Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C5H9NO3S |
Molecular Weight | 163.195 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)N[C@@H](CS)C(O)=O
InChI
InChIKey=PWKSKIMOESPYIA-BYPYZUCNSA-N
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
Molecular Formula | C5H9NO3S |
Molecular Weight | 163.195 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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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 |
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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 |
|
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 |
|
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 |
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 |
---|---|---|---|---|
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 |
|
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 |
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 |
---|---|---|
40 mg single, intranasal Studied dose Dose: 40 mg Route: intranasal Route: single Dose: 40 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
40 mg single, intranasal Studied dose Dose: 40 mg Route: intranasal Route: single Dose: 40 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
40 mg single, intranasal Studied dose Dose: 40 mg Route: intranasal Route: single Dose: 40 mg Sources: |
unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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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
by
admin
on
Edited
Mon Mar 31 17:51:38 GMT 2025
by
admin
on
Mon Mar 31 17:51:38 GMT 2025
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Record UNII |
WYQ7N0BPYC
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175776
Created by
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EU-Orphan Drug |
EU/3/04/259
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FDA ORPHAN DRUG |
158102
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WHO-VATC |
QR05CB01
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NDF-RT |
N0000008867
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FDA ORPHAN DRUG |
275909
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NDF-RT |
N0000175960
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WHO-ATC |
V03AB23
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NDF-RT |
N0000175961
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WHO-VATC |
QS01XA08
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WHO-VATC |
QV03AB23
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NDF-RT |
N0000175547
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FDA ORPHAN DRUG |
401713
Created by
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FDA ORPHAN DRUG |
370012
Created by
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LIVERTOX |
NBK548401
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NDF-RT |
N0000175429
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FDA ORPHAN DRUG |
664418
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DSLD |
528 (Number of products:1468)
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WHO-ATC |
R05CB01
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WHO-ATC |
S01XA08
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WHO-ESSENTIAL MEDICINES LIST |
4.2
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NCI_THESAURUS |
C74536
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FDA ORPHAN DRUG |
309110
Created by
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FDA ORPHAN DRUG |
20787
Created by
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FDA ORPHAN DRUG |
148401
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NCI_THESAURUS |
C275
Created by
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FDA ORPHAN DRUG |
479415
Created by
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Code System | Code | Type | Description | ||
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28939
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PRIMARY | |||
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C26668
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NO STRUCTURE GIVEN | |||
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DB06151
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PRIMARY | |||
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100000092261
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PRIMARY | |||
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m1353
Created by
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PRIMARY | Merck Index | ||
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210-498-3
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PRIMARY | |||
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WYQ7N0BPYC
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PRIMARY | |||
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SUB05229MIG
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PRIMARY | |||
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1535
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PRIMARY | |||
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78236
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PRIMARY | |||
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12035
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PRIMARY | |||
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CHEMBL600
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PRIMARY | |||
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197
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PRIMARY | RxNorm | ||
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111180
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PRIMARY | |||
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47911
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PRIMARY | |||
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616-91-1
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PRIMARY | |||
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DTXSID5020021
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PRIMARY | |||
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66
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PRIMARY | |||
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WYQ7N0BPYC
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PRIMARY | |||
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3003
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PRIMARY | |||
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ACETYLCYSTEINE
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PRIMARY | |||
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1009005
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PRIMARY | |||
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D000111
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PRIMARY | |||
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Acetylcysteine
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PRIMARY | |||
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C200
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
N-acetylcysteine inhibited the TNF-?-stimulated production of cytokines and chemokines
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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RACEMATE -> ENANTIOMER | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT | |||
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EXCRETED UNCHANGED |
URINE
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TRANSPORTER -> SUBSTRATE |
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Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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