U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C3H7NO2S
Molecular Weight 121.158
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Cysteine

SMILES

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

InChI

InChIKey=XUJNEKJLAYXESH-REOHCLBHSA-N
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

HIDE SMILES / InChI

Molecular Formula C3H7NO2S
Molecular Weight 121.158
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003545

Cysteine (cysteine hydrochloride is a salt) is a thiol-containing amino acid that is oxidized to form cystine. Cysteine is synthesized from methionine via the trans-sulfuration pathway in the adult, but newborn infants lack the enzyme, cystathionase, necessary to effect this conversion. Therefore, cysteine is generally considered to be an essential amino acid in infants.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CYSTEINE HYDROCHLORIDE

Approved Use

Cysteine Hydrochloride Injection, USP 0.5 gram is indicated for use only after dilution as an additive to Aminosyn (a crystalline amino acid solution) to meet the intravenous amino acid nutritional requirements of infants receiving total parenteral nutrition.

Launch Date

1986
Doses

Doses

DosePopulationAdverse events​
121 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 121 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 121 mg/kg, 1 times / day
Sources:
unhealthy, 34±6 weeks
Health Status: unhealthy
Age Group: 34±6 weeks
Sex: M+F
Sources:
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Disc. AE: Embolism pulmonary, Vein disorder NOS...
AEs leading to
discontinuation/dose reduction:
Embolism pulmonary
Vein disorder NOS
Thrombosis
Blood urea nitrogen increased
Acid base balance abnormal
Hyperammonemia
Aluminium abnormal NOS
Sources:
AEs

AEs

AESignificanceDosePopulation
Acid base balance abnormal Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Aluminium abnormal NOS Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Blood urea nitrogen increased Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Embolism pulmonary Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Hyperammonemia Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Thrombosis Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
Vein disorder NOS Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Use of proteasome inhibitors to examine processing of antigens for major histocompatibility complex class I presentation.
2001
The extracellular calcium-sensing receptor dimerizes through multiple types of intermolecular interactions.
2001 Feb 16
Ligand-independent dimerization and activation of the oncogenic Xmrk receptor by two mutations in the extracellular domain.
2001 Feb 2
Functional role of critical stripe residues in transmembrane span 7 of the serotonin transporter. Effects of Na+, Li+, and methanethiosulfonate reagents.
2001 Feb 9
Newly synthesized human delta opioid receptors retained in the endoplasmic reticulum are retrotranslocated to the cytosol, deglycosylated, ubiquitinated, and degraded by the proteasome.
2001 Feb 9
The toxoplasma micronemal protein MIC4 is an adhesin composed of six conserved apple domains.
2001 Feb 9
Reactive oxygen species and caspase activation mediate silica-induced apoptosis in alveolar macrophages.
2001 Jan
Protein metabolism at the crossroads?
2001 Jan
PMP22 related congenital hypomyelination neuropathy.
2001 Jan
Novel therapy in the treatment of scleroderma.
2001 Jan
Retinoids as ligands and coactivators of protein kinase C alpha.
2001 Jan
Biosynthesis and shedding of epiglycanin: a mucin-type glycoprotein of the mouse TA3Ha mammary carcinoma cell.
2001 Jan 1
The molecular mechanism of lead inhibition of human porphobilinogen synthase.
2001 Jan 12
The loop region covering the iron-sulfur cluster in bovine adrenodoxin comprises a new interaction site for redox partners.
2001 Jan 12
The human homolog of Saccharomyces cerevisiae Apg7p is a Protein-activating enzyme for multiple substrates including human Apg12p, GATE-16, GABARAP, and MAP-LC3.
2001 Jan 19
Cathepsin B-like cysteine proteases confer intestinal cysteine protease activity in Haemonchus contortus.
2001 Jan 26
The proteasome regulates receptor-mediated endocytosis of interleukin-2.
2001 Jan 5
Visualization of synaptic markers in the optic neuropils of Drosophila using a new constrained deconvolution method.
2001 Jan 8
Characterization of electrically evoked [3H]-D-aspartate release from hippocampal slices.
2001 Mar
Activation of the cyclin-dependent kinase CTDK-I requires the heterodimerization of two unstable subunits.
2001 Mar 16
Functional rescue of the nephrogenic diabetes insipidus-causing vasopressin V2 receptor mutants G185C and R202C by a second site suppressor mutation.
2001 Mar 16
Identification of internal autoproteolytic cleavage sites within the prosegments of recombinant procathepsin B and procathepsin S. Contribution of a plausible unimolecular autoproteolytic event for the processing of zymogens belonging to the papain family.
2001 Mar 16
Recombinant cytochrome rC557 obtained from Escherichia coli cells expressing a truncated Thermus thermophilus cycA gene. Heme inversion in an improperly matured protein.
2001 Mar 2
The transport activity of the Na+-Ca2+ exchanger NCX1 expressed in HEK 293 cells is sensitive to covalent modification of intracellular cysteine residues by sulfhydryl reagents.
2001 Mar 23
Requirements and effects of palmitoylation of rat PLD1.
2001 Mar 23
Agonist-induced conformational changes at the cytoplasmic side of transmembrane segment 6 in the beta 2 adrenergic receptor mapped by site-selective fluorescent labeling.
2001 Mar 23
Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite.
2001 Mar 30
Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens.
2001 Mar 30
Crystal structure of the "cab"-type beta class carbonic anhydrase from the archaeon Methanobacterium thermoautotrophicum.
2001 Mar 30
Amino acid residues in the PSI domain and cysteine-rich repeats of the integrin beta2 subunit that restrain activation of the integrin alpha(X)beta(2).
2001 Mar 9
Different metabolizing ability of thiol reactants in human and rat blood: biochemical and pharmacological implications.
2001 Mar 9
Redox properties and coordination structure of the heme in the co-sensing transcriptional activator CooA.
2001 Mar 9
Zinc release from the CH2C6 zinc finger domain of FILAMENTOUS FLOWER protein from Arabidopsis thaliana induces self-assembly.
2001 Mar 9
Patents

Sample Use Guides

Cysteine Hydrochloride Injection, USP 0.5 gram is intended for use only after dilution in Aminosyn (a crystalline amino acid solution). Each 10 mL of Cysteine Hydrochloride Injection, USP 0.5 gram should be combined aseptically with 12.5 grams of amino acids, such as that present in 250 mL of Aminosyn 5%. The admixture is then diluted with 250 mL of dextrose 50% or such lesser volume as indicated. Equal volumes of Aminosyn 5% and dextrose 50% produce a final solution which contains Aminosyn 2.5% in dextrose 25%, which is suitable for administration by central venous infusion. Administration of the final admixture should begin within one hour of mixing due to the oxidative degradation of cysteine in the higher pH environment of the amino acid and dextrose admixture. Otherwise, the admixture should be refrigerated immediately and used within 12 hours of the time of mixing.
Route of Administration: Intravenous
N-acetyl-L-cysteine (NAC) (1 µM ~ 1 mM) and cysteine (10 µM ~ 1 mM) increased [Ca(2+)]i in human neutrophils in a concentration-dependent manner. In Ca(2+)-free buffer, NAC- and cysteine-induced [Ca(2+)]i increase in human neutrophils completely disappeared, suggesting that NAC- and cysteine-mediated increase in [Ca(2+)]i in human neutrophils occur through Ca(2+) influx. NAC- and cysteine-induced [Ca(2+)]i increase was effectively inhibited by calcium channel inhibitors SKF96365 (10 µM) and ruthenium red (20 µM). In Na(+)-free HEPES, both NAC and cysteine induced a marked increase in [Ca(2+)]i in human neutrophils, arguing against the possibility that Na(+)-dependent intracellular uptake of NAC and cysteine is necessary for their [Ca(2+)]i increasing activity. The results show that NAC and cysteine induce [Ca(2+)]i increase through Ca(2+) influx in human neutrophils via SKF96365- and ruthenium red-dependent way.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:39 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:39 GMT 2025
Record UNII
K848JZ4886
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Cysteine
HSDB   II   INCI   INN   MART.   MI   VANDF   WHO-DD  
INCI   INN  
Official Name English
L-CYSTEINE
FHFI   JAN   VANDF  
Preferred Name English
Cysteine [WHO-DD]
Common Name English
CYSTEINE [HSDB]
Common Name English
CYSTEINUM
HPUS  
Common Name English
NSC-8746
Code English
CYSTEINE [MART.]
Common Name English
ACETYLCYSTEINE IMPURITY B [EP IMPURITY]
Common Name English
L-2-AMINO-3-MERCAPTOPROPIONIC ACID
Common Name English
L-CYSTEINE [FHFI]
Common Name English
CYSTEINE [VANDF]
Common Name English
R-2-AMINO-3-MERCAPTOPROPIONIC ACID
Systematic Name English
CYSTEINE [II]
Common Name English
CYSTEINE [MI]
Common Name English
FEMA NO. 3263
Code English
cysteine [INN]
Common Name English
(R)-2-AMINO-3-MERCAPTOPROPANOIC ACID
Systematic Name English
CYSTEINE, L-
Systematic Name English
E 920
Code English
L-CYSTEINE [VANDF]
Common Name English
CYSTEINUM [HPUS]
Common Name English
L-CYSTEINE [JAN]
Common Name English
Classification Tree Code System Code
LOINC 2180-8
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
DSLD 1135 (Number of products:91)
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 38484-2
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 25892-1
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
FDA ORPHAN DRUG 79693
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
JECFA EVALUATION L-CYSTEINE
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 15139-9
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
DSLD 2404 (Number of products:441)
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 34277-4
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
NCI_THESAURUS C29596
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
NCI_THESAURUS C68442
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 20641-7
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 25891-3
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 25893-9
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
LOINC 15133-2
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
CFR 21 CFR 172.320
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
CFR 21 CFR 184.1271
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
Code System Code Type Description
CHEBI
17561
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
HSDB
2109
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-158-2
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
WIKIPEDIA
CYSTEINE
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
CHEBI
35235
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
FDA UNII
K848JZ4886
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
NCI_THESAURUS
C29609
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
SMS_ID
100000083990
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
CHEBI
15356
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
NSC
8746
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
MERCK INDEX
m4048
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY Merck Index
PUBCHEM
5862
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
DRUG BANK
DB00151
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
ChEMBL
CHEMBL863
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
CHEBI
29950
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
EVMPD
SUB23325
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
MESH
D003545
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
JECFA MONOGRAPH
1409
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
DAILYMED
K848JZ4886
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
CAS
52-90-4
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
RXCUI
3024
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID8022876
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
DRUG CENTRAL
769
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
EVMPD
SUB06879MIG
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
INN
6162
Created by admin on Mon Mar 31 18:24:39 GMT 2025 , Edited by admin on Mon Mar 31 18:24:39 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
DERIVATIVE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY