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

Details

Stereochemistry ABSOLUTE
Molecular Formula C3H7NO2S
Molecular Weight 121.1594
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYSTEINE

SMILES

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

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

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

5.30236801E11
Doses

Doses

DosePopulationAdverse events​
121 mg/kg 1 times / day multiple, intravenous (total daily dose)
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
n = 6
Health Status: unhealthy
Condition: Parenteral nutrition
Age Group: 34±6 weeks
Sex: M+F
Population Size: 6
Sources:
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
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: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Acid base balance abnormal Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
Aluminium abnormal NOS Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
Blood urea nitrogen increased Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
Embolism pulmonary Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
Hyperammonemia Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
Thrombosis Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
Vein disorder NOS Disc. AE
22 mg/g aminoacid 1 times / day multiple, intravenous (total daily dose)
Recommended
Dose: 22 mg/g aminoacid, 1 times / day
Route: intravenous
Route: multiple
Dose: 22 mg/g aminoacid, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Parenteral nutrition
Sources: Page: p.1
PubMed

PubMed

TitleDatePubMed
DsbD-catalyzed transport of electrons across the membrane of Escherichia coli.
2001 Feb 2
Role of calcium-dependent protease(s) in globulization of isolated rat lens cortical fiber cells.
2001 Jan
Reactive oxygen species and caspase activation mediate silica-induced apoptosis in alveolar macrophages.
2001 Jan
The cellular chamber of doom.
2001 Jan
Covalent and noncovalent interactions mediate metabotropic glutamate receptor mGlu5 dimerization.
2001 Jan
The predominant form in which neurofilament subunits undergo axonal transport varies during axonal initiation, elongation, and maturation.
2001 Jan
Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans.
2001 Jan
Autocrine expression of activated transforming growth factor-beta(1) induces apoptosis in normal rat liver.
2001 Jan
Regulation of proteolysis.
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
Homocysteine and thiol metabolites in vitamin B12 deficiency.
2001 Jan
Role of aminothiols as a component of the plasma antioxidant system and relevance to homocysteine-mediated vascular disease.
2001 Jan
Interferon gamma regulates accumulation of the proteasome activator PA28 and immunoproteasomes at nuclear PML bodies.
2001 Jan
Retinoids as ligands and coactivators of protein kinase C alpha.
2001 Jan
Distinct T cell developmental consequences in humans and mice expressing identical mutations in the DLAARN motif of ZAP-70.
2001 Jan 1
Tec kinase signaling in T cells is regulated by phosphatidylinositol 3-kinase and the Tec pleckstrin homology domain.
2001 Jan 1
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 Jan 1
Cloning and functional expression of a degradation-resistant novel isoform of p27Kip1.
2001 Jan 1
Biosynthesis and shedding of epiglycanin: a mucin-type glycoprotein of the mouse TA3Ha mammary carcinoma cell.
2001 Jan 1
Crystal structure of an enzyme-substrate complex provides insight into the interaction between human arylsulfatase A and its substrates during catalysis.
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
Visualization of synaptic markers in the optic neuropils of Drosophila using a new constrained deconvolution method.
2001 Jan 8
T-cell antigen receptors in Atlantic cod (Gadus morhua l.): structure, organisation and expression of TCR alpha and beta genes.
2001 Mar
Characterization of electrically evoked [3H]-D-aspartate release from hippocampal slices.
2001 Mar
Agonistic induction of a covalent dimer in a mutant of natriuretic peptide receptor-A documents a juxtamembrane interaction that accompanies receptor activation.
2001 Mar 16
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
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 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
The cytosolic O-acetylserine(thiol)lyase gene is regulated by heavy metals and can function in cadmium tolerance.
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
Binding of levosimendan, a calcium sensitizer, to cardiac troponin C.
2001 Mar 23
Hypersulfated low molecular weight heparin with reduced affinity for antithrombin acts as an anticoagulant by inhibiting intrinsic tenase and prothrombinase.
2001 Mar 30
Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite.
2001 Mar 30
Synergistic activation of caspase-3 by m-calpain after neonatal hypoxia-ischemia: a mechanism of "pathological apoptosis"?
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
The structure of the C4C4 ring finger of human NOT4 reveals features distinct from those of C3HC4 RING fingers.
2001 Mar 30
Direct demonstration that homotetrameric chaperone SecB undergoes a dynamic dimer-tetramer equilibrium.
2001 Mar 9
Calpain mutants with increased Ca2+ sensitivity and implications for the role of the C(2)-like domain.
2001 Mar 9
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
The putative glutathione peroxidase gene of Plasmodium falciparum codes for a thioredoxin peroxidase.
2001 Mar 9
Rare somatic p53 mutation identified in breast cancer: a case report.
2001 Mar-Apr
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.
Name Type Language
CYSTEINE
HSDB   II   INCI   INN   MART.   MI   VANDF   WHO-DD  
INCI   INN  
Official Name English
CYSTEINE [HSDB]
Common Name English
CYSTEINUM
HPUS  
Common Name English
NSC-8746
Code English
CYSTEINE [MART.]
Common Name English
L-2-AMINO-3-MERCAPTOPROPIONIC ACID
Common Name English
L-CYSTEINE [FHFI]
Common Name English
CYSTEINE [VANDF]
Common Name English
L-CYSTEINE
FHFI   JAN   VANDF  
Systematic Name English
R-2-AMINO-3-MERCAPTOPROPIONIC ACID
Systematic Name English
CYSTEINE [II]
Common Name English
CYSTEINE [WHO-DD]
Common Name English
CYSTEINE [MI]
Common Name English
CYSTEINE [INCI]
Common Name English
FEMA NO. 3263
Code English
CYSTEINE [INN]
Common Name English
(R)-2-AMINO-3-MERCAPTOPROPANOIC ACID
Systematic Name English
ACETYLCYSTEINE IMPURITY B [EP]
Common 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 Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
DSLD 1135 (Number of products:91)
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 38484-2
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 25892-1
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
FDA ORPHAN DRUG 79693
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
JECFA EVALUATION L-CYSTEINE
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 15139-9
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
DSLD 2404 (Number of products:441)
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 34277-4
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
NCI_THESAURUS C29596
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
NCI_THESAURUS C68442
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 20641-7
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 25891-3
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 25893-9
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
LOINC 15133-2
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
CFR 21 CFR 172.320
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
CFR 21 CFR 184.1271
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
Code System Code Type Description
HSDB
2109
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-158-2
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
WIKIPEDIA
CYSTEINE
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
FDA UNII
K848JZ4886
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
NCI_THESAURUS
C29609
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
MERCK INDEX
M4048
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY Merck Index
PUBCHEM
5862
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
DRUG BANK
DB00151
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL863
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
EVMPD
SUB23325
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
MESH
D003545
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
CAS
52-90-4
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
RXCUI
3024
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY RxNorm
EPA CompTox
52-90-4
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
DRUG CENTRAL
769
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
EVMPD
SUB06879MIG
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY
INN
6162
Created by admin on Fri Jun 25 23:53:57 UTC 2021 , Edited by admin on Fri Jun 25 23:53:57 UTC 2021
PRIMARY