Methylchloroisothiazolinone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name

DrugBank Accession Number

DB14197

Background

Methylchloroisothiazolinone (MCI) is an isothiazolinone commonly used as a preservative with antibacterial and antifungal properties. It is found within many commercially available cosmetics, lotions, and makeup removers. It is also a known dermatological sensitizer and allergen; some of its side effects include flaky or scaly skin, breakouts, redness or itchiness, and moderate to severe swelling in the eye area. The American Contact Dermatitis Society named Methylchloroisothiazolinone the Contact Allergen of the Year for 2013.

Sensitivity to Methylchloroisothiazolinone may be identified with a clinical patch test.

Type

Small Molecule

Groups

Approved, Experimental

Structure

Similar Structures

Weight: Average: 149.59
Monoisotopic: 148.9702126
Chemical Formula: C₄H₄ClNOS

Synonyms

4-Isothiazolin-3-one, 5-chloro-2-methyl-
5-Chloro-2-methyl-3(2H)-isothiazolone
5-Chloro-N-methylisothiazolin-3-one

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Pharmacology

Indication: Methylchloroisothiazolinone is approved for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

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Pharmacodynamics: Not Available
Mechanism of action: Not Available
Absorption: Not Available
Volume of distribution: Not Available
Protein binding: Not Available
Metabolism: Not Available
Route of elimination: Not Available
Half-life: Not Available
Clearance: Not Available
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Toxicity: Not Available
Pathways: Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">: Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">: This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions: No interactions found.

Products

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Anti-Bacterial Multi-Purpose Cleaning Wipes	Methylchloroisothiazolinone (0.9 mg/1001) + Benzalkonium chloride (150 mg/1001) + Bronopol (50 mg/1001) + Ethanol (0.4 mL/1001) + Methylisothiazolinone (0.3 mg/1001)	Cloth	Topical	Publishers Clearing House LLC	2020-07-01	Not applicable
Anti-Bacterial Multi-Purpose Cleaning Wipes	Methylchloroisothiazolinone (0.9 mg/1001) + Benzalkonium chloride (150 mg/1001) + Bronopol (50 mg/1001) + Ethanol (0.4 mL/1001) + Methylisothiazolinone (0.3 mg/1001)	Cloth	Topical	Wenzhou Guanshang Paper Co., Ltd	2020-07-01	Not applicable
Hand Sanitizing Wipes	Methylchloroisothiazolinone (0.0009 g/100g) + Benzalkonium chloride (0.13 g/100g) + Bronopol (0.03 g/100g) + Methylisothiazolinone (0.0003 g/100g)	Patch	Topical	ZHEJIANG HUASHUN TECHNOLOGY CO.,LTD	2020-09-21	Not applicable
Hand Sanitizing Wipes	Methylchloroisothiazolinone (0.0009 g/100g) + Benzalkonium chloride (0.13 g/100g) + Bronopol (0.03 g/100g) + Methylisothiazolinone (0.0003 g/100g)	Patch	Topical	ZHEJIANG HUASHUN TECHNOLOGY CO.,LTD	2020-09-21	Not applicable
T.R.U.E. Test Thin-Layer Rapid Use Patch Test	Methylchloroisothiazolinone (3 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h) + p-tert-Butylphenol-formaldehyde resin (low molecular weight) (36 ug/48h)	Kit	Cutaneous	SmartPractice Denmark ApS	2012-03-01	Not applicable

Chemical Identifiers

UNII: DEL7T5QRPN
CAS number: 26172-55-4
InChI Key: DHNRXBZYEKSXIM-UHFFFAOYSA-N
InChI: InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3
IUPAC Name: 5-chloro-2-methyl-2,3-dihydro-1,2-thiazol-3-one
SMILES: CN1SC(Cl)=CC1=O

References

General References

Puangpet P, Chawarung A, McFadden JP: Methylchloroisothiazolinone/Methylisothiazolinone and methylisothiazolinone allergy. Dermatitis. 2015 Mar-Apr;26(2):99-102. doi: 10.1097/DER.0000000000000105. [Article]
Yu SH, Sood A, Taylor JS: Patch Testing for Methylisothiazolinone and Methylchloroisothiazolinone-Methylisothiazolinone Contact Allergy. JAMA Dermatol. 2016 Jan;152(1):67-72. doi: 10.1001/jamadermatol.2015.3606. [Article]
Castanedo-Tardana MP, Zug KA: Methylisothiazolinone. Dermatitis. 2013 Jan-Feb;24(1):2-6. doi: 10.1097/DER.0b013e31827edc73. [Article]

External Links

ChemSpider: 30800
RxNav: 1367119
ChEBI: 53621
ChEMBL: CHEMBL1738962
ZINC: ZINC000002002061
Wikipedia: Methylchloroisothiazolinone

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Cloth	Topical
Patch	Topical
Kit	Cutaneous

Prices

Not Available

Patents

Not Available

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	50.0 mg/mL	ALOGPS
logP	0.85	ALOGPS
logP	1.35	Chemaxon
logS	-0.48	ALOGPS
pKa (Strongest Basic)	-6.9	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	20.31 Å²	Chemaxon
Rotatable Bond Count	0	Chemaxon
Refractivity	44.52 m³·mol^-1	Chemaxon
Polarizability	13.12 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-0900000000-d60e65c496f39f961714
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-2900000000-b086e918f24136c70309
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-2900000000-3b6e47a4af77f8ffdd7a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03dj-9400000000-0a69a72245a860dc31fd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9000000000-835da521d7b1fe713f1c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-9000000000-aa52ec06c35433052733
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	111.6435761	predicted	DarkChem Lite v0.1.0
[M-H]-	123.78804	predicted	DeepCCS 1.0 (2019)
[M+H]+	112.9684761	predicted	DarkChem Lite v0.1.0
[M+H]+	126.302795	predicted	DeepCCS 1.0 (2019)
[M+Na]+	112.3358761	predicted	DarkChem Lite v0.1.0
[M+Na]+	134.48045	predicted	DeepCCS 1.0 (2019)

Drug created at July 03, 2018 22:12 / Updated at June 22, 2021 18:16

Methylchloroisothiazolinone

Identification

Structure for Methylchloroisothiazolinone (DB14197)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)