U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ACETYLCYSTEINE

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

HIDE SMILES / InChI

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

Curator's Comment: http://forum.parkinson.org/topic/20369-cerebrospinal-fluid-concentrations-of-n-acetylcysteine-after-oral-administration-in-parkinsons-disease/

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nacystelyn

Approved Use

Unknown
Secondary
ACETADOTE

Approved Use

ACETADOTE, 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 Date

1.07481602E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.27 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Depression (below serious, 1 patient)
Sources:
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)
Dry mouth (below serious, 1 patient)
Constipation (below serious, 2 patients)
Dizziness (below serious, 1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
strong [Inhibition 10000 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Dose-finding and 24-h monitoring for efficacy and safety of aerosolized Nacystelyn in cystic fibrosis.
2002 Feb
Patents

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
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 Wed Jul 05 22:46:20 UTC 2023
Edited
by admin
on Wed Jul 05 22:46:20 UTC 2023
Record UNII
WYQ7N0BPYC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETYLCYSTEINE
EP   HSDB   II   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
ACETYLCYSTEINE [EP MONOGRAPH]
Common Name English
(R)-N-ACETYLCYSTEINE
Systematic Name English
N-ACETYL CYSTEINE
Systematic Name English
ACETADOTE
Brand Name English
RK-0202
Code English
L-CYSTEINE, N-ACETYL-
Systematic Name English
ACETYLCYSTEINE [HSDB]
Common Name English
NAC
Common Name English
Acetylcysteine [WHO-DD]
Common Name English
5052
Code English
RESPAIRE
Brand Name English
ORISTAR NALC
Brand Name English
acetylcysteine [INN]
Common Name English
MERCAPTURIC ACID
Brand Name English
N-ACETYL-3-MERCAPTOALANINE
Systematic Name English
CYSTEINE, N-ACETYL-, L-
Systematic Name English
N-ACETYLCYSTEINE
Systematic Name English
TIXAIR
Brand Name English
ACETYL CYSTEINE [INCI]
Common Name English
BRONCHOLYSIN
Brand Name English
ACETYLCYSTEINE [ORANGE BOOK]
Common Name English
ACETYL CYSTEINE
INCI  
INCI  
Official Name English
CETYLEV
Brand Name English
FLUIMICIL
Brand Name English
N-ACETYL-L-CYSTEINE
Systematic Name English
ACETYLCYSTEINE [MART.]
Common Name English
ACETYLCYSTEINE [USP MONOGRAPH]
Common Name English
ACETYLCYSTEINE [VANDF]
Common Name English
SYNTEMUCOL
Brand Name English
MUCOSIL
Brand Name English
NSC-111180
Code English
ACETYLCYSTEINE [USP-RS]
Common Name English
FLUIMUCETIN
Brand Name English
ACETYLCYSTEINE [USAN]
Common Name English
N-ACETYI-L-CYSTEINE
Common Name English
ACETYLCYSTEINE [JAN]
Common Name English
N-ACETYL-(R)-CYSTEINE
Systematic Name English
ACETYLCYSTEINE [MI]
Common Name English
ACETYLCYSTEINE [II]
Common Name English
MUCOMYST
Brand Name English
Classification Tree Code System Code
NDF-RT N0000175776
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
EU-Orphan Drug EU/3/04/259
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 158102
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-VATC QR05CB01
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NDF-RT N0000008867
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 275909
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NDF-RT N0000175960
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-ATC V03AB23
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NDF-RT N0000175961
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-VATC QS01XA08
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-VATC QV03AB23
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NDF-RT N0000175547
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 401713
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 370012
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
LIVERTOX NBK548401
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NDF-RT N0000175429
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 664418
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
DSLD 528 (Number of products:1468)
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-ATC R05CB01
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-ATC S01XA08
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 4.2
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NCI_THESAURUS C74536
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 309110
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 20787
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 148401
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NCI_THESAURUS C275
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
FDA ORPHAN DRUG 479415
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
Code System Code Type Description
CHEBI
28939
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
NCI_THESAURUS
C26668
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
NO STRUCTURE GIVEN
DRUG BANK
DB06151
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
SMS_ID
100000092261
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
MERCK INDEX
M1353
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
210-498-3
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
DAILYMED
WYQ7N0BPYC
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
EVMPD
SUB05229MIG
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
INN
1535
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
CHEBI
78236
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
PUBCHEM
12035
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL600
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
RXCUI
197
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY RxNorm
NSC
111180
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
CHEBI
47911
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
CAS
616-91-1
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID5020021
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
DRUG CENTRAL
66
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
FDA UNII
WYQ7N0BPYC
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
HSDB
3003
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
WIKIPEDIA
ACETYLCYSTEINE
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
RS_ITEM_NUM
1009005
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
MESH
D000111
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
LACTMED
Acetylcysteine
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
NCI_THESAURUS
C200
Created by admin on Wed Jul 05 22:46:20 UTC 2023 , Edited by admin on Wed Jul 05 22:46:20 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
N-acetylcysteine inhibited the TNF-α-stimulated production of cytokines and chemokines
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC