Identification

Name
Parachlorophenol
Accession Number
DB13154
Type
Small Molecule
Groups
Approved
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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Camphorated Para Chlorophenol LiqParachlorophenol (35 %) + Camphor (65 %)LiquidDentalSultan Healthcare1985-12-312013-06-18Canada
CaustinerfParachlorophenol (.96 mg) + Camphor (1.56 mg) + Formaldehyde (2.16 mg) + Lidocaine (4.32 mg)TabletDentalSeptodont1972-12-312000-08-03Canada
Cresophene LiqParachlorophenol (300 mg) + Camphor (649 mg) + Dexamethasone (1 mg) + Thymol (50 mg)LiquidDentalSeptodont1978-12-31Not applicableCanada
Categories
UNII
3DLC36A01X
CAS number
106-48-9
Weight
Average: 128.556
Monoisotopic: 128.002892489
Chemical Formula
C6H5ClO
InChI Key
WXNZTHHGJRFXKQ-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
Pharmacodynamics
Not 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.

TargetActionsOrganism
USodium channel protein type 4 subunit alphaNot AvailableHuman
Absorption

absorbed from gastrointestinal tract.

Volume of distribution
Not Available
Protein binding
Not 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 life
Not Available
Clearance
Not 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 organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Sciencelab [Link]
  2. Pubchem [Link]
  3. Pubchem [Link]
  4. TOXNET [Link]
  5. ChemSpider [Link]
External Links
KEGG Drug
D00149
KEGG Compound
C02124
PubChem Compound
4684
PubChem Substance
347829264
ChemSpider
13875219
ChEBI
28078
ChEMBL
CHEMBL57053
HET
4CH
PDB Entries
3lb3 / 4awu / 4df2 / 5m8w

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidDental
TabletDental
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-004i-8900000000-f5b8d40439248259fba6
GC-MS Spectrum - EI-BGC-MSsplash10-004i-9800000000-3a8b74727039919cacc4
GC-MS Spectrum - EI-BGC-MSsplash10-004i-5900000000-7c45de518d13780605c4
GC-MS Spectrum - EI-BGC-MSsplash10-004i-5900000000-4855b919f4b9bab8519f
GC-MS Spectrum - EI-BGC-MSsplash10-004i-9800000000-32ffdbba762c4f0fc609
Mass Spectrum (Electron Ionization)MSsplash10-004i-9600000000-55d86628a011109663e2
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
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-edd6b8e255429561226b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-edd6b8e255429561226b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-4f6d51ee33067bb474ab
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-099706b387a703bff163
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-1900000000-51fe6ac2fa9bed9bb10a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-2900000000-a2fb225f178a8a1f4345
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-9600000000-ec3022a622bccb6ec3fb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05r0-9400000000-1debf82a3dd9a5d2c117
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05r3-9200000000-a2b07eb09c8d6ed52d74
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0690-9100000000-657bec677b116442fc42
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014l-9000000000-ad1f7056f8d05e405129
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gbc-9000000000-c791cec8d419b63d8d59

Taxonomy

Description
This compound belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Halophenols
Direct Parent
P-chlorophenols
Alternative Parents
Chlorobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
4-chlorophenol / 1-hydroxy-2-unsubstituted benzenoid / Halobenzene / Chlorobenzene / Monocyclic benzene moiety / Aryl halide / Aryl chloride / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monochlorophenol (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 pr...
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, prostagland...
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), methotre...
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 November 09, 2017 05:19