Tantum verde

Benzydamine

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: B2
Routes of administration	Oral, topical
ATC code	A01AD02 (WHO) G02CC03 (WHO) M01AX07 (WHO) M02AA05 (WHO)
Legal status
Legal status	UK: General sales list (GSL, OTC)
Pharmacokinetic data
Protein binding	<20%
Biological half-life	13 hours
Excretion	Renal
Identifiers
IUPAC name 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
CAS Number	642-72-8 Y
PubChem CID	12555
ChemSpider	12036 Y
UNII	4O21U048EF
KEGG	D07516 Y
ChEMBL	CHEMBL12610 Y
ECHA InfoCard	100.010.354
Chemical and physical data
Formula	C19H23N3O
Molar mass	309.405 g/mol
3D model (Jmol)	Interactive image
SMILES n2c(OCCCN(C)C)c1ccccc1n2Cc3ccccc3
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 Y Key:CNBGNNVCVSKAQZ-UHFFFAOYSA-N Y

Benzydamine (also known as Tantum Verde and branded in some countries as Difflam), available as the hydrochloride salt, is a locally-acting nonsteroidal anti-inflammatory drug (NSAID) with local anaesthetic and analgesic properties for pain relief and anti-inflammatory treatment of inflammatory conditions of the mouth and throat.

It may be used alone or as an adjunct to other therapy giving the possibility of increased therapeutic effect with little risk of interaction.

In some markets, the drug is supplied as an over-the-counter cream (Lonol in Mexico from Boehringer Ingelheim) used for topical treatment of musculoskeletal system disorders: sprains, strains, bursitis, tendinitis, synovitis, myalgia, periarthritis.

Studies indicate that benzydamine has notable in vitro antibacterial activity and also shows synergism in combination with other antibiotics, especially tetracyclines, against antibiotic-resistant strains of Staphylococcus aureus and Pseudomonas aeruginosa.

There are no contraindications to the use of benzydamine except for known hypersensitivity.

Benzydamine is well tolerated. Occasionally oral tissue numbness or stinging sensations may occur, as well as itching, a skin rash, skin swelling or redness, difficulty breathing and wheezing.

It selectively binds to inflamed tissues (Prostaglandin synthetase inhibitor) and is normally free of adverse systemic effects. Unlike other NSAIDs, it does not inhibit cyclooxygenase or lipooxygenase, and is not ulcerogenic.

Benzydamine has been used recreationally. In overdosages it acts a deliriant and CNS stimulant. Such use, particularly among teenagers, has been reported in Poland, Brazil and Romania.

Synthesis starts with the reaction of the N-benzyl derivative from methyl anthranilate with nitrous acid to give the N-nitroso derivative. Reduction by means of sodium thiosulfate leads to the transient hydrazine (3), which undergoes spontaneous internal hydrazide formation. Treatment of the enolate of this amide with 3-chloro-1-dimethylamkino propane gives benzydamine (5).