Resorcinol

Identification

Brand Names
Acnomel, Resinol, Rezamid, Vagisil Original Formula
Generic Name
Resorcinol
DrugBank Accession Number
DB11085
Background

Resorcinol is a 1,3-isomer (or meta-isomer) of benzenediol with the formula C6H4(OH)2. It is used as an antiseptic and disinfectant in topical pharmaceutical products in the treatment of skin disorders and infections such as acne, seborrheic dermatitis, eczema, psoriasis, corns, calluses, and warts. It exerts a keratolytic activity. Resorcinol works by helping to remove hard, scaly, or roughened skin.

Although it is primarily indicated for use as a topical application, resorcinol also possesses a well-documented anti-thyroidal activity that is generally not relied upon for any kind of formal therapeutic indication.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 110.1106
Monoisotopic: 110.036779436
Chemical Formula
C6H6O2
Synonyms
  • 1,3-Benzenediol
  • 1,3-Dihydroxybenzene
  • 1,3-Dihydroxybenzol
  • m-Hydroquinone
  • m-hydroxyphenol
  • Resorcinol
  • Resorzin
External IDs
  • C.I.-76505
  • FEMA NO. 3589
  • NSC-1571

Pharmacology

Indication

Contemporary therapeutic uses for resorcinol primarily revolve around the use of the phenol derivative as an active ingredient in topical antiseptics 2,1,5,6 or as topical antibacterial skin treatment products for conditions like acne, seborrheic dermatitis, eczema, and others 3,2,1,5,6.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAcne vulgaris••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter 6,4. Resorcinol interferes with the iodination of tyrosine and the oxidation of iodide 6,4. In an in vitro study involving lactoperoxidase (LPO) and thyroid peroxidase (TPO), it was shown that the mechanism of these two enzymes can become irreversibly inhibited by way of a suicide inactivation by resorcinol 6,4.

It is believed that the Fe3+ of the porphyrin residue of the peroxidase to is oxidised to Fe4+ by hydrogen peroxide with the transfer of an oxygen radical 6,4. In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme 6,4. The latter radical can bind, in a pH-dependent reaction, covalently and irreversibly to the resorcinol radical formed during regular oxidation of resorcinol and this reduces the activity of the enzyme greatly 6,4. While the inactivation of the enzyme and the binding of resorcinol to the enzyme may be largely increased by the presence of 0.1 nM iodide, increasing the iodide concentration to 5 mM reduced the resorcinol binding to the enzyme by one quarter but increased the enzyme activity, determined as the rate of iodination of tyrosine, more than proportionally from 6.2% to 44.7% 6,4. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated 6,4.

Ultimately, such in vitro and in vivo data propose that the anti-thyroidal activity of resorcinol is caused by inhibition of thyroid peroxidase enzymes, resulting in decreased thyroid hormone production and increased proliferation due to an increase in the secretion of TSH (thyroid stimulating hormone) 6,4. The iodination process is catalyzed by a haem-containing enzyme, and resorcinol is known to form covalent bonds with haem 6,4.

Despite the legitimacy of this pharmacodynamic profile in resorcinol, the therapeutic uses for which it may be formally indicated for at this time do not actually rely upon any of these mechanisms or dynamics, which are primarily elicited only upon systemic exposure to resorcinol or particularly high overdosage of the agent. This is especially true, considering resorcinol is most commonly available as topical applications to the public.

Mechanism of action

Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the effectiveness of the agent in treating various topical, dermatological conditions by eliciting antibacterial and keratolytic actions appears to stem from resorcinol's propensity for protein precipitation 2,3. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compound's ability to precipitate cutaneous proteins from the treated skin 3.

TargetActionsOrganism
UThyroid peroxidaseNot AvailableHumans
Absorption

The dermal absorption of resorcinol seems to be low (< 1%) when applied on healthy and intact skin 7. The agent absorbed very slightly under normal conditions & the absorption was lower when applied to the scalp than to clean shaven skin due to a strong fixation by the hair 1.

Volume of distribution

Specific data regarding the volume of distribution of resorcinol is not readily available, although it is believed that the compound's volume of distribution is considered large, owing to resorcinol's profile as a lipid-soluble compound 1.

Protein binding

Specific data regarding the protein binding of resorcinol is not readily available.

Metabolism

Specific data regarding the metabolism of resorcinol is not readily available, although the major metabolite of resorcinol found in the urine was its glucuronide 1.

Route of elimination

Specific data regarding the route of elimination of resorcinol is not readily available, although the major metabolite of resorcinol found in the urine was its glucuronide 1.

Half-life

Specific data regarding the half-life of resorcinol is not readily available, although, in one case of dermal exposure, an adult male with a 90% phenol exposure had an elimination half-life of about 14 hours 1.

Clearance

Specific data regarding the clearance of resorcinol is not readily available, although it is generally believed that the relatively low topical absorption or resorcinol does not result in an extensive systemic presence and clearance 7,1.

Adverse Effects
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Toxicity

Effects in man include CNS effects, mainly in persons who have used creams containing high levels of resorcinol, effects on the erythrocytes (especially methaemoglobinaemia, mainly in babies and infants) and, after prolonged exposure, effects on the thyroid gland (like goiter or especially chronic myxoedema) 6. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol 6. In persons suffering from resorcinol poisoning, the symptoms included anemia, spleen siderosis, and fatty degeneration of the liver and kidneys 6.

