MECYSTEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H9NO2S
Molecular Weight	135.185
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)[C@@H](N)CS

InChI

InChIKey=MCYHPZGUONZRGO-VKHMYHEASA-N

InChI=1S/C4H9NO2S/c1-7-4(6)3(5)2-8/h3,8H,2,5H2,1H3/t3-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C4H9NO2S
Molecular Weight	135.185
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con2033689.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22908983 | https://www.ncbi.nlm.nih.gov/pubmed/6185664

Mecysteine is used as a mucolytic in respiratory disorders associated with productive cough. Mecysteine is known as a mucolytic agent, it breaks down mucus. It works by breaking some of the chemical bonds between the molecules in mucus. It is given orally in a usual dose of 200 mg three times daily before meals reduced to 200 mg twice daily after 6 weeks. A rapid clinical effect can be achieved by giving 200 mg four times daily for the first 2 days. Mecysteine has also been given by inhalation.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mucus glycoproteins 2 Target ID: Mucus glycoproteins Sources: https://www.ncbi.nlm.nih.gov/pubmed/6185664	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con2033689.pdf http://www.ndrugs.com/?s=visclair http://www.netdoctor.co.uk/medicines/lungs/a7749/visclair/	Primary	Approved 8429	VISCLAIR Approved Use Visclair is used together with other medicines to help in the treatment of conditions in which thick mucus is a problem. e.g. chronic obstructive pulmonary disease, sinusitis (inflamed nasal tubes), secretory otitis and in the symptomatic relief of cough with sputum or phlegm.
Sinusitis 26 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1381465588312.pdf	Primary	Approved 8429	VISCLAIR Approved Use Visclair is used together with other medicines to help in the treatment of conditions in which thick mucus is a problem. e.g. chronic obstructive pulmonary disease, sinusitis (inflamed nasal tubes), secretory otitis and in the symptomatic relief of cough with sputum or phlegm.
Secretory otitis 2 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1381465588312.pdf	Primary	Approved 8429	VISCLAIR Approved Use Visclair is used together with other medicines to help in the treatment of conditions in which thick mucus is a problem. e.g. chronic obstructive pulmonary disease, sinusitis (inflamed nasal tubes), secretory otitis and in the symptomatic relief of cough with sputum or phlegm.

PubMed

Title	Date	PubMed
Water-soluble organosulfur compounds of garlic inhibit fatty acid and triglyceride syntheses in cultured rat hepatocytes.	2001 Apr	11383692
The formation of malodorous dimethyl oligosulphides in treated groundwater: the role of biofilms and potential precursors.	2001 May	11329675
lcd from Streptococcus anginosus encodes a C-S lyase with alpha,beta-elimination activity that degrades L-cysteine.	2002 Dec	12480900
Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3.	2003 Feb 6	12556160
Redox inversion of helicity in propeller-shaped molecules derived from s-methyl cysteine and methioninol.	2003 Mar 6	12605496
Synthesis and biological activity of photoactivatable N-ras peptides and proteins.	2003 Oct 22	14558822
Effect of five cysteine-containing compounds on three lipogenic enzymes in Balb/cA mice consuming a high saturated fat diet.	2004 Sep	15669759
Immobilized metal affinity beads for ferritin adsorption.	2005	16001724
Cysteine methyl ester modified glassy carbon spheres for removal of toxic heavy metals from aqueous media.	2005 Aug 7	16027914
Synthesis of pipecolic acid-based spiro bicyclic lactam scaffolds as beta-turn mimics.	2005 Jul 22	16018691
Maillard reaction products derived from thiol compounds as inhibitors of enzymatic browning of fruits and vegetables: the structure-activity relationship.	2005 Jun	16037314
The role of hydrogen bonding in the selectivity of L-cysteine methyl ester (CYSM) and L-cysteine ethyl ester (CYSE) for chloride ion.	2005 Mar	15683788
Kinetics and mechanistic studies of the hydrolysis of diisocyanate-derived bis-thiocarbamates of cysteine methyl ester.	2006 Mar	16544937
Mathematical modelling and simulation of adsorption processes at spherical microparticles.	2006 Mar 13	16456905
Kinetics of Cisplatin and its monohydrated complex with sulfur-containing compounds designed for local otoprotective administration.	2006 Nov	17060685
Observation of cysteine thiolate and -S...H-O intermolecular hydrogen bond.	2006 Nov 23	17107110
Electrospray ionization and triple quadrupole tandem mass spectrometry study of some biologically relevant homo- and heterodimeric cadmium thiolate conjugates.	2006 Oct	16872835
One-electron reduction of S-nitrosothiols in aqueous medium.	2006 Oct 15	17015170
Removal of toxic metal-ion pollutants from water by using chemically modified carbon powders.	2006 Oct 20	17441101
Antidiabetic zinc(II)-N-acetyl-L-cysteine complex: evaluations of in vitro insulinomimetic and in vivo blood glucose-lowering activities.	2007	18057552
Reduction of vanadium(V) to vanadium(IV) by NADPH, and vanadium(IV) to vanadium(III) by cysteine methyl ester in the presence of biologically relevant ligands.	2007 Aug	17574763
Antioxidative and anti-inflammatory effects of four cysteine-containing agents in striatum of MPTP-treated mice.	2007 Jul-Aug	17574387
Facile discrimination of aldose enantiomers by reversed-phase HPLC.	2007 Jun	17541189
Antiinflammatory and antifibrogenic effects of s-ethyl cysteine and s-methyl cysteine in the kidney of diabetic mice.	2007 May	17440992
Protective and alleviative effects from 4 cysteine-containing compounds on ethanol-induced acute liver injury through suppression of oxidation and inflammation.	2007 Sep	17995665
Synthesis, docking and anti-tumor activity of beta-L-1,3-thiazolidine pyrimidine nucleoside analogues.	2007 Sep	17897066
A viable synthesis of N-methyl cysteine.	2008	18008337
The uptake and fate of vanadyl ion in ascidian blood cells and a detailed hypothesis for the mechanism and location of biological vanadium reduction. A visible and X-ray absorption spectroscopic study.	2008 Apr	18234345
Radioprotectant and radiosensitizer effects on sterility of gamma-irradiated bone.	2008 Aug	18484147
Characterization, reactivity and photosensitizing properties of the triplet excited state of alpha-lapachone.	2008 Nov 28	18989476
Optical activity and chiral memory of thiol-capped CdTe nanocrystals.	2009 Aug 5	19588974
Inhibitory effects of cysteine and cysteine derivatives on germination of sporangiospores and hyphal growth of different Zygomycetes.	2009 Sep	19381868
Redetermination of di-μ-sulfido-bis-{[(2R)-2-acet-oxy-2-amino-ethane-1-thiol-ato-κN,S]oxidomolybdenum(V)}.	2010 Apr 24	21579054
Neuroimaging in the clinical diagnosis of dementia: observations from a memory disorders clinic.	2010 Aug	20670380
hi2-1, a QTL which improves harvest index, earliness and alters metabolite accumulation of processing tomatoes.	2010 Nov	20680612
Gold nanoparticles conjugated to benzoylmercaptoacetyltriglycine and L-cysteine methylester.	2010 Oct 1	20630534

Patents

Sample Use Guides

In Vivo Use Guide

It is given orally in a usual dose of 200 mg three times daily before meals reduced to 200 mg twice daily after 6 weeks. A rapid clinical effect can be achieved by giving 200 mg four times daily for the first 2 days.

Route of Administration: Oral

In Vitro Use Guide

The effects of L-cysteine methyl ester (Mecysteine) on behavior of mucus glycoproteins in canine tracheal secretory cells were investigated histologically and histochemically. Low concentrations (10(-7) and 10(-6)M) of L-cysteine methyl ester produced, as histological changes, decreases in the total goblet cell number and the thickness of the acini of submucosal glands, and an increase in the acinar inner diameter. On the other hand, L-cysteine methyl ester at 10(-5) and 10(-4)M produced an increase in the thickness of the acini and a slight decrease in the acinar inner diameter.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:23:30 UTC 2023` Edited by `admin` on `Fri Dec 15 16:23:30 UTC 2023`
Record UNII	RQ6L463N3B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MECYSTEINE

Official Name

English

mecysteine [INN]

Common Name

English

CYSTEINE METHYL ESTER

Systematic Name

English

METHYL ESTER OF CYSTEINE

Common Name

English

Mecysteine [WHO-DD]

Common Name

English

METHYL CYSTEINE

Systematic Name

English

MECYSTEINE [MI]

Common Name

English

METHYL L-CYSTEINATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C74536