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Hexetidine
Hexetidine
Hexetidine
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Hexetidine
Clinical data
Trade namesBactidol, others
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Not to be used by pregnant women
Routes of
administration		Topical (mouthwash)
ATC code
Legal status
Legal status
Identifiers
  • 1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidin-5-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.012 Edit this at Wikidata
Chemical and physical data
FormulaC21H45N3
Molar mass339.612 g·mol−1
3D model (JSmol)
  • CCCCC(CC)CN1CC(CN(C1)CC(CC)CCCC)(C)C
  • InChI=1S/C22H46N2/c1-7-11-13-20(9-3)15-23-17-22(5,6)18-24(19-23)16-21(10-4)14-12-8-2/h20-21H,7-19H2,1-6H3 ☒N
  • Key:ZSHBZCXOMHHPCE-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Hexetidine is an anti-bacterial and anti-fungal agent commonly used in both veterinary and human medicine. It is a local anesthetic, astringent and deodorant and has antiplaque effects.[1]

Hexetidine (then as insecticide) patent application was filed in 1945 and granted in 1947 to Murray Senkus of Commercial Solvents Corporation.[2]

Hexetidine is the medicinal ingredient in Sterisol, which is labelled for the symptomatic treatment of: streptococcal pharyngitis ('strep throat'), tonsillitis, pharyngitis, laryngitis, gingivitis, ulcerative stomatitis, oral thrush and Vincent's angina; postoperative hygiene following tonsillectomy, throat or oral surgery. Hexetidine is not the same as Chlorhexidine, another chemical commonly used in mouthwash, or the antimicrobial drug Hexedene (C22H45N3).[3]

In the UK, hexetidine is the active ingredient in the medicated mouthwash branded Oraldene. In Canada, hexetidine was the active ingredient in the medicated mouthwash branded Steri/sol which has been discontinued. It used to be produced by McNeil Consumer Healthcare, a division of Johnson & Johnson (originally Warner–Lambert, then marketed by Pfizer after its acquisition since 2007). Oraldene contains 0.1 g/100 ml of hexetidine. In some European countries, the gargle solution and mouth spray in bottles of 40 ml named Hexoral (by Mcneil) also contains 0.2% hexetidine as its active compound. In Greece it is called Hexalen mouth wash[4] (also available in spray). Hexetidine can also be found in the mouthwash Bactidol (by Mcneil) which is sold in many Asian countries. In Germany, hexetidine vaginal suppositories branded Vagi-Hex are available to be used for vaginal antisepsis. They are also used in late pregnancy for reducing neonatal infectious mortality and morbidity due to group B streptococcal infections;[5] nonetheless, hexetidine is to be used with care during pregnancy, and its vaginal use is counter-indicated in the first three months of pregnancy.[6]

Hexetidine

References

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Hexetidine

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from Grokipedia
Hexetidine is a synthetic heterocyclic compound with the molecular formula C21H45N3 and a molecular weight of 339.6 g/mol, belonging to the diazinane class and exhibiting broad-spectrum bactericidal and fungicidal activity. Originally developed as an in the 1940s, it later found applications as an in . Primarily utilized in topical formulations, hexetidine serves as a local anti-infective agent with additional mild , , and properties on mucosal surfaces. In human medicine, hexetidine is most commonly employed as a 0.1% for , disinfection of the buccal and pharyngeal mucosa, and prevention of bacterial, fungal, and yeast infections in the oral cavity. It is also used topically for treating vaginal and minor mucosal infections, with applications in for similar purposes. Commercial products containing hexetidine, such as certain mouth rinses, provide short-term relief from conditions like and plaque accumulation, and may serve as an alternative to for patients with allergies.

Uses

Oral applications

Hexetidine is primarily utilized as a 0.1% for the treatment of local bacterial, fungal, and yeast infections within the oral cavity, including conditions such as , , and aphthous ulcers. A double-blind, -controlled crossover study found no significant difference between hexetidine and in managing symptoms of minor aphthous ulceration. Additionally, it effectively targets the microflora associated with aphthous ulceration, aiding in symptom relief and infection control. In daily routines, hexetidine plays a key role in reducing plaque accumulation and preventing halitosis due to its properties. It has been shown to lower plaque levels compared to in randomized trials, supporting its use as an adjunct to mechanical cleaning for maintaining oral health. Formulations like Bactidol, containing 0.1% hexetidine, are commonly recommended for these purposes, providing broad support for plaque control and breath freshening. For throat infections such as and , hexetidine is applied via gargling with 10-15 ml of the undiluted 0.1% solution twice daily. This dosing regimen is indicated for symptomatic relief in minor oropharyngeal infections, including . Evidence from clinical studies highlights hexetidine's ability to reduce oral microbial load, particularly against and Candida albicans at concentrations of 1 mg/ml. In vitro assessments confirm its effectiveness in eliminating C. albicans from oral surfaces, such as , outperforming controls like . These effects contribute to its utility in preventing and treating oral infections.

