CYSTINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12N2O4S2
Molecular Weight	240.3
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LEVWYRKDKASIDU-IMJSIDKUSA-N

InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C6H12N2O4S2
Molecular Weight	240.3
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00138
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7276953 | https://www.ncbi.nlm.nih.gov/pubmed/27306219 | https://www.ncbi.nlm.nih.gov/pubmed/28297659

Cystine is the oxidized dimer form of the amino acid cysteine. Cystine serves two biological functions, a site of redox reactions and a mechanical linkage that allows proteins to retain their 3-dimensional structure. It is common in many foods such as eggs, meat, dairy products, and whole grains as well as skin, horns and hair. Human hair and skin contain approximately 10–14% cystine by mass. Cysteine supplements are sometimes marketed as anti-aging products with claims of improved skin elasticity. Cysteine is more easily absorbed by the body than cystine, so most supplements contain cysteine rather than cystine. N-acetyl-cysteine (NAC) is better absorbed than other cysteine or cystine supplements.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cystine/glutamate transporter 10 Target ID: CHEMBL1075149 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28070112	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27306219	Secondary		Not Provided 511	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27306219	Secondary		Not Provided 511	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17376	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17376
ChemicalBook	CB5242140	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5242140
eMolecules	496171	https://www.emolecules.com/cgi-bin/more?vid=496171
MolPort	MolPort-001-779-797	https://www.molport.com/shop/molecule-link/MolPort-001-779-797

PubMed

Title	Date	PubMed
Effects of metal ions on the oxidation and nitrosation of cysteine residues in proteins and enzymes.	2001	11219014
Synthesis of monensin derivatives and their effect on the activity of ricin A-chain immunotoxins.	2001	11217376
Blood glutathione and cysteine concentrations in twin children.	2001 Apr	11368428
Histological and histochemical observations in the stomach of the Senegal sole, Solea senegalensis.	2001 Apr	11332707
Cystinuria type I: identification of eight new mutations in SLC3A1.	2001 Apr	11260385
Visualising the activity of the cystine-glutamate antiporter in glial cells using antibodies to aminoadipic acid, a selectively transported substrate.	2001 Apr 1	11284017
Cysteinylation of MHC class II ligands: peptide endocytosis and reduction within APC influences T cell recognition.	2001 Apr 1	11254711
Hounsfield unit density in the determination of urinary stone composition.	2001 Aug	11489691
An efficient refolding method for the preparation of recombinant human prethrombin-2 and characterization of the recombinant-derived alpha-thrombin.	2001 Aug	11481045
Urinary sulfur compounds in Down syndrome.	2001 Aug	11468253
Solid phase assay of urine cystine supersaturation in the presence of cystine binding drugs.	2001 Aug	11458118
Identification and characterization of a new mammalian glutaredoxin (thioltransferase), Grx2.	2001 Aug 10	11397793
The activation of dopamine D4 receptors inhibits oxidative stress-induced nerve cell death.	2001 Aug 15	11487630
Location and mechanism of alpha 2,6-sialyltransferase dimer formation. Role of cysteine residues in enzyme dimerization, localization, activity, and processing.	2001 Aug 3	11356854
Solution structure of the satiety factor, CART, reveals new functionality of a well-known fold.	2001 Aug 7	11478874
[Toxic epidermal necrolysis (drug-induced Lyell's syndrome). 2. Treatment].	2001 Feb 16	11236525
A DNA polymerase with specificity for five base pairs.	2001 Feb 28	11456786
Thermosipho geolei sp. nov., a thermophilic bacterium isolated from a continental petroleum reservoir in Western Siberia.	2001 Jul	11491329
Laminar distribution of nicotinic receptor subtypes in cortical regions in schizophrenia.	2001 Jul	11470559
Medical and surgical therapy of the cystine stone patient.	2001 Jul	11429493
Metabolism of S-nitrosoglutathione by endothelial cells.	2001 Jul	11406512
Role of the cystine-knot motif at the C-terminus of rat mucin protein Muc2 in dimer formation and secretion.	2001 Jul 1	11415450
Hyperglycemia in diabetic rats reduces the glutathione content in the aortic tissue.	2001 Jul 20	11508646
Cystinuria in the dog: clinical studies during 14 years of medical treatment.	2001 Jul-Aug	11467594
Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide.	2001 Jul-Aug	11448590
Configuration and racemization determination of cysteine residues in peptides by chiral derivatization and HPLC: application to oxytocin peptides.	2001 Jun	11461045
Effect of fudosteine, a new cysteine derivative, on mucociliary transport.	2001 Jun	11428670
Cystine calculi in children: the results of a metabolic evaluation and response to medical therapy.	2001 Jun	11371943
Self-assembling, cystine-derived, fused nanotubes based on spirane architecture: design, synthesis, and crystal structure of cystinospiranes.	2001 Jun 20	11403591
Monitoring of the subtraction process in solid-phase representational difference analysis: characterization of a candidate drug.	2001 Jun 27	11418239
Human cystine/glutamate transporter: cDNA cloning and upregulation by oxidative stress in glioma cells.	2001 Jun 6	11406111
Folding screening assayed by proteolysis: application to various cystine deletion mutants of vascular endothelial growth factor.	2001 Mar	11342715
Role of stone analysis in metabolic evaluation and medical treatment of nephrolithiasis.	2001 Mar	11325090
[Spider and scorpion toxins as the ion channel blocker].	2001 Mar	11268643
True ileal digestibility of amino acids in sow's milk for 17-day-old pigs.	2001 Mar	11263831
Three-dimensional structure of human follicle-stimulating hormone.	2001 Mar	11222739
Human lens thioltransferase: cloning, purification, and function.	2001 Mar	11222536
Molecular cloning of preproinsulin cDNAs from several osteoglossomorphs and a cyprinid.	2001 Mar 28	11306171
Methylmercury inhibits the in vitro uptake of the glutathione precursor, cystine, in astrocytes, but not in neurons.	2001 Mar 9	11245823
[Leber's hereditary optic neuropathy].	2001 Mar-Apr	11510171
Evaluation of urinary carnitine and taurine excretion in 5 cystinuric dogs with carnitine and taurine deficiency.	2001 Mar-Apr	11300604
Extracorporeal shock wave lithotripsy in children. Efficacy, complications and long-term follow-up.	2001 May	11464043
A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid.	2001 May	11428546
Energy utilization of low-protein diets in growing pigs.	2001 May	11374546
Synthetic peptides derived from the beta2-beta3 loop of Raphanus sativus antifungal protein 2 that mimic the active site.	2001 May	11350601
Evolution and classification of cystine knot-containing hormones and related extracellular signaling molecules.	2001 May	11328851
Human cystinuria-related transporter: localization and functional characterization.	2001 May	11318953
Design of Gram-negative selective antimicrobial peptides.	2001 May 15	11341843
Synthesis of diaminosuberic acid derivatives via ring-closing alkyne metathesis.	2001 May 18	11348148
Pediatric urolithiasis in Armenia: a study of 198 patients observed from 1991 to 1999.	2001 Sep	11511987

