U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula 2C6H3Cl3O.C4H10N2
Molecular Weight 481.028
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICLOFENOL PIPERAZINE

SMILES

C1CNCCN1.OC2=C(Cl)C=C(Cl)C(Cl)=C2.OC3=C(Cl)C=C(Cl)C(Cl)=C3

InChI

InChIKey=BNVFYGMONODIGW-UHFFFAOYSA-N
InChI=1S/2C6H3Cl3O.C4H10N2/c2*7-3-1-5(9)6(10)2-4(3)8;1-2-6-4-3-5-1/h2*1-2,10H;5-6H,1-4H2

HIDE SMILES / InChI

Molecular Formula C4H10N2
Molecular Weight 86.1356
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H3Cl3O
Molecular Weight 197.446
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

2,4,5-Trichlorophenol is a grey flake or needle-shaped solid. It is used as an intermediate in the manufacture of the herbicide 2,4,5-Trichlorophenoxyacetic Acid (2,4,5-T) and as a fungicide and bactericide. 2,4,5-trichlorophenol (triclofenol piperazine, Ranestol) is an antifungal agent, which was also used against light hookworm infections. Thirty persons who were positive for hookworm eggs in their stools were treated with 50 mg/kg of triclofenol piperazine dissolved in 5 per cent polyethylene glycol Ranestol® in soft gelatin capsules. Nineteen of these showed 77 to 100 % reduction in egg count average when compared with the pre-treatment counts. Side reactions were limited to mild and transient nausea in 23, vomiting in 7, transient abdominal cramps and headache in 2 each. 2,4,5-trichlorophenol complexed with dicyclohexylamine was used for treatment of experimental mycosis. From the mycological and clinical evaluation the conclusion can be drawn that the effect of phenol in lipophilic ointment is comparable to that of clotrimazole.

Approval Year

PubMed

PubMed

TitleDatePubMed
Purification and Properties of Component B of 2,4,5-Trichlorophenoxyacetate Oxygenase from Pseudomonas cepacia AC1100.
1995 Sep
Reactions of 2,4,6-trichlorophenol on model fly ash: oxidation to CO and CO2, condensation to PCDD/F and conversion into related compounds.
2001 Feb-Mar
Fate of the herbicides 2,4,5-T, atrazine, and DNOC in a shallow, anaerobic aquifer investigated by in situ passive diffusive emitters and laboratory batch experiments.
2001 Nov-Dec
Evidence of differences in the biotransformation of organic contaminants in three species of freshwater invertebrates.
2002
Electrochemical removal of p-nonylphenol from dilute solutions using a carbon fiber anode.
2002 Jul
Impact of protein binding on the availability and cytotoxic potency of organochlorine pesticides and chlorophenols in vitro.
2002 Jun 14
Biological monitoring of 2,4,5-trichlorophenol (II): evaluation of an enzyme-linked immunosorbent assay for the analysis of water, urine, and serum samples.
2002 Nov
Products of aqueous chlorination of 4-nonylphenol and their estrogenic activity.
2002 Oct
A disappearance model for the prediction of trichlorophenol ozonation.
2003 Apr
Polychlorinated dibenzo-p-dioxins and dibenzofurans in the air of Seveso, Italy, 26 years after the explosion.
2003 Apr 15
Maternal serum dioxin levels and birth outcomes in women of Seveso, Italy.
2003 Jun
Isolation of a glucosyltransferase from Arabidopsis thaliana active in the metabolism of the persistent pollutant 3,4-dichloroaniline.
2003 May
Treatment of trichlorophenol by catalytic oxidation process.
2003 May
Narrow-band irradiation of a homologous series of chlorophenols on TiO2: charge-transfer complex formation and reactivity.
2004 Jul 6
Hydrophilic and hydrophobic sorption of organic acids by variable charge soils: effect of chemical acidity and acidic functional group.
2004 Oct 15
Ultrasonic dehalogenation and toxicity reduction of trichlorophenol.
2005 Jan
Quantification of phenolic metabolites of environmental chemicals in human urine using gas chromatography-tandem mass spectrometry and isotope dilution quantification.
2005 Jun 25
Hydroxyl free radical reactivity toward aqueous chlorinated phenols.
2005 Mar
Functional importance of the family 1 glucosyltransferase UGT72B1 in the metabolism of xenobiotics in Arabidopsis thaliana.
2005 May
Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry.
2006 Feb 2
Fenton degradation of organic pollutants in the presence of low-molecular-weight organic acids: cooperative effect of quinone and visible light.
2006 Jan 15
Using the dual-mode model to describe adsorption of organic pollutants onto an organoclay.
2006 Jul 1
Role of plant activity and contaminant speciation in aquatic plant assimilation of 2,4,5-trichlorophenol.
2006 Jun
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Age- and concentration-dependent elimination half-life of 2,3,7,8-tetrachlorodibenzo-p-dioxin in Seveso children.
2006 Oct
Serum concentrations of chlorinated dibenzo-p-dioxins and dibenzofurans among former Michigan trichlorophenol and pentachlorophenol workers.
2007 Sep
Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria x ananassa) achene and receptacle.
2008
Novel application of modified multiwalled carbon nanotubes as a solid phase extraction adsorbent for the determination of polyhalogenated organic pollutants in aqueous solution.
2008 Apr
Pentachlorophenol and cancer risk: focusing the lens on specific chlorophenols and contaminants.
2008 Aug
Chlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyl profiles of workers with trichlorophenol and pentachlorophenol exposures.
2008 Aug
Automated on-line column-switching HPLC-MS/MS method for measuring environmental phenols and parabens in serum.
2008 Aug 15
Evaluation of various tests for the diagnosis of soil contamination by 2,4,5-trichlorophenol (2,4,5-TCP).
2008 Dec
Molecular characterization of brominated persistent pollutants using extended X-ray absorption fine structure (EXAFS) spectroscopy.
2008 Feb
Fluorescence quenching of versatile fluorescent probes based on strongly electron-donating distyrylbenzenes responsive to aromatic chlorinated and nitro compounds, boronic acid and Ca(2+).
2008 Jan
Acidogenic sequencing batch reactor start-up procedures for induction of 2,4,6-trichlorophenol dechlorination.
2008 Mar
Dioxins and cardiovascular disease mortality.
2008 Nov
A margin-of-exposure approach to assessment of noncancer risks of dioxins based on human exposure and response data.
2008 Oct
Metabolic fate of [14C] chlorophenols in radish (Raphanus sativus), lettuce (Lactuca sativa), and spinach (Spinacia oleracea).
2008 Sep 24
Patents

Sample Use Guides

Triclofenol piperazine was administered as a salt consisting of 82 per cent 2,4,5-triclofenol and 18 percent piperazine which was enclosed in a soft gelatin capsule consisting of a 5 per cent solution of the drug in polyethylene glycol 400. The capsules contained 250 or 100 mg. (base) of the salt. It was administered with Coca Cola which was followed by hard candy. Each patient received a single dose of 50 mg./kg. of body weight.
Route of Administration: Oral
2,4,5-trichlorophenol (2,4,5-TCP) at concentrations from 25-600 ppm increased the size and granularity of the lymphocytes. 2,4,5-TCP induced the strongest and 4,5-DCC induced the weakest changes in these parameters. Moreover, 2,4,5-TCP induced the greatest loss of lymphocyte viability, which was statistically significant at concentrations of 125 and 600 ppm.
Substance Class Chemical
Created
by admin
on Sat Dec 17 01:32:16 UTC 2022
Edited
by admin
on Sat Dec 17 01:32:16 UTC 2022
Record UNII
444YK71BIV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICLOFENOL PIPERAZINE
INN   MI   USAN  
USAN   INN  
Official Name English
CN-5834-5931B
Code English
RANESTOL
Brand Name English
TRICLOFENOL PIPERAZINE [MI]
Common Name English
triclofenol piperazine [INN]
Common Name English
PHENOL, 2,4,5-TRICHLORO-, COMPD. WITH PIPERAZINE (2:1)
Systematic Name English
NSC-77747
Code English
CN-5834-5931-B
Code English
Piperazine compound (1:2) with 2,4,5-trichlorophenol
Common Name English
TRICLOFENOL PIPERAZINE [USAN]
Common Name English
CI-416
Code English
IN-29-5931B
Code English
IN 29-5931B
Code English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C152737
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
CAS
5714-82-9
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
FDA UNII
444YK71BIV
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
NSC
77747
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
MERCK INDEX
M975
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY Merck Index
ChEMBL
CHEMBL2107709
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
EPA CompTox
DTXSID50972607
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
INN
1226
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
PUBCHEM
21952
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
EVMPD
SUB11273MIG
Created by admin on Sat Dec 17 01:32:16 UTC 2022 , Edited by admin on Sat Dec 17 01:32:16 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY