MECYSTEINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H9NO2S.ClH
Molecular Weight	171.646
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=WHOHXJZQBJXAKL-DFWYDOINSA-N

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 846

Conditions

Condition	Modality	Highest Phase	Product
Chronic obstructive pulmonary disease 175 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 8583	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 8583	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 8583	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.

Doses

Dose	Population	Adverse events
1200 mg 2 times / day multiple, oral Highest studied dose Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/350498/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/350498/	Other AEs: Heartburn, Nausea... Other AEs: Heartburn (13.3%) Nausea (13.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/350498/

AEs

AE	Significance	Dose	Population
Heartburn	13.3%	1200 mg 2 times / day multiple, oral Highest studied dose Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/350498/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/350498/
Nausea	13.3%	1200 mg 2 times / day multiple, oral Highest studied dose Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/350498/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/350498/

PubMed

Title	Date	PubMed
hi2-1, a QTL which improves harvest index, earliness and alters metabolite accumulation of processing tomatoes.	2010-11	20680612
Gold nanoparticles conjugated to benzoylmercaptoacetyltriglycine and L-cysteine methylester.	2010-10-01	20630534
Neuroimaging in the clinical diagnosis of dementia: observations from a memory disorders clinic.	2010-08	20670380
Redetermination of di-μ-sulfido-bis-{[(2R)-2-acet-oxy-2-amino-ethane-1-thiol-ato-κN,S]oxidomolybdenum(V)}.	2010-04-24	21579054
A new method for the detection and characterization of alpha-lipoic acid mixed disulphides.	2010-04	20109104
Synthesis, structural characterisation and anti-proliferative activity of NHC gold amino acid and peptide conjugates.	2009-09-21	20449149
Inhibitory effects of cysteine and cysteine derivatives on germination of sporangiospores and hyphal growth of different Zygomycetes.	2009-09	19381868
Optical activity and chiral memory of thiol-capped CdTe nanocrystals.	2009-08-05	19588974
In vitro glutathione conjugation of methyl iodide in rat, rabbit, and human blood and tissues.	2009-05	19519152
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009-02	19014974
Equilibrium and kinetic investigations of the interaction of model platinum(II) complex with DNA constituents in reference to the antitumour activity: complex-formation reactions of [Pd(N,N-diethylethylenediamine)(H2O)2]2+ with ligands of biological significance and displacement reactions of DNA constituents.	2009	19696935
Characterization, reactivity and photosensitizing properties of the triplet excited state of alpha-lapachone.	2008-11-28	18989476
Radioprotectant and radiosensitizer effects on sterility of gamma-irradiated bone.	2008-08	18484147
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.	2008-04	18234345
A viable synthesis of N-methyl cysteine.	2008	18008337
Protective and alleviative effects from 4 cysteine-containing compounds on ethanol-induced acute liver injury through suppression of oxidation and inflammation.	2007-09	17995665
Synthesis, docking and anti-tumor activity of beta-L-1,3-thiazolidine pyrimidine nucleoside analogues.	2007-09	17897066
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.	2007-08	17574763
Facile discrimination of aldose enantiomers by reversed-phase HPLC.	2007-06	17541189
Antiinflammatory and antifibrogenic effects of s-ethyl cysteine and s-methyl cysteine in the kidney of diabetic mice.	2007-05	17440992
Antioxidative and anti-inflammatory effects of four cysteine-containing agents in striatum of MPTP-treated mice.	2007-02-15	17574387
Antidiabetic zinc(II)-N-acetyl-L-cysteine complex: evaluations of in vitro insulinomimetic and in vivo blood glucose-lowering activities.	2007	18057552
Observation of cysteine thiolate and -S...H-O intermolecular hydrogen bond.	2006-11-23	17107110
Kinetics of Cisplatin and its monohydrated complex with sulfur-containing compounds designed for local otoprotective administration.	2006-11	17060685
Removal of toxic metal-ion pollutants from water by using chemically modified carbon powders.	2006-10-20	17441101
One-electron reduction of S-nitrosothiols in aqueous medium.	2006-10-15	17015170
Electrospray ionization and triple quadrupole tandem mass spectrometry study of some biologically relevant homo- and heterodimeric cadmium thiolate conjugates.	2006-10	16872835
Mathematical modelling and simulation of adsorption processes at spherical microparticles.	2006-03-13	16456905
Kinetics and mechanistic studies of the hydrolysis of diisocyanate-derived bis-thiocarbamates of cysteine methyl ester.	2006-03	16544937
Cysteine methyl ester modified glassy carbon spheres for removal of toxic heavy metals from aqueous media.	2005-08-07	16027914
Synthesis of pipecolic acid-based spiro bicyclic lactam scaffolds as beta-turn mimics.	2005-07-22	16018691
Maillard reaction products derived from thiol compounds as inhibitors of enzymatic browning of fruits and vegetables: the structure-activity relationship.	2005-06	16037314
The role of hydrogen bonding in the selectivity of L-cysteine methyl ester (CYSM) and L-cysteine ethyl ester (CYSE) for chloride ion.	2005-03	15683788
Immobilized metal affinity beads for ferritin adsorption.	2005	16001724
Effect of five cysteine-containing compounds on three lipogenic enzymes in Balb/cA mice consuming a high saturated fat diet.	2004-09	15669759
Synthesis and biological activity of photoactivatable N-ras peptides and proteins.	2003-10-22	14558822
Redox inversion of helicity in propeller-shaped molecules derived from s-methyl cysteine and methioninol.	2003-03-06	12605496
Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3.	2003-02-06	12556160
lcd from Streptococcus anginosus encodes a C-S lyase with alpha,beta-elimination activity that degrades L-cysteine.	2002-12	12480900
The formation of malodorous dimethyl oligosulphides in treated groundwater: the role of biofilms and potential precursors.	2001-05	11329675
Water-soluble organosulfur compounds of garlic inhibit fatty acid and triglyceride syntheses in cultured rat hepatocytes.	2001-04	11383692

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 `Mon Mar 31 17:49:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:40 GMT 2025`
Record UNII	33RG619160
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MECYSTEINE HYDROCHLORIDE

Common Name

English

METHYL L-CYSTEINE HYDROCHLORIDE

Preferred Name

English

MECYSTEINE HYDROCHLORIDE [MI]

Common Name

English

MECYSTEINE HYDROCHLORIDE [MART.]

Common Name

English

L-CYSTEINE METHYL ESTER HYDROCHLORIDE

Systematic Name

English

METHYL (R)-2-AMINO-3-MERCAPTOPROPANOATE HYDROCHLORIDE

Systematic Name

English

ACDRILE

Common Name

English

METHYL L-CYSTEINE HYDROCHLORIDE [JAN]

Common Name

English

Mecysteine hydrochloride [WHO-DD]

Common Name

English

ACTIOL

Common Name

English

L-CYSTEINE, METHYL ESTER, HYDROCHLORIDE

Systematic Name

English

NSC-161611

Code

English

Code System Code Type Description

MESH

C017507