mercaptamine   Click here for help

GtoPdb Ligand ID: 7440

Synonyms: CI-9148 | Cystagon® | Cystaran® | cysteamine hydrochloride | L-1573
Approved drug PDB Ligand
mercaptamine is an approved drug (FDA (1994), EMA (1997))
Compound class: Synthetic organic
Comment: Mercaptamine is the simplest stable aminothiol, and a degradation product of the amino acid cysteine.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 64.82
Molecular weight 77.03
XLogP 0.11
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCCS
Isomeric SMILES NCCS
InChI InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
InChI Key UFULAYFCSOUIOV-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
The bitartrate and hydrochloride salt forms are indicated for the treatment of neuropathic cystinosis, and to treat radiation sickness. Link to ClinicalTrials.gov to view currently registered trials assessing efficacy of this drug for additional indications.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The inherited lysosomal storage disease, cystinosis is characterized by the abnormal accumulation of the amino acid cystine and arises through inheritance of mutations in the lysosomal cystine transporter gene (CTNS, O60931). Intracellular cystine accumulation and crystallization causes widespread tissue damage. The free thiol group of cysteamine cleaves the disulphide bond in cystine, thereby allowing excretion of the cystine byproducts.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
European Medicines Agency (EMA)