U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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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 of CYSTINE

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

Description
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.

Originator

Sources: Journal of the American Chemical Society Volume 19, Issue 5, Pages382-4, Journal , 1897

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
An algorithm for mapping positively selected members of quasispecies-type viruses.
2001
Histological and histochemical observations in the stomach of the Senegal sole, Solea senegalensis.
2001 Apr
Homologues of archaeal rhodopsins in plants, animals and fungi: structural and functional predications for a putative fungal chaperone protein.
2001 Apr 2
[Toxic epidermal necrolysis (drug-induced Lyell's syndrome). 2. Treatment].
2001 Feb 16
The role of disulfide bridge in the folding and stability of the recombinant human prion protein.
2001 Jan 26
Hyperglycemia in diabetic rats reduces the glutathione content in the aortic tissue.
2001 Jul 20
Cystinuria in the dog: clinical studies during 14 years of medical treatment.
2001 Jul-Aug
Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide.
2001 Jul-Aug
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
How does hexachlorobenzene treatment affect liver uroporphyrinogen decarboxylase?
2001 Jun
Electroanalytical exploitation of quinone-thiol interactions: application to the selective determination of cysteine.
2001 Mar
Three-dimensional structure of human follicle-stimulating hormone.
2001 Mar
Effect of oxygen on induction of the cystine transporter by bacterial lipopolysaccharide in mouse peritoneal macrophages.
2001 Mar 30
Human cystinuria-related transporter: localization and functional characterization.
2001 May
Design of Gram-negative selective antimicrobial peptides.
2001 May 15
Patents

Sample Use Guides

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
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.
Name Type Language
L-CYSTINE
FCC  
Preferred Name English
CYSTINE
EP   INCI   INN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD  
INN   INCI   USAN  
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
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DSLD 2409 (Number of products:212)
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LOINC 34278-2
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DSLD 76 (Number of products:12)
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LOINC 2180-8
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NCI_THESAURUS C29596
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CFR 21 CFR 172.320
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Code System Code Type Description
MESH
D003553
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PRIMARY
RS_ITEM_NUM
1161586
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PRIMARY
DRUG BANK
DB00138
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PRIMARY
EVMPD
SUB01541MIG
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PRIMARY
EPA CompTox
DTXSID2046418
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PRIMARY
WIKIPEDIA
CYSTINE
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PRIMARY
DRUG CENTRAL
4130
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NSC
13203
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PRIMARY
MERCK INDEX
m4049
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PRIMARY Merck Index
CHEBI
16283
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PRIMARY
RXCUI
3036
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PRIMARY RxNorm
SMS_ID
100000091082
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PRIMARY
FDA UNII
48TCX9A1VT
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PRIMARY
DAILYMED
48TCX9A1VT
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PRIMARY
NCI_THESAURUS
C29610
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PRIMARY
CHEBI
17376
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PRIMARY
PUBCHEM
67678
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PRIMARY
ECHA (EC/EINECS)
200-296-3
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PRIMARY
EVMPD
SUB41569
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PRIMARY
CHEBI
35491
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PRIMARY
CAS
56-89-3
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PRIMARY
CHEBI
50058
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PRIMARY
ChEMBL
CHEMBL590540
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PRIMARY
INN
7922
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PRIMARY