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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
SynonymLanguageCode
(R,R)-3,3'-dithiobis(2-aminopropanoic acid)Not AvailableNot Available
L-alpha-Diamino-beta-dithiolactic acidNot AvailableNot Available
L-DicysteineNot AvailableNot Available
β,β'-dithiodialanineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
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[C@H](N)C(O)=O)C(O)=O
Mass Specshow(2.96 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsDicarboxylic Acids and Derivatives; Polyols; Organic Disulfides; Polyamines; Enolates; Carboxylic Acids; Monoalkylamines
Substituentsdicarboxylic acid derivative; organic disulfide; polyol; polyamine; enolate; carboxylic acid; amine; primary aliphatic amine; organonitrogen compound; primary amine
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.7309
Blood Brain Barrier - 0.5098
Caco-2 permeable - 0.7541
P-glycoprotein substrate Non-substrate 0.606
P-glycoprotein inhibitor I Non-inhibitor 0.9749
P-glycoprotein inhibitor II Non-inhibitor 1.0
Renal organic cation transporter Non-inhibitor 0.9521
CYP450 2C9 substrate Non-substrate 0.9012
CYP450 2D6 substrate Non-substrate 0.8371
CYP450 3A4 substrate Non-substrate 0.8232
CYP450 1A2 substrate Non-inhibitor 0.8924
CYP450 2C9 substrate Non-inhibitor 0.8968
CYP450 2D6 substrate Non-inhibitor 0.9149
CYP450 2C19 substrate Non-inhibitor 0.9101
CYP450 3A4 substrate Non-inhibitor 0.6103
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.995
Ames test Non AMES toxic 0.5429
Carcinogenicity Non-carcinogens 0.781
Biodegradation Ready biodegradable 0.628
Rat acute toxicity 2.0474 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9839
hERG inhibition (predictor II) Non-inhibitor 0.9707
Pharmacoeconomics
ManufacturersNot Available
Packagers
  • Mason Distributors
  • Tyson & Associates Inc.
Dosage formsNot Available
Prices
Unit descriptionCostUnit
L-alanine 600 mg capsule0.35USDcapsule
A-ketoglut acid 500 mg capsule0.31USDcapsule
Amino acid capsule0.08USDcapsule
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 solubility1.68e+01 g/lALOGPS
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 area126.64ChemAxon
rotatable bond count7ChemAxon
refractivity54.87ChemAxon
polarizability22.77ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot 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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD03636
KEGG CompoundC00491
ChEBI16283
ChEMBLCHEMBL863
PharmGKBPA449176
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/lcy_0088.shtml
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Cystine/glutamate transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cystine/glutamate transporter Q9UPY5 Details

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
  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
  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
  4. Bridges CC, Zalups RK: Cystine and glutamate transport in renal epithelial cells transfected with human system x(-) ©. Kidney Int. 2005 Aug;68(2):653-64. Pubmed
  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

2. Cystinosin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cystinosin O60931 Details

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

3. B(0,+)-type amino acid transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
B(0,+)-type amino acid transporter 1 P82251 Details

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
  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

4. Neutral and basic amino acid transport protein rBAT

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Neutral and basic amino acid transport protein rBAT Q07837 Details

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
  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

1. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 11:19