- Accession Number
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.
- Small Molecule
- Average: 110.1106
- Chemical Formula
- External IDs
- FEMA NO. 3589
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Contemporary therapeutic uses for resorcinol primarily revolve around the use of the phenol derivative as an active ingredient in topical antiseptics 2,1,5 or as topical antibacterial skin treatment products for conditions like acne, seborrheic dermatitis, eczema, and others 3,2,1,5.
- Associated Conditions
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
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 5,4. Resorcinol interferes with the iodination of tyrosine and the oxidation of iodide 5,4. 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 5,4.
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 5,4. 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 5,4. 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 5,4. 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% 5,4. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated 5,4.
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) 5,4. The iodination process is catalyzed by a haem-containing enzyme, and resorcinol is known to form covalent bonds with haem 5,4.
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.
Target Actions Organism UThyroid peroxidase Not Available Humans
The dermal absorption of resorcinol seems to be low (< 1%) when applied on healthy and intact skin 6. 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.
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.
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.
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 6,1.
- Adverse Effects
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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) 5. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol 5. In persons suffering from resorcinol poisoning, the symptoms included anemia, spleen siderosis, and fatty degeneration of the liver and kidneys 5.
- Affected organisms
- Humans and other mammals
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- 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.
Drug Interaction Abacavir Abacavir may decrease the excretion rate of Resorcinol which could result in a higher serum level. Abaloparatide The therapeutic efficacy of Abaloparatide can be decreased when used in combination with Resorcinol. Aceclofenac Aceclofenac may decrease the excretion rate of Resorcinol which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Resorcinol which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Resorcinol which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Resorcinol which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Resorcinol which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Resorcinol which could result in a higher serum level. Acrivastine Acrivastine may decrease the excretion rate of Resorcinol which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Resorcinol which could result in a higher serum level.Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more
- Food Interactions
- No interactions found.
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- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acne Aid Gel Resorcinol (1.25 %) + Chloroxylenol (.375 %) + Octasulfur (2.5 %) Gel Topical Stiefel Laboratories, Inc. 1966-12-31 1998-07-09 Acne Drying Topical Resorcinol (2 g/100mL) + Octasulfur (8 g/100mL) Lotion Topical Only Yourx, Inc. 2014-08-26 Not applicable Acne Treatment maximum strength CVS Resorcinol (2 g/100g) + Octasulfur (8 g/100g) Cream Topical CVS Health 2014-12-26 Not applicable Acnomel Skin Tone Cream Resorcinol (2 %) + Isopropyl alcohol (11 %) + Octasulfur (8 %) Cream Topical Numark Laboratories, Inc. 1992-12-31 2004-07-30 Acnotex acne Treatment Resorcinol (20 mg/1mL) + Octasulfur (80 mg/1mL) Lotion Topical Genesis 2011-07-07 2015-03-01 Adult Acnomel Resorcinol (20 mg/1g) + Octasulfur (80 mg/1g) Cream Topical Numark Brands, Inc 1946-10-08 Not applicable Adult Acnomel Tinted Resorcinol (2 g/100g) + Octasulfur (8 g/100g) Cream Topical Denison Pharmaceuticals, Inc. 2017-01-01 Not applicable Anti Itch Resorcinol (2 g/100g) + Benzocaine (5 g/100g) Cream Topical Walgreen Company 2006-03-02 2021-03-31 Anti-Itch Regular Strength Resorcinol (2 g/100g) + Benzocaine (5 g/100g) Cream Topical Walgreens 2020-01-09 Not applicable Assured Feminine Anti-itch Resorcinol (2 g/100g) + Benzocaine (5 g/100g) Cream Topical Greenbrier International, Inc. 2017-03-31 Not applicable
- ATC Codes
- D10AX02 — Resorcinol
- D10AX — Other anti-acne preparations for topical use
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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.
- Organic compounds
- Super Class
- Sub Class
- Direct Parent
- Alternative Parents
- 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Organooxygen compounds / Hydrocarbon derivatives
- 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)
- CAS number
- InChI Key
- IUPAC Name
- General References
- NIH Toxnet: Resorcinol Profile [Link]
- Drugs.com: Resorcinol Profile [Link]
- Resorcinol Peel as a Part of a Facial Rejuvenation Program [Link]
- INCHEM: Resorcinol Profile [Link]
- Resorcinol - Wiley Online Library Resource [File]
- TUKES Finnish Safety and Chemicals Agency: Evaluation Report for Resorcinol [File]
- PDB Entries
- 1evr / 1qiz / 2oly / 2olz / 2om0 / 2om1 / 2omh / 2omi / 2w44 / 3aqt … show 7 more
- Download (73.5 KB)
- Not Available
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 8 g Cream Topical Ointment Topical Solution Topical 0.15 g/15ml Paste Topical Liquid Topical Solution Cutaneous 1 g/100g Lotion Topical Ointment Rectal Solution Topical 5 g Lotion Topical 5 g Ointment Topical 4 g Cream Topical; Vaginal Lotion Topical 3 g Gel Cutaneous 2 % w/w Lotion Topical 2.8 % Ointment Topical 5 g Gel Topical Solution Topical
- Not Available
- Not Available
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 82.3 mg/mL ALOGPS logP 0.7 ALOGPS logP 1.37 ChemAxon logS -0.13 ALOGPS pKa (Strongest Acidic) 9.26 ChemAxon pKa (Strongest Basic) -5.7 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 0 ChemAxon Refractivity 30.02 m3·mol-1 ChemAxon Polarizability 10.75 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET Features
- Not Available
- Mass Spec (NIST)
- Not Available
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- Thyroid peroxidase
- Molecular Weight
- 102961.63 Da
- 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. [PubMed:24383450]
Drug created on December 03, 2015 16:51 / Updated on February 21, 2021 18:52