivative. This is next reduced by sodium thiosulfate to give transient hydrazine. This hydrazine can then undergo spontaneous internal hydrazide formation. Treating this resultant enolate with 3-chloro-1-dimethylamkino propane ultimately yields benzydamine.
- Mechanism of action
Despite being categorized as a non-steroidal anti-inflammatory drug (NSAID), benzydamine demonstrates various mechanisms of action that differ from those of traditional aspirin-like NSAIDs. In particular, benzydamine predominantly acts by inhibiting the synthesis of pro inflammatory cytokines like tumour necrosis factor-alpha (TNF-α) and interleukin-1β (IL-1β) without largely affecting other pro inflammatory cytokines (ie. such as IL-6 and IL-8) or anti-inflammatory cytokines (ie. like IL-10 or IL-1 receptor antagonist). 3,5
Moreover, benzydamine is largely a weak inhibitor of prostaglandin synthesis as it has been shown to effectively inhibit cyclooxygenase (COX) and lipoxygenase enzyme activity only at concentrations of 1mM or greater. Considering most contemporary usages of benzydamine are topical applications that are generally not well absorbed through the skin and/or non-specialized mucosae, benzydamine does not often achieve the kind of absorption or blood concentrations necessary to cause any extraneous distant systemic effects or COX inhibition, allowing it to localize its action. 3,5
Additionally, it is also hypothesized that benzydamine is capable of inhibiting the oxidative burst of neutrophils and membrane stabilization. These actions are exhibited by the substance’s ability to inhibit the release of granules from neutrophils and to stabilize lysosomes. 3,5
Furthermore, benzydamine is capable of a local anaesthetic effect that may be related to its capability for inhibiting the release of inflammatory mediators like substance P and calcitonin gene related peptide from sensory nerve endings. Since substance P is capable of causing the release of histamine from mast cells, benzydamine’s prevention of substance P release further contributes to an anti-inflammatory effect. 3,5
Benzydamine also demonstrates a non-specific antibacterial activity against various bacterial strains that are resistant to broad-spectrum antibiotics such as ampicillin, chloramphenicol, and tetracycline at concentrations of about 3 mmol/L. Combinatorial use of benzydamine and other antibiotics like tetracycline and chloramphenicol are also synergistic against antibiotic resistant strains of Staphylococcus aureus and Pseudomonas aeruginosa. 3
- Absorption
Oral doses of benzydamine are well absorbed and plasma drug concentrations reach a peak fairly rapidly and then decline with a half-life of approximately 13 hours. When applied topically, although the local drug concentrations are relatively large, the systemic absorption of topically applied benzydamine is relatively low compared to oral doses. This low topical absorption contributes to a decreased potential for any systemic drug side-effects when benzydamine is administered in this way. 6
- Volume of distribution
- Protein binding
Benzydamine exhibits < 20% plasma protein binding after oral administration 6,3.
- Metabolism
Benzydamine is primarily metabolized by oxidation, dealkylation, and conjugation into hydroxy, dealkylated, and N-oxide metabolites 6,3.
In general, however, when used at the recommended doses the levels at which benzydamine is absorbed or exposed into the body are usually not sufficient to produce systemic pharmacological effects [L
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- Route of elimination
The relatively high lipid solubility of the weak base benzydamine is thought to be associated with considerable passive resorption within the renal tubule, which suggests that only approximately 5% of benzydamine is excreted unchanged in the urine 1. At the same time however, other studies have suggested that considerably larger amounts (50-65%) of the drug is excreted unchanged in urine 4.
While several inactive oxidized metabolites of benzydamine are excreted in urine, the benzydamine N-oxide metabolite can remain in plasma and demonstrate a half-life that is longer than the parent benzydamine compound 1.
Nevertheless, it is generally believed that excretion occurs mainly through urine and is mostly in the form of inactive metabolites or conjugation products 8.
- Half-life
Approximately 13 h after oral administration 6, with a terminal half life of about 7.7 h 3.
- Clearance
Benzydamine demonstrateas a systemic clearance of 170 ml/min 3.
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
A possible adverse reaction associated with the use of the mouthwash or oromucosal spray formulations of benzymadine is potential numbness and/or stinging in the mouth and/or throat 5,6.
Some possible adverse reactions that tend to be associated more with topical cream formulations of benzymadine include increased sensitivity to sunlight, and localized itching, skin rash, redness, or swelling 7.
The prescribing information for all formulations of benzymadine however, warn against the possibility of severe allergic reaction (anaphylaxis) associated with swelling of the throat and mouth, difficulty in swallowing, speaking, and breathing, or wheezing 5,6,7.
As benzydamine is a non-steroidal anti-inflammatory drug (NSAID), it is necessary to determine if a patient is allergic to NSAIDs before considering its use 5,6,7.
Intoxication is expected as a consequence of accidental ingestion of large quantities of benzydamine (over 300 mg ingestion). Other symptoms associated with overdose of ingested benzydamine include gastrointestinal and central nervous system symptoms like nausea, vomiting, abdominal pain, oesophageal irritation, dizziness, hallucinations, agitation, anxiety, and irritability 6.
The official prescribing information for benzydamine generally suggest that benzydamine mouthwashes and sprays should not be used in pregnancy 6,7 . Similarly, the official prescribing information for benzydamine also generally suggest that benzydamine mouthwashes and sprays should not be used during lactation unless considered essential by a physician 6,7.
The prescribing information for topical cream formulations of benzydamine note that benzydamine cream should not be used in pregnancy or lactation unless considered necessary by the physician 5.
Overall, non-clinical data reveal no special hazards for humans based on conventional studies of safety pharmacology, repeated toxicity, genotoxicity, cardiogenic potential, and toxicity to reproduction 5. Additionally, there is no evidence of teratogenic effects in animal studies 6.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Benzydamine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Benzydamine is combined with Abciximab. Acarbose Benzydamine may decrease the excretion rate of Acarbose which could result in a higher serum level. Acebutolol Benzydamine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Benzydamine. Acemetacin The risk or severity of adverse effects can be increased when Acemetacin is combined with Benzydamine. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Benzydamine is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Benzydamine. Acetazolamide Acetazolamide may increase the excretion rate of Benzydamine which could result in a lower serum level and potentially a reduction in efficacy. Acetohexamide The protein binding of Acetohexamide can be decreased when combined with Benzydamine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Benzydamine hydrochloride K2GI407R4Q 132-69-4 HNNIWKQLJSNAEQ-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataPharixia Mouthwash Buccal Pendopharm Division Of Pharmascience Inc 1996-12-02 Not applicable Canada 
Pharixia Alcohol Free Mouthwash Buccal Pendopharm Division Of Pharmascience Inc 2020-07-13 Not applicable Canada Sun-benz - Liq 0.15% Liquid Dental; Oral Sun Pharmaceutical Industries Inc. 1997-04-03 2011-07-29 Canada Tantum Mouthwash Buccal Valeant Canada Lp Valeant Canada S.E.C. 1993-12-31 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataApo-benzydamine Oral Rinse Mouthwash Buccal Apotex Corporation 1998-11-09 Not applicable Canada Novo-benzydamine Mouthwash; Solution Buccal; Oral Novopharm Limited 2008-06-03 2018-05-17 Canada Novo-benzydamine - Oral Rinse Liquid; Mouthwash Buccal; Oral Novopharm Limited 1997-02-06 2015-10-26 Canada Nu-benzydamine Oral Rinse Liquid Buccal Nu Pharm Inc Not applicable Not applicable Canada Odan-benzydamine Mouthwash Buccal Odan Laboratories Ltd 2017-08-11 Not applicable Canada PMS-benzydamine Mouthwash Buccal Pharmascience Inc 1999-04-30 Not applicable Canada Ratio-benzydamine Solution Oral Ratiopharm Inc Division Of Teva Canada Limited 1997-03-24 2010-05-21 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- ATC Codes
- A01AD02 — Benzydamine
- A01AD — Other agents for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- M01AX — Other antiinflammatory and antirheumatic agents, non-steroids
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- M02AA — Antiinflammatory preparations, non-steroids for topical use
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- G02CC — Antiinflammatory products for vaginal administration
- G02C — OTHER GYNECOLOGICALS
- G02 — OTHER GYNECOLOGICALS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Alimentary Tract and Metabolism
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antiinflammatory Products for Vaginal Administration
- Drugs that are Mainly Renally Excreted
- Genito Urinary System and Sex Hormones
- Heterocyclic Compounds, Fused-Ring
- Indazoles
- Mouthwashes and Gargles
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Pyrazoles
- Stomatological Preparations
- Throat Preparations
- Topical Products for Joint and Muscular Pain
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as indazoles. These are compounds containing an indazole, which is structurally characterized by a pyrazole fused to a benzene.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrazoles
- Sub Class
- Indazoles
- Direct Parent
- Indazoles
- Alternative Parents
- Alkyl aryl ethers / Benzene and substituted derivatives / Pyrazoles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzopyrazole / Ether / Heteroaromatic compound / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 4O21U048EF
- CAS number
- 642-72-8
- InChI Key
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- {3-[(1-benzyl-1H-indazol-3-yl)oxy]propyl}dimethylamine
- SMILES
- CN(C)CCCOC1=NN(CC2=CC=CC=C2)C2=CC=CC=C12
References
- General References
- Baldock GA, Brodie RR, Chasseaud LF, Taylor T, Walmsley LM, Catanese B: Pharmacokinetics of benzydamine after intravenous, oral, and topical doses to human subjects. Biopharm Drug Dispos. 1991 Oct;12(7):481-92. [PubMed:1932611]
- Silvestrini B, Barcellona PS, Garau A, Catanese B: Toxicology of benzydamine. Toxicol Appl Pharmacol. 1967 Jan;10(1):148-59. [PubMed:6031923]
- Quane PA, Graham GG, Ziegler JB: Pharmacology of benzydamine. Inflammopharmacology. 1998;6(2):95-107. doi: 10.1007/s10787-998-0026-0. [PubMed:17694367]
- Catanese B, Grasso A, Silverstrini B: Studies on the absorption and elimination of benzydamine in the mouse, rat, dog, and man. Arzneimittelforschung. 1966 Oct;16(10):1354-7. [PubMed:6014929]
- Electronic Medicines Compedium Difflam (Benzydamine Hydrochloride) Spray Monograph [Link]
- Electronic Medicines Compedium Benzydamine Hydrochloride 0.15% w/v Mouthwash Monograph [Link]
- Electronic Medicines Compedium Difflam (Benzydamine Hydrochloride) 3% Cream Monograph [Link]
- Benzydamine - Tantum Verde [Link]
- External Links
- PubChem Compound
- 12555
- PubChem Substance
- 310265011
- ChemSpider
- 12036
- BindingDB
- 50103598
- 1425
- ChEBI
- 94563
- ChEMBL
- CHEMBL12610
- ZINC
- ZINC000002020083
- Wikipedia
- Benzydamine
- AHFS Codes
- 52:28.00 — Mouthwashes and Gargles
- 52:08.20 — Nonsteroidal Anti-inflammatory Agents
- MSDS
- Download (343 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Impacted Third Molar Tooth 1 4 Completed Other Intubation Complications 1 4 Completed Prevention Post Operative Nausea and Vomiting (PONV) / Sore Throat 1 4 Completed Prevention Sore Throat 1 4 Completed Supportive Care Pain / Quality of Life 1 3 Completed Supportive Care Head and Neck Carcinoma / Mucositis 1 3 Completed Treatment Radiation Effects / Stomatitis 1 3 Unknown Status Prevention For Intervention 1 1 Completed Other Healthy Volunteers 2 1 Completed Other Healthy Women 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Rinse Oral 22.5 mg/15mL Spray Oral 0.3 mg/0.2mL Solution Solution Oral 0.15 g Rinse Oral 120 ml Spray 0.15 % Gel 50 gr Tablet, coated 50 mg Rinse Oral 1.5 mg/ml Rinse Oral 0.15 % Tablet, film coated 50 mg Solution Buccal; Oral 0.3 g Cream Vaginal 0.5 g Solution Topical; Vaginal 100 mg Solution Buccal; Oral 0.15 g Spray Oral 1.5 mg/ml Spray Oral 3 mg/ml Solution Buccal; Oral 150 mg Rinse Oral 300 mg/200ml Rinse Oral 120 mg/100ml Lozenge 3 mg Mouthwash 1.5 mg/1mL Mouthwash Oral 1.5 mg/1mL Spray Oral 3 mg/1mL Spray Oral 45 mg/30ml Rinse Oral 0.12 % Spray Oral 0.12 % Rinse Oral 600 mg Solution Oral 18 mg/15mL Spray Oral 15 ml Rinse Oral 180 mg Spray Oral 46 mg Cream 5 % Gel 5 % Gel Topical 5 G Injection, solution Intramuscular 5 mg/5ml Ointment Topical 3 % Ointment Topical 5 G Pill 50 MG Solution / drops Oral 3 % Suppository 100 MG Suppository 50 MG Suppository Rectal 25 mg Spray Oral 0.15 % Cream Vaginal 0.5 % Granule, for solution 500 MG Solution Vaginal 0.1 % Solution, concentrate 500 MG/10ML Mouthwash Oral 150 mg/100mL Spray Oral 150 mg/100mL Tablet, soluble Oral 3 mg Spray Oral 45 mg Rinse Oral 120 mg Rinse Oral 0.3 % Spray Oral 0.3 % Mouthwash; solution Buccal; Oral Liquid; mouthwash Buccal; Oral Liquid Buccal Mouthwash Buccal Rinse Oral 0.15 g/100ml Spray Oral 0.15 g/100ml Solution Oral Rinse Oral 12 % Liquid Dental; Oral Lozenge Oral Cream Topical 5 % Rinse Oral 180 mg/120ml Rinse Oral 0.045 g/30ml Paste, dentifrice Dental 0.5 % Rinse Oral Gel 50 g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 320°F MSDS water solubility Miscible MSDS - Predicted Properties
Property Value Source Water Solubility 0.0491 mg/mL ALOGPS logP 3.78 ALOGPS logP 3.66 ChemAxon logS -3.8 ALOGPS pKa (Strongest Basic) 9.26 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 30.29 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 105.56 m3·mol-1 ChemAxon Polarizability 35.62 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on September 15, 2015 13:55 / Updated on October 21, 2020 01:55
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