Benzydamine

Identification

Summary

Benzydamine is a locally-acting NSAID indicated for the symptomatic relief of pain in acute sore throat and for the symptomatic relief of oropharyngeal mucositis caused by radiation therapy.

Brand Names

Pharixia, Tantum

Generic Name

Benzydamine

DrugBank Accession Number

DB09084

Background

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

Similar Structures

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

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Associated Conditions

Associated Therapies

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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

The volume of distribution of benzydamine is 10 L ^1,3.

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

Hover over products below to view reaction partners

Benzydamine
- Benzydamine N-oxide
- Norbenzydamine

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

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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.

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
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Abacavir	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.
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.
Acetylsalicylic acid	The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Benzydamine.

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Food Interactions

No interactions found.

Products

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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
Pharixia	Mouthwash	0.15 % w/v	Buccal	Pendopharm Division Of Pharmascience Inc	1996-12-02	Not applicable
Pharixia Alcohol Free	Mouthwash	0.15 % w/v	Buccal	Pendopharm Division Of Pharmascience Inc	2020-07-13	Not applicable
Sun-benz - Liq 0.15%	Liquid	.15 %	Dental; Oral	Sun Pharmaceutical Industries Inc.	1997-04-03	2011-07-29
Tantum	Mouthwash	0.15 % w/v	Buccal	Bausch Health, Canada Inc.	1993-12-31	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-benzydamine Oral Rinse	Mouthwash	0.15 %	Buccal	Apotex Corporation	1998-11-09	Not applicable
Novo-benzydamine	Mouthwash; Solution	1.5 mg / mL	Buccal; Oral	Novopharm Limited	2008-06-03	2018-05-17
Novo-benzydamine - Oral Rinse	Liquid; Mouthwash	1.5 mg / mL	Buccal; Oral	Novopharm Limited	1997-02-06	2015-10-26
Nu-benzydamine Oral Rinse	Liquid	0.15 %	Buccal	Nu Pharm Inc	Not applicable	Not applicable
Odan-benzydamine	Mouthwash	0.15 % w/v	Buccal	Odan Laboratories Ltd	2017-08-11	Not applicable
PMS-benzydamine	Mouthwash	0.15 % w/v	Buccal	Pharmascience Inc	1999-04-30	Not applicable
Ratio-benzydamine	Solution	0.15 %	Oral	Ratiopharm Inc Division Of Teva Canada Limited	1997-03-24	2010-05-21

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
ดีโทรท สเปรย์ 0.3% (กลิ่นมิ้นท์)	Spray	3 mg/1ml	Oral	บริษัท อินเตอร์ไทย ฟาร์มาซูติเคิ้ล แมนูแฟคเจอริ่ง จำกัด จำกัด	2017-12-02	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ANDOREX GARGARA, 200 ML	Benzydamine hydrochloride (22.5 mg/15mL) + Chlorhexidine gluconate (18 mg/15mL)	Rinse	Oral	PHARMACTİVE İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ANDOREX SPREY, 30 ML	Benzydamine hydrochloride (0.3 mg/0.2mL) + Chlorhexidine gluconate (0.24 mg/0.2mL)	Spray	Oral	PHARMACTİVE İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
BUCALIV® ULTRA	Benzydamine hydrochloride (0.15 g) + Cetylpyridinium chloride (0.05 g)	Solution	Buccal; Oral	LABORATORIO FRANCO COLOMBIANO LAFRANCOL S.A.S.	2018-03-16	Not applicable
CLİORO % 0,15 + % 0,12 GARGARA	Benzydamine hydrochloride (300 mg/200ml) + Chlorhexidine gluconate (240 mg/200ml)	Rinse	Oral	HELBA İLAÇ İÇ VE DIŞ SAN. TİC. LTD. ŞTİ.	2020-08-14	Not applicable
CLIORO ORAL SPREY, 1 ADET	Benzydamine hydrochloride (45 mg/30ml) + Chlorhexidine gluconate (36 mg/30ml)		Oral	HELBA İLAÇ İÇ VE DIŞ SAN. TİC. LTD. ŞTİ.	2020-08-14	Not applicable
CLODER PLUS 30 ML ORAL SPREY	Benzydamine hydrochloride (45 mg/30ml) + Chlorhexidine gluconate (36 mg/30ml)		Oral	NOBEL İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
CLODER PLUS GARGARA, 200 ML	Benzydamine hydrochloride (150 mg/100ml) + Chlorhexidine gluconate (120 mg/100ml)	Rinse	Oral	NOBEL İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ENMIKS GARGARA , 200 ML	Benzydamine hydrochloride (0.15 %) + Chlorhexidine gluconate (0.12 %)	Rinse	Oral	BİLİM İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ENMIKS ORAL SPREY ,30 ML	Benzydamine hydrochloride (45 mg/30ml) + Chlorhexidine gluconate (36 mg/30ml)	Spray	Oral	BİLİM İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
FARDOBEN %0,15+%0,12 GARGARA, 200 ML	Benzydamine hydrochloride (0.15 %) + Chlorhexidine gluconate (0.12 %)	Rinse	Oral	Deva Holding A.S.	2020-08-14	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
TANTUM %5 JEL, 100 G	Benzydamine (5 %)	Gel	Topical	ANGELİNİ İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
TANTUM %5 JEL, 50 G	Benzydamine (5 %)	Gel	Topical	ANGELİNİ İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
TANTUM VERDE % 0,15 120 ML GARGARA	Benzydamine hydrochloride (180 mg/120ml)	Rinse	Oral	ANGELİNİ İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
TANTUM VERDE 0,045 GR 30 ML SPREY	Benzydamine hydrochloride (0.045 g/30ml)	Rinse	Oral	ANGELİNİ İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable

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. [Article]
Silvestrini B, Barcellona PS, Garau A, Catanese B: Toxicology of benzydamine. Toxicol Appl Pharmacol. 1967 Jan;10(1):148-59. [Article]
Quane PA, Graham GG, Ziegler JB: Pharmacology of benzydamine. Inflammopharmacology. 1998;6(2):95-107. doi: 10.1007/s10787-998-0026-0. [Article]
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. [Article]
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
RxNav: 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	Completed	Treatment	Sore Throat	1
3	Unknown Status	Prevention	For Intervention	1
1	Completed	Other	Healthy Volunteers	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Rinse	Oral
Mouthwash	Buccal	0.15 %
Solution	Oral
Solution	Oral	0.15 g
Tablet, coated		50 mg
Gel	Oral
Spray	Transmucosal
Solution	Topical	0.15 g
Tablet, film coated	Oral
Tablet	Buccal	3 mg
Tablet	Oral	3 mg
Solution	Buccal; Oral
Powder	Topical; Vaginal	0.498 g
Powder	Topical; Vaginal	5.3 g
Solution	Buccal; Oral	0.3 g
Cream	Vaginal	0.5 g
Solution	Topical; Vaginal	100 mg
Solution	Buccal; Oral	0.15 g
Spray	Oral
Solution	Buccal; Oral	150 mg
Spray, metered	Oral
Gel	Oral
Solution	Oral
Injection, solution	Intramuscular
Ointment	Topical
Pill
Solution / drops	Oral
Suppository	Rectal
Powder, for solution	Vaginal
Cream	Vaginal
Douche	Vaginal
Mouthwash	Oral
Spray	Oral
Tablet, soluble	Oral
Mouthwash; solution	Buccal; Oral	1.5 mg / mL
Liquid; mouthwash	Buccal; Oral	1.5 mg / mL
Liquid	Buccal	0.15 %
Mouthwash	Buccal	0.15 % w/v
Spray, metered	Oral
Solution	Oral	0.15 %
Tablet	Transmucosal
Tablet	Transmucosal
Lozenge	Oral
Liquid	Dental; Oral	.15 %
Lozenge	Oral
Cream	Topical
Gel	Topical
Granule, for solution	Vaginal
Solution	Vaginal
Mouthwash	Oral
Pastille	Oral
Paste, dentifrice	Dental
Rinse	Oral
Powder	Vaginal
Spray	Oral	1.5 mg/1ml
Spray	Oral	3 mg/1ml
Lozenge	Oral	3 mg

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 19:55 / Updated on June 23, 2021 06:08

Benzydamine

Identification

Structure for Benzydamine (DB09084)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra