Methylchloroisothiazolinone

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

Identification

Name
Methylchloroisothiazolinone
Accession Number
DB14197
Type
Small Molecule
Groups
Approved, Experimental
Description

Methylchloroisothiazolinone, also referred to as MCI, is a preservative with antibacterial and antifungal effects within the group of isothiazolinones. 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.

Structure
Thumb
Synonyms
  • 4-Isothiazolin-3-one, 5-chloro-2-methyl-
  • 5-Chloro-2-methyl-3(2H)-isothiazolone
  • 5-Chloro-N-methylisothiazolin-3-one
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
T.R.U.E. Test Thin-Layer Rapid Use Patch TestMethylchloroisothiazolinone (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) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (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)KitSmartPractice Denmark ApS2012-03-01Not applicableUs
Categories
UNII
DEL7T5QRPN
CAS number
26172-55-4
Weight
Average: 149.59
Monoisotopic: 148.9702126
Chemical Formula
C4H4ClNOS
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

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.

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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Puangpet P, Chawarung A, McFadden JP: Methylchloroisothiazolinone/Methylisothiazolinone and methylisothiazolinone allergy. Dermatitis. 2015 Mar-Apr;26(2):99-102. doi: 10.1097/DER.0000000000000105. [PubMed:25757082]
  2. 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. [PubMed:26536492]
  3. Castanedo-Tardana MP, Zug KA: Methylisothiazolinone. Dermatitis. 2013 Jan-Feb;24(1):2-6. doi: 10.1097/DER.0b013e31827edc73. [PubMed:23340392]
External Links
ChemSpider
30800
ChEBI
53621
ChEMBL
CHEMBL1738962
Wikipedia
Methylchloroisothiazolinone

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Kit
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility50.0 mg/mLALOGPS
logP0.85ALOGPS
logP1.35ChemAxon
logS-0.48ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.52 m3·mol-1ChemAxon
Polarizability13.12 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

Drug created on July 03, 2018 16:12 / Updated on November 02, 2018 07:51