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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H8NO3S.Na
Molecular Weight 185.177
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETYLCYSTEINE SODIUM

SMILES

[Na+].CC(=O)N[C@@H](CS)C([O-])=O

InChI

InChIKey=KVXPBDQWIXGZEL-WCCKRBBISA-M
InChI=1S/C5H9NO3S.Na/c1-3(7)6-4(2-10)5(8)9;/h4,10H,2H2,1H3,(H,6,7)(H,8,9);/q;+1/p-1/t4-;/m0./s1

HIDE SMILES / InChI

Description

Acetylcysteine (also known as N-acetylcysteine or N-acetyl-L-cysteine or NAC) is primarily used as a mucolytic agent and in the management of acetaminophen poisoning. Acetylcysteine likely protects the liver by maintaining or restoring the glutathione levels, or by acting as an alternate substrate for conjugation with, and thus detoxification of, the reactive metabolite. Nacystelyn (NAL), a recently-developed lysine salt of N-acetylcysteine (NAC) is known to have excellent mucolytic capabilities and is used to treat cystic fibrosis (CF) lung disease. NAC as a precursor to the antioxidant glutathione modulates glutamatergic, neurotrophic, and inflammatory pathways. The potential applications of NAC to facilitate recovery after traumatic brain injury, cerebral ischemia, and in treatment of cerebrovascular vasospasm after subarachnoid hemorrhage. Acetylcysteine serves as a prodrug to L-cysteine, which is a precursor to the biologic antioxidant, glutathione, and hence administration of acetylcysteine replenishes glutathione stores. L-cysteine also serves as a precursor to cystine, which in turn serves as a substrate for the cystine-glutamate antiporter on astrocytes hence increasing glutamate release into the extracellular space. Acetylcysteine also possesses some anti-inflammatory effects possibly via inhibiting NF-κB through redox activation of the nuclear factor kappa kinases thereby modulating cytokine synthesis. NAC is associated with reduced levels of inflammatory cytokines and acts as a substrate for glutathione synthesis. These actions are believed to converge upon mechanisms promoting cell survival and growth factor synthesis, leading to increased neurite sprouting.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nacystelyn
Secondary
ACETADOTE

Cmax

ValueDoseCo-administeredAnalytePopulation
26.5 μg/mL
11 g single, oral
ACETYLCYSTEINE plasma
Homo sapiens
3.47 mg/L
400 mg single, oral
ACETYLCYSTEINE plasma
Homo sapiens
0.68 mg/L
200 mg single, oral
ACETYLCYSTEINE plasma
Homo sapiens
2.57 mg/L
600 mg single, oral
ACETYLCYSTEINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
186 μg × h/mL
11 g single, oral
ACETYLCYSTEINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
18.1 h
11 g single, oral
ACETYLCYSTEINE plasma
Homo sapiens
2.27 h
600 mg single, oral
ACETYLCYSTEINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
23.5%
11 g single, oral
ACETYLCYSTEINE plasma
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
hepatic injury: Acetadote should be administered within 8 hours from acetaminophen ingestion for maximal protection against hepatic injury for patients whose serum acetaminophen levels fall above the “possible” toxicity line on the Rumack-Matthew nomogram (line connecting 150 mcg/mL at 4 hours with 50 mcg/mL at 12 hours cystic fibrosis: patients inhaled either from two (4 mg) to eight puffs (16 mg) of a single dose of NAL from the range, administered in an open-label fashion, or 12 puffs of active NAL (24 mg) versus 12 puffs of placebo,
Route of Administration: Other
In Vitro Use Guide
It was studied the alteration of cellular properties during in vitro hematopoietic differentiation of human iPSCs and the ability of N-acetylcysteine (NAC), a potent free radical scavenger, to prevent such alterations. IPSCs were differentiated towards hematopoietic cells in the presence of 1 mM NAC. Intracellular reactive oxygen species (ROS), nitric oxide (NO), senescence, apoptosis and mitochondrial membrane potential (MMP) were evaluated at 1 and 3 weeks of differentiation. NAC administration improved hematopoietic differentiation of iPSCs in terms of production of CD34, CD45 and CD43 positive cells.