U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MECYSTEINE HYDROCHLORIDE

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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
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.
Primary
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

PubMed

TitleDatePubMed
Water-soluble organosulfur compounds of garlic inhibit fatty acid and triglyceride syntheses in cultured rat hepatocytes.
2001 Apr
The formation of malodorous dimethyl oligosulphides in treated groundwater: the role of biofilms and potential precursors.
2001 May
lcd from Streptococcus anginosus encodes a C-S lyase with alpha,beta-elimination activity that degrades L-cysteine.
2002 Dec
Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3.
2003 Feb 6
Redox inversion of helicity in propeller-shaped molecules derived from s-methyl cysteine and methioninol.
2003 Mar 6
Synthesis and biological activity of photoactivatable N-ras peptides and proteins.
2003 Oct 22
Effect of five cysteine-containing compounds on three lipogenic enzymes in Balb/cA mice consuming a high saturated fat diet.
2004 Sep
Immobilized metal affinity beads for ferritin adsorption.
2005
Cysteine methyl ester modified glassy carbon spheres for removal of toxic heavy metals from aqueous media.
2005 Aug 7
Synthesis of pipecolic acid-based spiro bicyclic lactam scaffolds as beta-turn mimics.
2005 Jul 22
Maillard reaction products derived from thiol compounds as inhibitors of enzymatic browning of fruits and vegetables: the structure-activity relationship.
2005 Jun
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
Kinetics and mechanistic studies of the hydrolysis of diisocyanate-derived bis-thiocarbamates of cysteine methyl ester.
2006 Mar
Mathematical modelling and simulation of adsorption processes at spherical microparticles.
2006 Mar 13
Kinetics of Cisplatin and its monohydrated complex with sulfur-containing compounds designed for local otoprotective administration.
2006 Nov
Observation of cysteine thiolate and -S...H-O intermolecular hydrogen bond.
2006 Nov 23
Electrospray ionization and triple quadrupole tandem mass spectrometry study of some biologically relevant homo- and heterodimeric cadmium thiolate conjugates.
2006 Oct
One-electron reduction of S-nitrosothiols in aqueous medium.
2006 Oct 15
Removal of toxic metal-ion pollutants from water by using chemically modified carbon powders.
2006 Oct 20
Antidiabetic zinc(II)-N-acetyl-L-cysteine complex: evaluations of in vitro insulinomimetic and in vivo blood glucose-lowering activities.
2007
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
Antioxidative and anti-inflammatory effects of four cysteine-containing agents in striatum of MPTP-treated mice.
2007 Jul-Aug
Facile discrimination of aldose enantiomers by reversed-phase HPLC.
2007 Jun
Antiinflammatory and antifibrogenic effects of s-ethyl cysteine and s-methyl cysteine in the kidney of diabetic mice.
2007 May
Protective and alleviative effects from 4 cysteine-containing compounds on ethanol-induced acute liver injury through suppression of oxidation and inflammation.
2007 Sep
Synthesis, docking and anti-tumor activity of beta-L-1,3-thiazolidine pyrimidine nucleoside analogues.
2007 Sep
A viable synthesis of N-methyl cysteine.
2008
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
Radioprotectant and radiosensitizer effects on sterility of gamma-irradiated bone.
2008 Aug
Characterization, reactivity and photosensitizing properties of the triplet excited state of alpha-lapachone.
2008 Nov 28
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
Optical activity and chiral memory of thiol-capped CdTe nanocrystals.
2009 Aug 5
Aurintricarboxylic acid inhibits influenza virus neuraminidase.
2009 Feb
In vitro glutathione conjugation of methyl iodide in rat, rabbit, and human blood and tissues.
2009 May
Inhibitory effects of cysteine and cysteine derivatives on germination of sporangiospores and hyphal growth of different Zygomycetes.
2009 Sep
Synthesis, structural characterisation and anti-proliferative activity of NHC gold amino acid and peptide conjugates.
2009 Sep 21
A new method for the detection and characterization of alpha-lipoic acid mixed disulphides.
2010 Apr
Redetermination of di-μ-sulfido-bis-{[(2R)-2-acet-oxy-2-amino-ethane-1-thiol-ato-κN,S]oxidomolybdenum(V)}.
2010 Apr 24
Neuroimaging in the clinical diagnosis of dementia: observations from a memory disorders clinic.
2010 Aug
hi2-1, a QTL which improves harvest index, earliness and alters metabolite accumulation of processing tomatoes.
2010 Nov
Gold nanoparticles conjugated to benzoylmercaptoacetyltriglycine and L-cysteine methylester.
2010 Oct 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Mecysteine has also been given by inhalation.
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.
Name Type Language
MECYSTEINE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common 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
METHYL L-CYSTEINE HYDROCHLORIDE
JAN  
Systematic Name English
Code System Code Type Description
MESH
C017507
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
FDA UNII
33RG619160
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
SMS_ID
100000086184
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
CAS
18598-63-5
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
NSC
161611
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
MERCK INDEX
m7126
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY Merck Index
CAS
5714-80-7
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
29144
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
EVMPD
SUB03110MIG
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046520
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
RXCUI
235828
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
242-435-0
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-208-6
Created by admin on Fri Dec 15 15:11:36 GMT 2023 , Edited by admin on Fri Dec 15 15:11:36 GMT 2023
ALTERNATIVE