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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Resorcinol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Resorcinol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Resorcinol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Resorcinol which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Resorcinol which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
No interactions found.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
T3 PIMPLE GELGel2 % w/wCutaneousHOE PHARMACEUTICALS SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Acne Aid GelResorcinol (1.25 %) + Chloroxylenol (.375 %) + Octasulfur (2.5 %)GelTopicalStiefel Laboratories, Inc.1966-12-311998-07-09Canada flag
Acne Drying TopicalResorcinol (2 g/100mL) + Octasulfur (8 g/100mL)LotionTopicalOnly Yourx, Inc.2014-08-26Not applicableUS flag
Acne Treatment maximum strength CVSResorcinol (2 g/100g) + Octasulfur (8 g/100g)CreamTopicalCVS Health2014-12-26Not applicableUS flag
Acnomel Skin Tone CreamResorcinol (2 %) + Isopropyl alcohol (11 %) + Octasulfur (8 %)CreamTopicalNumark Laboratories, Inc.1992-12-312004-07-30Canada flag
Acnotex acne TreatmentResorcinol (20 mg/1mL) + Octasulfur (80 mg/1mL)LotionTopicalGenesis2011-07-072015-03-01US flag

Categories

ATC Codes
D10AX02 — ResorcinolS01AX06 — Resorcinol
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
resorcinols, benzenediol (CHEBI:27810) / a benzenediol (CPD-623)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
YUL4LO94HK
CAS number
108-46-3
InChI Key
GHMLBKRAJCXXBS-UHFFFAOYSA-N
InChI
InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
IUPAC Name
benzene-1,3-diol
SMILES
OC1=CC(O)=CC=C1

References

General References
  1. NIH Toxnet: Resorcinol Profile [Link]
  2. Drugs.com: Resorcinol Profile [Link]
  3. Resorcinol Peel as a Part of a Facial Rejuvenation Program [Link]
  4. INCHEM: Resorcinol Profile [Link]
  5. DailyMed Label: BENZOCAINE AND RESORCINOL cream [Link]
  6. Resorcinol - Wiley Online Library Resource [File]
  7. TUKES Finnish Safety and Chemicals Agency: Evaluation Report for Resorcinol [File]
Human Metabolome Database
HMDB0032037
KEGG Drug
D00133
KEGG Compound
C01751
PubChem Compound
5054
PubChem Substance
347827890
ChemSpider
4878
BindingDB
26189
RxNav
35382
ChEBI
27810
ChEMBL
CHEMBL24147
ZINC
ZINC000000002028
PDBe Ligand
RCO
Wikipedia
Resorcinol
PDB Entries
1evr / 1qiz / 2oly / 2olz / 2om0 / 2om1 / 2omh / 2omi / 2w44 / 3aqt
show 8 more
MSDS
Download (73.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical
OintmentTopical
LiquidTopical0.8 % w/w
PasteTopical
LiquidTopical
SolutionCutaneous
LotionTopical
OintmentRectal
CreamTopical; Vaginal
GelCutaneous2 % w/w
OintmentTopical5 g
GelTopical
SolutionTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility82.3 mg/mLALOGPS
logP0.7ALOGPS
logP1.37Chemaxon
logS-0.13ALOGPS
pKa (Strongest Acidic)9.26Chemaxon
pKa (Strongest Basic)-5.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity30.02 m3·mol-1Chemaxon
Polarizability10.75 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
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-MSsplash10-03di-3900000000-523ce2d2022aff1e8307
GC-MS Spectrum - EI-BGC-MSsplash10-08gi-9600000000-0e7d24e90c380c2fbaf5
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9500000000-02f0a9b7ce8b4af47473
GC-MS Spectrum - EI-BGC-MSsplash10-03e9-9300000000-fcd22d3e2208eda085dd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f83-3960000000-6169d32b43f71f4abe1a
Mass Spectrum (Electron Ionization)MSsplash10-03di-8900000000-3771649f063971fd96f3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-6e5d7d00af5e0ff154d5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-390a7eb266152d83c925
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-9600000000-bee997565f57f9a1f2c5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mo-9200000000-bf4513727158205d6e54
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gvo-9000000000-c3a11376740204985f58
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-6e64b39732b3a34689d2
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]-116.3295973
predicted
DarkChem Lite v0.1.0
[M-H]-116.4733973
predicted
DarkChem Lite v0.1.0
[M-H]-116.5034973
predicted
DarkChem Lite v0.1.0
[M-H]-116.3921973
predicted
DarkChem Lite v0.1.0
[M-H]-117.683075
predicted
DeepCCS 1.0 (2019)
[M+H]+117.9115973
predicted
DarkChem Lite v0.1.0
[M+H]+117.5463973
predicted
DarkChem Lite v0.1.0
[M+H]+117.4441973
predicted
DarkChem Lite v0.1.0
[M+H]+118.3914973
predicted
DarkChem Lite v0.1.0
[M+H]+120.16533
predicted
DeepCCS 1.0 (2019)
[M+Na]+116.8823973
predicted
DarkChem Lite v0.1.0
[M+Na]+116.8861973
predicted
DarkChem Lite v0.1.0
[M+Na]+116.8865973
predicted
DarkChem Lite v0.1.0
[M+Na]+116.9566973
predicted
DarkChem Lite v0.1.0
[M+Na]+128.78416
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Interacting drug is a metabolite: oxidized metabolite of resorcinol is an irreversible inhibitor of the enzyme via covalent binding at the active site
General Function
Peroxidase activity
Specific Function
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name
TPO
Uniprot ID
P07202
Uniprot Name
Thyroid peroxidase
Molecular Weight
102961.63 Da
References
  1. Paul KB, Hedge JM, Rotroff DM, Hornung MW, Crofton KM, Simmons SO: Development of a thyroperoxidase inhibition assay for high-throughput screening. Chem Res Toxicol. 2014 Mar 17;27(3):387-99. doi: 10.1021/tx400310w. Epub 2014 Jan 14. [Article]

Drug created at December 03, 2015 16:51 / Updated at February 03, 2022 06:26