Identification
NameParachlorophenol
Accession NumberDB13154
TypeSmall Molecule
GroupsApproved
Description

P-chlorophenol is a white crystals with a strong phenol odor. Slightly soluble to soluble in water, depending on the isomer, and denser than water. Noncombustible.

Structure
Thumb
Synonyms
4-Chlorophenol
4-chlorphenol
p-Chlorophenol
External IDs NSC-2877
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Camphorated Para Chlorophenol LiqLiquidDentalSultan Healthcare1985-12-312013-06-18Canada
CaustinerfTabletDentalSeptodont1972-12-312000-08-03Canada
Cresophene LiqLiquidDentalSeptodont1978-12-31Not applicableCanada
Categories
UNII3DLC36A01X
CAS number106-48-9
WeightAverage: 128.556
Monoisotopic: 128.002892489
Chemical FormulaC6H5ClO
InChI KeyWXNZTHHGJRFXKQ-UHFFFAOYSA-N
InChI
InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
IUPAC Name
4-chlorophenol
SMILES
OC1=CC=C(Cl)C=C1
Pharmacology
Indication

Used as an intermediate in organic synthesis of dyes and drugs. Local antibacterial agent in root canal therapy, as topical antiseptic in ointments

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

The major mode of action of chlorophenols appears to be the uncoupling of oxidative phosphorylation. The strength of the uncoupling effect is related to the degree of chlorination: PCP is the strongest inhibitor of oxidative phosphorylation, MCP the weakest. To a lesser extent, inhibition of oxidative phosphorylation is affected by the positions of the chlorine atoms on the molecule.

TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium channel protein type 4 subunit alphaProteinunknownNot AvailableHumanP35499 details
Related Articles
Absorption

absorbed from gastrointestinal tract.

Volume of distributionNot Available
Protein bindingNot Available
Metabolism

P-Chlorophenol yields p-chloroanisole in guinea pigs. P-Chlorophenol yields 4-chlorocatechol p-chloro phenyl-beta-D-glucuronide & p-chlorphenyl sulfate in rabbits. P-Chlorophenol yields p-chlorophenyl sulfate in rats.

Route of elimination

87% of 4-chlorophenol was excreted in urine of dogs as sulfate and glucuronide.

Half lifeNot Available
ClearanceNot Available
Toxicity

Signs and symptoms in human : When undiluted, it whitens & cauterizes the skin & mucous membranes. 4-chlorophenol was shown to permeate the skin. It produces damage at a threshold concentration of 0.75% (w/v).

Routes of Entry: Absorbed through skin. Eye contact. Toxicity to Animals: Acute oral toxicity (LD50): 367 mg/kg [Mouse]. Acute dermal toxicity (LD50): 1500 mg/kg [Rat]. Chronic Effects on Humans: CARCINOGENIC EFFECTS: Classified 2B (Possible for human.) by IARC. DEVELOPMENTAL TOXICITY: Classified Reproductive system/toxin/male, Development toxin [POSSIBLE]. May cause damage to the following organs: liver, brain, gastrointestinal tract, upper respiratory tract, central nervous system (CNS). Other Toxic Effects on Humans: Very hazardous in case of skin contact (irritant).

Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Sciencelab [Link]
  2. Pubchem [Link]
  3. Pubchem [Link]
  4. TOXNET [Link]
  5. ChemSpider [Link]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletDental
LiquidDental
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.0 mg/mLALOGPS
logP2.37ALOGPS
logP2.27ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.84 m3·mol-1ChemAxon
Polarizability12.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-8900000000-f5b8d40439248259fba6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-9800000000-3a8b74727039919cacc4View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-5900000000-7c45de518d13780605c4View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-5900000000-4855b919f4b9bab8519fView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-9800000000-32ffdbba762c4f0fc609View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0900000000-edd6b8e255429561226bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0900000000-edd6b8e255429561226bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0900000000-4f6d51ee33067bb474abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0900000000-099706b387a703bff163View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-1900000000-51fe6ac2fa9bed9bb10aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-2900000000-a2fb225f178a8a1f4345View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9600000000-ec3022a622bccb6ec3fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05r0-9400000000-1debf82a3dd9a5d2c117View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05r3-9200000000-a2b07eb09c8d6ed52d74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0690-9100000000-657bec677b116442fc42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014l-9000000000-ad1f7056f8d05e405129View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gbc-9000000000-c791cec8d419b63d8d59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-004i-9600000000-55d86628a011109663e2View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentP-chlorophenols
Alternative ParentsChlorobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
Substituents4-chlorophenol / 1-hydroxy-2-unsubstituted benzenoid / Halobenzene / Chlorobenzene / Monocyclic benzene moiety / Aryl halide / Aryl chloride / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsmonochlorophenol (CHEBI:28078 ) / a chloroaromatic compound (CPD-10870 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Voltage-gated sodium channel activity
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeleta...
Gene Name:
SCN4A
Uniprot ID:
P35499
Uniprot Name:
Sodium channel protein type 4 subunit alpha
Molecular Weight:
208059.175 Da
References
  1. Leuwer M, Haeseler G, Hecker H, Bufler J, Dengler R, Aronson JK: An improved model for the binding of lidocaine and structurally related local anaesthetics to fast-inactivated voltage-operated sodium channels, showing evidence of cooperativity. Br J Pharmacol. 2004 Jan;141(1):47-54. Epub 2003 Dec 8. [PubMed:14662728 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Uniprot Name:
Solute carrier organic anion transporter family member 1B1
Molecular Weight:
76447.99 Da
References
  1. UniProt [Link]
  2. ChEMBL [Link]
  3. ChEMBL [Link]
  4. KEGG [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Uniprot Name:
Solute carrier organic anion transporter family member 1B3
Molecular Weight:
77402.175 Da
References
  1. UniProt [Link]
  2. ChEMBL [Link]
Drug created on December 02, 2016 11:51 / Updated on September 01, 2017 12:29