Identification

Name
Acetylcysteine
Accession Number
DB06151
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. It is a derivative of cysteine with an acetyl group attached to the amino group of cysteine. NAC is essentially a prodrug that is converted to cysteine (in the intestine by the enzyme aminoacylase 1) and absorbed in the intestine into the blood stream. Cysteine is a key constituent to glutathione and hence administration of acetylcysteine replenishes glutathione stores. Acetylcysteine can also be used as a general antioxidant which can help mitigate symptoms for a variety of diseases exacerbated by reactive oxygen species (ROS). For instance, acetylcysteine is commonly used in individuals with renal impairment to prevent the precipitation of acute renal failure. Acetylcysteine has been shown to have efficacy in treating mild to moderate traumatic brain injury including ischemic brain injury, particularly in reducing neuronal losses, and also reducing cognitive and neurological symptoms when administered promptly after injury. N-acetylcysteine is now widely used in the treatment of HIV, and it has reported efficacy in chronic obstructive pulmonary disease and contrast-induced nephropathy. Acetylcysteine is also being successfully used to treat a variety of neuropsychiatric and neurodegenerative disorders including cocaine, cannabis, and smoking addictions, Alzheimer's and Parkinson's diseases, autism, compulsive and grooming disorders, schizophrenia, depression, and bipolar disorder. Recent data also shows that N-acetylcysteine inhibits muscle fatigue and can be used to enhance performance in endurance events and in exercise and endurance training.

Acetylcysteine is also undergoing clinical trials as RK-0202, an oral rinse for the prevention and treatment of mucositis. It is comprised of acetylcysteine in a polymer matrix.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 163.195
Monoisotopic: 163.030313849
Chemical Formula
C5H9NO3S
Synonyms
  • (2R)-2-acetylamino-3-sulfanylpropanoic acid
  • (R)-2-acetylamino-3-mercaptopropanoic acid
  • (R)-mercapturic acid
  • Acetilcisteina
  • Acetylcysteine
  • Acetylcysteinum
  • L-acetylcysteine
  • L-α-acetamido-β-mercaptopropionic acid
  • Mercapturic acid
  • N-acetyl-L-(+)-cysteine
  • N-acetyl-L-cysteine
  • N-acetylcysteine
  • NAC
External IDs
  • 5052
  • NSC-111180
  • RK-0202

Pharmacology

Indication

Acetylcysteine is used mainly as a mucolytic and in the management of paracetamol (acetaminophen) overdose.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Acetylcysteine has been shown to reduce the extent of liver injury following acetaminophen overdose. It is most effective when given early, with benefit seen principally in patients treated within 8-10 hours of the overdose. 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.

Mechanism of action

Acetylcysteine protects against acetaminophen overdose-induced hepatotoxicity by maintaining or restoring hepatic concentrations of glutathione. It does this by producing the glutathione precursor L-cysteine. Glutathione is required to inactivate an intermediate metabolite (N-acetyl-p-benzoquinoneimine or NAPQI) of acetaminophen that is thought to be hepatotoxic. In acetaminophen overdose cases, excessive quantities of this metabolite are formed because the primary metabolic (glucuronide and sulfate conjugation) pathways become saturated. Acetylcysteine may act by reducing the metabolite to the parent compound and/or by providing sulfhydryl for conjugation of the metabolite. Experimental evidence also suggests that a sulfhydryl-containing compound such as acetylcysteine may also directly inactivate the metabolite. The mechanisms of action for acetylcysteine’s well-known mucolytic effects are different. In particular, when inhaled, acetylcysteine (and its metabolic byproduct cysteine) exerts its mucolytic action through its free sulfhydryl group, which reduces the disulfide bonds in the mucus matrix and lowers mucus viscosity. This action increases with increasing pH and is most significant at pH 7 to 9. The mucolytic action of acetylcysteine is not affected by the presence of DNA. Acetylcysteine is also an antioxidant and reduces oxidative stress. 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. This glutamate in turn acts on mGluR2/3 receptors, and at higher doses of acetylcysteine, mGluR5. Glutathione also modulates the NMDA receptor by acting at the redox site. These effects on glutamate and NMDA signaling appear to explain some of the positive neuropsychotropic effects associated with NAC. 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.

TargetActionsOrganism
AGlutathione synthetase
stimulator
Humans
ACystine/glutamate transporter
activator
Humans
UNAPQI (N-acetyl-p-benzoquinone imine)
reducer
Humans
UAminoacylase-1
ligand
Humans
UInhibitor of nuclear factor kappa-B kinase subunit beta
inhibitor
Humans
UInhibitor of nuclear factor kappa-B kinase subunit alpha
inhibitor
Humans
UGlutamate receptor ionotropic, NMDA 2B
activator
Humans
UGlutamate receptor ionotropic, NMDA 1
activator
Humans
UGlutamate receptor ionotropic, NMDA 2A
activator
Humans
UGlutamate receptor ionotropic, NMDA 2D
activator
Humans
UGlutamate receptor ionotropic, NMDA 3A
activator
Humans
Absorption

Bioavailability is 6–10% following oral administration and less than 3% following topical administration.

Volume of distribution
Not Available
Protein binding

83%

Metabolism

Hepatic. Deacetylated by the liver to cysteine and subsequently metabolized.

Route of elimination
Not Available
Half-life

5.6 hours (adults), 11 hours (neonates)

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Single intravenous doses of acetylcysteine at 1000 mg/kg in mice, 2445 mg/kg in rats, 1500 mg/kg in guinea pigs, 1200 mg/kg in rabbits and 500 mg/kg in dogs were lethal. Symptoms of acute toxicity were ataxia, hypoactivity, labored respiration, cyanosis, loss of righting reflex and convulsions.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AmbrisentanThe excretion of Ambrisentan can be decreased when combined with Acetylcysteine.
AsunaprevirThe excretion of Asunaprevir can be decreased when combined with Acetylcysteine.
AtorvastatinThe excretion of Atorvastatin can be decreased when combined with Acetylcysteine.
AxitinibThe excretion of Axitinib can be decreased when combined with Acetylcysteine.
BenzylpenicillinThe excretion of Benzylpenicillin can be decreased when combined with Acetylcysteine.
BosentanThe excretion of Bosentan can be decreased when combined with Acetylcysteine.
CaspofunginThe excretion of Caspofungin can be decreased when combined with Acetylcysteine.
CerivastatinThe excretion of Cerivastatin can be decreased when combined with Acetylcysteine.
CholecystokininThe excretion of Cholecystokinin can be decreased when combined with Acetylcysteine.
Cholic AcidThe excretion of Cholic Acid can be decreased when combined with Acetylcysteine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

International/Other Brands
Fluimucil / Lysox / Mucolysin (Zambon)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcetadoteInjection, solution200 mg/1mLIntravenousCumberland Pharmaceuticals2004-06-042011-01-21US flag
AcetadoteInjection, solution200 mg/1mLIntravenousCumberland Pharmaceuticals Inc.2004-01-23Not applicableUS flag
AcetylcysteineInjection200 mg/1mLIntravenousPaddock Laboratories, LLC2013-10-152021-02-01US flag
AcetylcysteineInjection200 mg/1mLIntravenousPaddock Laboratories, LLC2012-12-20Not applicableUS flag
Acetylcysteine InjectionSolutionIntravenous; Oral; Respiratory (inhalation)Teligent Ou2009-08-18Not applicableCanada flag
Acetylcysteine SolutionSolutionIntravenous; Oral; Respiratory (inhalation)Sandoz Canada Incorporated2001-04-27Not applicableCanada flag
Acetylcysteine Solution USPSolutionIntravenous; Oral; Respiratory (inhalation)Teligent Ou2018-01-26Not applicableCanada flag
CetylevTablet, effervescent500 mg/1OralArbor Pharmaceuticals2016-06-272019-04-01US flag
CetylevTablet, effervescent2.5 g/1OralArbor Pharmaceuticals2017-02-132019-04-01US flag
CetylevTablet, effervescent2.5 g/1OralArbor Pharmaceuticals2016-06-272019-04-01US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcetylcysteineSolution200 mg/1mLOral; Respiratory (inhalation)West-Ward Pharmaceuticals Corp.1996-05-012014-04-03US flag
AcetylcysteineInhalant200 mg/1mLRespiratory (inhalation)AMERICAN REGENT, INC.1995-10-01Not applicableUS flag
AcetylcysteineInhalant200 mg/1mLOral; Respiratory (inhalation)Cardinal Health2011-05-06Not applicableUS flag
AcetylcysteineSolution200 mg/1mLOral; Respiratory (inhalation)Physicians Total Care, Inc.2009-06-29Not applicableUS flag
AcetylcysteineSolution200 mg/1mLOral; Respiratory (inhalation)Fresenius Kabi USA, LLC2012-09-01Not applicableUS flag
AcetylcysteineSolution100 mg/1mLOral; Respiratory (inhalation)Fresenius Kabi USA, LLC2014-03-31Not applicableUS flag
AcetylcysteineSolution200 mg/1mLOral; Respiratory (inhalation)Hospira, Inc.2005-06-01Not applicableUS flag
AcetylcysteineInhalant200 mg/1mLRespiratory (inhalation)AMERICAN REGENT, INC.1995-10-01Not applicableUS flag
AcetylcysteineSolution200 mg/1mLOral; Respiratory (inhalation)Hospira Worldwide, Inc.1989-05-012009-04-05US flag
AcetylcysteineInhalant100 mg/1mLRespiratory (inhalation)AMERICAN REGENT, INC.1995-10-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Parvolex Liq IV 200mg/mlLiquidIntravenousBioniche Pharma (Canada) Ltd1994-12-311996-11-08Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
L-Methyl MC NACAcetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1)Tablet, coatedOralVirtus Pharmaceuticals2014-04-092015-02-15US flag
Levomefolate Calcium Acetylcysteine and Mecobalamin AlgalAcetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) + Schizochytrium DHA oil (90.314 mg/1)Tablet, coatedOralVirtus Pharmaceuticals2014-05-092015-02-15US flag
Levomefolate Calcium Acetylcysteine Mecobalamin AlgalAcetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) + Schizochytrium DHA oil (90.314 mg/1)TabletOralMethod Pharmaceuticals2015-04-012015-04-01US flag
Levomefolate Calcium, Acetylcysteine, Mecobalamin and AlgalAcetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) + Schizochytrium DHA oil (90.314 mg/1)TabletOralVirtus Pharmaceuticals2013-06-132015-02-15US flag
Medi-10Acetylcysteine (200 mg/1) + Cholecalciferol (1000 [iU]/1) + Chromium picolinate (1 mg/1) + Levomefolate calcium (2.5 mg/1) + Lipoic acid (200 mg/1) + Mecobalamin (2.5 mg/1) + Nicotinamide (10 mg/1) + Pyridoxal phosphate (20 mg/1) + Resveratrol (83 mg/1) + Ubidecarenone (16 mg/1)CapsuleOralMedicap Laboratories Inc.2015-05-012016-01-12US flag
MethazelAcetylcysteine (50 mg/1) + Folic acid (1 mg/1) + Lipoic acid (50 mg/1) + Mecobalamin (2.5 mg/1) + Pyridoxal phosphate (50 mg/1) + Coenzyme q10, (2z)- (25 mg/1)CapsuleOralSterling-Knight Pharmaceuticals, LLC2015-10-122019-12-01US flag

Categories

ATC Codes
R05CB01 — AcetylcysteineS01XA08 — AcetylcysteineV03AB23 — Acetylcysteine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-L-alpha-amino acids
Alternative Parents
Cysteine and derivatives / Acetamides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Alkylthiols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Acetamide / Aliphatic acyclic compound / Alkylthiol / Carbonyl group / Carboxamide group / Carboxylic acid / Cysteine or derivatives / Hydrocarbon derivative / Monocarboxylic acid or derivatives / N-acyl-l-alpha-amino acid
show 8 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
L-cysteine derivative, N-acetyl-L-amino acid, acetylcysteine (CHEBI:28939)

Chemical Identifiers

UNII
WYQ7N0BPYC
CAS number
616-91-1
InChI Key
PWKSKIMOESPYIA-BYPYZUCNSA-N
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
IUPAC Name
(2R)-2-acetamido-3-sulfanylpropanoic acid
SMILES
CC(=O)N[[email protected]@H](CS)C(O)=O

References

Synthesis Reference

Rolf-Dieter Juch, Gerd Birrenbach, Christian Pflugshaupt, "Solid, fast-soluble pharmaceutical preparation containing S-(carboxymethyl)-L-cysteine and/or N-acetylcysteine." U.S. Patent US5401514, issued November, 1990.

US5401514
General References
  1. Bachert C, Hormann K, Mosges R, Rasp G, Riechelmann H, Muller R, Luckhaupt H, Stuck BA, Rudack C: An update on the diagnosis and treatment of sinusitis and nasal polyposis. Allergy. 2003 Mar;58(3):176-91. [PubMed:12653791]
  2. Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. [PubMed:9624310]
  3. Breitkreutz R, Pittack N, Nebe CT, Schuster D, Brust J, Beichert M, Hack V, Daniel V, Edler L, Droge W: Improvement of immune functions in HIV infection by sulfur supplementation: two randomized trials. J Mol Med (Berl). 2000;78(1):55-62. [PubMed:10759030]
  4. Dawson AH, Henry DA, McEwen J: Adverse reactions to N-acetylcysteine during treatment for paracetamol poisoning. Med J Aust. 1989 Mar 20;150(6):329-31. [PubMed:2716644]
  5. Fulghesu AM, Ciampelli M, Muzj G, Belosi C, Selvaggi L, Ayala GF, Lanzone A: N-acetyl-cysteine treatment improves insulin sensitivity in women with polycystic ovary syndrome. Fertil Steril. 2002 Jun;77(6):1128-35. [PubMed:12057717]
  6. Jones AL: Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: a critical review. J Toxicol Clin Toxicol. 1998;36(4):277-85. [PubMed:9711192]
Human Metabolome Database
HMDB0001890
KEGG Drug
D00221
KEGG Compound
C06809
PubChem Compound
12035
PubChem Substance
99443235
ChemSpider
11540
BindingDB
50420190
RxNav
197
ChEBI
28939
ChEMBL
CHEMBL600
ZINC
ZINC000003589203
Therapeutic Targets Database
DNC000981
PharmGKB
PA448033
PDBe Ligand
SC2
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Acetylcysteine
AHFS Codes
  • 92:12.00 — Antidotes
PDB Entries
207l / 2j1g / 2j2p / 2j58 / 5hpm / 5icx / 5nn4
FDA label
Download (238 KB)
MSDS
Download (59.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAdipose Tissue Atrophy / Atrophy of Breast / Breast; Atrophy / Breast; Deformity, Congenital / Graft Loss1
4Active Not RecruitingTreatmentAsthma1
4Active Not RecruitingTreatmentPilon Fracture1
4CompletedDiagnosticAnatomic renal artery stenosis / Chronic Kidney Disease (CKD) / Pulmonary Cancer / Pulmonary Embolism1
4CompletedDiagnosticGastric Mucosal Lesion1
4CompletedDiagnosticInsulin Resistance Syndrome X / Pancreatic Beta Cell Function1
4CompletedDiagnosticStomach Neoplasms1
4CompletedPreventionAdverse Effects / Contrast Induced Nephropathy (CIN) / Kidney Diseases / Prophylaxis of Contrast-induced nephropathy / Renal Failure1
4CompletedPreventionContrast media reaction / Kidney Diseases1
4CompletedPreventionHepatectomy / Reperfusion Injury1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amend
  • American Regent
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Boehringer Ingelheim Ltd.
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • Cumberland Pharmaceuticals
  • Hospira Inc.
  • Luitpold Pharmaceuticals Inc.
  • Roxane Labs
  • Spectrum Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet100 mg
Tablet200 mg
Tablet600 mg
SolutionOral200 mg/10mL
GranuleOral2 g
Injection, solutionIntravenous200 mg/1mL
GranuleOral0.2 g
GranuleOral200 mg
GranuleOral600 mg
Powder, for solutionOral2 g
Tablet, effervescentOral600 mg/1
InhalantOral; Respiratory (inhalation)100 mg/1mL
InhalantOral; Respiratory (inhalation)200 mg/1mL
InhalantRespiratory (inhalation)100 mg/1mL
InhalantRespiratory (inhalation)200 mg/1mL
InjectionIntravenous200 mg/1mL
Injection, solutionIntravenous6 g/30mL
SolutionIntravenous; Oral; Respiratory (inhalation)
Granule, effervescentOral100 mg
InjectionIntravenous300 mg/3ml
Powder, for solutionOral600 mg
Granule, effervescentOral200 mg
SolutionIntravenous0.25 g/mL
Tablet, effervescent600 mg
SolutionIntravenous10.4 g/L
SolutionIntravenous4.15 g
Injection, solutionIntravenous
Powder, for solutionOral1200 mg
Powder, for solutionOral900 mg
Syrup4 %
PowderOral1200 mg
Granule200 mg
Capsule200 mg
Solution300 mg/3ml
PowderOral900 mg
PowderOral600 mg
Powder600 mg
Powder; powder, for solution; powder, for suspensionOral200 MG
Powder; powder, for solution; powder, for suspensionOral600 MG
Powder; powder, for solution; powder, for suspensionOral100 MG
Tablet, effervescent900 mg
Solution / dropsOphthalmic50 mg/ml
Tablet, effervescentOral2.5 g/1
Tablet, effervescentOral500 mg/1
Tablet, effervescent400 mg
Powder1200 mg
Tablet, effervescentOral25 mg
Tablet, effervescentOral50 mg
Syrup200 mg/5ml
SolutionOral200 mg
Granule100 MG/5ML
Granule, for solutionOral100 MG
Granule, for solutionOral200 MG
Granule, for solutionOral600 MG
Syrup100 MG/5ML
Syrup600 MG/15ML
SyrupOral2 g
PowderOral0.6 g
GranuleOral6.6667 g
SyrupOral4 g
Tablet, coatedOral
TabletOral
CapsuleOral
Powder900 mg
Granule600 mg
GranuleOral0.6 g
GranuleOral100 mg
Tablet, effervescentOral1200 mg
Tablet, effervescentOral900 mg
Syrup150 ml
Powder200 mg
Syrup100 ml
Tablet, effervescent1200 mg
SolutionIntravenous; Oral; Respiratory (inhalation)200 mg
SolutionOral; Respiratory (inhalation)100 mg/1mL
SolutionOral; Respiratory (inhalation)200 mg/1mL
LiquidIntravenous; Oral; Respiratory (inhalation)
Powder, for solutionOral100 mg
Granule, effervescent400 mg
Granule
Syrup20 mg/ml
Powder, for solutionOral0.2 g
Tablet, effervescent200 mg
Tablet, effervescentOral600 MG
Tablet, effervescentOral200 MG
Tablet, for solution; tablet, for suspensionOral200 MG
SyrupOral0.15 g
SyrupOral0.3 g
Powder
GranuleOral200 mg/5ml
Granule100 mg
LiquidIntravenous
Powder, for solutionOral200 mg
Tablet
PowderOral300 mg
Prices
Unit descriptionCostUnit
Mucomyst-10 10% Solution 30ml Vial25.99USD vial
Acetylcysteine 20% Solution 10ml Vial22.99USD vial
Acetylcysteine 10% Solution 30ml Vial19.99USD vial
Mucomyst 20% Solution 30ml Vial18.99USD vial
Acetylcysteine 20% Solution 30ml Vial17.99USD vial
Acetylcysteine 20% Solution 4ml Vial16.99USD vial
Acetylcysteine 10% Solution 10ml Vial8.66USD vial
Acetadote 200 mg/ml vial6.65USD ml
Acetylcysteine powder3.07USD g
N-acetyl-l-cysteine powder0.84USD g
Mucomyst 20 % Solution0.75USD ml
Acetylcysteine 20 % Solution0.68USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8399445No2013-03-192025-08-24US flag
US8722738No2014-05-132032-04-06US flag
US8653061No2014-02-182025-08-24US flag
US8148356No2012-04-032026-05-21US flag
US8747894No2014-06-102032-05-08US flag
US9327028No2016-05-032031-07-21US flag
US9427421No2016-08-302032-05-08US flag
US9561204No2017-02-072032-05-08US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)109-110Martin, T.A. and Waller, C.W.; US. Patent 3,184,505; May 18, 1965; assigned to Mead Johnson & Company.
pKa9.52 (at 25 °C)SERJEANT & DEMPSEY (1979)
Predicted Properties
PropertyValueSource
Water Solubility5.09 mg/mLALOGPS
logP-0.03ALOGPS
logP-0.71ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.67 m3·mol-1ChemAxon
Polarizability15.34 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Download (8.35 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0i00-2970000000-d817070e3a42f5e63ec5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-01ox-9000000000-192b8907b32f1e180c72
GC-MS Spectrum - GC-MSGC-MSsplash10-0i00-2970000000-d817070e3a42f5e63ec5
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-b0d92bfcc2536077a6fc
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-9000000000-f305286cee84e6ae992b
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0a4l-9000000000-b10b4a2a6383336db871
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Stimulator
General Function
Protein homodimerization activity
Specific Function
Not Available
Gene Name
GSS
Uniprot ID
P48637
Uniprot Name
Glutathione synthetase
Molecular Weight
52384.325 Da
References
  1. Martensson J, Gustafsson J, Larsson A: A therapeutic trial with N-acetylcysteine in subjects with hereditary glutathione synthetase deficiency (5-oxoprolinuria). J Inherit Metab Dis. 1989;12(2):120-30. [PubMed:2502672]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Cystine:glutamate antiporter activity
Specific Function
Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name
SLC7A11
Uniprot ID
Q9UPY5
Uniprot Name
Cystine/glutamate transporter
Molecular Weight
55422.44 Da
References
  1. Dean O, Giorlando F, Berk M: N-acetylcysteine in psychiatry: current therapeutic evidence and potential mechanisms of action. J Psychiatry Neurosci. 2011 Mar;36(2):78-86. doi: 10.1503/jpn.100057. [PubMed:21118657]
Kind
Small molecule
Organism
Humans
Pharmacological action
Unknown
Actions
Reducer
References
  1. Jones AL: Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: a critical review. J Toxicol Clin Toxicol. 1998;36(4):277-85. [PubMed:9711192]
  2. Prescott LF, Critchley JA: The treatment of acetaminophen poisoning. Annu Rev Pharmacol Toxicol. 1983;23:87-101. [PubMed:6347057]
  3. Marzullo L: An update of N-acetylcysteine treatment for acute acetaminophen toxicity in children. Curr Opin Pediatr. 2005 Apr;17(2):239-45. [PubMed:15800420]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Metallopeptidase activity
Specific Function
Involved in the hydrolysis of N-acylated or N-acetylated amino acids (except L-aspartate).
Gene Name
ACY1
Uniprot ID
Q03154
Uniprot Name
Aminoacylase-1
Molecular Weight
45884.705 Da
References
  1. Uttamsingh V, Keller DA, Anders MW: Acylase I-catalyzed deacetylation of N-acetyl-L-cysteine and S-alkyl-N-acetyl-L-cysteines. Chem Res Toxicol. 1998 Jul;11(7):800-9. [PubMed:9671543]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Scaffold protein binding
Specific Function
Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...
Gene Name
IKBKB
Uniprot ID
O14920
Uniprot Name
Inhibitor of nuclear factor kappa-B kinase subunit beta
Molecular Weight
86563.245 Da
References
  1. Oka S, Kamata H, Kamata K, Yagisawa H, Hirata H: N-acetylcysteine suppresses TNF-induced NF-kappaB activation through inhibition of IkappaB kinases. FEBS Lett. 2000 Apr 28;472(2-3):196-202. [PubMed:10788610]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Scaffold protein binding
Specific Function
Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...
Gene Name
CHUK
Uniprot ID
O15111
Uniprot Name
Inhibitor of nuclear factor kappa-B kinase subunit alpha
Molecular Weight
84638.88 Da
References
  1. Oka S, Kamata H, Kamata K, Yagisawa H, Hirata H: N-acetylcysteine suppresses TNF-induced NF-kappaB activation through inhibition of IkappaB kinases. FEBS Lett. 2000 Apr 28;472(2-3):196-202. [PubMed:10788610]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic site...
Gene Name
GRIN2B
Uniprot ID
Q13224
Uniprot Name
Glutamate receptor ionotropic, NMDA 2B
Molecular Weight
166365.885 Da
References
  1. Lipton SA, Choi YB, Takahashi H, Zhang D, Li W, Godzik A, Bankston LA: Cysteine regulation of protein function--as exemplified by NMDA-receptor modulation. Trends Neurosci. 2002 Sep;25(9):474-80. [PubMed:12183209]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
Molecular Weight
105371.945 Da
References
  1. Lipton SA, Choi YB, Takahashi H, Zhang D, Li W, Godzik A, Bankston LA: Cysteine regulation of protein function--as exemplified by NMDA-receptor modulation. Trends Neurosci. 2002 Sep;25(9):474-80. [PubMed:12183209]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of sub...
Gene Name
GRIN2A
Uniprot ID
Q12879
Uniprot Name
Glutamate receptor ionotropic, NMDA 2A
Molecular Weight
165281.215 Da
References
  1. Lipton SA, Choi YB, Takahashi H, Zhang D, Li W, Godzik A, Bankston LA: Cysteine regulation of protein function--as exemplified by NMDA-receptor modulation. Trends Neurosci. 2002 Sep;25(9):474-80. [PubMed:12183209]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Nmda glutamate receptor activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine.
Gene Name
GRIN2D
Uniprot ID
O15399
Uniprot Name
Glutamate receptor ionotropic, NMDA 2D
Molecular Weight
143750.685 Da
References
  1. Lipton SA, Choi YB, Takahashi H, Zhang D, Li W, Godzik A, Bankston LA: Cysteine regulation of protein function--as exemplified by NMDA-receptor modulation. Trends Neurosci. 2002 Sep;25(9):474-80. [PubMed:12183209]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Lipton SA, Choi YB, Takahashi H, Zhang D, Li W, Godzik A, Bankston LA: Cysteine regulation of protein function--as exemplified by NMDA-receptor modulation. Trends Neurosci. 2002 Sep;25(9):474-80. [PubMed:12183209]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Daily A, Monks NR, Leggas M, Moscow JA: Abrogation of microcystin cytotoxicity by MAP kinase inhibitors and N-acetyl cysteine is confounded by OATPIB1 uptake activity inhibition. Toxicon. 2010 Apr 1;55(4):827-37. doi: 10.1016/j.toxicon.2009.11.019. Epub 2009 Nov 24. [PubMed:19944114]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Aslamkhan AG, Han YH, Yang XP, Zalups RK, Pritchard JB: Human renal organic anion transporter 1-dependent uptake and toxicity of mercuric-thiol conjugates in Madin-Darby canine kidney cells. Mol Pharmacol. 2003 Mar;63(3):590-6. [PubMed:12606766]

Drug created on January 15, 2008 09:45 / Updated on September 24, 2020 02:08

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