Hexylresorcinol

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofMouth irritation••• •••••••••••
Treatment ofOrofacial pain••• •••••••••••
Prophylaxis ofSkin infections••• •••••••••••
Symptomatic treatment ofSore throat••• ••••••••••
Treatment ofSore throat••• •••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
UDNA topoisomerase 1
inhibitor
Humans
UProtein-glutamine gamma-glutamyltransferase 2
inhibitor
Humans
UTyrosinase
inhibitor
Humans
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

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Antiseptic Sore Throat Loz. (lemon Flavour)Lozenge2.4 mg / lozOralH.J. Sutton Industries Ltd.1997-01-241999-03-23Canada flag
Antiseptic Sore Throat Loz(honey Eucalyp.fl)Lozenge2.4 mg / lozOralH.J. Sutton Industries Ltd.1997-01-031999-03-23Canada flag
Antiseptic Sore Throat Loz(mint Menthol Flv)Lozenge2.4 mg / lozOralH.J. Sutton Industries Ltd.1997-01-031999-03-23Canada flag
Antiseptic Throat Lozenges (with Hexylresorcinol)Lozenge2.4 mgOralH.J. Sutton Industries Ltd.1997-01-032013-07-05Canada flag
AvaptaSpray1 mg/1mLOralNeel Products LLC2012-08-162015-10-13US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AnubisMedHexylresorcinol (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)LiquidTopicalANUBIS COSMETICS SL2022-11-042027-07-01US flag
AvaptaHexylresorcinol (1 mg/1mL) + Benzalkonium chloride (0.2 mg/1mL) + Zinc chloride (2 mg/1mL)SprayOralNeel Products LLC2012-08-162015-10-13US flag
AvaptaHexylresorcinol (1 mg/1mL) + Allantoin (5 mg/1mL) + Camphor (9 mg/1mL) + Menthol (4 mg/1mL)SprayTopicalNeel Products LLC2012-08-062015-10-13US flag
Green Guard Sore Throat ReliefHexylresorcinol (2.4 mg/1) + Menthol (4.5 mg/1)LozengeOralUnifirst First Aid Corporation2008-12-302015-01-26US flag
Medi-First Plus Sore Throat MaxHexylresorcinol (2.4 mg/1) + Menthol (4.5 mg/1)LozengeOralUnifirst First Aid Corporation2008-12-302014-01-08US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
S.T.37Hexylresorcinol (1.1 mg/1mL)SolutionOral; TopicalNumark Brands, Inc1929-11-20Not applicableUS flag

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
  1. 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]
  2. 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]
  3. Maplestone PA, Mukerji AK: Hexylresorcinol as an Anthelmintic. Ind Med Gaz. 1932 Nov;67(11):610-612. [Article]
  4. DailyMed: S.T.37-hexylresorcinol solution monograph [Link]
  5. Electronic Medicines Compendium: Strepsils (hexylresorcinol) Extra Triple Action Blackcurrant Lozenges Monograph [Link]
  6. Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
  7. NIH Toxnet: Hexylresorcinol Profile [Link]
  8. IPCS INCHEM 4-Hexylresorcinol Profile [Link]
  9. Health Products Regulatory Authority of Ireland: Summary of Product Characteristics for Hexylresorcinol [File]
  10. University of Utah College of Pharmacy: Topical Analgesic and Anaesthetic Agents Drug Class Review [File]
Human Metabolome Database
HMDB0032567
PubChem Compound
3610
PubChem Substance
347827952
ChemSpider
21106121
BindingDB
50292636
RxNav
5321
ChEBI
93749
ChEMBL
CHEMBL443605
ZINC
ZINC000001576892
Wikipedia
Hexylresorcinol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedPreventionPostoperative Sorethroat / Sore Throat1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidTopical
SprayOral
SprayOral1 mg/1mL
SprayTopical
LozengeOral2.4 mg / loz
LozengeOral
LozengeOral2 mg/1
SolutionTopical1.1 mg/1mL
SolutionOral; Topical1.1 mg/1mL
LozengeOral
LozengeOral3.5 mg
LozengeOral3.5 mg / loz
LozengeOral2.4 mg/1
LozengeOral2.4 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.454 mg/mLALOGPS
logP3.77ALOGPS
logP4.1Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.55Chemaxon
pKa (Strongest Basic)-5.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity58.07 m3·mol-1Chemaxon
Polarizability22.98 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00fr-8900000000-4e5e556980dc8bd1d331
GC-MS Spectrum - EI-BGC-MSsplash10-00di-0900000000-5e9f9f102fe32a7d43f9
Mass Spectrum (Electron Ionization)MSsplash10-00di-2900000000-6308ed79d3b6955a1373
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fu-9800000000-4bd80941445d618c439d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-22927a4b82450fa12ced
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0900000000-47988e0288afddf5485d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9200000000-1c20c1c5d7dc4ed75d9c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0600-1900000000-a528bd6d25312d8b9c5f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aou-9600000000-17201ee8db9c468382c0
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-155.4638995
predicted
DarkChem Lite v0.1.0
[M-H]-156.2972995
predicted
DarkChem Lite v0.1.0
[M-H]-156.2388995
predicted
DarkChem Lite v0.1.0
[M-H]-149.9519
predicted
DeepCCS 1.0 (2019)
[M+H]+157.8058995
predicted
DarkChem Lite v0.1.0
[M+H]+158.5971995
predicted
DarkChem Lite v0.1.0
[M+H]+158.1430995
predicted
DarkChem Lite v0.1.0
[M+H]+153.92775
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.1212995
predicted
DarkChem Lite v0.1.0
[M+Na]+156.0716995
predicted
DarkChem Lite v0.1.0
[M+Na]+156.8175995
predicted
DarkChem Lite v0.1.0
[M+Na]+163.29646
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Poly(a) rna binding
Specific 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 singl...
Gene Name
TOP1
Uniprot ID
P11387
Uniprot Name
DNA topoisomerase 1
Molecular Weight
90725.19 Da
References
  1. Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins.
Gene Name
TGM2
Uniprot ID
P21980
Uniprot Name
Protein-glutamine gamma-glutamyltransferase 2
Molecular Weight
77328.21 Da
References
  1. Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA ...
Gene Name
TYR
Uniprot ID
P14679
Uniprot Name
Tyrosinase
Molecular Weight
60392.69 Da
References
  1. Hexylresorcinol: Providing Skin Benefits by Modulating Multiple Molecular Targets [Link]

Drug created at December 03, 2015 16:51 / Updated at March 29, 2024 03:23