acetylcysteine   Click here for help

GtoPdb Ligand ID: 10945

Synonyms: Ilube® (eye drops) | N-A-C Sustain® | N-Acetyl-cysteine | N-Acetyl-L-cysteine | NAC | Parvolex®
Approved drug PDB Ligand
acetylcysteine is an approved drug (FDA (1963), UK (1992))
Compound class: Synthetic organic
Comment: Acetylcysteine is a prodrug for L-cysteine synthesis, and L-cysteine is a precursor to the biologic antioxidant glutathione. Hence adminstration of acetylcysteine replenishes glutathione stores.
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 CDK toolkit. 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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 105.2
Molecular weight 163.03
XLogP -0.13
No. Lipinski's rules broken 0
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.

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Canonical SMILES SC[C@@H](C(=O)O)NC(=O)C
Isomeric SMILES SC[C@@H](C(=O)O)NC(=O)C
InChI InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
InChI Key PWKSKIMOESPYIA-BYPYZUCNSA-N
No information available.
Summary of Clinical Use Click here for help
Acetylcysteine is used to help prevent or reduce liver damage caused by acetaminophen (paracetamol) overdose. The EMA has designated acetylcysteine as an orphan drug for the treatment of pseudomyxoma peritonei (2018), where it is expected to dissolve mucus in the lungs so making it easier to clear. Acetylcysteine has been used for this action in patients with cystic fibrosis, but its efficacy in this condition has been questioned [2]. It is also indicated for the relief of dry eye syndromes associated with deficient tear secretion, impaired or abnormal mucus production (i.e. applied topically as eye drops as artificial tears with mucolytic and lubricant properties)
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)