Patents

Sample Use Guides

In Vivo Use Guide

The subjects in the C/T group were orally administered an amino acid supplement, which contained 700 mg cystine and 280 mg theanine (total weight, 1.7 g; Ajinomoto, Tokyo, Japan), once a day starting 1 week before and ending at the same time as the administration of S-1 (a total of 35 days)

Route of Administration: Oral

In Vitro Use Guide

200,000 hTERT-HME cell were plated in 6-well plates and switched to cystine-deprived media for 12 hr prior to FACS analysis. CMDCFDA and C11-BODIPY581/591 (Molecular Probes; Thermo Fisher) were used to detect total and lipid ROS, respectively. Following deprivation of cystine for 12 hr, cells were washed with PBS, loaded with either CMDCFDA (10 mM) or C11 BODIPY (2 mM) in DPBS for 30 min, trypsinized with 0.25% Trypsin-EDTA, resuspended inPBSwith1%FBS, and analyzed using an AttuneNxT flow cytometer (Thermo Fisher). Dyes were excited using a blue 488-nm laser, and emission was recorded on BL1 (530/30) for a minimum of 5,000 cells per sample.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:59:50 GMT 2025` Edited by `admin` on `Wed Apr 02 09:59:50 GMT 2025`
Record UNII	48TCX9A1VT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

L-CYSTINE

Preferred Name

English

CYSTINE

Official Name

English

CYSTINE [EP MONOGRAPH]

Common Name

English

ACETYLCYSTEINE IMPURITY A [EP IMPURITY]

Common Name

English

S-CYSTEINYL CYSTEINE

Systematic Name

English

CYSTINE, L-

Common Name

English

TYROSINE IMPURITY C [EP IMPURITY]

Common Name

English

CYSTINE [MI]

Common Name

English

3,3-DISULFANEDIYLBIS((2R)-2-AMINOPROPANOIC ACID)

Systematic Name

English

L-CYSTINE [FCC]

Common Name

English

Cystine [WHO-DD]

Common Name

English

cystine [INN]

Common Name

English

NSC-13203

Code

English

L-CYSTINE [JAN]

Common Name

English

CYSTINE [USP-RS]

Common Name

English

CYSTINE [USAN]

Common Name

English

CYSTINE [VANDF]

Common Name

English

CYSTINE [MART.]

Common Name

English

Classification Tree Code System Code

LOINC

27027-2