CHLOROXYLENOL

First approved in 1960

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H9ClO
Molecular Weight	156.609
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(O)=CC(C)=C1Cl

InChI

InChIKey=OSDLLIBGSJNGJE-UHFFFAOYSA-N

InChI=1S/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3

HIDE SMILES / InChI

Description
Sources: http://www.cleaninginstitute.org/assets/1/Page/American%20Cleaning%20Institute%20Comments%20on%20chloroxylenolProposed%20FDA%20Amendment%20of%20TFM1.pdf
Curator's Comment: description was created based on several sources, including https://www.uwlax.edu/urc/JUR-online/PDF/2000/Koecher_and_Krenke.pdf

Chloroxylenol is used as a preservative in cooling fluids, cosmetics, topical medications, urinary antiseptics and metal working fluids. Products containing Chloroxylenol are used for cleaning and disinfecting wounds, abrasions and abscesses, for minor cuts and scratches, insect bites, burns, inflammation of the skin. It is also found in hair conditioners, toilet cleaners, deodorants, soaps and paste. New use cases continue to be identified. Chloroxylenol has been shown to be effective at reducing the number of pathogenic bacteria in clinical environments. Chloroxylenol has been reviewed and is permitted for use within the European Union (EU) in cosmetic products and is also permitted for use in a number of topical pharmaceutical products as licensed by the UK Medicines and Health Regulatory Agency. Chloroxylenol could cause mild skin irritation in some individuals, or cause an allergic reaction in others. Developed in Europe in the 1920s and used in the United States since the 1950s, Chloroxylenol is one of the most mature antimicrobial agents

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e4b3d43d-7333-4623-bc05-d50b132cfac5	Preventing		Approved 8429	ANTIMICROBIAL HAND LOTION SOAP 652 Approved Use Unknown

PubMed

Title	Date	PubMed
Structural requirements for voltage-dependent block of muscle sodium channels by phenol derivatives.	2001 Apr	11309264
Assessment of resistance towards biocides following the attachment of micro-organisms to, and growth on, surfaces.	2001 Aug	11473589
Female condom reuse in Lusaka, Zambia: evidence from 12 cases.	2001 Dec	11796810
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.	2001 Feb	11266322
[Determination of 4-chloro-3,5-dimethyl phenol in antiseptics and synthetic products by scanning thin-layer chromatography].	2001 Jul	12545501
Determination of the antibacterial efficacy of several antiseptics tested on skin by an 'ex-vivo' test.	2001 Mar	11232776
Phenol derivatives accelerate inactivation kinetics in one inactivation-deficient mutant human skeletal muscle Na(+) channel.	2001 Mar 23	11282107
Determination of phenolic disinfectant agents in commercial formulations by liquid chromatography.	2001 May-Jun	11417646
Comparative susceptibility of resident and transient hand bacteria to para-chloro-meta-xylenol and triclosan.	2002	12147083
Sonochemical degradation of aromatic organic pollutants.	2002	11952182
Guideline for Hand Hygiene in Health-Care Settings. Recommendations of the Healthcare Infection Control Practices Advisory Committee and the HICPAC/SHEA/APIC/IDSA Hand Hygiene Task Force. Society for Healthcare Epidemiology of America/Association for Professionals in Infection Control/Infectious Diseases Society of America.	2002 Oct 25	12418624
Contamination of toothbrush at different time intervals and effectiveness of various disinfecting solutions in reducing the contamination of toothbrush.	2002 Sep	12435003
Allergenicity evaluation of p-chloro-m-cresol and p-chloro-m-xylenol by non-radioactive murine local lymph-node assay and multiple-dose guinea pig maximization test.	2003 Aug 28	12927380
Use of the 'ex vivo' test to study long-term bacterial survival on human skin and their sensitivity to antisepsis.	2004	15546405
Comparative analysis of antibiotic and antimicrobial biocide susceptibility data in clinical isolates of methicillin-sensitive Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa between 1989 and 2000.	2004	15357719
An improved model for the binding of lidocaine and structurally related local anaesthetics to fast-inactivated voltage-operated sodium channels, showing evidence of cooperativity.	2004 Jan	14662728
Efficacy of surgical preparation solutions in foot and ankle surgery.	2005 May	15866959
The effects of biocides (antiseptics and disinfectants) on the endospores of Rhinosporidium seeberi.	2006 Apr	16687856
Antifungal activity of antimicrobial-impregnated devices.	2006 Apr	16524420
Expression profiling of estrogen-responsive genes in breast cancer cells treated with alkylphenols, chlorinated phenols, parabens, or bis- and benzoylphenols for evaluation of estrogenic activity.	2006 May 25	16280211
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Allergic contact dermatitis to chloroxylenol.	2006 Sep	16956470
Predicting dermal permeability of biocides in commercial cutting fluids using a LSER approach.	2007 Dec 10	18029120
Determinants of disease presentation and outcome during cryptococcosis: the CryptoA/D study.	2007 Feb	17284154
Risk factors for HIV infection in males who have sex with males (MSM) in Bangladesh.	2007 Jul 12	17625020
Chloroxylenol.	2007 Jun	17498419
A review of anti-septic agents for pre-operative skin preparation.	2007 Oct-Dec	18165724
Contact sensitivity to preservatives in the UK, 2004-2005: results of multicentre study.	2007 Sep	17680865
Evaluation of estrogenic activity of organic biocides using ER-binding and YES assay.	2007 Sep	17408834
Patch testing experience with 1000 patients.	2007 Sep-Oct	17921610
Susceptibility pattern of some clinical bacterial isolates to selected antibiotics and disinfectants.	2008	19004240
Mineralization of the biocide chloroxylenol by electrochemical advanced oxidation processes.	2008 Apr	18262595
In-vitro activity and in-vivo efficacy of catheters impregnated with chloroxylenol and thymol against uropathogens.	2008 Feb	18042195
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.	2008 Oct	18822043
Occupation-related contact dermatitis in North American health care workers referred for patch testing: cross-sectional data, 1998 to 2004.	2008 Sep-Oct	18845116
Identification of three classes of heteroaromatic compounds with activity against intracellular Trypanosoma cruzi by chemical library screening.	2009	19238193
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009 Dec 2	19956587
Hand dermatitis: a focus on allergic contact dermatitis to biocides.	2009 Jul	19580920
Degradation of the biocide 4-chloro-3,5-dimethylphenol in aqueous medium with ozone in combination with ultraviolet irradiation: operating conditions influence and mechanism.	2009 Nov	19818989
Newborn care practices among slum dwellers in Dhaka, Bangladesh: a quantitative and qualitative exploratory study.	2009 Nov 17	19919700
The antiviral action of common household disinfectants and antiseptics against murine hepatitis virus, a potential surrogate for SARS coronavirus.	2009 Oct	19692148
Vaginal practices of HIV-negative Zimbabwean women.	2010	20871844
Determination of phenolic disinfectants in consumer products by capillary electrophoresis with amperometric detection.	2010 Aug	20819284
Screening level ecological risk assessment for phenols in surface water of the Taihu Lake.	2010 Aug	20557922
Drug structure-transport relationships.	2010 Dec	21107662
A case of intermittent explosive disorder.	2010 Jan	21694793
Vaginal practices and associations with barrier methods and gel use among Sub-Saharan African women enrolled in an HIV prevention trial.	2010 Jun	20352318
Preliminary phytochemical screening and in vitro antioxidant activities of the aqueous extract of Helichrysum longifolium DC.	2010 May 14	20470421
Evaluation of the tissue toxicity of antiseptics by the hen's egg test on the chorioallantoic membrane (HETCAM).	2010 May 18	20562059

Patents

Sample Use Guides

In Vivo Use Guide

soap

Route of Administration: Topical

In Vitro Use Guide

Unknown

Name

Type

Language

CHLOROXYLENOL

Official Name

English

PARACHLOROMETOXYLENOL

Common Name

English

NSC-4971

Code

English

CHLOROXYLENOL [USP-RS]

Common Name

English

PARACHLOROMETAXYLENOL

Systematic Name

English

CHLOROXYLENOL [MI]

Common Name

English

CHLOROXYLENOL [INCI]

Common Name

English

Chloroxylenol [WHO-DD]

Common Name

English

CHLOROXYLENOL [VANDF]

Common Name

English

4-Chloro-3,5-xylenol

Systematic Name

English

CHLOROXYLENOL [USP MONOGRAPH]

Common Name

English

CHLOROXYLENOL [USAN]

Common Name

English

CHLOROXYLENOL [HSDB]

Common Name

English

PHENOL, 4-CHLORO-3,5-DIMETHYL-

Systematic Name

English

chloroxylenol [INN]

Common Name

English

CHLOROXYLENOL [II]

Common Name

English

4-CHLORO-3,5-DIMETHYLPHENOL

Systematic Name

English

PARACHLOROMETOXYLENOL [VANDF]

Common Name

English

P-CHLORO-M-XYLENOL

Common Name

English

CHLOROXYLENOL [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.538