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

Details

Stereochemistry ACHIRAL
Molecular Formula C13H11ClO
Molecular Weight 218.679
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOROPHENE

SMILES

OC1=C(CC2=CC=CC=C2)C=C(Cl)C=C1

InChI

InChIKey=NCKMMSIFQUPKCK-UHFFFAOYSA-N
InChI=1S/C13H11ClO/c14-12-6-7-13(15)11(9-12)8-10-4-2-1-3-5-10/h1-7,9,15H,8H2

HIDE SMILES / InChI

Molecular Formula C13H11ClO
Molecular Weight 218.679
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Chlorophene is a halogenated phenolic compound that functions as a biocide and preservative in cosmetics. In Europe, the maximum authorized concentration allowed for Chlorophene is 0.2%. The glucuronic acid conjugate, the sulfate ester conjugate, and two other minor metabolites of Chlorophene were profiled in rat urine during pharmacokinetic tests. Chlorophene is incompletely absorbed through rat skin. In several anumal species these chemicals exhibited low oral toxicity. Some evidence of toxicity was found in short-term oral toxicity studies in mice and rats with nephropathy as the principal finding. Rats and mice dosed with Chlorophene for 2 years had a dose-related and sex-related increase in the severity of nephropathy. In another set of animal tests Chlorophene was found to be an ocular irritant. There was no readily available inhalation profile for Chlorophene. Chlorophene was severely irritating to rabbits in most dermal irritation studies. Chlorophene was found to be mutagenic in four in-vitro mammalian test systems. However, neoplasms were not observed in rats treated with Chlorophene for 2 years but, in mice treated similarly a significant incidence of neoplasms was observed. A 1-year National Toxicology Program (NTP) study concluded that Chlorophene was a cutaneous irritant and a weak skin tumor promoter but had no activity as an initiator or complete carcinogen. Some reactions to Chlorophene occurred in some, but not all, clinical dermal sensitization tests.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Disposition of o-benzyl-p-chlorophenol in male rats.
1986
Prechronic toxicity of o-benzyl-p-chlorophenol in rats and mice.
1986 Nov
Chronic nephropathy and renal carcinogenicity of o-benzyl-p-chlorophenol in F344/N rats and B6C3F1 mice.
1995 Sep
Determination of phenolic disinfectant agents in commercial formulations by liquid chromatography.
2001 May-Jun
Effects of high temperature and disinfectants on the viability of Sarcocystis neurona sporocysts.
2002 Dec
Ecotoxicological evaluation of the biocidal agents sodium o-phenylphenol, sodium o-benzyl-p-chlorophenol, and sodium p-tertiary amylphenol.
2005 Feb
In vitro cytotoxicity assessment of the biocidal agents sodium o-phenylphenol, sodium o-benzyl-p-chlorophenol, and sodium p-tertiary amylphenol using established fish cell lines.
2006 Oct
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
2008 Oct
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011 Mar 28
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:55:07 GMT 2023
Edited
by admin
on Sat Dec 16 17:55:07 GMT 2023
Record UNII
7560BB0BO3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOROPHENE
HSDB   MART.   MI   USAN  
USAN  
Official Name English
CLOROPHENE [USAN]
Common Name English
NSC-59989
Code English
ORTHO-BENZYL-PARA-CHLOROPHENOL
Systematic Name English
clorofene [INN]
Common Name English
PHENOL, 4-CHLORO-2-(PHENYLMETHYL)-
Systematic Name English
4-Chloro-α-phenyl-O-cresol
Common Name English
CLOROPHENE [MI]
Common Name English
SANTOPHEN 1
Brand Name English
2-BENZYL-4-CHLOROPHENOL
Systematic Name English
4-CHLORO-2-BENZYLPHENOL
Systematic Name English
BENZYL CHLORO PHENOL
Systematic Name English
Clorofene [WHO-DD]
Common Name English
CHLOROPHENE
INCI  
INCI  
Official Name English
CLOROFENE
INN   WHO-DD  
INN  
Official Name English
CHLOROPHENE [INCI]
Common Name English
CLOROPHENE [MART.]
Common Name English
O-BENZYL-P-CHLOROPHENOL
Common Name English
5-CHLORO-2-HYDROXYDIPHENYLMETHANE
Common Name English
CLOROPHENE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45494
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
EPA PESTICIDE CODE 62201
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
Code System Code Type Description
NSC
59989
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
MERCK INDEX
m3664
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY Merck Index
MESH
C004660
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
EVMPD
SUB06762MIG
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
CAS
120-32-1
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
FDA UNII
7560BB0BO3
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
INN
2100
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
HSDB
5179
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
SMS_ID
100000084028
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
RXCUI
21290
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
204-385-8
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID5020154
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
PUBCHEM
8425
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL1328919
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
NCI_THESAURUS
C65342
Created by admin on Sat Dec 16 17:55:08 GMT 2023 , Edited by admin on Sat Dec 16 17:55:08 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY