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
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68003545
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.
CNS Activity
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | CYSTEINE HYDROCHLORIDE Approved UseCysteine 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 Date1986 |
Doses
Dose | Population | Adverse 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: |
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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 Sources: Page: p.1Vein disorder NOS Thrombosis Blood urea nitrogen increased Acid base balance abnormal Hyperammonemia Aluminium abnormal NOS |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
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The neuroprotective effects of phytoestrogens on amyloid beta protein-induced toxicity are mediated by abrogating the activation of caspase cascade in rat cortical neurons. | 2001 Feb 16 |
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DsbD-catalyzed transport of electrons across the membrane of Escherichia coli. | 2001 Feb 2 |
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The protease inhibitor, MG132, blocks maturation of the amyloid precursor protein Swedish mutant preventing cleavage by beta-Secretase. | 2001 Feb 9 |
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Homocysteine inhibits inactivation of factor Va by activated protein C. | 2001 Feb 9 |
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Expression of gamma-glutamyl transpeptidase protects ramos B cells from oxidation-induced cell death. | 2001 Feb 9 |
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RNA passes through the hole of the protein hexamer in the complex with the Escherichia coli Rho factor. | 2001 Feb 9 |
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Role of calcium-dependent protease(s) in globulization of isolated rat lens cortical fiber cells. | 2001 Jan |
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Reactive oxygen species and caspase activation mediate silica-induced apoptosis in alveolar macrophages. | 2001 Jan |
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The cellular chamber of doom. | 2001 Jan |
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Covalent and noncovalent interactions mediate metabotropic glutamate receptor mGlu5 dimerization. | 2001 Jan |
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The predominant form in which neurofilament subunits undergo axonal transport varies during axonal initiation, elongation, and maturation. | 2001 Jan |
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Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans. | 2001 Jan |
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Autocrine expression of activated transforming growth factor-beta(1) induces apoptosis in normal rat liver. | 2001 Jan |
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Regulation of proteolysis. | 2001 Jan |
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Protein metabolism at the crossroads? | 2001 Jan |
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PMP22 related congenital hypomyelination neuropathy. | 2001 Jan |
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Novel therapy in the treatment of scleroderma. | 2001 Jan |
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Homocysteine and thiol metabolites in vitamin B12 deficiency. | 2001 Jan |
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Role of aminothiols as a component of the plasma antioxidant system and relevance to homocysteine-mediated vascular disease. | 2001 Jan |
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Interferon gamma regulates accumulation of the proteasome activator PA28 and immunoproteasomes at nuclear PML bodies. | 2001 Jan |
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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 |
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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 |
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Cloning and functional expression of a degradation-resistant novel isoform of p27Kip1. | 2001 Jan 1 |
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Biosynthesis and shedding of epiglycanin: a mucin-type glycoprotein of the mouse TA3Ha mammary carcinoma cell. | 2001 Jan 1 |
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Crystal structure of an enzyme-substrate complex provides insight into the interaction between human arylsulfatase A and its substrates during catalysis. | 2001 Jan 12 |
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Lysosomal prenylcysteine lyase is a FAD-dependent thioether oxidase. | 2001 Jan 26 |
|
Visualization of synaptic markers in the optic neuropils of Drosophila using a new constrained deconvolution method. | 2001 Jan 8 |
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T-cell antigen receptors in Atlantic cod (Gadus morhua l.): structure, organisation and expression of TCR alpha and beta genes. | 2001 Mar |
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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 |
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Activation of the cyclin-dependent kinase CTDK-I requires the heterodimerization of two unstable subunits. | 2001 Mar 16 |
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Functional rescue of the nephrogenic diabetes insipidus-causing vasopressin V2 receptor mutants G185C and R202C by a second site suppressor mutation. | 2001 Mar 16 |
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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 |
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A proteome analysis of the cadmium response in Saccharomyces cerevisiae. | 2001 Mar 16 |
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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 |
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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 |
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The cytosolic O-acetylserine(thiol)lyase gene is regulated by heavy metals and can function in cadmium tolerance. | 2001 Mar 23 |
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Requirements and effects of palmitoylation of rat PLD1. | 2001 Mar 23 |
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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 |
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Hypersulfated low molecular weight heparin with reduced affinity for antithrombin acts as an anticoagulant by inhibiting intrinsic tenase and prothrombinase. | 2001 Mar 30 |
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Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite. | 2001 Mar 30 |
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Synergistic activation of caspase-3 by m-calpain after neonatal hypoxia-ischemia: a mechanism of "pathological apoptosis"? | 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 |
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Direct demonstration that homotetrameric chaperone SecB undergoes a dynamic dimer-tetramer equilibrium. | 2001 Mar 9 |
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Calpain mutants with increased Ca2+ sensitivity and implications for the role of the C(2)-like domain. | 2001 Mar 9 |
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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 |
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Different metabolizing ability of thiol reactants in human and rat blood: biochemical and pharmacological implications. | 2001 Mar 9 |
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The putative glutathione peroxidase gene of Plasmodium falciparum codes for a thioredoxin peroxidase. | 2001 Mar 9 |
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Rare somatic p53 mutation identified in breast cancer: a case report. | 2001 Mar-Apr |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27610031
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.
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LOINC |
2180-8
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DSLD |
1135 (Number of products:91)
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38484-2
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25892-1
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FDA ORPHAN DRUG |
79693
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JECFA EVALUATION |
L-CYSTEINE
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15139-9
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2404 (Number of products:441)
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34277-4
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NCI_THESAURUS |
C29596
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NCI_THESAURUS |
C68442
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20641-7
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25891-3
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25893-9
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15133-2
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CFR |
21 CFR 172.320
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CFR |
21 CFR 184.1271
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200-158-2
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CYSTEINE
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C29609
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100000083990
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m4048
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DB00151
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3024
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DTXSID8022876
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769
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SUB06879MIG
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6162
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ACTIVE MOIETY
PARENT (METABOLITE)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)