Vaginal and other topical uses

Hexetidine serves as a topical for treating vaginal infections, including caused by pathogens such as (formerly Haemophilus vaginalis) and, to a lesser extent, due to Candida species. In one study of 155 cases treated with hexetidine vaginal (Sterisil), 83.5% of 79 G. vaginalis infections achieved clinical cure, while only 4 of 34 moniliasis cases showed both clinical and mycological resolution, indicating moderate efficacy against fungal elements. It is commonly formulated as a 0.1% , , or tablet for direct application to the vaginal mucosa, providing localized disinfection without significantly disrupting beneficial lactobacilli. For preventive applications, hexetidine is used in gynecological and obstetric settings to reduce bacterial load prior to procedures or during high-risk pregnancies. A five-day regimen of 20 mg hexetidine suppositories daily in cases of impending reduced vaginal bacteria by five log CFU/ml and cervical bacteria by nearly three log CFU/ml, sparing lactobacilli and lowering risks in over 11,000 deliveries. Typical dosing involves one 10 mg vaginal tablet applied twice daily (morning and bedtime) for 3–7 days, or 10–20 mg daily as suppositories for preoperative antisepsis, effectively preventing postoperative infections in the vaginal and cervical areas. Beyond vaginal applications, hexetidine finds use in dermatological contexts as a topical for superficial infections, leveraging its broad-spectrum activity against and fungi. A preliminary demonstrated its therapeutic efficacy in various dermatoses when applied topically, supporting its role in managing minor cutaneous fungal or bacterial conditions. It is also incorporated into intimate products for deodorizing effects, aiding in odor control through its and properties during localized mucosal or application. The agent's limited systemic absorption—negligible amounts enter the bloodstream from vaginal or topical sites—enhances its safety profile for these localized treatments, but use during or requires consultation with a physician to ensure benefits outweigh potential risks.

Veterinary applications

Hexetidine is employed in veterinary to manage oral infections in companion animals, particularly in dogs and cats, through formulations such as plaque-prevention gels applied directly to the teeth and . These gels create a barrier to inhibit bacterial and reduce plaque and tartar accumulation, thereby aiding in the prevention of periodontal issues and associated halitosis. They are typically applied weekly using a disposable applicator, with a generous amount spread along the gum line on both sides of the mouth, following veterinary guidance to ensure safe use in small animals. In wound care, hexetidine serves as an for disinfection and prevention of secondary infections in and companion animals, including dogs, cats, and . It is incorporated into medicated washes like Triocil, formulated at a concentration of 5 mg/L, which is applied topically to cuts, abrasions, and irritated after wetting the animal's to cleanse and promote healing while targeting gram-positive and . For antifungal applications, hexetidine addresses (such as ringworm) and yeast infections in , leveraging its activity against superficial mycotic pathogens in topical solutions, lotions, or shampoos suitable for dermal use in affected animals. Dosage adjustments are essential across species to minimize irritation, with low concentrations recommended for topical applications—such as in horse shampoos—to balance efficacy and safety in smaller animals like cats, where more dilute solutions prevent mucosal or skin sensitivity. Hexetidine's inclusion in veterinary products, including oral care rinses and washes, reflects regulatory approvals in various countries for animal use, often as over-the-counter options for routine management. This broad-spectrum activity against and fungi supports its role in preventing infections without systemic absorption concerns in topical veterinary contexts.

