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Identification
NameL-Cystine
Accession NumberDB00138  (NUTR00023)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

A covalently linked dimeric nonessential amino acid formed by the oxidation of cysteine. Two molecules of cysteine are joined together by a disulfide bridge to form cystine. [PubChem]

Structure
Thumb
Synonyms
(R,R)-3,3'-dithiobis(2-aminopropanoic acid)
L-alpha-Diamino-beta-dithiolactic acid
L-Dicysteine
β,β'-dithiodialanine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII48TCX9A1VT
CAS number56-89-3
WeightAverage: 240.3
Monoisotopic: 240.023848262
Chemical FormulaC6H12N2O4S2
InChI KeyInChIKey=LEVWYRKDKASIDU-SEFKMRKONA-N
InChI
InChI=1/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-/s2
IUPAC Name
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
SMILES
N[C@@H](CSSC[[email protected]](N)C(O)=O)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Dialkyldisulfide
  • Organic disulfide
  • Sulfenyl compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationIt has been claimed that L-cysteine has anti-inflammatory properties, that it can protect against various toxins, and that it might be helpful in osteoarthritis and rheumatoid arthritis. More research will have to be done before L-cysteine can be indicated for any of these conditions. Research to date has mostly been in animal models.
PharmacodynamicsL-Cystine is a covalently linked dimeric nonessential amino acid formed by the oxidation of cysteine. Two molecules of cysteine are joined together by a disulfide bridge to form cystine. Cystine is a chemical substance which naturally occurs as a deposit in the urine, and can form a calculus (hard mineral formation) when deposited in the kidney. The compound produced when two cysteine molecules linked by a disulfide (S-S) bond. Cystine is required for proper vitamin B6 utilization and is also helpful in the healing of burns and wounds, breaking down mucus deposits in illnesses such as bronchitis as well as cystic fibrosis. Cysteine also assists in the supply of insulin to the pancreas, which is needed for the assimilation of sugars and starches. It increases the level of glutathione in the lungs, liver, kidneys and bone marrow, and this may have an anti-aging effect on the body by reducing age-spots etc.
Mechanism of actionCertain conditions, e.g. an acetaminophen overdose, deplete hepatic glutathione and subject the tissues to oxidative stress resulting in loss of cellular integrity. L-Cystine serves as a major precursor for synthesis of glutathione.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityWith typical doses of 1 to 1.5 grams daily, the most commonly reported side effects have been gastrointestinal, such as nausea. There are rare reports of cystine renal stone formation, Single injections of L-cysteine (0.6-1.5 g/kg) into 4-day-old pups resulted in massive damage to cortical neurons, permanent retinal dystrophy, atrophy of the brain and hyperactivity.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7309
Blood Brain Barrier-0.5098
Caco-2 permeable-0.7541
P-glycoprotein substrateNon-substrate0.606
P-glycoprotein inhibitor INon-inhibitor0.9749
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9521
CYP450 2C9 substrateNon-substrate0.9012
CYP450 2D6 substrateNon-substrate0.8371
CYP450 3A4 substrateNon-substrate0.8232
CYP450 1A2 substrateNon-inhibitor0.8924
CYP450 2C9 inhibitorNon-inhibitor0.8968
CYP450 2D6 inhibitorNon-inhibitor0.9149
CYP450 2C19 inhibitorNon-inhibitor0.9101
CYP450 3A4 inhibitorNon-inhibitor0.6103
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.995
Ames testNon AMES toxic0.5429
CarcinogenicityNon-carcinogens0.781
BiodegradationReady biodegradable0.628
Rat acute toxicity2.0474 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9839
hERG inhibition (predictor II)Non-inhibitor0.9707
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
  • Mason Distributors
  • Tyson & Associates Inc.
Dosage formsNot Available
Prices
Unit descriptionCostUnit
L-alanine 600 mg capsule0.35USD capsule
A-ketoglut acid 500 mg capsule0.31USD capsule
Amino acid capsule0.08USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point260.5 dec °CPhysProp
water solubility190 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-5.08CHMELIK,J ET AL. (1991)
pKa1MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility16.8 mg/mLALOGPS
logP-3.2ALOGPS
logP-5.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity54.87 m3·mol-1ChemAxon
Polarizability22.77 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (2.96 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0950000000-a803bc05843192dd737dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kb-0940000000-f82b905ef9e7c9e47552View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9850000000-49b9a52a8387d6d6f272View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014j-1970000000-9576699202733d4fd7edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0890000000-51a32ee40240e45646bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9700000000-4054924ddfb90f120e67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9100000000-085d45702e61de0f8e4dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000x-9000000000-ae0f516d71e6a49fe52fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Peter Stehle, Peter Furst, Werner Fekl, “N,N’-bis-L-amino acid-L-cystine-peptide containing amino acid preparations for oral parenteral nutrition.” U.S. Patent US4968696, issued February, 1964.

US4968696
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (72 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Cystine:glutamate antiporter activity
Specific Function:
Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name:
SLC7A11
Uniprot ID:
Q9UPY5
Molecular Weight:
55422.44 Da
References
  1. Tomi M, Hosoya K, Takanaga H, Ohtsuki S, Terasaki T: Induction of xCT gene expression and L-cystine transport activity by diethyl maleate at the inner blood-retinal barrier. Invest Ophthalmol Vis Sci. 2002 Mar;43(3):774-9. [PubMed:11867597 ]
  2. Hosoya K, Tomi M, Ohtsuki S, Takanaga H, Saeki S, Kanai Y, Endou H, Naito M, Tsuruo T, Terasaki T: Enhancement of L-cystine transport activity and its relation to xCT gene induction at the blood-brain barrier by diethyl maleate treatment. J Pharmacol Exp Ther. 2002 Jul;302(1):225-31. [PubMed:12065721 ]
  3. Ruiz E, Siow RC, Bartlett SR, Jenner AM, Sato H, Bannai S, Mann GE: Vitamin C inhibits diethylmaleate-induced L-cystine transport in human vascular smooth muscle cells. Free Radic Biol Med. 2003 Jan 1;34(1):103-10. [PubMed:12498985 ]
  4. Bridges CC, Zalups RK: Cystine and glutamate transport in renal epithelial cells transfected with human system x(-) (c). Kidney Int. 2005 Aug;68(2):653-64. [PubMed:16014042 ]
  5. Tomi M, Funaki T, Abukawa H, Katayama K, Kondo T, Ohtsuki S, Ueda M, Obinata M, Terasaki T, Hosoya K: Expression and regulation of L-cystine transporter, system xc-, in the newly developed rat retinal Muller cell line (TR-MUL). Glia. 2003 Sep;43(3):208-17. [PubMed:12898700 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-cystine transmembrane transporter activity
Specific Function:
Cystine/H(+) symporter thought to transport cystine out of lysosomes. Plays an important role in melanin synthesis, possibly by preventing melanosome acidification and subsequent degradation of tyrosinase TYR.
Gene Name:
CTNS
Uniprot ID:
O60931
Molecular Weight:
41737.6 Da
References
  1. Kalatzis V, Cherqui S, Antignac C, Gasnier B: Cystinosin, the protein defective in cystinosis, is a H(+)-driven lysosomal cystine transporter. EMBO J. 2001 Nov 1;20(21):5940-9. [PubMed:11689434 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Peptide antigen binding
Specific Function:
Involved in the high-affinity, sodium-independent transport of cystine and neutral and dibasic amino acids (system b(0,+)-like activity). Thought to be responsible for the high-affinity reabsorption of cystine in the kidney tubule.
Gene Name:
SLC7A9
Uniprot ID:
P82251
Molecular Weight:
53480.81 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-cystine transmembrane transporter activity
Specific Function:
Involved in the high-affinity, sodium-independent transport of cystine and neutral and dibasic amino acids (system B(0,+)-like activity). May function as an activator of SLC7A9 and be involved in the high-affinity reabsorption of cystine in the kidney tubule.
Gene Name:
SLC3A1
Uniprot ID:
Q07837
Molecular Weight:
78851.4 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular Weight:
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23