Identification
- Summary
Phenol is an antiseptic and disinfectant used in a variety of settings.
- Generic Name
- Phenol
- DrugBank Accession Number
- DB03255
- Background
Phenol is an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. Phenol has been used to disinfect skin and to relieve itching. Phenol is also used as an oral analgesic or anesthetic in products such as Chloraseptic to treat pharyngitis. Additionally, phenol and its related compounds are used in surgical ingrown toenail treatment, a process termed phenolization. Research indicates that parental exposure to phenol and its related compounds are positively associated with spontaneous abortion. During the second world war, phenol injections were used as a means of execution by the Nazis. Phenol is a toxic compound whose vapours are corrosive to the skin, eyes, and respiratory tract.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Phenol (DB03255)
- Weight
- Average: 94.1112
Monoisotopic: 94.041864814 - Chemical Formula
- C6H6O
- Synonyms
- Acide carbolique
- Acide phénique
- Benzenol
- Carbolic acid
- Carbolsäure
- Fenol
- Hydroxybenzene
- Karbolsäure
- Monohydroxybenzene
- Oxybenzene
- Phenic Acid
- Phenol
- Phenyl alcohol
- Phenyl hydroxide
- Phenylic acid
- Phenylic alcohol
- PHOH
- External IDs
- ENT-1814
- NSC-36808
Pharmacology
- Indication
Phenol is primarily indicated for minor sore throat pain, sore mouth, minor mouth irritation, and pain associated with canker sores. Additionally, phenol is indicated in the treatment of focal spasticity.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Phenol is a potent proteolytic agent. Concentrations in the 5% to 7% range dissolve tissue on contact via proteolysis. In high concentrations when injected next to a nerve, phenol produces a chemical neurolysis which is nonselective across nerve fiber size and most prominent on its outer aspect. Local anesthetic effects occur within 5-10 minutes.
Target Actions Organism USerum albumin Not Available Humans UThermolysin Not Available Bacillus thermoproteolyticus - Absorption
Phenol is rapidly absorbed through the skin and into the lungs.
- Volume of distribution
At I5 min after exposure, the liver contained the highest level of phenol, consisting mainly of free phenol. After 82 minutes post administration, phenol is uniformly distributed in the liver, blood, kidneys, lungs, along with the heart, testes, thymus and the spleen. With the passage of time, the proportion of free to conjugated phenol changed. By 360 minutes most phenol appears in conjugated forms.
- Protein binding
Not Available
- Metabolism
Phenyl sulfate, phenyl glucuronide, quinol sulfate, and quinol glucuronide were detected in human beings as phenol metabolites.
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- Route of elimination
The kidney is the primary route of elimination of phenol.
- Half-life
Not Available
- Clearance
In rabbits, 72% is excreted in the urine, 1% in the feces, 4% in the carcass following sacrifice, and trace amounts were exhaled.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Mouse, Subcutaneous, LD50: 0.3-0.35 g/kg. (Duplay and Cazin, 1891; Tollens, 1905). Rat, Subcutaneous, LD50: 0.45. (Deichmann and Witherup, 1944). Rat, Oral, LD50: 0.53. (Deichmann and Witherup, 1944). Rat, Oral, LD50: 0.65. (Flickinger, 1976). Rat, Cutaneous, LD50: 0.67. (Conning and Hayes, 1970).
- Pathways
Pathway Category Sulfite Oxidase Deficiency Disease Sulfate/Sulfite Metabolism Metabolic - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Phenol. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Phenol. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Phenol. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Phenol. Acetic acid The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Phenol. Acetyl sulfisoxazole The risk or severity of methemoglobinemia can be increased when Acetyl sulfisoxazole is combined with Phenol. Adagrasib The risk or severity of methemoglobinemia can be increased when Adagrasib is combined with Phenol. Afatinib The risk or severity of methemoglobinemia can be increased when Afatinib is combined with Phenol. Aldesleukin The risk or severity of methemoglobinemia can be increased when Aldesleukin is combined with Phenol. Alectinib The risk or severity of methemoglobinemia can be increased when Alectinib is combined with Phenol. 
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- 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.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Phenol 6% Solution 6 % Intramuscular Sandoz Canada Incorporated 1993-12-31 2017-08-01 Canada 
Sterile Diluent for Allergenic Extract Injection, solution 0.004 mL/1mL Intradermal; Subcutaneous Antigen Laboratories, Inc. 1974-03-23 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ABC Sore Throat Menthol Flavor Spray 1.4 g/100mL Oral Amerisource Bergen 2023-01-23 Not applicable US ABC Sore Throat Menthol Flavor Spray 1.4 g/100mL Oral Amerisource Bergen 2022-12-26 Not applicable US Aseptil Rojo Spray 1.4 mg/100mL Topical Menper Distributors, Inc. 2012-02-21 Not applicable US Care One Sore Throat Spray 1.4 g/100mL Oral American Sales Company 2003-11-19 2016-12-06 US Castellani Paint Liquid 15 mg/1mL Topical Pedinol Pharmacal, Inc. 1972-01-01 Not applicable US Castellani Paint Liquid 15 mg/1mL Topical Physicians Total Care, Inc. 2008-05-15 Not applicable US Castellani Paint Liquid 15 mg/1mL Topical Stratus Pharmaceuticals 2014-04-01 Not applicable US Castellani Paint Liquid 15 mg/1mL Topical Pedinol Pharmacal, Inc. 1972-01-01 Not applicable US Castellani Paint 1.5% Liquid 15 mg/1mL Topical The Podiatree Company 2013-07-01 Not applicable US Castellani Paint 1.5% Liquid 15 mg/1mL Topical The Podiatree Company 2013-07-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Abridge Cold Sore Treatment Phenol (15 mg/1g) + Menthol (10 mg/1g) + Petrolatum (892 mg/1g) + Synthetic camphor (30 mg/1g) Cream Topical Ranir LLC 2020-02-24 Not applicable US Absorbine Jr Pro Cream Phenol (15 mg/1g) + Lidocaine (40 mg/1g) Cream Topical Clarion Brands, Llc 2023-02-15 Not applicable US Absorbine Jr Pro No Mess Roll-on Plus Phenol (15 mg/1g) + Lidocaine (40 mg/1g) Cream Topical Clarion Brands, Llc 2023-02-15 Not applicable US Ambix First Aid Phenol (0.005 g/1g) + Dyclonine hydrochloride (0.005 g/1g) Cream Topical Suite K Value Added Services LLC 2013-08-19 2013-08-20 US Ambix First Aid Phenol (0.005 g/1g) + Dyclonine hydrochloride (0.005 g/1g) Cream Topical Organics Corporation Of America Dba Ambix Laboratories 2013-08-22 Not applicable US Anbesol Gel Phenol (0.5 %) + Benzocaine (6.4 %) Gel Oral Wyeth Ltd. 1993-12-31 2004-08-04 Canada Anbesol Liquid Phenol (0.45 %) + Benzocaine (6.5 %) + Camphor (0.25 %) + Levomenthol (0.25 %) Liquid Buccal Wyeth Ltd. 1992-12-31 2006-07-24 Canada Anbesol Maximum Strength Liquid Phenol (0.45 %) + Benzocaine (20.0 %) + Camphor (0.25 %) + Levomenthol (0.25 %) Liquid Oral Wyeth Ltd. 1992-12-31 2006-07-24 Canada Au Kah Chuen Skin Lotion Phenol (0.5 %) + Camphor (2 %) + Levomenthol (1 %) Lotion Topical Wing Quon Enterprises Ltd. Not applicable Not applicable Canada Balzarol Ont Phenol (250 mg / 100 g) + Allantoin (200 mg / 100 g) + Benzocaine (1 g / 100 g) Ointment Topical Rolmex International Inc. 1978-12-31 2008-07-09 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dermagesic Phenol (1.4 mg/100mL) + Diphenhydramine hydrochloride (1 mg/100mL) Liquid Topical Llorens Pharmaceuticals International Division 2009-02-01 2014-01-20 US Liver supplement Phenol (0.8 g/100g) Powder Oral Bionutrigen Co., Ltd. 2011-09-15 Not applicable US Preferred Plus Medicated Lip Balm Phenol (4 mg/1g) + Menthol (7 mg/1g) + Synthetic camphor (17 mg/1g) Stick Topical Kinray 2007-02-28 Not applicable US
Categories
- ATC Codes
- C05BB05 — Phenol
- C05BB — Sclerosing agents for local injection
- C05B — ANTIVARICOSE THERAPY
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Anesthetics
- Anesthetics, Local
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiseptics and Disinfectants
- Antivaricose Therapy
- Benzene Derivatives
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Dermatologicals
- Disinfectants
- Miscellaneous Therapeutic Agents
- Nervous System
- Pharmaceutical Preparations
- Pharmaceutical Solutions
- Phenol and Derivatives
- Phenols
- Sclerosing Agents for Local Injection
- Sclerosing Solutions
- Solutions
- Throat Preparations
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- 1-hydroxy-4-unsubstituted benzenoids
- Direct Parent
- 1-hydroxy-4-unsubstituted benzenoids
- Alternative Parents
- 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
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols (CHEBI:15882) / a phenol (PHENOL)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 339NCG44TV
- CAS number
- 108-95-2
- InChI Key
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
- IUPAC Name
- phenol
- SMILES
- OC1=CC=CC=C1
References
- Synthesis Reference
http://en.wikipedia.org/wiki/Phenols#Synthesisofphenols
- General References
- Chen X, Chen M, Xu B, Tang R, Han X, Qin Y, Xu B, Hang B, Mao Z, Huo W, Xia Y, Xu Z, Wang X: Parental phenols exposure and spontaneous abortion in Chinese population residing in the middle and lower reaches of the Yangtze River. Chemosphere. 2013 Sep;93(2):217-22. doi: 10.1016/j.chemosphere.2013.04.067. Epub 2013 May 25. [Article]
- Gracies JM, Elovic E, McGuire J, Simpson DM: Traditional pharmacological treatments for spasticity. Part I: Local treatments. Muscle Nerve Suppl. 1997;6:S61-91. [Article]
- Babich H, Davis DL: Phenol: a review of environmental and health risks. Regul Toxicol Pharmacol. 1981 Jun;1(1):90-109. [Article]
- External Links
- Human Metabolome Database
- HMDB0000228
- KEGG Drug
- D00033
- KEGG Compound
- C15584
- PubChem Compound
- 996
- PubChem Substance
- 46508193
- ChemSpider
- 971
- BindingDB
- 26187
- 33290
- ChEBI
- 15882
- ChEMBL
- CHEMBL14060
- ZINC
- ZINC000005133329
- PharmGKB
- PA450913
- PDBe Ligand
- IPH
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Phenol
- PDB Entries
- 1ai0 / 1ai7 / 1aiy / 1fjw / 1foh / 1jhx / 1jhy / 1li2 / 1lph / 1mpj … show 97 more
- MSDS
- Download (51.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Pilonidal Sinus of Natal Cleft / Pilonidal Sinus Without Abscess 1 4 Recruiting Treatment Knee Pain Chronic / Osteoarthritis of the Knee 1 4 Recruiting Treatment Pilonidal Sinus of Natal Cleft / Pilonidal Sinus Without Abscess 1 4 Withdrawn Treatment Pain, Chronic 1 2 Not Yet Recruiting Prevention Prophylaxis of migraine headaches 1 2 Unknown Status Supportive Care Interactable Malignant Perineal Pain 1 2 Unknown Status Treatment Alzheimer's Disease (AD) 1 1 Terminated Basic Science Asthma, Allergic / Healthy Subjects (HS) 1 1 Unknown Status Treatment Back pain 1 0 Recruiting Prevention Hearing Loss, Idiopathic Sudden Sensorineural / Intratympanic Steroid Injection / Menière's Disease 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- ALK-Abello Inc.
- Allergy Laboratories Inc.
- Anachemia Canada
- Antigen Laboratories Inc.
