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 |
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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 effect of cysteine on the altered expression of class alpha and mu glutathione S-transferase genes in the rat liver during protein-calorie malnutrition. | 2000 Oct 18 |
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Use of proteasome inhibitors to examine processing of antigens for major histocompatibility complex class I presentation. | 2001 |
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Purification of 20S proteasomes. | 2001 |
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The crystal structure of human placenta growth factor-1 (PlGF-1), an angiogenic protein, at 2.0 A resolution. | 2001 Apr 13 |
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The extracellular calcium-sensing receptor dimerizes through multiple types of intermolecular interactions. | 2001 Feb 16 |
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Kinetics of CO and NO ligation with the Cys(331)-->Ala mutant of neuronal nitric-oxide synthase. | 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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Ligand-independent dimerization and activation of the oncogenic Xmrk receptor by two mutations in the extracellular domain. | 2001 Feb 2 |
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The glutathione transferase structural family includes a nuclear chloride channel and a ryanodine receptor calcium release channel modulator. | 2001 Feb 2 |
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Degradation of nucleosome-associated centromeric histone H3-like protein CENP-A induced by herpes simplex virus type 1 protein ICP0. | 2001 Feb 23 |
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The toxoplasma micronemal protein MIC4 is an adhesin composed of six conserved apple domains. | 2001 Feb 9 |
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Insect immunity. Constitutive expression of a cysteine-rich antifungal and a linear antibacterial peptide in a termite insect. | 2001 Feb 9 |
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Reaction of human myoglobin and nitric oxide. Heme iron or protein sulfhydryl (s) nitrosation dependence on the absence or presence of oxygen. | 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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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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Interferon gamma regulates accumulation of the proteasome activator PA28 and immunoproteasomes at nuclear PML bodies. | 2001 Jan |
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Retinoids as ligands and coactivators of protein kinase C alpha. | 2001 Jan |
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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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The tumor suppressor PTEN is phosphorylated by the protein kinase CK2 at its C terminus. Implications for PTEN stability to proteasome-mediated degradation. | 2001 Jan 12 |
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Glutaredoxin protects cerebellar granule neurons from dopamine-induced apoptosis by activating NF-kappa B via Ref-1. | 2001 Jan 12 |
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The Rela(p65) subunit of NF-kappaB is essential for inhibiting double-stranded RNA-induced cytotoxicity. | 2001 Jan 12 |
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The molecular mechanism of lead inhibition of human porphobilinogen synthase. | 2001 Jan 12 |
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Identification and characterization of a Drosophila nuclear proteasome regulator. A homolog of human 11 S REGgamma (PA28gamma ). | 2001 Jan 12 |
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A proposed common structure of substrates bound to mitochondrial processing peptidase. | 2001 Jan 19 |
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Mutations that affect ligand binding to the Escherichia coli aspartate receptor: implications for transmembrane signaling. | 2001 Jan 26 |
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Cathepsin B-like cysteine proteases confer intestinal cysteine protease activity in Haemonchus contortus. | 2001 Jan 26 |
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Tigerinins: novel antimicrobial peptides from the Indian frog Rana tigerina. | 2001 Jan 26 |
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Helix packing of functionally important regions of the cardiac Na(+)-Ca(2+) exchanger. | 2001 Jan 5 |
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The proteasome regulates receptor-mediated endocytosis of interleukin-2. | 2001 Jan 5 |
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African swine fever virus protease, a new viral member of the SUMO-1-specific protease family. | 2001 Jan 5 |
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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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Characterization of electrically evoked [3H]-D-aspartate release from hippocampal slices. | 2001 Mar |
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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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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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Crystal structure of the "cab"-type beta class carbonic anhydrase from the archaeon Methanobacterium thermoautotrophicum. | 2001 Mar 30 |
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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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Zinc release from the CH2C6 zinc finger domain of FILAMENTOUS FLOWER protein from Arabidopsis thaliana induces self-assembly. | 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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Expression-independent consumption of substrates in cell-free expression system from Escherichia coli. | 2001 Nov 17 |
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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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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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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CYSTEINE
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DTXSID8022876
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SUB06879MIG
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6162
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ACTIVE MOIETY
PARENT (METABOLITE)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
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SALT/SOLVATE (PARENT)