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Details

Stereochemistry ACHIRAL
Molecular Formula C4H4ClNOS
Molecular Weight 149.599
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLCHLOROISOTHIAZOLINONE

SMILES

CN1SC(Cl)=CC1=O

InChI

InChIKey=DHNRXBZYEKSXIM-UHFFFAOYSA-N
InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3

HIDE SMILES / InChI
Molecular Formula C4H4ClNOS
Molecular Weight 149.599
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: DOI: 10.1007/978-3-642-55706-4_7 http://ec.europa.eu/consumers/sectors/cosmetics/files/pdf/mci_mi/mci_mi_pc_en.pdf Methylisothiazolinone/Methylchloroisothiazolinone (Kathon CG) Allergy: An Updated Review.

Methylchloroisothiazolinone is an active ingredient in many preservatives marketed under various brand names. It is effective against gram-positive and gram-negative bacteria, yeast, and fungi. Pure Methylchloroisothiazolinone is not commercially available. Kathon CG contains a mixture of Methylisothiazolinone (MI) and Methylchloroisothiazolinone (MCI) in ratio 3:1. Kathon was used in various rinse-off and leave-on formulations including hair products, shampoos, skin care products, bath products, eye and facial makeup, wet wipes and suntan products. The Commission envisages amending Annex V of the Cosmetics Regulation (EC) No. 1223/2009 to restrict the use of methylchloroisothiazolinone to rinse-off products, as suggested by the SCCS.

Originator

Approval Year

1988
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8429
TRUE Test

Approved Use

5-chloro-2-methyl-4-isothiazolin-3-one (1.05% to 1.25% w/w) and 2-methyl-4-isothiazolin-3-one (0.25% to 0.40% w/w) in a 3:1 ratio at a concentration of 1.5% in aqueous magnesium salts are used to formulate patch #17
PubMed

PubMed

TitleDatePubMed
Audit of Finn Chamber patch test preparation.
2002 Dec
Involvement of oxidative stress in apoptosis induced by a mixture of isothiazolinones in normal human keratinocytes.
2003 Aug
Coupling of contact sensitizers to thiol groups is a key event for the activation of monocytes and monocyte-derived dendritic cells.
2003 Feb
Contact sensitization to 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one in children.
2003 Oct
Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione.
2004 Jan 19
Effect of glutathione on the covalent binding of the 13C-labeled skin sensitizer 5-chloro-2-methylisothiazol-3-one to human serum albumin: identification of adducts by nuclear magnetic resonance, matrix-assisted laser desorption/ionization mass spectrometry, and nanoelectrospray tandem mass spectrometry.
2004 Sep
From experiment to theory: molecular orbital parameters to interpret the skin sensitization potential of 5-chloro-2-methylisothiazol-3-one and 2-methylisothiazol-3-one.
2005 Feb
GSH depletion, protein S-glutathionylation and mitochondrial transmembrane potential hyperpolarization are early events in initiation of cell death induced by a mixture of isothiazolinones in HL60 cells.
2006 Feb
Airborne allergic contact dermatitis to methylchloroisothiazolinone/methylisothiazolinone in ironing water.
2008 Mar
Role of intracellular calcium and S-glutathionylation in cell death induced by a mixture of isothiazolinones in HL60 cells.
2009 Mar
Consumer exposure to biocides--identification of relevant sources and evaluation of possible health effects.
2010 Feb 3
Prevalence and cause of methylisothiazolinone contact allergy.
2010 Sep
B cell increases and ex vivo IL-2 production as secondary endpoints for the detection of sensitizers in non-radioisotopic local lymph node assay using flow cytometry.
2012 Mar 25
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.
2015 Mar 1
Patents

