Acetylcysteine
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
Structure for Acetylcysteine (DB06151)
- 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.
Target Actions Organism AGlutathione synthetase stimulatorHumans ACystine/glutamate transporter activatorHumans UNAPQI (N-acetyl-p-benzoquinone imine) reducerHumans UAminoacylase-1 ligandHumans UInhibitor of nuclear factor kappa-B kinase subunit beta inhibitorHumans UInhibitor of nuclear factor kappa-B kinase subunit alpha inhibitorHumans UGlutamate receptor ionotropic, NMDA 2B activatorHumans UGlutamate receptor ionotropic, NMDA 1 activatorHumans UGlutamate receptor ionotropic, NMDA 2A activatorHumans UGlutamate receptor ionotropic, NMDA 2D activatorHumans UGlutamate receptor ionotropic, NMDA 3A activatorHumans - 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.
Drug Interaction Unlock Additional DataAmbrisentan The excretion of Ambrisentan can be decreased when combined with Acetylcysteine. Asunaprevir The excretion of Asunaprevir can be decreased when combined with Acetylcysteine. Atorvastatin The excretion of Atorvastatin can be decreased when combined with Acetylcysteine. Axitinib The excretion of Axitinib can be decreased when combined with Acetylcysteine. Benzylpenicillin The excretion of Benzylpenicillin can be decreased when combined with Acetylcysteine. Bosentan The excretion of Bosentan can be decreased when combined with Acetylcysteine. Caspofungin The excretion of Caspofungin can be decreased when combined with Acetylcysteine. Cerivastatin The excretion of Cerivastatin can be decreased when combined with Acetylcysteine. Cholecystokinin The excretion of Cholecystokinin can be decreased when combined with Acetylcysteine. Cholic Acid The excretion of Cholic Acid can be decreased when combined with Acetylcysteine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- International/Other Brands
- Fluimucil / Lysox / Mucolysin (Zambon)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAcetadote Injection, solution 200 mg/1mL Intravenous Cumberland Pharmaceuticals Inc. 2004-01-23 Not applicable US 
Acetadote Injection, solution 200 mg/1mL Intravenous Cumberland Pharmaceuticals 2004-06-04 2011-01-21 US Acetylcysteine Injection 200 mg/1mL Intravenous Paddock Laboratories, LLC 2013-10-15 2021-02-01 US Acetylcysteine Injection 200 mg/1mL Intravenous Paddock Laboratories, LLC 2012-12-20 Not applicable US Acetylcysteine Injection Solution Intravenous; Oral; Respiratory (inhalation) Teligent Ou 2009-08-18 Not applicable Canada 
Acetylcysteine Solution Solution Intravenous; Oral; Respiratory (inhalation) Sandoz Canada Incorporated 2001-04-27 Not applicable Canada Acetylcysteine Solution USP Solution Intravenous; Oral; Respiratory (inhalation) Teligent Ou 2018-01-26 Not applicable Canada Cetylev Tablet, effervescent 2.5 g/1 Oral Arbor Pharmaceuticals 2016-06-27 2019-04-01 US Cetylev Tablet, effervescent 500 mg/1 Oral Arbor Pharmaceuticals 2016-06-27 2019-04-01 US Cetylev Tablet, effervescent 2.5 g/1 Oral Arbor Pharmaceuticals 2017-02-13 2019-04-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAcetylcysteine Inhalant 200 mg/1mL Oral; Respiratory (inhalation) Cardinal Health 2011-05-06 Not applicable US Acetylcysteine Injection 200 mg/1mL Intravenous Akorn, Inc. 2015-03-25 Not applicable US Acetylcysteine Solution 200 mg/1mL Oral; Respiratory (inhalation) Fresenius Kabi USA, LLC 2012-09-01 Not applicable US Acetylcysteine Solution 200 mg/1mL Oral; Respiratory (inhalation) Hospira, Inc. 2005-06-01 Not applicable US Acetylcysteine Solution 100 mg/1mL Oral; Respiratory (inhalation) West-Ward Pharmaceuticals Corp. 1996-05-01 2014-04-03 US Acetylcysteine Inhalant 200 mg/1mL Respiratory (inhalation) AMERICAN REGENT, INC. 1995-10-01 Not applicable US Acetylcysteine Solution 100 mg/1mL Oral; Respiratory (inhalation) Hospira Worldwide, Inc. 1989-05-01 2009-04-05 US Acetylcysteine Inhalant 100 mg/1mL Respiratory (inhalation) AMERICAN REGENT, INC. 1995-10-01 Not applicable US Acetylcysteine Injection, solution 200 mg/1mL Intravenous Cadila Healthcare Limited 2019-01-17 Not applicable US Acetylcysteine Solution 200 mg/1mL Oral; Respiratory (inhalation) West-Ward Pharmaceuticals Corp. 1996-05-01 2014-04-03 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataParvolex Liq IV 200mg/ml Liquid Intravenous Bioniche Pharma (Canada) Ltd 1994-12-31 1996-11-08 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image L-Methyl MC NAC Acetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) Tablet, coated Oral Virtus Pharmaceuticals 2014-04-09 2015-02-15 US Levomefolate Calcium Acetylcysteine and Mecobalamin Algal Acetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) + Schizochytrium DHA oil (90.314 mg/1) Tablet, coated Oral Virtus Pharmaceuticals 2014-05-09 2015-02-15 US Levomefolate Calcium Acetylcysteine Mecobalamin Algal Acetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) + Schizochytrium DHA oil (90.314 mg/1) Tablet Oral Method Pharmaceuticals 2015-04-01 2015-04-01 US Levomefolate Calcium, Acetylcysteine, Mecobalamin and Algal Acetylcysteine (600 mg/1) + Levomefolate calcium (6 mg/1) + Mecobalamin (2 mg/1) + Schizochytrium DHA oil (90.314 mg/1) Tablet Oral Virtus Pharmaceuticals 2013-06-13 2015-02-15 US Medi-10 Acetylcysteine (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) Capsule Oral Medicap Laboratories Inc. 2015-05-01 2016-01-12 US Methazel Acetylcysteine (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) Capsule Oral Sterling-Knight Pharmaceuticals, LLC 2015-10-12 2019-12-01 US
Categories
- ATC Codes
- R05CB01 — Acetylcysteine
- R05CB — Mucolytics
- R05C — EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
- R05 — COUGH AND COLD PREPARATIONS
- R — RESPIRATORY SYSTEM
- S01XA — Other ophthalmologicals
- S01X — OTHER OPHTHALMOLOGICALS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Amino Acids
- Amino Acids, Neutral
- Amino Acids, Peptides, and Proteins
- Amino Acids, Sulfur
- Anti-Infective Agents
- Antidote for Acetaminophen Overdose
- Antidotes
- Antioxidants
- Compounds used in a research, industrial, or household setting
- Cough and Cold Preparations
- Cysteine
- Decreased Respiratory Secretion Viscosity
- Expectorants
- Free Radical Scavengers
- Increased Glutathione Concentration
- OATP1B1/SLCO1B1 Inhibitors
- Ophthalmologicals
- Protective Agents
- Reduction Activity
- Respiratory System Agents
- Sensory Organs
- Sulfhydryl Compounds
- Sulfur Compounds
- 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
- 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]
- Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. [PubMed:9624310]
- 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]
- 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]
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0001890
- KEGG Drug
- D00221
- KEGG Compound
- C06809
- PubChem Compound
- 12035
- PubChem Substance
- 99443235
- ChemSpider
- 11540
- BindingDB
- 50420190
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Asthma 1 4 Active Not Recruiting Treatment Pilon Fracture 1 4 Completed Diagnostic Anatomic renal artery stenosis / Chronic Kidney Disease (CKD) / Pulmonary Cancer / Pulmonary Embolism 1 4 Completed Diagnostic Gastric Mucosal Lesion 1 4 Completed Diagnostic Insulin Resistance Syndrome X / Pancreatic Beta Cell Function 1 4 Completed Diagnostic Stomach Neoplasms 1 4 Completed Prevention Adverse Effects / Contrast Induced Nephropathy (CIN) / Kidney Diseases / Prophylaxis of Contrast-induced nephropathy / Renal Failure 1 4 Completed Prevention Contrast media reaction / Kidney Diseases 1 4 Completed Prevention Hepatectomy / Reperfusion Injury 1 4 Completed Prevention Postoperative Acute Kidney Injury After Off-pump Coronary Artery Bypass Graft 1
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
Form Route Strength Tablet 100 mg Tablet 200 mg Tablet 600 mg Solution Oral 200 mg/10mL Solution Oral Granule Oral 2 g Injection, solution Intravenous 200 mg/1mL Granule Oral 0.2 g Granule Oral 200 mg Granule Oral 600 mg Powder, for solution Oral 2 g Powder, for solution Oral 100 mg/5g Powder, for solution Oral 200 mg/1g Tablet, effervescent Oral 600 mg/1 Tablet, soluble Oral 100 mg Tablet, soluble Oral 200 mg Tablet, soluble Oral 600 mg Capsule Inhalant Oral; Respiratory (inhalation) 100 mg/1mL Inhalant Oral; Respiratory (inhalation) 200 mg/1mL Inhalant Respiratory (inhalation) 100 mg/1mL Inhalant Respiratory (inhalation) 200 mg/1mL Injection Intravenous 200 mg/1mL Injection, solution Intravenous 6 g/30mL Solution Intravenous; Oral; Respiratory (inhalation) Granule, effervescent Oral 100 mg Injection Intravenous 300 mg/3ml Powder, for solution Oral 600 mg Granule, effervescent Oral 200 mg Solution Intravenous 0.25 g/mL Tablet, effervescent 600 mg Solution Intravenous 10.4 g/L Solution Intravenous 4.15 g Injection, solution Intravenous Powder, for solution Oral 1200 mg Powder, for solution Oral 900 mg Syrup 4 % Powder Oral 1200 mg Granule 200 mg Capsule 200 mg Solution 300 mg/3ml Powder Oral 900 mg Powder Oral 600 mg Powder 600 mg Powder; powder, for solution; powder, for suspension Oral 200 MG Powder; powder, for solution; powder, for suspension Oral 600 MG Powder; powder, for solution; powder, for suspension Oral 100 MG Tablet, effervescent 900 mg Solution / drops Ophthalmic 5 g/100mL Solution / drops Ophthalmic 50 mg/ml Tablet, effervescent Oral 2.5 g/1 Tablet, effervescent Oral 500 mg/1 Tablet, effervescent 400 mg Powder 1200 mg Tablet, effervescent Oral 25 mg Tablet, effervescent Oral 50 mg Syrup 200 mg/5ml Injection, solution 300 mg/3mL Solution / drops Ophthalmic 10 g/100mL Injection, solution, concentrate Parenteral 20 % Granule, for solution Oral 200 mg/1g Solution Oral 200 mg Granule 100 MG/5ML Granule, for solution Oral 100 MG Granule, for solution Oral 200 MG Granule, for solution Oral 600 MG Syrup 100 MG/5ML Syrup 600 MG/15ML Syrup Oral 2 g Powder Oral 0.6 g Granule Oral 6.6667 g Syrup Oral 4 g Capsule 600 mg Granule, for solution Oral 600 mg/5g Injection, solution 5 g/25mL Solution Oral 20 mg/ml Tablet, effervescent Oral Tablet, coated Oral Tablet Oral Capsule Oral Powder 900 mg Granule 600 mg Granule, for solution Oral 200 mg/3g Injection, powder, for solution 200 mg/3g Powder, for solution 600 mg Granule Oral 0.6 g Granule Oral 100 mg Tablet, effervescent Oral 1200 mg Tablet, effervescent Oral 900 mg Syrup 150 ml Powder 200 mg Syrup 100 ml Granule, for solution Oral 100 mg/6g Tablet, effervescent 1200 mg Injection, solution 1 g/5mL Injection, solution 300 mg/1.5mL Tablet, coated Oral 600 mg Solution Intravenous; Oral; Respiratory (inhalation) 200 mg Solution Oral; Respiratory (inhalation) 100 mg/1mL Solution Oral; Respiratory (inhalation) 200 mg/1mL Liquid Intravenous; Oral; Respiratory (inhalation) Powder, for solution Oral 100 mg Granule, effervescent 400 mg Granule Granule, for solution Oral 200 mg/5g Syrup 20 mg/ml Granule, for solution Oral 600 mg/7g Powder, for solution Oral 0.2 g Tablet, effervescent 200 mg Tablet, effervescent Oral 600 MG Tablet, effervescent Oral 200 MG Tablet, for solution; tablet, for suspension Oral Tablet, for solution; tablet, for suspension Oral 200 MG Powder Parenteral Syrup Oral 0.15 g Syrup Oral 0.3 g Powder Granule Oral 200 mg/5ml Granule 100 mg Liquid Intravenous Powder, for solution Oral 200 mg Solution; spray Nasal 1 g/100mL Granule, for solution Oral 100 mg/5g Tablet Powder Oral 300 mg - Prices
Unit description Cost Unit Mucomyst-10 10% Solution 30ml Vial 25.99USD vial Acetylcysteine 20% Solution 10ml Vial 22.99USD vial Acetylcysteine 10% Solution 30ml Vial 19.99USD vial Mucomyst 20% Solution 30ml Vial 18.99USD vial Acetylcysteine 20% Solution 30ml Vial 17.99USD vial Acetylcysteine 20% Solution 4ml Vial 16.99USD vial Acetylcysteine 10% Solution 10ml Vial 8.66USD vial Acetadote 200 mg/ml vial 6.65USD ml Acetylcysteine powder 3.07USD g N-acetyl-l-cysteine powder 0.84USD g Mucomyst 20 % Solution 0.75USD ml Acetylcysteine 20 % Solution 0.68USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS8399445 No 2013-03-19 2025-08-24 US US8722738 No 2014-05-13 2032-04-06 US US8653061 No 2014-02-18 2025-08-24 US US8148356 No 2012-04-03 2026-05-21 US US8747894 No 2014-06-10 2032-05-08 US US9327028 No 2016-05-03 2031-07-21 US US9427421 No 2016-08-30 2032-05-08 US US9561204 No 2017-02-07 2032-05-08 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 109-110 Martin, T.A. and Waller, C.W.; US. Patent 3,184,505; May 18, 1965; assigned to Mead Johnson & Company. pKa 9.52 (at 25 °C) SERJEANT & DEMPSEY (1979) - Predicted Properties
Property Value Source Water Solubility 5.09 mg/mL ALOGPS logP -0.03 ALOGPS logP -0.71 ChemAxon logS -1.5 ALOGPS pKa (Strongest Acidic) 3.82 ChemAxon pKa (Strongest Basic) -1.5 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 66.4 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 37.67 m3·mol-1 ChemAxon Polarizability 15.34 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Download (8.35 KB)
- Spectra
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
- 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
- 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]
Unknown
Reducer
References
- 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]
- Prescott LF, Critchley JA: The treatment of acetaminophen poisoning. Annu Rev Pharmacol Toxicol. 1983;23:87-101. [PubMed:6347057]
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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 October 29, 2020 19:26
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
![]({"CS-Molecular-Health-1.jpg":"/assets/ads/CS-Molecular-Health-1-19e76f023997d5ac198da2cb9976457f7b9ba733f0ea8a780fe21191c759e8fa.jpg","Drug-Dev-2.jpg":"/assets/ads/Drug-Dev-2-7c3039d93245f493c23278efbf759e4f933848a676262d579087d5cc516af179.jpg","Drug-Search-3.jpg":"/assets/ads/Drug-Search-3-7346c33d2133f62b46cbfbbe2b666e78f955c6847e242692c6081fec37c4d10d.jpg","PM-3.jpg":"/assets/ads/PM-3-13494ac4c996d71619127a11f685681418d4280832dec162c0b2c9c8bc2eda50.jpg","OD-Webinar-1.jpg":"/assets/ads/OD-Webinar-1-f9357f6d57fef5e411aa1c0439ef46c86d9151214434659d096eeed6407b799b.jpg","DDI-3.jpg":"/assets/ads/DDI-3-12808cf864d540ad43757b10b08fc52ae93e793b0c6e81345555187b2840ad09.jpg","EMR-2.jpg":"/assets/ads/EMR-2-adacf8de3f42cb06d6676d06fce611c29781db6ad30776cd18b72a7d8e69f0c8.jpg","Covid.jpg":"/assets/ads/Covid-eed8f17668b0308db62ce3c656f5e2f562376e9185ae08dda5ce6ed9ab0bbd1f.jpg","CS-Molecular-Health-2.jpg":"/assets/ads/CS-Molecular-Health-2-22f41f94b3f87e44a1dcaa8f6c03dc411ab69558efd4f3148ff9bb6adaa956dc.jpg","PM-5.jpg":"/assets/ads/PM-5-d0dc031e0fa0d0097d912eff07b7e80b27b867264dd5b055e379a57bfa2a8723.jpg","DDI-4.jpg":"/assets/ads/DDI-4-313b9c374b937fd78bb2ade652b9b030abb9e6cb90efd35833f793e384e8185b.jpg","Discover-1.jpg":"/assets/ads/Discover-1-b48ae6a3872eeb442f4c22a9a1d867428c83a917ec78a8c3ff4e02f84c5d4fef.jpg","Discover-2.jpg":"/assets/ads/Discover-2-6e7759998ee0fdc234cd84eea962f2480f0c7dafadabd785924918420decb102.jpg","Repurpose-1.jpg":"/assets/ads/Repurpose-1-265fbec40f0eac18d51d3ec4f558c10cb623d834ea75e0296259e458b72ee6d4.jpg","Repurpose-2.jpg":"/assets/ads/Repurpose-2-d12bd1d18b92d36eab60e71e6fd59acf04ef60a53783570e11eef397a0e0f4f5.jpg","PM-6.jpg":"/assets/ads/PM-6-3ae66e41f7ae1e851a0910be89141cf2533509b46df6379464efc885d5ee2f07.jpg","Drug-Search-4.jpg":"/assets/ads/Drug-Search-4-2a9102bd41f16e8c40c9d8044d1dcb6f206ff80107cc269aa83d02ea683bc829.jpg","DDI-5.jpg":"/assets/ads/DDI-5-fa1c287946f4044094c723161577cb5ac631f9cd1217446e510dc79ace6cb94e.jpg","TH-1.jpg":"/assets/ads/TH-1-55a9077bb39e8c38a68c67b555b8091d21a9d41b1c21c7daed3fe53e6f9f3c97.jpg","TH-2.jpg":"/assets/ads/TH-2-1d488747fa4af00ab970a48dba0b228b054d166aa22c1760a310e2b72dd22589.jpg"})
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates