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Identification
Name Cysteamine
Accession Number DB00847 (APRD00896)
Type small molecule
Groups approved
Description

A radiation-protective agent that oxidizes in air to form cystamine. It can be given intravenously or orally to treat radiation sickness. The bitartrate has been used for the oral treatment of nephropathic cystinosis. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(2-Mercaptoethyl)amine
2-Amino-1-ethanethiol
2-Aminoethanethiol
2-Aminoethyl mercaptan
2-Mercaptoethanamine
Aminoethyl mercaptan
beta-Aminoethanethiol
beta-MEA
beta-Mercaptoethylamine
Cisteamina
Cysteamide
Cysteamin
Cysteamine hydrochloride
Cysteinamine
Decarboxycysteine
Ethanethiolamine
MEA
Mercamine
Mercaptamin
Thioethanolamine
First Prev Next Last
Salts Not Available
Brand names
Name Company
Becaptan
Cystavision
Lambraten
Lambratene
Mecramine
Mercamin
Merkamin
Riacon
Brand mixtures Not Available
Categories
  • Radiation-Protective Agents
  • Nephropathic cystinosis therapy
CAS number 60-23-1
Weight Average: 77.149
Monoisotopic: 77.029919919
Chemical Formula C2H7NS
InChI Key InChIKey=UFULAYFCSOUIOV-UHFFFAOYSA-N
InChI
InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
Plain Text
IUPAC Name
2-aminoethane-1-thiol
SMILES
NCCS
Plain Text
Mass Spec show (7.29 KB)
Taxonomy
Kingdom Organic
Classes
  • Aliphatic and Aryl Amines
Substructures
  • Aliphatic and Aryl Amines
  • Thiols
Pharmacology
Indication Given intravenously or orally to treat radiation sickness. The bitartrate has been used for the oral treatment of nephropathic cystinosis and cystinurea.
Pharmacodynamics People born without the ability to metabolize the amino acid cystine suffer from cystinosis, a rare inherited disorder characterized by the deposition and accumulation of cystine crystals throughout the body. These crystals cause considerable damage, particularly in the kidney. Kidney failure can occur by the age of 10 in untreated patients. Cysteamine prevents the accumulation of cystine crystals and is prescribed to prevent further kidney damage. Cysteamine helps to convert cystine into less harmful chemical forms that can be removed from cells.
Mechanism of action The free thiol cysteamine depletes cystinotic leukocytes and other cells of cystine, whose accumulation is considered the cause of organ damage in cystinosis. Cysteamine cleaves the disulfide bond with cystine to produce molecules that can escape the metabolic defect in cystinosis and cystinuria.
Absorption Not Available
Volume of distribution
  • 156 L
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance
  • apparent plasma cl=1.2 L/min
Toxicity Symptoms of overdose may include convulsions (seizures), increased thirst and unusual tiredness or weakness.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Mylan pharmaceuticals inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Cystagon 150 mg capsule 1.28 USD capsule
Cystagon 50 mg capsule 0.44 USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 98 °C PhysProp
logP 0.1 Not Available
Predicted Properties
Property Value Source
water solubility 2.35e+01 g/l ALOGPS
logP 0.01 ALOGPS
logP -0.42 ChemAxon
logS -0.52 ALOGPS
pKa (strongest acidic) 9.42 ChemAxon
pKa (strongest basic) 10.4 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 26.02 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 22.39 ChemAxon
polarizability 8.65 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Lukashin BP, Grebeniuk AN: [Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice] Radiats Biol Radioecol. 2001 May-Jun;41(3):310-2. Pubmed
External Links
Resource Link
KEGG Drug D03634 Link_out
KEGG Compound C01678 Link_out
PubChem Compound 6058 Link_out
PubChem Substance 46507730 Link_out
ChemSpider 5834 Link_out
BindingDB 7968 Link_out
ChEBI 17141 Link_out
ChEMBL 17141 Link_out
Therapeutic Targets Database DAP001297 Link_out
PharmGKB PA449171 Link_out
Drugs.com http://www.drugs.com/cdi/cysteamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Cysteamine Link_out
ATC Codes
  • A16AA04
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (73.7 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. cystine

Pharmacological action: unknown
Actions: cleavage

References:
  1. Omran Z, Kay G, Di Salvo A, Knott RM, Cairns D: PEGylated derivatives of cystamine as enhanced treatments for nephropathic cystinosis. Bioorg Med Chem Lett. 2011 Jan 1;21(1):45-7. Epub 2010 Nov 21. Pubmed

2. Somatostatin

Pharmacological action: unknown
Actions: binder

Somatostatin inhibits the release of somatotropin

Organism class: human
UniProt ID: P61278 Link_out
Gene: SST Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ahren B, Bottcher G, Ekman R, Sundler F: Cysteamine and the endocrine pancreas: immunocytochemical, immunochemical, and functional aspects. Cell Tissue Res. 1989 Apr;256(1):159-66. Pubmed
  2. McIntosh CH, Bakich V, Bokenfohr K, DiScala-Guenot D, Kwok YN, Brown JC: Cysteamine-induced reduction in gastrointestinal somatostatin: evidence for a region-specific loss in immunoreactivity. Regul Pept. 1988 Jun;21(3-4):205-18. Pubmed
  3. Terry LC, Craig R: Cysteamine effects on monoamines, dopamine-beta-hydroxylase and the hypothalamic-pituitary axis. Neuroendocrinology. 1985 Dec;41(6):467-75. Pubmed
  4. McIntosh C, Bakich V, Trotter T, Kwok YN, Nishimura E, Pederson R, Brown J: Effect of cysteamine on secretion of gastrin and somatostatin from the rat stomach. Gastroenterology. 1984 May;86(5 Pt 1):834-8. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Neuropeptide Y receptor type 2

Pharmacological action: unknown
Actions: other/unknown

Receptor for neuropeptide Y and peptide YY. The rank order of affinity of this receptor for pancreatic polypeptides is PYY > NPY > PYY (3-36) > NPY (2-36) > [Ile-31, Gln-34] PP > [Leu- 31, Pro-34] NPY > PP, [Pro-34] PYY and NPY free acid

Organism class: human
UniProt ID: P49146 Link_out
Gene: NPY2R
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Li W, Hexum TD: Cysteamine selectively enhances neuropeptide Y2 receptor binding activity. Biochem Biophys Res Commun. 1992 Apr 15;184(1):380-6. Pubmed
Enzymes

1. Myeloperoxidase

Actions: substrate

Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity

UniProt ID: P05164 Link_out
Gene: MPO Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Svensson BE: Abilities of peroxidases to catalyse peroxidase-oxidase oxidation of thiols. Biochem J. 1988 Dec 15;256(3):757-62. Pubmed
  2. Svensson BE, Graslund A, Strom G, Moldeus P: Thiols as peroxidase substrates. Free Radic Biol Med. 1993 Feb;14(2):167-75. Pubmed
  3. Svensson BE, Lindvall S: Myeloperoxidase-oxidase oxidation of cysteamine. Biochem J. 1988 Jan 15;249(2):521-30. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19