Patents

US5750402 A
1

Sample Use Guides

In Vivo Use Guide
3 mcg of 5-chloro-2-methyl-4-isothiazolin-3-one (1.05% to 1.25% w/w) and 2-methyl-4-isothiazolin-3-one (0.25% to 0.40%w/w) in a 3:1 ratio per patch. Schedule patients to return approximately 48 hours after patch test application to have the panels removed.
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: Kathon is active at concentrations of 2.25–9 mg/mL active ingredients against a wide range of bacteria and fungi. https://www.google.ru/url?sa=t&rct=j&q=&esrc=s&source=web&cd=6&ved=0ahUKEwinisCBq8bPAhXI8ywKHWDrAJ8QFghGMAU&url=https%3A%2F%2Ffaculty.psau.edu.sa%2Ffiledownload%2Fdoc-7-pdf-61f3024ed641390e498517b310f7a378-original.pdf&usg=AFQjCNETPmioZMn6G6wNkDUJ6dSIgh59tA&sig2=uKNYTfPwwpRk83zu8Y96zA&bvm=bv.134495766,d.bGg
5-Chloro-2-methyl-4-isothiazolin-3-one inhibited growth in all test strains of Salmonella typhimurium without activation. A statistically significant increase in the number of revertants in strain TA100 was observed without activation at concentrations of 0.20, 0.25 and 0.30 ug/plate and in 2 of the 3 trials at 0.10 ug/plate.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:34 UTC 2023
Edited
by admin
on Fri Dec 15 15:50:34 UTC 2023
Record UNII
DEL7T5QRPN
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYLCHLOROISOTHIAZOLINONE
II   INCI   MART.   VANDF  
INCI  
Official Name English
5-CHLORO-2-METHYL-3-ISOTHIAZOLONE
Systematic Name English
METHYLCHLOROISOTHIAZOLINONE [II]
Common Name English
METHYLCHLOROISOTHIAZOLINONE [MART.]
Common Name English
5-CHLOR-2-METHYL-4-ISOTHIAZOLIN-3-ONE
Common Name English
A-33
Code English
METHYLCHLOROISOTHIAZOLINONE [MI]
Common Name English
3(2H)-ISOTHIAZOLONE, 5-CHLORO-2-METHYL-
Systematic Name English
5-CHLORO-N-METHYLISOTHIAZOLONE
Systematic Name English
METHYLCHLOROISOTHIAZOLINONE [INCI]
Common Name English
Methylchloroisothiazolinone [WHO-DD]
Common Name English
5-CHLORO-2-METHYL-2H-ISOTHIAZOL-3-ONE
Systematic Name English
5-CHLORO-2-METHYL-ISOTHIAZOL-3-ONE
Systematic Name English
5-CHLORO-2-METHYL-3(2H)-ISOTHIAZOLONE
Systematic Name English
N-METHYL-5-CHLOROISOTHIAZOLONE
Systematic Name English
N-METHYL-5-CHLOROISOTHIAZOLIN-3-ONE
Systematic Name English
METHYLCHLOROISOTHIAZOLINONE [VANDF]
Common Name English
HS 818
Code English
NEOLONE 950
Brand Name English
5-CHLORO-2-METHYLISOTHIAZOLIN-3-ONE
Systematic Name English
5-CHLORO-2-METHYL-4-ISOTHIAZOLIN-3-ONE
Systematic Name English
4-ISOTHIAZOLIN-3-ONE, 5-CHLORO-2-METHYL-
Systematic Name English
A 33
Code English
5-CHLORO-N-METHYLISOTHIAZOLIN-3-ONE
Systematic Name English
HS-818
Code English
2-METHYL-5-CHLOROISOTHIAZOLIN-3-ONE
Systematic Name English
2-METHYL-5-CHLORO-3-ISOTHIAZOLONE
Systematic Name English
5-CHLORO-2-METHYL-3(2H)-ISOTHIAZOLINONE
Systematic Name English
Classification Tree Code System Code
Food Contact Sustance Notif, (FCN No.) FCN NO. 704
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 999
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 569
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
EPA PESTICIDE CODE 107103
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 675
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
CFR 21 CFR 176.170
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
CFR 21 CFR 175.320
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
Code System Code Type Description
MESH
C011421
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
EVMPD
SUB23424
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
DRUG BANK
DB14197
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
FDA UNII
DEL7T5QRPN
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
RXCUI
1367119
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY Increased Histamine Release [PE]
MERCK INDEX
m7433
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
SMS_ID
100000088728
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
CHEBI
53621
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
PUBCHEM
33344
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
WIKIPEDIA
METHYLCHLOROISOTHIAZOLINONE
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
247-500-7
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
CFR
21 CFR 176.300
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
CAS
26172-55-4
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
HSDB
8270
Created by admin on Fri Dec 15 15:50:35 UTC 2023 , Edited by admin on Fri Dec 15 15:50:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID9034286
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
DAILYMED
DEL7T5QRPN
Created by admin on Fri Dec 15 15:50:34 UTC 2023 , Edited by admin on Fri Dec 15 15:50:34 UTC 2023
PRIMARY
Related Record Type Details
Structure of METHYLCHLOROISOTHIAZOLINONE
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