Hexylresorcinol
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Identification
- Summary
Hexylresorcinol is an ingredient used to relieve irritation, pain, and prevent infection.
- Generic Name
- Hexylresorcinol
- DrugBank Accession Number
- DB11254
- Background
Hexylresorcinol is a substituted dihydroxybenzene. It exhibits antiseptic, anthelmintic, and local anesthetic properties. It can be found in topical applications for minor skin infections and in oral solutions or throat lozenges for pain relief and first aid antiseptic.
The compound may also be used commonly in various commercial cosmetic anti-aging creams while ongoing studies research the possibility of using hexylresorcinol as an anti-cancer therapy - indications all of which require further study and testing at the current moment.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 194.2701
Monoisotopic: 194.13067982 - Chemical Formula
- C12H18O2
- Synonyms
- 4-hexyl-1,3-benzenediol
- 4-hexylresorcinol
- Hexylresorcinol
- External IDs
- E-586
- INS NO.586
- INS-586
- NSC-1570
Pharmacology
- Indication
Hexylresorcinol is predominantly employed as the active ingredient in lotions, sprays, or lozenges indicated as a (a) topical antiseptic to help prevent skin infection in minor cuts, scrapes, or burns, or (b) as an antiseptic and local anesthetic for the relief of a sore throat and its associated pain 4,5.
In addition, hexylresorcinol is used as an active ingredient in various commercial cosmetic skincare products as an anti-aging cream 6 while other studies have looked into whether or not the compound could be used effectively as an anti-inflammatory agent or even as an anti-cancer therapy 6.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Mouth irritation ••• ••• •••••••• Treatment of Orofacial pain ••• ••• •••••••• Prophylaxis of Skin infections ••• ••• •••••••• Symptomatic treatment of Sore throat ••• ••• ••••••• Treatment of Sore throat ••• ••• •••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Hexylresorcinol is a phenol derivative, and in typical therapeutic usage is primarily a local anesthetic for topical use on the mucous membranes of the mouth and throat 9. The local anesthetic like properties of hexylresorcinol is likely due to its sodium channel blocking effects 9. The agent also demonstrates mild antiseptic activity as well as an apparent anti-inflammatory, demulcent action 9.
- Mechanism of action
When acting as an oral anesthetic for relieving sore throats, it is generally believed that hexylresorcinol is possibly capable of blocking voltage-gated neuronal sodium channels, which in turn would inhibit the initiation and conduction of nerve impulses for feeling or transmitting pain signals in the local area to which the hexylresorcinol is applied 10.
As an antiseptic agent, studies have demonstrated that hexylresorcinol is capable of eliciting actions like reducing or inhibiting the generation of bacterial biofilm, interfering with bacterial cell chain formation, reducing bacterial adherence of the pharynx, inhibition of glycolytic enzyme and pH drops, and alteration of cell surface hydrophobicity 2. Unfortunately, there are either antibiotics that function even more effectively at formally treating bacterial growth or there are also other plant-derived phenolic compounds similar to hexylresorcinol that elicit stronger such mechanisms of action 2. Nevertheless, it is useful for hexylresorcinol to have both anesthetic and certain antiseptic actions for its use in treating various relatively self-limiting scrapes and sore throats that are treated by the over-the-counter products that feature the compound. Early studies in the 1930s and 1940s suggested that there were more effective medicines over hexylresorcinol that could be employed for their anthelmintic effects 3.
As an anti-inflammatory and anti-aging agent, some studies have shown that it may be possible for hexylresorcinol to inhibit the phosphorylation of the immune response mediator NF-kappaB and also elicit a significant skin lightening effect owing to a strong inhibitory effect on tyrosinase and peroxidase and a stimulatory effect on glutathione and E-cadherin syntheses 6. It is proposed that hexylresorcinol can bind to tyrosinase directly and inhibits its enzyme activity 6. Literature data suggests that low glutathione levels relates to the deposition of melanin in the skin of humans and other animals, while high glutathione levels inhibit melanogenesis 6. And ultimately, it is also reported that glutathione depletion increases tyrosinase activity in human melanoma cells, which makes hexylresorcinol's effects on tyrosinase desirable 6.
Finally, there are ongoing studies that have reported hexylresorcinol's abilities to induce the differentiation of SCC-9 squamous cell cell-line by way of the modulation of the E2F-mediated signaling pathway and suppress the growth of squamous cell carcinoma SCC-9 cells in a dose-dependent manner 6. Moreover, such studies have also shown that hexylresorcinol is seemingly capable of dose-dependent induction of SCC-9 cell apoptosis as well as the inhibition of transglutaminase-2 enzyme activity which can facilitate chemotherapy resistance 6.
Target Actions Organism ATyrosinase inhibitorHumans UDNA topoisomerase 1 inhibitorHumans UProtein-glutamine gamma-glutamyltransferase 2 inhibitorHumans - Absorption
Owing to the poor absorption of hexylresorcinol, systemic exposure and symptoms are unusual 7.
- Volume of distribution
Readily accessible data regarding the volume of distribution of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area 5,9,10.
- Protein binding
Readily accessible data regarding the protein binding of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area 5,9,10.
- Metabolism
Regarding the metabolism of hexylresorcinol, it has been reported that excretion of the compound in the urine is largely in the form of an ethereal sulfate conjugate 7.
- Route of elimination
When two men received doses of 1 g of hexylresorcinol, an average of 18% of the dose was recovered in the urine within the first 12 hours - thereafter, the compound was not detected in urine samples 7.
- Half-life
Readily accessible data regarding the half-life of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area 5,9,10.
- Clearance
Readily accessible data regarding the clearance of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area 5,9,10.
- Adverse Effects
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- Toxicity
In the over-the-counter antiseptic and oral analgesic sprays and lozenges that hexylresorcinol is typically employed as the active ingredient, it is noted that overdosage of the agent may cause minor gastrointestinal irritation 5,9,10.
The probable oral LD50 of hexylresorcinol in humans has been estimated to be between 500 and 5000 mg/kg body weight, between 1 oz and 1 pint (or 1 lbs) for a 70 kg person 7,8.
- 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.Not Available
- Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Antiseptic Sore Throat Loz. (lemon Flavour) Lozenge 2.4 mg / loz Oral H.J. Sutton Industries Ltd. 1997-01-24 1999-03-23 Canada Antiseptic Sore Throat Loz(honey Eucalyp.fl) Lozenge 2.4 mg / loz Oral H.J. Sutton Industries Ltd. 1997-01-03 1999-03-23 Canada Antiseptic Sore Throat Loz(mint Menthol Flv) Lozenge 2.4 mg / loz Oral H.J. Sutton Industries Ltd. 1997-01-03 1999-03-23 Canada Antiseptic Throat Lozenges (with Hexylresorcinol) Lozenge 2.4 mg Oral H.J. Sutton Industries Ltd. 1997-01-03 2013-07-05 Canada Avapta Spray 1 mg/1mL Oral Neel Products LLC 2012-08-16 2015-10-13 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AnubisMed Hexylresorcinol (1 g/50mL) + Ammonia (2.75 g/50mL) + Ascorbyl glucoside (0.25 g/50mL) + Ethanol (6.3 mL/50mL) + Ethylhexylglycerin (0.025 g/50mL) + Glycolic acid (17 g/50mL) + Hydroxyethyl cellulose (0.34875 g/50mL) + Isopropyl alcohol (0.75 g/50mL) + Kojic acid (2.5 g/50mL) + Lactic acid (5 g/50mL) + Phenoxyethanol (0.225 g/50mL) + Propylene glycol (0.5 g/50mL) + Salicylic acid (1 g/50mL) + Water (7.333 mL/50mL) Liquid Topical ANUBIS COSMETICS SL 2022-11-04 2027-07-01 US Avapta Hexylresorcinol (1 mg/1mL) + Allantoin (5 mg/1mL) + Camphor (9 mg/1mL) + Menthol (4 mg/1mL) Spray Topical Neel Products LLC 2012-08-06 2015-10-13 US Avapta Hexylresorcinol (1 mg/1mL) + Benzalkonium chloride (0.2 mg/1mL) + Zinc chloride (2 mg/1mL) Spray Oral Neel Products LLC 2012-08-16 2015-10-13 US Green Guard Sore Throat Relief Hexylresorcinol (2.4 mg/1) + Menthol (4.5 mg/1) Lozenge Oral Unifirst First Aid Corporation 2008-12-30 2015-01-26 US Medi-First Plus Sore Throat Max Hexylresorcinol (2.4 mg/1) + Menthol (4.5 mg/1) Lozenge Oral Unifirst First Aid Corporation 2008-12-30 2014-01-08 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image S.T.37 Hexylresorcinol (1.1 mg/1mL) Solution Oral; Topical Numark Brands, Inc 1929-11-20 Not applicable US
Categories
- ATC Codes
- R02AA12 — Hexylresorcinol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Resorcinols
- Alternative Parents
- 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Resorcinol
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- R9QTB5E82N
- CAS number
- 136-77-6
- InChI Key
- WFJIVOKAWHGMBH-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3
- IUPAC Name
- 4-hexylbenzene-1,3-diol
- SMILES
- CCCCCCC1=C(O)C=C(O)C=C1
References
- General References
- McNally D, Shephard A, Field E: Randomised, double-blind, placebo-controlled study of a single dose of an amylmetacresol/2,4-dichlorobenzyl alcohol plus lidocaine lozenge or a hexylresorcinol lozenge for the treatment of acute sore throat due to upper respiratory tract infection. J Pharm Pharm Sci. 2012;15(2):281-94. [Article]
- Mace S, Truelstrup Hansen L, Rupasinghe HPV: Anti-Bacterial Activity of Phenolic Compounds against Streptococcus pyogenes. Medicines (Basel). 2017 May 1;4(2). pii: medicines4020025. doi: 10.3390/medicines4020025. [Article]
- Maplestone PA, Mukerji AK: Hexylresorcinol as an Anthelmintic. Ind Med Gaz. 1932 Nov;67(11):610-612. [Article]
- DailyMed: S.T.37-hexylresorcinol solution monograph [Link]
- Electronic Medicines Compendium: Strepsils (hexylresorcinol) Extra Triple Action Blackcurrant Lozenges Monograph [Link]
- Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
- NIH Toxnet: Hexylresorcinol Profile [Link]
- IPCS INCHEM 4-Hexylresorcinol Profile [Link]
- Health Products Regulatory Authority of Ireland: Summary of Product Characteristics for Hexylresorcinol [File]
- University of Utah College of Pharmacy: Topical Analgesic and Anaesthetic Agents Drug Class Review [File]
- External Links
- Human Metabolome Database
- HMDB0032567
- PubChem Compound
- 3610
- PubChem Substance
- 347827952
- ChemSpider
- 21106121
- BindingDB
- 50292636
- 5321
- ChEBI
- 93749
- ChEMBL
- CHEMBL443605
- ZINC
- ZINC000001576892
- Wikipedia
- Hexylresorcinol
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Prevention Postoperative Sorethroat / Sore Throat 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical Spray Oral Spray Oral 1 mg/1mL Spray Topical Lozenge Oral 2.4 mg / loz Lozenge Oral Lozenge Oral 2 mg/1 Solution Topical 1.1 mg/1mL Solution Oral; Topical 1.1 mg/1mL Lozenge Oral Lozenge Oral 3.5 mg Lozenge Oral 3.5 mg / loz Lozenge Oral 2.4 mg/1 Lozenge Oral 2.4 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.454 mg/mL ALOGPS logP 3.77 ALOGPS logP 4.1 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 9.55 Chemaxon pKa (Strongest Basic) -5.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 58.07 m3·mol-1 Chemaxon Polarizability 22.98 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.4638995 predictedDarkChem Lite v0.1.0 [M-H]- 156.2972995 predictedDarkChem Lite v0.1.0 [M-H]- 156.2388995 predictedDarkChem Lite v0.1.0 [M-H]- 149.9519 predictedDeepCCS 1.0 (2019) [M+H]+ 157.8058995 predictedDarkChem Lite v0.1.0 [M+H]+ 158.5971995 predictedDarkChem Lite v0.1.0 [M+H]+ 158.1430995 predictedDarkChem Lite v0.1.0 [M+H]+ 153.92775 predictedDeepCCS 1.0 (2019) [M+Na]+ 156.1212995 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.0716995 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.8175995 predictedDarkChem Lite v0.1.0 [M+Na]+ 163.29646 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine (By similarity). In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone (PubMed:28661582)
- Specific Function
- copper ion binding
- Gene Name
- TYR
- Uniprot ID
- P14679
- Uniprot Name
- Tyrosinase
- Molecular Weight
- 60392.69 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a single-strand break via transesterification at a target site in duplex DNA. The scissile phosphodiester is attacked by the catalytic tyrosine of the enzyme, resulting in the formation of a DNA-(3'-phosphotyrosyl)-enzyme intermediate and the expulsion of a 5'-OH DNA strand. The free DNA strand then rotates around the intact phosphodiester bond on the opposing strand, thus removing DNA supercoils. Finally, in the religation step, the DNA 5'-OH attacks the covalent intermediate to expel the active-site tyrosine and restore the DNA phosphodiester backbone (By similarity). Regulates the alternative splicing of tissue factor (F3) pre-mRNA in endothelial cells. Involved in the circadian transcription of the core circadian clock component BMAL1 by altering the chromatin structure around the ROR response elements (ROREs) on the BMAL1 promoter
- Specific Function
- ATP binding
- Gene Name
- TOP1
- Uniprot ID
- P11387
- Uniprot Name
- DNA topoisomerase 1
- Molecular Weight
- 90725.19 Da
References
- Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Calcium-dependent acyltransferase that catalyzes the formation of covalent bonds between peptide-bound glutamine and various primary amines, such as gamma-amino group of peptide-bound lysine, or mono- and polyamines, thereby producing cross-linked or aminated proteins, respectively (PubMed:23941696, PubMed:31991788, PubMed:9252372). Involved in many biological processes, such as bone development, angiogenesis, wound healing, cellular differentiation, chromatin modification and apoptosis (PubMed:1683874, PubMed:27270573, PubMed:7935379, PubMed:9252372, PubMed:28198360). Acts as a protein-glutamine gamma-glutamyltransferase by mediating the cross-linking of proteins, such as ACO2, HSPB6, FN1, HMGB1, RAP1GDS1, SLC25A4/ANT1, SPP1 and WDR54 (PubMed:23941696, PubMed:24349085, PubMed:29618516, PubMed:30458214). Under physiological conditions, the protein cross-linking activity is inhibited by GTP; inhibition is relieved by Ca(2+) in response to various stresses (PubMed:18092889, PubMed:7592956, PubMed:7649299). When secreted, catalyzes cross-linking of proteins of the extracellular matrix, such as FN1 and SPP1 resulting in the formation of scaffolds (PubMed:12506096). Plays a key role during apoptosis, both by (1) promoting the cross-linking of cytoskeletal proteins resulting in condensation of the cytoplasm, and by (2) mediating cross-linking proteins of the extracellular matrix, resulting in the irreversible formation of scaffolds that stabilize the integrity of the dying cells before their clearance by phagocytosis, thereby preventing the leakage of harmful intracellular components (PubMed:7935379, PubMed:9252372). In addition to protein cross-linking, can use different monoamine substrates to catalyze a vast array of protein post-translational modifications: mediates aminylation of serotonin, dopamine, noradrenaline or histamine into glutamine residues of target proteins to generate protein serotonylation, dopaminylation, noradrenalinylation or histaminylation, respectively (PubMed:23797785, PubMed:30867594). Mediates protein serotonylation of small GTPases during activation and aggregation of platelets, leading to constitutive activation of these GTPases (By similarity). Plays a key role in chromatin organization by mediating serotonylation and dopaminylation of histone H3 (PubMed:30867594, PubMed:32273471). Catalyzes serotonylation of 'Gln-5' of histone H3 (H3Q5ser) during serotonergic neuron differentiation, thereby facilitating transcription (PubMed:30867594). Acts as a mediator of neurotransmission-independent role of nuclear dopamine in ventral tegmental area (VTA) neurons: catalyzes dopaminylation of 'Gln-5' of histone H3 (H3Q5dop), thereby regulating relapse-related transcriptional plasticity in the reward system (PubMed:32273471). Regulates vein remodeling by mediating serotonylation and subsequent inactivation of ATP2A2/SERCA2 (By similarity). Also acts as a protein deamidase by mediating the side chain deamidation of specific glutamine residues of proteins to glutamate (PubMed:20547769, PubMed:9623982). Catalyzes specific deamidation of protein gliadin, a component of wheat gluten in the diet (PubMed:9623982). May also act as an isopeptidase cleaving the previously formed cross-links (PubMed:26250429, PubMed:27131890). Also able to participate in signaling pathways independently of its acyltransferase activity: acts as a signal transducer in alpha-1 adrenergic receptor-mediated stimulation of phospholipase C-delta (PLCD) activity and is required for coupling alpha-1 adrenergic agonists to the stimulation of phosphoinositide lipid metabolism (PubMed:8943303)
- Specific Function
- calcium ion binding
- Gene Name
- TGM2
- Uniprot ID
- P21980
- Uniprot Name
- Protein-glutamine gamma-glutamyltransferase 2
- Molecular Weight
- 77328.21 Da
References
- Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
Drug created at December 03, 2015 16:51 / Updated at October 21, 2024 08:50