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
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
Molecular Formula | C5H8NO3S |
Molecular Weight | 162.187 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24683506
Curator's Comment: http://forum.parkinson.org/topic/20369-cerebrospinal-fluid-concentrations-of-n-acetylcysteine-after-oral-administration-in-parkinsons-disease/
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27738742 |
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Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11380598 |
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Target ID: P48637 Gene ID: 2937.0 Gene Symbol: GSS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2502672 |
|||
Target ID: Q9UPY5 Gene ID: 23657.0 Gene Symbol: SLC7A11 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21118657 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Nacystelyn Approved UseUnknown |
|||
Secondary | ACETADOTE Approved UseACETADOTE, administered intravenously within 8 to 10 hours after ingestion of a potentially hepatotoxic quantity of acetaminophen, is indicated to prevent or lessen hepatic injury. Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26.5 μg/mL |
11 g single, oral dose: 11 g route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.68 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2029805 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2.57 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2029805 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
3.47 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2029805 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
186 μg × h/mL |
11 g single, oral dose: 11 g route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.27 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3803419 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18.1 h |
11 g single, oral dose: 11 g route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.5% |
11 g single, oral dose: 11 g route of administration: Oral experiment type: SINGLE co-administered: |
ACETYLCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
11 g single, oral Highest studied dose Dose: 11 g Route: oral Route: single Dose: 11 g Sources: |
healthy, adult n = 29 Health Status: healthy Age Group: adult Population Size: 29 Sources: |
|
1200 mg 2 times / day multiple, oral Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: Trichotillomania Population Size: 20 Sources: |
Other AEs: Rash, Depression... Other AEs: Rash (below serious, 1 patient) Sources: Depression (below serious, 1 patient) |
3000 mg multiple, oral (total daily dose) Dose: 3000 mg Route: oral Route: multiple Dose: 3000 mg Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: Pathologic Skin Picking Population Size: 35 Sources: |
Other AEs: Nausea, Dry mouth... Other AEs: Nausea (below serious, 5 patients) Sources: Dry mouth (below serious, 1 patient) Constipation (below serious, 2 patients) Dizziness (below serious, 1 patient) |
900 mg 3 times / day multiple, oral Dose: 900 mg, 3 times / day Route: oral Route: multiple Dose: 900 mg, 3 times / day Sources: |
unhealthy n = 5 Health Status: unhealthy Condition: Obsessive-Compulsive Disorder Population Size: 5 Sources: |
Other AEs: Skin rash... Other AEs: Skin rash (below serious, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Depression | below serious, 1 patient | 1200 mg 2 times / day multiple, oral Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: Trichotillomania Population Size: 20 Sources: |
Rash | below serious, 1 patient | 1200 mg 2 times / day multiple, oral Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: Trichotillomania Population Size: 20 Sources: |
Dizziness | below serious, 1 patient | 3000 mg multiple, oral (total daily dose) Dose: 3000 mg Route: oral Route: multiple Dose: 3000 mg Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: Pathologic Skin Picking Population Size: 35 Sources: |
Dry mouth | below serious, 1 patient | 3000 mg multiple, oral (total daily dose) Dose: 3000 mg Route: oral Route: multiple Dose: 3000 mg Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: Pathologic Skin Picking Population Size: 35 Sources: |
Constipation | below serious, 2 patients | 3000 mg multiple, oral (total daily dose) Dose: 3000 mg Route: oral Route: multiple Dose: 3000 mg Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: Pathologic Skin Picking Population Size: 35 Sources: |
Nausea | below serious, 5 patients | 3000 mg multiple, oral (total daily dose) Dose: 3000 mg Route: oral Route: multiple Dose: 3000 mg Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: Pathologic Skin Picking Population Size: 35 Sources: |
Skin rash | below serious, 1 patient | 900 mg 3 times / day multiple, oral Dose: 900 mg, 3 times / day Route: oral Route: multiple Dose: 900 mg, 3 times / day Sources: |
unhealthy n = 5 Health Status: unhealthy Condition: Obsessive-Compulsive Disorder Population Size: 5 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/19944114/ Page: 1.0 |
strong [Inhibition 10000 uM] |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23319348
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.
Substance Class |
Chemical
Created
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Edited
Fri Dec 15 18:29:14 GMT 2023
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Record UNII |
NRD80R06FB
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Record Status |
Validated (UNII)
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Record Version |
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