Identification

Name
Phenol
Accession Number
DB03255  (EXPT01917)
Type
Small Molecule
Groups
Approved, Experimental
Description

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.

Structure
Thumb
Synonyms
  • Acide carbolique
  • Acide phenique
  • Benzenol
  • Carbolic acid
  • Carbolsaeure
  • Hydroxybenzene
  • Karbolsaeure
  • Monohydroxybenzene
  • Oxybenzene
  • Phenic Acid
  • Phenol
  • Phenyl alcohol
  • Phenyl hydroxide
  • Phenylic Acid
  • Phenylic alcohol
  • PHOH
External IDs
ENT-1814 / NSC-36808
Product Ingredients
IngredientUNIICASInChI Key
Phenyl hydrogen sulfate2L4RKM5351937-34-8CTYRPMDGLDAWRQ-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Diluent for Allergenic Extract - Sterile Normal Saline with PhenolInjection, solutionPercutaneous; SubcutaneousHollister Stier Laboratories Llc1979-08-01Not applicableUs
Diluent for Allergenic Extract - Sterile Normal Saline with PhenolInjection, solutionPercutaneous; SubcutaneousHollister Stier Laboratories Llc1979-08-01Not applicableUs
Phenol 6%Solution6 %OtherSandoz Canada Incorporated1993-12-31Not applicableCanada
Sterile Diluent for Allergenic ExtractInjection, solution.004 mL/mLIntradermal; SubcutaneousAntigen Laboratories, Inc.1974-03-23Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aseptil RojoLiquid1 mg/mLOralMenper Distributors2012-02-21Not applicableUs
Care One Sore ThroatSpray1.4 g/100mLOralAmerican Sales Company2003-11-192017-11-30Us
Castellani PaintLiquid15 mg/mLTopicalPedinol Pharmacal, Inc.1972-01-01Not applicableUs
Castellani PaintLiquid15 mg/mLTopicalPhysicians Total Care, Inc.2008-05-15Not applicableUs
Castellani PaintLiquid15 mg/mLTopicalStratus Pharmaceuticals2014-04-01Not applicableUs
Castellani PaintLiquid15 mg/mLTopicalPedinol Pharmacal, Inc.1972-01-01Not applicableUs
Castellani Paint 1.5%Liquid15 mg/mLTopicalThe Podiatree Company2013-07-01Not applicableUs
Castellani Paint 1.5%Liquid15 mg/mLTopicalThe Podiatree Company2013-07-01Not applicableUs
Cepastat CherryLozenge14.5 mg/1OralInsight Pharmaceuticals2009-06-292017-12-22Us
Cepastat Extra StrengthLozenge29 mg/1OralInsight Pharmaceuticals2009-07-07Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Liver supplementPowder.8 g/100gOralBionutrigen Co., Ltd.2011-09-15Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ambix First AidPhenol (.005 g/g) + Dyclonine hydrochloride (.005 g/g)CreamTopicalOrganics Corporation Of America Dba Ambix Laboratories2013-08-22Not applicableUs
Anbesol GelPhenol (0.5 %) + Benzocaine (6.4 %)GelOralWyeth Ltd.1993-12-312004-08-04Canada
Anbesol LiquidPhenol (0.45 %) + Benzocaine (6.5 %) + Camphor (0.25 %) + Menthol (0.25 %)LiquidBuccalWyeth Ltd.1992-12-312006-07-24Canada
Anbesol Maximum Strength LiquidPhenol (0.45 %) + Benzocaine (20.0 %) + Camphor (0.25 %) + Menthol (0.25 %)LiquidOralWyeth Ltd.1992-12-312006-07-24Canada
Au Kah Chuen Skin LotionPhenol (0.5 %) + Camphor (2 %) + Menthol (1 %)LotionTopicalWing Quon Enterprises Ltd.Not applicableNot applicableCanada
Balzarol OntPhenol (250 mg) + Allantoin (200 mg) + Benzocaine (1 g)OintmentTopicalRolmex International Inc.1978-12-312008-07-09Canada
Banana Boat Medicated Lip BalmPhenol (0.5 %) + Camphor (0.25 %) + Menthol (0.6 %)StickTopicalThe Banana Boat Company1997-04-142000-09-13Canada
Bite ReliefPhenol (2 %) + Benzocaine (7.95 %) + Camphor (0.1 %) + Menthol (1 %)LiquidTopicalPic Corporation1986-12-311997-11-24Canada
Blistex DctPhenol (0.48 %) + Camphor (0.38 %) + Menthol (0.6 %) + Octinoxate (7.3 %) + Oxybenzone (4.5 %)OintmentTopicalBlistex Corporation1995-12-31Not applicableCanada
Blistex LipPhenol (.5 g/100g) + Camphor (.5 g/100g) + Dimethicone (1.1 g/100g) + Menthol (.6 g/100g)OintmentTopicalHART Health1995-08-09Not applicableUs
Categories
UNII
339NCG44TV
CAS number
108-95-2
Weight
Average: 94.1112
Monoisotopic: 94.041864814
Chemical Formula
C6H6O
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

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.

Structured Indications
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.

TargetActionsOrganism
UThermolysinNot AvailableGeobacillus stearothermophilus
ULysozymeNot AvailableEnterobacteria phage T4
UNicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
USerum albuminNot AvailableHuman
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.

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.

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).

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Sulfate/Sulfite MetabolismMetabolic
Sulfite oxidase deficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
HyaluronidaseThe risk or severity of adverse effects can be increased when Hyaluronidase is combined with Phenol.Approved, Investigational
Technetium Tc-99m tilmanoceptPhenol may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

http://en.wikipedia.org/wiki/Phenols#Synthesisofphenols

General References
  1. 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. [PubMed:23714150]
  2. Gracies JM, Elovic E, McGuire J, Simpson DM: Traditional pharmacological treatments for spasticity. Part I: Local treatments. Muscle Nerve Suppl. 1997;6:S61-91. [PubMed:9826983]
  3. Babich H, Davis DL: Phenol: a review of environmental and health risks. Regul Toxicol Pharmacol. 1981 Jun;1(1):90-109. [PubMed:6764550]
External Links
Human Metabolome Database
HMDB00228
KEGG Drug
D00033
KEGG Compound
C15584
PubChem Compound
996
PubChem Substance
46508193
ChemSpider
971
BindingDB
26187
ChEBI
15882
ChEMBL
CHEMBL14060
PharmGKB
PA450913
HET
IPH
Drugs.com
Drugs.com Drug Page
Wikipedia
Phenol
ATC Codes
D08AE03 — PhenolR02AA19 — PhenolC05BB05 — PhenolN01BX03 — Phenol
AHFS Codes
  • 52:16.00 — Local Anesthetics
PDB Entries
1ai0 / 1ai7 / 1aiy / 1fjw / 1foh / 1jhx / 1jhy / 1li2 / 1lph / 1mpj
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MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Unknown StatusTreatmentBack Pain1
Not AvailableActive Not RecruitingTreatmentPilonidal Sinus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
GelOral
LiquidBuccal
LiquidOral
LiquidOral1 mg/mL
StickTopical
OintmentTopical
PasteTopical
CreamTopical
LotionTopical
LiquidTopical15 mg/mL
LozengeOral14.5 mg/1
LozengeOral29 mg/1
SprayOral3.5 mg/.7mL
SpongeTopical
SprayOral
Injection, solutionPercutaneous; Subcutaneous
LiquidIntradermal; Percutaneous; Subcutaneous
LiquidSubcutaneous
StickTopical.68 g/7g
LiquidTopical1.5 g/100mL
SprayOral1.4 mL/100mL
LiquidTopical
PowderOral.8 g/100g
SalveTopical
SprayOral1.4 g/177mL
SolutionTopical
LiquidTopical1.4 %
SprayOral1.4 mg/mL
SolutionOther6 %
LiquidIntradermal; Subcutaneous
LiquidOral.25 mg/100mL
GelTopical
SprayOral1.4 mg/100mL
SprayOral1.5 g/100mL
LiquidOral1.5 g/100mL
SprayOral1.4 g/100mL
LiquidOral1.4 g/100mL
SprayOral10.268 mg/100mL
SprayOral10.628 mg/100mL
Injection, solutionIntradermal; Subcutaneous
Injection, solutionIntradermal; Subcutaneous.004 mL/mL
PlasterTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)40.9 °CPhysProp
boiling point (°C)181.8 °CPhysProp
water solubility8.28E+004 mg/L (at 25 °C)SOUTHWORTH,GR & KELLER,JL (1986)
logP1.46HANSCH,C ET AL. (1995)
logS0ADME Research, USCD
pKa9.99 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility46.6 mg/mLALOGPS
logP1.39ALOGPS
logP1.67ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.04 m3·mol-1ChemAxon
Polarizability9.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9931
Blood Brain Barrier+0.9076
Caco-2 permeable+0.9326
P-glycoprotein substrateNon-substrate0.8082
P-glycoprotein inhibitor INon-inhibitor0.979
P-glycoprotein inhibitor IINon-inhibitor0.9917
Renal organic cation transporterNon-inhibitor0.8704
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.6114
CYP450 2C9 inhibitorNon-inhibitor0.9654
CYP450 2D6 inhibitorNon-inhibitor0.9746
CYP450 2C19 inhibitorNon-inhibitor0.8981
CYP450 3A4 inhibitorNon-inhibitor0.9523
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8695
Ames testNon AMES toxic0.9454
CarcinogenicityNon-carcinogens0.7594
BiodegradationReady biodegradable0.7488
Rat acute toxicity2.5044 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8468
hERG inhibition (predictor II)Non-inhibitor0.9666
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0udi-3900000000-97dfa3be718a9ee7ace4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00kf-9000000000-6fb456992902a13931f9
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-78c83ab6ff1d3dfdbec6
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-89b0c430b8924ee2afde
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-fc01d0ad6740cfd70e13
GC-MS Spectrum - EI-BGC-MSsplash10-006w-9000000000-c8b41f2899ca8cc9d4bc
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-db80d8b605e20595c679
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-3900000000-97dfa3be718a9ee7ace4
Mass Spectrum (Electron Ionization)MSsplash10-00kf-9000000000-40b376f4e58c23369a01
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0006-9000000000-e67da0571423f0e6b4b8
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-9000000000-e0f57b1e970d0d46597e
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0006-9000000000-e67da0571423f0e6b4b8
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-00kf-9000000000-7bfe3b897e928a8f3a2c
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , PositiveLC-MS/MSsplash10-0006-9000000000-78c83ab6ff1d3dfdbec6
MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-0006-9000000000-89b0c430b8924ee2afde
MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , PositiveLC-MS/MSsplash10-0006-9000000000-fc01d0ad6740cfd70e13
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0006-9000000000-ca4fa5905cccbfeab33a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols (CHEBI:15882) / a phenol (PHENOL)

Targets

Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Metalloendopeptidase activity
Specific Function
Extracellular zinc metalloprotease.
Gene Name
nprS
Uniprot ID
P43133
Uniprot Name
Thermolysin
Molecular Weight
60616.22 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Details
2. Lysozyme
Kind
Protein
Organism
Enterobacteria phage T4
Pharmacological action
Unknown
General Function
Lysozyme activity
Specific Function
Endolysin with lysozyme activity that degrades host peptidoglycans and participates with the holin and spanin proteins in the sequential events which lead to the programmed host cell lysis releasin...
Gene Name
E
Uniprot ID
P00720
Uniprot Name
Endolysin
Molecular Weight
18691.385 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
Specific Function
Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6-dimethylbenzimidazole (DMB).
Gene Name
cobT
Uniprot ID
Q05603
Uniprot Name
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase
Molecular Weight
36612.305 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11334365]

Drug created on June 13, 2005 07:24 / Updated on January 14, 2018 10:04