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Identification
NamePhenol
Accession NumberDB03255  (EXPT01917)
Typesmall molecule
Groupsapproved, 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
SynonymLanguageCode
Acide carboliqueNot AvailableNot Available
Acide pheniqueNot AvailableNot Available
BenzenolNot AvailableNot Available
Carbolic acidNot AvailableNot Available
CarbolsaeureNot AvailableNot Available
HydroxybenzeneNot AvailableNot Available
KarbolsaeureNot AvailableNot Available
MonohydroxybenzeneNot AvailableNot Available
OxybenzeneNot AvailableNot Available
Phenic AcidNot AvailableNot Available
PhenolNot AvailableNot Available
Phenyl alcoholNot AvailableNot Available
Phenyl hydroxideNot AvailableNot Available
Phenylic AcidNot AvailableNot Available
Phenylic alcoholNot AvailableNot Available
PHOHNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
CARE ONE SORE THROATAmerican Sales Company
CEPASTAT EXTRA STRENGTHInsight Pharmaceuticals
CHLORASEPTIC SORE THROATPrestige Brands Holdings, Inc.
EQUALINE SORE THROATSupervalu Inc
GOOD NEIGHBOR PHARMACY SORE THROATAmerisource Bergen
HEALTHY ACCENTS SORE THROATDZA Brands LLC
Brand mixtures
Brand NameIngredients
Blistex Lip dimethicone, camphor, menthol, phenol
CHAPSTICK MEDICATEDcamphor, menthol, petrolatum, phenol
GermolenePhenol and Chlorhexidine
Murakami CamphenicPhenol and Camphor
OzonolPhenol and Zinc Oxide
Categories
CAS number108-95-2
WeightAverage: 94.1112
Monoisotopic: 94.041864814
Chemical FormulaC6H6O
InChI KeyISWSIDIOOBJBQZ-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
Mass Specshow(8.52 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentPhenols and Derivatives
Alternative parentsPolyamines; Enols
Substituentspolyamine; enol
Classification descriptionThis compound belongs to the phenols and derivatives. These are compounds containing a phenol moiety, which is a benzene bearing an hydroxyl group.
Pharmacology
IndicationPhenol 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.
PharmacodynamicsNot Available
Mechanism of actionPhenol 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.
AbsorptionPhenol 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 bindingNot Available
Metabolism

Phenyl sulfate, phenyl glucuronide, quinol sulfate, and quinol glucuronide were detected in human beings as phenol metabolites.

Route of eliminationThe kidney is the primary route of elimination of phenol.
Half lifeNot 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.

ToxicityMouse, 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9654
CYP450 2D6 substrate Non-inhibitor 0.9746
CYP450 2C19 substrate Non-inhibitor 0.8981
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point40.9 °CPhysProp
boiling point181.8 °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 solubility4.66e+01 g/lALOGPS
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 area20.23ChemAxon
rotatable bond count0ChemAxon
refractivity28.04ChemAxon
polarizability9.81ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis Reference

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

General Reference
  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 May 25. pii: S0045-6535(13)00665-6. doi: 10.1016/j.chemosphere.2013.04.067. Pubmed
  2. H. Babich, D.L. Davis, Phenol: A review of environmental and health risks. Regulatory Toxicology and Pharmacology, Volume 1, Issue 1, June 1981, Pages 90–109.
  3. 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
External Links
ResourceLink
KEGG DrugD00033
KEGG CompoundC00146
PubChem Compound996
PubChem Substance46508193
BindingDB26187
ChEBI15882
ChEMBLCHEMBL14060
PharmGKBPA450913
HETIPH
Drugs.comhttp://www.drugs.com/cdi/phenol-spray.html
WikipediaPhenol
ATC CodesN01BX03C05BB05R02AA19D08AE03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(51.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Thermolysin

Kind: protein

Organism: Geobacillus stearothermophilus

Pharmacological action: unknown

Components

Name UniProt ID Details
Thermolysin P43133 Details

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
  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

2. Lysozyme

Kind: protein

Organism: Enterobacteria phage T4

Pharmacological action: unknown

Components

Name UniProt ID Details
Lysozyme P00720 Details

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
  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

3. Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase

Kind: protein

Organism: Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)

Pharmacological action: unknown

Components

Name UniProt ID Details
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:20