Adverse effects

Common and rare effects

Hexetidine, when used as a or gargle, is generally well-tolerated, but users may experience mild of the and mucosa as a common effect during routine application. Taste disturbances, including (altered or bitter taste), and temporary oral numbness (transient anaesthesia) due to its local anesthetic properties are also reported, though infrequently in clinical settings. Rare effects encompass tongue or tooth discoloration, which occurs less frequently with hexetidine than with in comparative clinical trials. Other uncommon manifestations include mucosal , blistering, or ulceration at the application site, as well as dry mouth or increased salivation noted in post-marketing surveillance. Allergic reactions, such as or presenting as swelling, are very rare but have been documented. Clinical studies indicate that adverse effects like tooth staining and sensitivity are more pronounced with higher concentrations of hexetidine or prolonged use beyond recommended durations, typically 5-7 days. Users are advised to monitor for persistent irritation and discontinue use if severe symptoms develop, seeking medical advice for any signs of allergic response.

Overdose and toxicity

Acute overdose of hexetidine, often resulting from of large volumes of formulations containing the compound, can lead to severe mucosal in the oral cavity and , along with symptoms such as , , and general gastrointestinal upset primarily due to the alcohol content in alcoholic solutions; hexetidine itself at the concentrations used is unlikely to be toxic, and systemic effects are rare owing to the compound's poor absorption. In cases of alcoholic solutions, excessive ingestion may additionally produce signs of , including drowsiness and . No fatalities from hexetidine overdose have been reported. The oral LD50 in rats is approximately 610 mg/kg body weight, suggesting moderate . Chronic exposure to high doses over extended periods may result in localized mucosal due to prolonged contact, though significant systemic has not been observed in long-term studies, and no fatalities are documented. Management of overdose involves supportive care, such as thorough rinsing to alleviate local and monitoring for gastrointestinal symptoms; induction of should be avoided, and there is no specific . Immediate medical consultation or contact with a is advised for substantial ingestions. Special caution is warranted in children under 12 years and individuals with pre-existing mucosal sensitivities, as hexetidine products are not recommended for young children due to potential for heightened .

Pharmacology

Mechanism of action

Hexetidine is a cationic that primarily exerts its antimicrobial effects through disruption of microbial cell membranes, resulting in bactericidal and fungicidal activity against a broad spectrum of pathogens, including Gram-positive and as well as fungi. This membrane-disrupting action leads to leakage of cellular contents and rapid cell death at therapeutic concentrations typically ranging from 0.1% to 1% in topical formulations. The compound demonstrates strong activity against and yeast such as Candida albicans, achieving significant reductions in microbial counts at concentrations of 1 mg/mL, while its efficacy is comparatively weaker against many . Against C. albicans, hexetidine additionally interferes with fungal adherence to oral epithelial cells, further limiting colonization and infection. Beyond its properties, hexetidine exhibits mild local anesthetic effects upon application to mucous membranes, along with and actions that help alleviate oral discomfort and neutralize odor-causing compounds. These ancillary effects enhance its utility in managing minor oral infections and promoting without promoting microbial resistance, which remains short-lived and transient.

Pharmacokinetics

Hexetidine demonstrates minimal systemic absorption when applied topically to the oral or vaginal mucosa, with negligible systemic absorption, as no human absorption studies have been conducted and animal data suggest minimal uptake, allowing for primarily local therapeutic effects without significant entry into the bloodstream. Due to its cationic nature, it binds readily to mucous membranes, buccal tissues, and , promoting prolonged local retention rather than widespread distribution. Distribution of hexetidine is largely confined to the site of application, with no evidence of substantial systemic circulation or reported in available studies. Radiolabeled studies indicate retention on buccal and gingival tissues for 8 to 10 hours following a single oral rinse, and in some instances, detection persists up to 65 hours post-application, underscoring its localized action. This tissue adherence supports sustained antimicrobial activity at the application site while minimizing exposure to distant organs. Limited data exist on hexetidine owing to its low systemic absorption. Elimination primarily involves local desorption and degradation at the application site, with unabsorbed portions potentially swallowed and excreted fecally without further absorption in the . The plasma is not well-defined due to negligible systemic levels, but salivary elimination follows kinetics, with detectable concentrations persisting for up to 25 minutes post-rinse and varying inter-individually. Overall, the effective for local effects is on the order of hours, aligning with its intended topical use.

Chemistry

Structure and properties

Hexetidine is a synthetic featuring a hexahydropyrimidine (1,3-diazinane) ring core, substituted at the 5-position with both an amino group and a , while the atoms at positions 1 and 3 bear 2-ethylhexyl alkyl chains. This structure results in a mixture of stereoisomers due to chiral centers at the 5-position and the in the 2-ethylhexyl side chains. The IUPAC name for hexetidine is 1,3-bis(2-ethylhexyl)-5-methyl-1,3-diazinan-5-amine. The molecular formula of hexetidine is C21H45N3, with a molecular weight of 339.60 g/mol. At room temperature, hexetidine appears as a clear, colorless to pale yellow oily liquid, with a density of 0.889 g/mL at 25°C. Its boiling point is approximately 160°C under reduced pressure (0.4 mmHg), with an estimated normal boiling point around 388°C at 760 mmHg. Hexetidine exhibits low solubility in water, ranging from 0.1 to 1 g/L, but is freely soluble in organic solvents such as acetone, methanol, benzene, chloroform, and petroleum ether. The flash point is 70°C. Regarding stability, hexetidine is generally stable when stored in tightly closed containers in a cool, dry place, away from light and strong oxidizing agents, to which it is sensitive; it should not be handled with or equipment. The pKa value for its group is 8.3 at 25°C.

Synthesis

Hexetidine is synthesized through a multi-step process beginning with the formation of a substituted hexahydropyrimidine ring via a nitro-Mannich-type , followed by reduction of the nitro group to an amino functionality. The key intermediate, 1,3-bis(2-ethylhexyl)-5-nitro-5-methylhexahydropyrimidine, is prepared by reacting 2-ethylhexylamine with to generate an intermediate, which then undergoes addition with in the presence of a basic catalyst, such as or an base, typically at elevated temperatures around 50–70°C. This cyclization step leverages the reactivity of the primary amine and to build the 1,3-dialkylhexahydropyrimidine scaffold while incorporating the 5-nitro-5-methyl substituent, yielding the crude nitro compound in approximately 70–80% purity. The nitro intermediate is subsequently reduced to hexetidine via catalytic hydrogenation in a solvent like methanol, using Raney nickel as the catalyst at pressures exceeding 500 psi (preferably around 1,000 psi) and temperatures of 50–100°C, until hydrogen uptake ceases, typically within 1 hour. This process, outlined in U.S. Patent 3,054,797 granted in 1962, produces hexetidine with yields of 70–80% based on the nitro starting material, after filtration of the catalyst and removal of solvent by distillation. The resulting product is a mixture of stereoisomers due to the chiral center at the 5-position of the ring. Purification of the crude hexetidine is essential for pharmaceutical applications, as it is an oily liquid prone to side products from incomplete cyclization or over-condensation. A common method involves forming the sparingly soluble 1,5-naphthalenedisulfonate salt in an aqueous alcoholic medium (e.g., isopropyl alcohol-water mixtures), precipitating the salt, and regenerating the with dilute like , achieving 95–97% recovery of high-purity hexetidine. Alternative purification via or is possible but less favored industrially due to thermal sensitivity and lower efficiency. Challenges in the synthesis include minimizing side products like polymeric condensates during ring formation and managing stereoisomer distribution, which can affect and stability, though the process generally avoids complex separation of individual isomers.

History

Development and patents

Hexetidine was first synthesized in the mid-1940s by chemist Murray Senkus at Commercial Solvents Corporation, initially patented as part of the 5-aminohexahydropyrimidines with the application filed in 1944 and granted in 1945 (U.S. Patent 2,387,043). During the 1950s, researchers at the same company explored its potential as a broad-spectrum antiseptic, leveraging its antimicrobial properties. A key milestone in its development came with U.S. 3,054,797, granted in 1962 to Wilton O. Bell and Albert E. Neckar of Commercial Solvents Corporation, which detailed an improved process for synthesizing 5-aminohexahydropyrimidines, including hexetidine, via high-pressure to achieve higher purity and yield. Early studies in the confirmed its efficacy against oral pathogens such as and fungi, establishing its suitability for topical use. Initial human evaluations in the late assessed its safety and effectiveness as a 0.1% for treating minor oral infections and promoting . Hexetidine was first commercialized in January 1958 under the brand name Sterisil by Warner-Chilcott Laboratories, initially as a vaginal gel and later expanded to oral rinses, marking its entry into European and North American markets. In the 1970s, formulation advancements included U.S. Patent 3,749,721 (1973), which introduced a purification method using 1,5-naphthalenedisulfonate to produce high-purity hexetidine for pharmaceutical applications, enhancing stability and reducing impurities. Further evolution in the 1980s focused on synergistic combinations, such as European Patent EP0049830B1 (filed 1981, granted 1985), which described mouthwash formulations pairing hexetidine with zinc salts to inhibit dental plaque formation more effectively than either agent alone.

Regulatory status and availability

Hexetidine is approved as a topical for oral use in the through national marketing authorizations granted by member states, allowing its inclusion in mouthwashes and sprays for disinfection and . It is classified under the Anatomical Therapeutic Chemical (ATC) code A01AB12 for antiinfectives and antiseptics used in dental and oral conditions. In the United States, hexetidine was not included in the (FDA) OTC drug monograph for antigingivitis/antiplaque products due to insufficient marketing history, and it is no longer marketed for therapeutic oral use, having been withdrawn post-1980s amid the rise of alternative antiseptics. Approvals exist in various Asian and Pacific countries, including the , where it is registered as a household remedy for oral antisepsis. Hexetidine is widely available over-the-counter in formulations at a typical concentration of 0.1% for local infections and in , , and parts of and . Prescription requirements apply for vaginal suppositories or gels in select European regions, such as and , where it is used for vaginal antisepsis under brands like Vagi-Hex. Notable brand names include Bactidol in the , , and other Asian markets; Hextril and Hexoral across much of ; and Oraldene in the and . Globally, hexetidine maintains strong market presence in developing regions, including , , and , where it is distributed through pharmacies and retail outlets for everyday oral care. Its availability remains limited in , with no current over-the-counter or prescription formulations approved for human therapeutic use in the United States or . As of 2025, there have been no significant regulatory changes or new approvals reported for hexetidine in major markets.

Research

Antiviral properties

Hexetidine has demonstrated antiviral activity in several studies, primarily through disruption of viral envelopes and interference with processes, akin to its antibacterial mechanism, though the exact pathways remain incompletely characterized. A 2021 study evaluated hexetidine-containing (0.1% concentration) against using the European Standard EN14476 protocol on Vero E6 cells, showing a >5 log10 reduction in viral (equivalent to >99.99% inactivation) within 30 seconds of exposure under both clean and dirty conditions. Earlier lab tests from the same year, using as a surrogate, reported reductions in viral infectivity of up to 99.68% at full concentration and over 94% at 25% dilution after 15-30 seconds exposure in suspension assays on Vero E6 cells. Activity has also been observed against other viruses, including herpes simplex virus type 1 (HSV-1) and strains. In a 2016 in vitro analysis, non-cytotoxic concentrations of hexetidine (as a component of ) attenuated HSV-1 by over 100-fold after 30 seconds exposure in cell cultures, alongside similar reductions for highly pathogenic A/H5N1 and A/H1N1pdm. These findings support potential applications in oral rinses for reducing viral loads in the upper , particularly for enveloped viruses like those in protocols. Clinical evidence remains limited, with no dedicated Phase 4 trials identified for antiviral indications. A 2022 pilot involving 66 SARS-CoV-2-positive participants tested hexetidine as an oral rinse, observing a 69.2% conversion to negative RT-PCR in samples at 15 minutes post-application, though this did not reach compared to (p > 0.05). Despite these promising in vitro results, hexetidine lacks regulatory approval for antiviral use and is classified primarily as an for bacterial and fungal infections, with further clinical validation needed to establish efficacy against viruses.

Comparative efficacy

A 2011 systematic review of randomized controlled trials found that hexetidine significantly reduced plaque accumulation compared to in short-term use, but it was less effective than for long-term plaque control and gingival inflammation reduction, while exhibiting fewer adverse effects such as tooth staining. In a 2005 double-blind involving patients with , 0.1% hexetidine demonstrated equivalent reductions in plaque index, bleeding index, and gingival index to 0.1% after four weeks of use, but with significantly less tooth discoloration (P = 0.0035), indicating better tolerability. Compared to other antiseptics like (CPC), hexetidine shows similar short-term antimicrobial effects against oral bacteria, but exhibits superior activity against Candida species; for instance, 0.1% hexetidine achieved 100% inhibition against C. albicans and other Candida strains , outperforming typical 0.05-0.075% CPC formulations in consistency across species. A 2024 review confirmed hexetidine's strong efficacy against various Candida spp. in commercial mouthwashes. Overall, hexetidine serves as a cost-effective alternative to premium antiseptics like in resource-limited settings, where its wide availability and lower side-effect profile support adjunctive use for , but it is generally not considered first-line in developed markets favoring more potent agents. A 2024 study in critically ill patients found hexetidine effective in reducing oropharyngeal colonization risk, comparable to .

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