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

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
Hypersulfated low molecular weight heparin with reduced affinity for antithrombin acts as an anticoagulant by inhibiting intrinsic tenase and prothrombinase.
2001-03-30
Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite.
2001-03-30
Synergistic activation of caspase-3 by m-calpain after neonatal hypoxia-ischemia: a mechanism of "pathological apoptosis"?
2001-03-30
Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens.
2001-03-30
Crystal structure of the "cab"-type beta class carbonic anhydrase from the archaeon Methanobacterium thermoautotrophicum.
2001-03-30
The structure of the C4C4 ring finger of human NOT4 reveals features distinct from those of C3HC4 RING fingers.
2001-03-30
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.
2001-03-23
The cytosolic O-acetylserine(thiol)lyase gene is regulated by heavy metals and can function in cadmium tolerance.
2001-03-23
Requirements and effects of palmitoylation of rat PLD1.
2001-03-23
Agonist-induced conformational changes at the cytoplasmic side of transmembrane segment 6 in the beta 2 adrenergic receptor mapped by site-selective fluorescent labeling.
2001-03-23
Binding of levosimendan, a calcium sensitizer, to cardiac troponin C.
2001-03-23
Agonistic induction of a covalent dimer in a mutant of natriuretic peptide receptor-A documents a juxtamembrane interaction that accompanies receptor activation.
2001-03-16
Activation of the cyclin-dependent kinase CTDK-I requires the heterodimerization of two unstable subunits.
2001-03-16
Functional rescue of the nephrogenic diabetes insipidus-causing vasopressin V2 receptor mutants G185C and R202C by a second site suppressor mutation.
2001-03-16
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.
2001-03-16
Direct demonstration that homotetrameric chaperone SecB undergoes a dynamic dimer-tetramer equilibrium.
2001-03-09
Calpain mutants with increased Ca2+ sensitivity and implications for the role of the C(2)-like domain.
2001-03-09
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).
2001-03-09
Different metabolizing ability of thiol reactants in human and rat blood: biochemical and pharmacological implications.
2001-03-09
Redox properties and coordination structure of the heme in the co-sensing transcriptional activator CooA.
2001-03-09
Zinc release from the CH2C6 zinc finger domain of FILAMENTOUS FLOWER protein from Arabidopsis thaliana induces self-assembly.
2001-03-09
The putative glutathione peroxidase gene of Plasmodium falciparum codes for a thioredoxin peroxidase.
2001-03-09
Characterization of transsulfuration and cysteine biosynthetic pathways in the protozoan hemoflagellate, Trypanosoma cruzi. Isolation and molecular characterization of cystathionine beta-synthase and serine acetyltransferase from Trypanosoma.
2001-03-02
T-cell antigen receptors in Atlantic cod (Gadus morhua l.): structure, organisation and expression of TCR alpha and beta genes.
2001-03
Characterization of electrically evoked [3H]-D-aspartate release from hippocampal slices.
2001-03
DsbD-catalyzed transport of electrons across the membrane of Escherichia coli.
2001-02-02
The human homolog of Saccharomyces cerevisiae Apg7p is a Protein-activating enzyme for multiple substrates including human Apg12p, GATE-16, GABARAP, and MAP-LC3.
2001-01-19
Crystal structure of an enzyme-substrate complex provides insight into the interaction between human arylsulfatase A and its substrates during catalysis.
2001-01-12
Visualization of synaptic markers in the optic neuropils of Drosophila using a new constrained deconvolution method.
2001-01-08
Distinct T cell developmental consequences in humans and mice expressing identical mutations in the DLAARN motif of ZAP-70.
2001-01-01
Tec kinase signaling in T cells is regulated by phosphatidylinositol 3-kinase and the Tec pleckstrin homology domain.
2001-01-01
B cell receptor-stimulated mitochondrial phospholipase A2 activation and resultant disruption of mitochondrial membrane potential correlate with the induction of apoptosis in WEHI-231 B cells.
2001-01-01
Cloning and functional expression of a degradation-resistant novel isoform of p27Kip1.
2001-01-01
Biosynthesis and shedding of epiglycanin: a mucin-type glycoprotein of the mouse TA3Ha mammary carcinoma cell.
2001-01-01
Role of calcium-dependent protease(s) in globulization of isolated rat lens cortical fiber cells.
2001-01
Reactive oxygen species and caspase activation mediate silica-induced apoptosis in alveolar macrophages.
2001-01
The cellular chamber of doom.
2001-01
Covalent and noncovalent interactions mediate metabotropic glutamate receptor mGlu5 dimerization.
2001-01
The predominant form in which neurofilament subunits undergo axonal transport varies during axonal initiation, elongation, and maturation.
2001-01
Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans.
2001-01
Autocrine expression of activated transforming growth factor-beta(1) induces apoptosis in normal rat liver.
2001-01
Regulation of proteolysis.
2001-01
Protein metabolism at the crossroads?
2001-01
PMP22 related congenital hypomyelination neuropathy.
2001-01
Novel therapy in the treatment of scleroderma.
2001-01
Homocysteine and thiol metabolites in vitamin B12 deficiency.
2001-01
Role of aminothiols as a component of the plasma antioxidant system and relevance to homocysteine-mediated vascular disease.
2001-01
Interferon gamma regulates accumulation of the proteasome activator PA28 and immunoproteasomes at nuclear PML bodies.
2001-01
Retinoids as ligands and coactivators of protein kinase C alpha.
2001-01
Rare somatic p53 mutation identified in breast cancer: a case report.
2000-12-23
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
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