Clinical data | |
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Trade names | Maxtra Gargle, Difflam, Tantum |
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Routes of administration | Oral, topical |
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Pharmacokinetic data | |
Protein binding | <20% |
Elimination half-life | 13 hours |
Excretion | Kidney |
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ECHA InfoCard | 100.010.354 |
Chemical and physical data | |
Formula | C19H23N3O |
Molar mass | 309.413 g·mol−1 |
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Benzydamine (also known as Tantum Verde and branded in some countries as Maxtra Gargle, Difflam and Septabene), 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. [2] It falls under class of chemicals known as indazole.
It was synthesized in Italy in 1964 and marketed in 1966. [3]
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.
Benzydamine has been used recreationally. In overdosages it acts as a deliriant and CNS stimulant. [4] Such use, particularly among teenagers, has been reported in Brazil, [5] [6] Poland, [4] Romania, and Turkey.[ citation needed ]
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. [4] [7] It has powerful reinforcing effect and has cross sensitization with drugs of abuse such as heroin and cocaine in animals. It is hypothesized that it has cannabinoid agonistic activity. [8]
Benzydamine is poorly absorbed through skin [9] and vagina. [10]
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-dimethylamino propane gives benzydamine (5). Please note there is an error in this section: US3318905 states that the nitroso derivative is reduced with sodium hydrosulfite (sodium dithionite) and not with sodium hyposulfite (sodium thiosulfate), as shown in the above scheme and stated in text.
An interesting alternative synthesis of this substance starts by sequential reaction of N-benzylaniline with phosgene, and then with sodium azide to product the corresponding carbonyl azide. On heating, nitrogen is evolved and a separatable mixture of nitrene insertion product and the desired ketoindazole # results. The latter reaction appears to be a Curtius rearrangement type product to produce an N-isocyanate #, which then cyclizes. Alkylation of the enol with sodium methoxide and 3-dimethylaminopropyl chloride gives benzydamine.
Alternatively, use of chloroacetamide in the alkylation step followed by acid hydrolysis produces bendazac instead.
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. [14] [15]
It also has some cannabinoid activity in rats but has not been tested in humans. [8] It is also hypothesized to act on 5-HT2A receptors due to its structural similarity with serotonin. [3]
Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used orally or intravenously. It typically begins working within an hour.
Diclofenac, sold under the brand name Voltaren, among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammatory diseases such as gout. It is taken by mouth or rectally in a suppository, used by injection, or applied to the skin. Improvements in pain last for as much as eight hours. It is also available in combination with misoprostol in an effort to decrease stomach problems.
Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and lasts for up to twelve hours.
Anti-inflammatory or antiphlogistic is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as opposed to opioids, which affect the central nervous system to block pain signaling to the brain.
Mefenamic acid is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs), and is used to treat mild to moderate pain.
Oxaprozin, also known as oxaprozinum, is a nonsteroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis. Chemically, it is a propionic acid derivative. Safety and efficacy has been established in children over 6 years with juvenile rheumatoid arthritis only, and there is an increased risk of adverse reactions in the elderly population.
Eye drops or eyedrops are liquid drops applied directly to the surface of the eye usually in small amounts such as a single drop or a few drops. Eye drops usually contain saline to match the salinity of the eye. Drops containing only saline and sometimes a lubricant are often used as artificial tears to treat dry eyes or simple eye irritation such as itching or redness. Eye drops may also contain one or more medications to treat a wide variety of eye diseases. Depending on the condition being treated, they may contain steroids, antihistamines, sympathomimetics, beta receptor blockers, parasympathomimetics, parasympatholytics, prostaglandins, nonsteroidal anti-inflammatory drugs (NSAIDs), antibiotics, antifungals, or topical anesthetics.
Sodium thiosulfate is an inorganic compound with the formula Na2S2O3. Typically it is available as the white or colorless pentahydrate, Na2S2O3·5H2O. The solid is a crystalline substance that dissolves well in water.
Carprofen is a nonsteroidal anti-inflammatory drug (NSAID) of the carbazole and propionic acid class that was previously for use in humans and animals but is now only available to veterinarians for prescribing as a supportive treatment for various conditions in animals. Carprofen reduces inflammation by inhibition of COX-1 and COX-2; its specificity for COX-2 varies from species to species. Marketed under many brand names worldwide, carprofen is used as a treatment for inflammation and pain, including joint pain and postoperative pain.
Moxifloxacin is an antibiotic, used to treat bacterial infections, including pneumonia, conjunctivitis, endocarditis, tuberculosis, and sinusitis. It can be given by mouth, by injection into a vein, and as an eye drop.
Loxoprofen is a nonsteroidal anti-inflammatory drug (NSAID) in the propionic acid derivatives group, which also includes ibuprofen and naproxen among others. It is available in some countries for oral administration. A transdermal preparation was approved for sale in Japan in January 2006; medicated tape and gel formulations followed in 2008 and 2010.
Sulfacetamide is a sulfonamide antibiotic.
Amtolmetin guacil is a non-steroidal anti-inflammatory drug (NSAID). It is a prodrug of tolmetin sodium.
Bendazac is a nonsteroidal anti-inflammatory drug (NSAID) used for joint and muscular pain.
Acemetacin is a non-steroidal anti-inflammatory drug (NSAID) used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain. It is manufactured by Merck KGaA under the tradename Emflex, and is available in the UK and other countries as a prescription-only drug.
Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.
A drug class is a group of medications and other compounds that have similar chemical structures, the same mechanism of action, similar modes of action, and/or are used to treat the similar diseases. The Food and Drug Administration (FDA) has worked on classifying and licensing new medications for many years. However, the FDA's Drug Evaluation and Research Center categorizes these new medications based on both their chemical and therapeutic class.
Prostaglandin inhibitors are drugs that inhibit the synthesis of prostaglandin in human body. There are various types of prostaglandins responsible for different physiological reactions such as maintaining the blood flow in stomach and kidney, regulating the contraction of involuntary muscles and blood vessels, and act as a mediator of inflammation and pain. Cyclooxygenase (COX) and Phospholipase A2 are the major enzymes involved in prostaglandin production, and they are the drug targets for prostaglandin inhibitors. There are mainly 2 classes of prostaglandin inhibitors, namely non- steroidal anti- inflammatory drugs (NSAIDs) and glucocorticoids. In the following sections, the medical uses, side effects, contraindications, toxicity and the pharmacology of these prostaglandin inhibitors will be discussed.
An antiarthritic is any drug used to relieve or prevent arthritic symptoms, such as joint pain or joint stiffness. Depending on the antiarthritic drug class, it is used for managing pain, reducing inflammation or acting as an immunosuppressant. These drugs are typically given orally, topically or through administration by injection. The choice of antiarthritic medication is often determined by the nature of arthritis, the severity of symptoms as well as other factors, such as the tolerability of side effects.