- Dosage Forms
Form Route Strength Gel Oral Liquid Buccal Liquid Oral Solution Topical Spray Topical 1.4 mg/100mL Kit Topical Stick Topical Paste Topical Kit; ointment; stick Topical Cream Topical Lotion Topical Gel Topical Liquid Topical 15 mg/1mL Liquid Topical 0.8 % w/w Lozenge Oral 14.5 mg/1 Lozenge Oral 29 mg/1 Spray Oral 3.5 mg/0.7mL Sponge Topical Solution Solution Liquid Intradermal; Percutaneous; Subcutaneous Liquid Subcutaneous Solution Oral Stick Topical 0.68 g/7g Liquid Topical 1.5 g/100mL Solution Cutaneous Solution Buccal; Oropharyngeal 1.4 g Injection Submucosal 5 % Spray Oral 1.4 mg/100mL Solution Buccal; Oral 1.4 g Kit; liquid; ointment Buccal; Topical Ointment Topical Powder Oral 0.8 g/100g Liquid Topical Salve Topical Spray Oral 1.4 g/177mL Solution Topical Solution Auricular (otic) Liquid Topical 1.4 % Salve Topical 1.5 g/100g Spray Oral 1.4 mg/1mL Solution Intramuscular 6 % Solution / drops Auricular (otic) Liquid Intradermal; Subcutaneous Liquid Oral .25 mg/100mL Spray Oral 1.4 g/100g Spray Oral 1.4 g/100mL Spray Oral 1.5 g/100mL Liquid Oral 1.5 g/100mL Liquid Oral 1.4 g/100mL Injection, solution Intradermal; Subcutaneous Injection, solution Intradermal; Subcutaneous 0.004 mL/1mL Spray Oral 10.628 mg/100mL Rinse Oral 6 mg/1mL Spray Oral Spray Oral 7 mg/1mL Liquid Topical 6 mg/1mL Plaster Topical Solution 50 mg/1ml Liquid Dental - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 40.9 °C PhysProp boiling point (°C) 181.8 °C PhysProp water solubility 8.28E+004 mg/L (at 25 °C) SOUTHWORTH,GR & KELLER,JL (1986) logP 1.46 HANSCH,C ET AL. (1995) logS 0 ADME Research, USCD pKa 9.99 (at 25 °C) SERJEANT,EP & DEMPSEY,B (1979) - Predicted Properties
Property Value Source Water Solubility 46.6 mg/mL ALOGPS logP 1.39 ALOGPS logP 1.67 Chemaxon logS -0.31 ALOGPS pKa (Strongest Acidic) 10.02 Chemaxon pKa (Strongest Basic) -5.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 28.04 m3·mol-1 Chemaxon Polarizability 9.81 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9931 Blood Brain Barrier + 0.9076 Caco-2 permeable + 0.9326 P-glycoprotein substrate Non-substrate 0.8082 P-glycoprotein inhibitor I Non-inhibitor 0.979 P-glycoprotein inhibitor II Non-inhibitor 0.9917 Renal organic cation transporter Non-inhibitor 0.8704 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7558 CYP450 1A2 substrate Non-inhibitor 0.6114 CYP450 2C9 inhibitor Non-inhibitor 0.9654 CYP450 2D6 inhibitor Non-inhibitor 0.9746 CYP450 2C19 inhibitor Non-inhibitor 0.8981 CYP450 3A4 inhibitor Non-inhibitor 0.9523 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8695 Ames test Non AMES toxic 0.9454 Carcinogenicity Non-carcinogens 0.7594 Biodegradation Ready biodegradable 0.7488 Rat acute toxicity 2.5044 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8468 hERG inhibition (predictor II) Non-inhibitor 0.9666
Spectra
- Mass Spec (NIST)
- Download (8.52 KB)
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. [Article]
- Kind
- Protein
- Organism
- Bacillus thermoproteolyticus
- Pharmacological action
- Unknown
- General Function
- Metalloendopeptidase activity
- Specific Function
- Extracellular zinc metalloprotease.
- Gene Name
- npr
- Uniprot ID
- P00800
- Uniprot Name
- Thermolysin
- Molecular Weight
- 60103.515 Da
References
- English AC, Groom CR, Hubbard RE: Experimental and computational mapping of the binding surface of a crystalline protein. Protein Eng. 2001 Jan;14(1):47-59. doi: 10.1093/protein/14.1.47. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 05, 2023 06:28