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

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
Mechanisms of inhibitory effects of zinc and cadmium ions on agonist binding to adenosine A1 receptors in rat brain.
1999 Aug 15
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
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
DsbD-catalyzed transport of electrons across the membrane of Escherichia coli.
2001 Feb 2
Determination of disulfide bond assignments and N-glycosylation sites of the human gastrointestinal carcinoma antigen GA733-2 (CO17-1A, EGP, KS1-4, KSA, and Ep-CAM).
2001 Feb 23
Degradation of nucleosome-associated centromeric histone H3-like protein CENP-A induced by herpes simplex virus type 1 protein ICP0.
2001 Feb 23
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
Insect immunity. Constitutive expression of a cysteine-rich antifungal and a linear antibacterial peptide in a termite insect.
2001 Feb 9
Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans.
2001 Jan
Tec kinase signaling in T cells is regulated by phosphatidylinositol 3-kinase and the Tec pleckstrin homology domain.
2001 Jan 1
Cloning and functional expression of a degradation-resistant novel isoform of p27Kip1.
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 molecular mechanism of lead inhibition of human porphobilinogen synthase.
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
Tigerinins: novel antimicrobial peptides from the Indian frog Rana tigerina.
2001 Jan 26
Structural requirements for the stabilization of metarhodopsin II by the C terminus of the alpha subunit of transducin.
2001 Jan 26
Helix packing of functionally important regions of the cardiac Na(+)-Ca(2+) exchanger.
2001 Jan 5
The proteasome regulates receptor-mediated endocytosis of interleukin-2.
2001 Jan 5
African swine fever virus protease, a new viral member of the SUMO-1-specific protease family.
2001 Jan 5
Reconstitution of pterin-free inducible nitric-oxide synthase.
2001 Jan 5
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
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
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
Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens.
2001 Mar 30
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
Executioner caspase-3, -6, and -7 perform distinct, non-redundant roles during the demolition phase of apoptosis.
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 [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
L-CYSTEINE
FHFI   JAN   VANDF  
Systematic Name English
R-2-AMINO-3-MERCAPTOPROPIONIC ACID
Systematic Name English
CYSTEINE [II]
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
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 Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
DSLD 1135 (Number of products:91)
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 38484-2
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 25892-1
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
FDA ORPHAN DRUG 79693
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
JECFA EVALUATION L-CYSTEINE
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 15139-9
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
DSLD 2404 (Number of products:441)
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 34277-4
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
NCI_THESAURUS C29596
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
NCI_THESAURUS C68442
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 20641-7
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 25891-3
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 25893-9
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
LOINC 15133-2
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
CFR 21 CFR 172.320
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
CFR 21 CFR 184.1271
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
Code System Code Type Description
CHEBI
17561
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
HSDB
2109
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-158-2
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
WIKIPEDIA
CYSTEINE
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
CHEBI
35235
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
FDA UNII
K848JZ4886
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
NCI_THESAURUS
C29609
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
SMS_ID
100000083990
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
CHEBI
15356
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
NSC
8746
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
MERCK INDEX
m4048
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY Merck Index
PUBCHEM
5862
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
DRUG BANK
DB00151
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL863
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
CHEBI
29950
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
EVMPD
SUB23325
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
MESH
D003545
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
JECFA MONOGRAPH
1409
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
DAILYMED
K848JZ4886
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
CAS
52-90-4
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
RXCUI
3024
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8022876
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
DRUG CENTRAL
769
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
EVMPD
SUB06879MIG
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY
INN
6162
Created by admin on Fri Dec 15 16:18:33 UTC 2023 , Edited by admin on Fri Dec 15 16:18:33 UTC 2023
PRIMARY