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 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27306219	Secondary		Not Provided 504	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27306219	Secondary		Not Provided 504	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
MolPort	MolPort-001-779-797	https://www.molport.com/shop/molecule-link/MolPort-001-779-797
eMolecules	496171	https://www.emolecules.com/cgi-bin/more?vid=496171

PubMed

Title	Date	PubMed
Infrared analysis of urinary calculi by a single reflection accessory and a neural network interpretation algorithm.	2001	11427461
Capture and identification of folding intermediates of cystinyl proteins by cyanylation and mass spectrometry.	2001	11381521
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
Assignment of the disulfide bonds of huwentoxin-II by Edman degradation sequencing and stepwise thiol modification.	2001 Apr	11298747
Determination by liquid chromatography of free and total cysteine in human urine in the form of its S-quinolinium derivative.	2001 Apr 13	11355829
xCt cystine transporter expression in HEK293 cells: pharmacology and localization.	2001 Apr 20	11302733
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
[Cystine lithiasis: physiopathology and medical treatment].	2001 Feb	11296632
A DNA polymerase with specificity for five base pairs.	2001 Feb 28	11456786
The amino acid transport system b(o,+) and cystinuria.	2001 Jan-Mar	11396607
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
Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells.	2001 Jul 1	11425486
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
Estimation of the total sulfur amino acid requirement and the effect of betaine in diets deficient in total sulfur amino acids for the weanling pig.	2001 Jun	11424694
Partial restoration of lutropin activity by an intersubunit disulfide bond: implications for structure/function studies.	2001 Jun	11395930
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
Occurrence of the Asn45Ser mutation in the GPIX gene in a Belgian patient with Bernard Soulier syndrome.	2001 Mar	11297032
Disulfide bond structure of the AVR9 elicitor of the fungal tomato pathogen Cladosporium fulvum: evidence for a cystine knot.	2001 Mar 27	11297411
Molecular cloning of preproinsulin cDNAs from several osteoglossomorphs and a cyprinid.	2001 Mar 28	11306171
[Leber's hereditary optic neuropathy].	2001 Mar-Apr	11510171
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
The metabolism of sulphur in relation to the biochemistry of cystine and cysteine: its fundamental importance in biology. A cyclic interchange between their mono- and di-sulphides is the unique reaction creating life and intelligence.	2001 May	11388786
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 `Sat Dec 16 18:04:02 GMT 2023` Edited by `admin` on `Sat Dec 16 18:04:02 GMT 2023`
Record UNII	48TCX9A1VT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

L-CYSTINE

Systematic Name

English

CYSTINE [INCI]

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