Identification

Name
Cystine
Accession Number
DB00138  (NUTR00023)
Type
Small Molecule
Groups
Approved, 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.

Structure
Thumb
Synonyms
  • (R,R)-3,3'-dithiobis(2-aminopropanoic acid)
  • L-alpha-Diamino-beta-dithiolactic acid
  • L-Cystine
  • L-Dicysteine
  • β,β'-dithiodialanine
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Medi Msm (methyl Sulfonyl Methane)Cystine (.05 g/100g) + Biotin (.02 g/100g) + L-Cysteine (.02 g/100g) + L-Methionine (.02 g/100g) + Thiamine (.02 g/100g)PowderTopicalMbg Inc (Korea Institute of Science Development)2016-09-162017-09-16Us
Categories
UNII
48TCX9A1VT
CAS number
56-89-3
Weight
Average: 240.3
Monoisotopic: 240.023848262
Chemical Formula
C6H12N2O4S2
InChI Key
LEVWYRKDKASIDU-IMJSIDKUSA-N
InChI
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
IUPAC Name
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
SMILES
N[[email protected]@H](CSSC[[email protected]](N)C(O)=O)C(O)=O

Pharmacology

Indication

It 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.

Structured Indications
Not Available
Pharmacodynamics

L-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 action

Certain 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.

TargetActionsOrganism
UCystine/glutamate transporterNot AvailableHuman
UCystinosinNot AvailableHuman
UB(0,+)-type amino acid transporter 1Not AvailableHuman
UNeutral and basic amino acid transport protein rBATNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

With 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00192
KEGG Drug
D03636
KEGG Compound
C00491
PubChem Compound
67678
PubChem Substance
46506670
ChemSpider
60997
ChEBI
16283
ChEMBL
CHEMBL590540
PharmGKB
PA449176
PDRhealth
PDRhealth Drug Page
MSDS
Download (72 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Mason Distributors
  • Tyson & Associates Inc.
Dosage forms
FormRouteStrength
PowderTopical
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)260.5 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00kb-0950000000-a803bc05843192dd737d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00kb-0940000000-f82b905ef9e7c9e47552
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00di-9850000000-49b9a52a8387d6d6f272
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-014j-1970000000-9576699202733d4fd7ed
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kb-0950000000-a803bc05843192dd737d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9850000000-49b9a52a8387d6d6f272
GC-MS Spectrum - GC-MSGC-MSsplash10-014j-1970000000-9576699202733d4fd7ed
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kb-0930000000-7cb336c3f272fd0fcd6b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kb-0920000000-1c414573da4bbe4a66dd
Mass Spectrum (Electron Ionization)MSsplash10-000x-9000000000-ae0f516d71e6a49fe52f
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-0890000000-51a32ee40240e45646bc
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-9700000000-4054924ddfb90f120e67
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00di-9100000000-085d45702e61de0f8e4d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-cysteine-S-conjugates
Alternative Parents
L-alpha-amino acids / Dicarboxylic acids and derivatives / Dialkyldisulfides / Amino acids / Sulfenyl compounds / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
L-cysteine-s-conjugate / Alpha-amino acid / L-alpha-amino acid / Dicarboxylic acid or derivatives / Organic disulfide / Dialkyldisulfide / Amino acid / Sulfenyl compound / Carboxylic acid / Organopnictogen compound
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-cysteine derivative, cystine (CHEBI:16283)

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
Uniprot Name
Cystine/glutamate transporter
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 tyr...
Gene Name
CTNS
Uniprot ID
O60931
Uniprot Name
Cystinosin
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 reabsorptio...
Gene Name
SLC7A9
Uniprot ID
P82251
Uniprot Name
b(0,+)-type amino acid transporter 1
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 t...
Gene Name
SLC3A1
Uniprot ID
Q07837
Uniprot Name
Neutral and basic amino acid transport protein rBAT
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
Uniprot Name
Monocarboxylate transporter 10
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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:33