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 (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
Purification of 20S proteasomes.
2001
The crystal structure of human placenta growth factor-1 (PlGF-1), an angiogenic protein, at 2.0 A resolution.
2001 Apr 13
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
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
Molecular mechanism of hypoxia-inducible factor 1alpha -p300 interaction. A leucine-rich interface regulated by a single cysteine.
2001 Feb 2
The glutathione transferase structural family includes a nuclear chloride channel and a ryanodine receptor calcium release channel modulator.
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
The protease inhibitor, MG132, blocks maturation of the amyloid precursor protein Swedish mutant preventing cleavage by beta-Secretase.
2001 Feb 9
Homocysteine inhibits inactivation of factor Va by activated protein C.
2001 Feb 9
RNA passes through the hole of the protein hexamer in the complex with the Escherichia coli Rho factor.
2001 Feb 9
The toxoplasma micronemal protein MIC4 is an adhesin composed of six conserved apple domains.
2001 Feb 9
Insect immunity. Constitutive expression of a cysteine-rich antifungal and a linear antibacterial peptide in a termite insect.
2001 Feb 9
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
Purification and characterization of two hemolysins from Stichodactyla helianthus.
2001 Feb-Mar
Role of calcium-dependent protease(s) in globulization of isolated rat lens cortical fiber cells.
2001 Jan
The cellular chamber of doom.
2001 Jan
The predominant form in which neurofilament subunits undergo axonal transport varies during axonal initiation, elongation, and maturation.
2001 Jan
Regulation of proteolysis.
2001 Jan
PMP22 related congenital hypomyelination neuropathy.
2001 Jan
Homocysteine and thiol metabolites in vitamin B12 deficiency.
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
Regular exercise improves cognitive function and decreases oxidative damage in rat brain.
2001 Jan
Distinct T cell developmental consequences in humans and mice expressing identical mutations in the DLAARN motif of ZAP-70.
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
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
Glutaredoxin protects cerebellar granule neurons from dopamine-induced apoptosis by activating NF-kappa B via Ref-1.
2001 Jan 12
Selective degradation of oxidized calmodulin by the 20 S proteasome.
2001 Jan 12
A proposed common structure of substrates bound to mitochondrial processing peptidase.
2001 Jan 19
Visualization of synaptic markers in the optic neuropils of Drosophila using a new constrained deconvolution method.
2001 Jan 8
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
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
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
The structure of the C4C4 ring finger of human NOT4 reveals features distinct from those of C3HC4 RING fingers.
2001 Mar 30
The putative glutathione peroxidase gene of Plasmodium falciparum codes for a thioredoxin peroxidase.
2001 Mar 9
Executioner caspase-3, -6, and -7 perform distinct, non-redundant roles during the demolition phase of apoptosis.
2001 Mar 9
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 Fri Dec 15 16:18:32 GMT 2023
Edited
by admin
on Fri Dec 15 16:18:32 GMT 2023
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
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 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
DSLD 1135 (Number of products:91)
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 38484-2
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 25892-1
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
FDA ORPHAN DRUG 79693
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
JECFA EVALUATION L-CYSTEINE
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 15139-9
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
DSLD 2404 (Number of products:441)
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 34277-4
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
NCI_THESAURUS C29596
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
NCI_THESAURUS C68442
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 20641-7
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 25891-3
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 25893-9
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
LOINC 15133-2
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
CFR 21 CFR 172.320
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
CFR 21 CFR 184.1271
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
Code System Code Type Description
CHEBI
17561
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
HSDB
2109
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-158-2
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
WIKIPEDIA
CYSTEINE
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
CHEBI
35235
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
FDA UNII
K848JZ4886
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
NCI_THESAURUS
C29609
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
SMS_ID
100000083990
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
CHEBI
15356
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
NSC
8746
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
MERCK INDEX
m4048
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY Merck Index
PUBCHEM
5862
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
DRUG BANK
DB00151
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL863
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
CHEBI
29950
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
EVMPD
SUB23325
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
MESH
D003545
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
JECFA MONOGRAPH
1409
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
DAILYMED
K848JZ4886
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
CAS
52-90-4
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
RXCUI
3024
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8022876
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
DRUG CENTRAL
769
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
EVMPD
SUB06879MIG
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
INN
6162
Created by admin on Fri Dec 15 16:18:33 GMT 2023 , Edited by admin on Fri Dec 15 16:18:33 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
DERIVATIVE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
PRODRUG -> METABOLITE ACTIVE
Scientific Literature
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY