Acetylcysteine

Identification

Summary

Acetylcysteine is a medication that can be used as a mucolytic in patients with certain lung conditions and as an antidote for acetaminophen overdose.

Brand Names
Acetadote
Generic Name
Acetylcysteine
DrugBank Accession Number
DB06151
Background

Acetylcysteine is an antioxidant and glutathione inducer indicated for mucolytic therapy and the treatment of acetaminophen overdose.14,15,16,17 Acetylcysteine has also been studied for a wide variety of off-label indications with mixed results.8,9,10

Acetylcysteine was granted FDA approval on 14 September 1963.18

Type
Small Molecule
Groups
Approved, Investigational
Structure
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 indicated for mucolytic therapy and in the management of acetaminophen overdose.14,15,16,17

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcetaminophen overdose••••••••••••••••••••
Treatment ofAcetaminophen overdose•••••••••••••••••••••• ••••••••• •••••••••••
Treatment ofAcetaminophen overdose•••••••••••••••••••••• •••••••••• ••••••••
Used in combination to treatChronic rhinitisCombination Product in combination with: Tuaminoheptane (DB13238)•••••••••••••••••
Treatment ofCorneal diseases••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Acetylcysteine is indicated for mucolytic therapy and in the management of acetaminophen overdose.14,15,16,17 It has a short duration of action as it is given every 1-8 hours depending on route of administration, and has a wide therapeutic window.14,15,16,17 Patients should be counselled regarding diluting oral solutions in cola for taste masking,7 the risk of hypersensitivity, and the risk of upper gastrointestinal hemorrhage.14,15,16,17

Mechanism of action

A number of possible mechanisms for the mucolytic activity of acetylcysteine have been proposed. Acetylcysteine's sulfhydryl groups may hydrolize disulfide bonds within mucin, breaking down the oligomers, and making the mucin less viscous.11,16 Acetylcysteine has also been shown to reduce mucin secretion in rat models.11 It is an antioxidant in its own right but is also deacetylated to cysteine, which participates in the synthesis of the antioxidant glutathione.11 The antioxidant activity may also alter intracellular redox reactions, decreasing phosphorylation of EGFR and MAPK, which decrease transcription of the gene MUC5AC which produces mucin.11

In the case of acetaminophen overdoses, a portion of the drug is metabolized by CYP2E1 to form the potentially toxic metabolite N-acetyl-p-benzoquinone imine (NAPQI).16 The amount of NAPQI produced in an overdose saturates and depletes glutathione stores.16 The free NAPQI promiscuously binds to proteins in hepatocytes, leading to cellular necrosis.16 Acetylcysteine can directly conjugate NAPQI or provide cysteine for glutathione production and NAPQI conjugation.16

TargetActionsOrganism
AGlutathione synthetase
stimulator
Humans
ACystine/glutamate transporter
activator
Humans
UNAPQI (N-acetyl-p-benzoquinone imine)
reducer
Humans
UAminoacylase-1
substrate
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

An 11 g dose in the form of an effervescent tablet for solution reaches a mean Cmax of 26.5 µg/mL, with a Tmax of 2 hours, and an AUC of 186 µg*h/mL.17

Volume of distribution

The volume of distribution of acetylcysteine is 0.47 L/kg.15

Protein binding

Acetylcysteine is 66-97% protein bound in serum,15 usually to albumin.12

Metabolism

Acetylcysteine can be deacetylated by aminoacylase 1 or other undefined deacetylases before undergoing the normal metabolism of cysteine.1,5

Hover over products below to view reaction partners

Route of elimination

An oral dose of radiolabelled acetylcysteine is 13-38% recovered in the urine in the first 24 hours,15 while 3% is recovered in the feces.6

Half-life

The mean terminal half life of acetylcysteine in adults is 5.6 hours15 and in pre-term neonates is 11 hours.2

Clearance

Acetylcysteine has a mean clearance of 0.11 L/hr/kg.15

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with vomiting, nausea, bronchospasm, periorbital angioedema, and hypotension.3 Treat patients with symptomatic and supportive measures.15 Hemodialysis may remove some acetylcysteine from circulation as it is somewhat protein bound.15

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.
AtogepantThe serum concentration of Atogepant can be increased when it is 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.
Food Interactions
No interactions found.

Products

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International/Other Brands
Fluimucil / Lysox / Mucolysin (Zambon)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcetadoteInjection, solution200 mg/1mLIntravenousCumberland Pharmaceuticals Inc.2004-01-23Not applicableUS flag
AcetadoteInjection, solution200 mg/1mLIntravenousCumberland Pharmaceuticals2004-06-042011-01-21US flag
AcetylcysteineInjection200 mg/1mLIntravenousPaddock Laboratories, LLC2013-10-152021-02-01US flag
Acetylcysteine InjectionSolution200 mg / mLIntravenous; Oral; Respiratory (inhalation)Teligent Ou2009-08-182022-02-01Canada flag
Acetylcysteine InjectionSolution200 mg / mLIntravenousAuro Pharma IncNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcetylcysteineInjection200 mg/1mLIntravenousAkorn2015-03-25Not applicableUS flag
AcetylcysteineSolution200 mg/1mLOral; Respiratory (inhalation)Exela Pharma Sciences, LLC2023-11-13Not applicableUS flag
AcetylcysteineSolution100 mg/1mLOral; Respiratory (inhalation)West-Ward Pharmaceuticals Corp.1996-05-012014-04-03US flag
AcetylcysteineInhalant100 mg/1mLRespiratory (inhalation)AMERICAN REGENT, INC.1995-10-01Not applicableUS flag
AcetylcysteineInjection200 mg/1mLIntravenousAlmaject, Inc.2022-10-17Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ACETINPowder, for solutionOralHEALOL PHARMACEUTICALS SDN. BHD.2020-09-08Not applicableMalaysia flag
ACETIN-200Powder, for solutionOralHEALOL PHARMACEUTICALS SDN. BHD.2020-09-08Not applicableMalaysia flag
Acetylcysteine Sandoz Effervescent Tablet 200mgTablet, effervescent200 mgOralSANDOZ PRODUCTS MALAYSIA SDN. BHD.2020-09-08Not applicableMalaysia flag
Acetylcysteine Sandoz Effervescent Tablet 600mgTablet, effervescent600 mgOralSANDOZ PRODUCTS MALAYSIA SDN. BHD.2020-09-08Not applicableMalaysia flag
ACETYLCYSTEINE SANDOZ EFFERVESCENT TABLETS 600MGTablet, effervescent600 mgOralNOVARTIS (SINGAPORE) PTE LTD2014-07-30Not applicableSingapore flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AKE 1100 GLUKOZLU IV SOLOSYONU, 1000 MLAcetylcysteine (0.25 g/mL) + Alanine (4.5 g/mL) + Arginine (3.6 g/mL) + D-glucose monohydrate (66 g/mL) + Glycerin (3.61 g/mL) + Glycine (4.2 g/mL) + Histidine (3.6 g/mL) + Isoleucine (1.5 g/mL) + Leucine (2.52 g/mL) + Lysine monohydrate (2.476 g/mL) + Malic acid (2.64 g/mL) + Methionine (1.6 g/mL) + Phenylalanine (1.062 g/mL) + Potassium chloride (1.865 g/mL) + Proline (4.5 g/mL) + Threonine (1.32 g/mL) + Tryptophan (0.6 g/mL) + Zinc chloride (3 mg/mL)SolutionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.1995-03-082022-03-03Turkey flag
AKE 1100 GLUKOZLU IV SOLOSYONU, 500 MLAcetylcysteine (0.25 g/mL) + Alanine (4.5 g/mL) + Arginine (3.6 g/mL) + D-glucose monohydrate (66 g/mL) + Glycerin (3.61 g/mL) + Glycine (4.2 g/mL) + Histidine (3.6 g/mL) + Isoleucine (1.5 g/mL) + Leucine (2.52 g/mL) + Lysine monohydrate (2.476 g/mL) + Malic acid (2.64 g/mL) + Methionine (1.6 g/mL) + Phenylalanine (1.062 g/mL) + Potassium chloride (1.865 g/mL) + Proline (4.5 g/mL) + Threonine (1.32 g/mL) + Tryptophan (0.6 g/mL) + Zinc chloride (3 mg/mL)SolutionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.1995-03-082022-03-03Turkey flag
Amino - Mel "nephro" - InfusionsflascheAcetylcysteine (0.54 g/L) + Alanine (6.2 g/L) + Arginine (8.2 g/L) + Glycine (5.31 g/L) + Glycyltyrosine (3.16 g/L) + Histidine (9.8 g/L) + Isoleucine (5.8 g/L) + Leucine (12.8 g/L) + Lysine acetate (16.93 g/L) + Methionine (2 g/L) + Phenylalanine (3.5 g/L) + Proline (3 g/L) + Serine (7.6 g/L) + Threonine (8.2 g/L) + Tryptophan (3 g/L) + Tyrosine (0.6 g/L) + Valine (8.7 g/L)SolutionIntravenousFresenius Kabi Austria Gmb H1991-03-05Not applicableAustria flag
AMINOPLASMAL 15% IN 500ML GLASS BOTTLEAcetylcysteine (0.5 g/1000ml) + Alanine (22.35 g/1000ml) + Arginine (16.05 g/1000ml) + Aspartic acid (7.95 g/1000ml) + Glutamic acid (16.2 g/1000ml) + Glycine (19.2 g/1000ml) + Histidine (5.25 g/1000ml) + Isoleucine (5.85 g/1000ml) + Leucine (11.4 g/1000ml) + Lysine (7.95 g/1000ml) + Methionine (5.7 g/1000ml) + Phenylalanine (5.7 g/1000ml) + Proline (7.35 g/1000ml) + Serine (3 g/1000ml) + Threonine (5.4 g/1000ml) + Tryptophan (2.1 g/1000ml) + Tyrosine (0.5 g/1000ml) + Valine (7.2 g/1000ml)Injection, solutionIntravenousB.BRAUN MEDICAL INDUSTRIES SDN. BHD.2020-09-08Not applicableMalaysia flag
AMINOPLASMAL HEPA 10%-500ML GLASS BOTTLEAcetylcysteine (0.8 g/L) + Alanine (8.3 g/L) + Arginine (8.8 g/L) + Asparagine (0.55 g/L) + Aspartic acid (2.5 g/L) + Glutamic acid (5.7 g/L) + Glycine (6.3 g/L) + Histidine (4.7 g/L) + Isoleucine (8.8 g/L) + Leucine (13.6 g/L) + Lysine acetate (10.6 g/L) + Methionine (1.2 g/L) + N-acetyltyrosine (0.86 g/L) + Ornithine hydrochloride (1.66 g/L) + Phenylalanine (1.6 g/L) + Proline (7.1 g/L) + Serine (3.7 g/L) + Threonine (4.6 g/L) + Tryptophan (1.5 g/L) + Valine (10.6 g/L)Injection, solutionIntravenousB.BRAUN MEDICAL INDUSTRIES SDN. BHD.2020-09-08Not applicableMalaysia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ASTEIN 600 MG EFERVESAN TABLET, 20 ADETAcetylcysteine (600 mg)Tablet, effervescentOralRP FARMA İLAÇ KOZMETİK SAN. VE TİC.LTD.ŞTİ2020-07-21Not applicableTurkey flag
BRUNAC % 5 GÖZ DAMLASI, ÇÖZELTİAcetylcysteine (50 mg/ml)Solution / dropsOphthalmicBİO-GEN İLAÇ SAN.TİC.LTD. ŞTİ.2013-01-29Not applicableTurkey flag
FolcyteineAcetylcysteine (200 mg/1) + Calcium citrate tetrahydrate (47 mg/1) + Cholecalciferol (800 [iU]/1) + Folic acid (1000 ug/1) + Magnesium citrate (16 mg/1)TabletOralPureTek Corporation2023-09-14Not applicableUS flag
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

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)
Affected organisms
  • Humans and other mammals

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[C@@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. Cotgreave I, Moldeus P, Schuppe I: The metabolism of N-acetylcysteine by human endothelial cells. Biochem Pharmacol. 1991 Jun 21;42(1):13-6. doi: 10.1016/0006-2952(91)90674-t. [Article]
  2. Ahola T, Fellman V, Laaksonen R, Laitila J, Lapatto R, Neuvonen PJ, Raivio KO: Pharmacokinetics of intravenous N-acetylcysteine in pre-term new-born infants. Eur J Clin Pharmacol. 1999 Nov;55(9):645-50. doi: 10.1007/s002280050687. [Article]
  3. Mahmoudi GA, Astaraki P, Mohtashami AZ, Ahadi M: N-acetylcysteine overdose after acetaminophen poisoning. Int Med Case Rep J. 2015 Feb 27;8:65-9. doi: 10.2147/IMCRJ.S74563. eCollection 2015. [Article]
  4. Holdiness MR: Clinical pharmacokinetics of N-acetylcysteine. Clin Pharmacokinet. 1991 Feb;20(2):123-34. doi: 10.2165/00003088-199120020-00004. [Article]
  5. 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. [Article]
  6. Pei Y, Liu H, Yang Y, Yang Y, Jiao Y, Tay FR, Chen J: Biological Activities and Potential Oral Applications of N-Acetylcysteine: Progress and Prospects. Oxid Med Cell Longev. 2018 Apr 22;2018:2835787. doi: 10.1155/2018/2835787. eCollection 2018. [Article]
  7. Crouch BI, Caravati EM, Dandoy C: Effect of dilution with beverages on the smell and taste of oral acetylcysteine. Am J Health Syst Pharm. 2007 Sep 15;64(18):1965-8. doi: 10.2146/ajhp060568. [Article]
  8. Bass S, Zook N: Intravenous acetylcysteine for indications other than acetaminophen overdose. Am J Health Syst Pharm. 2013 Sep 1;70(17):1496-501. doi: 10.2146/ajhp120645. [Article]
  9. Thompson CA: Acetylcysteine's off-label use presents dosage-form issue. Am J Health Syst Pharm. 2007 Jul 1;64(13):1362, 1364, 1368. doi: 10.2146/news070062. [Article]
  10. Slattery KM, Dascombe B, Wallace LK, Bentley DJ, Coutts AJ: Effect of N-acetylcysteine on cycling performance after intensified training. Med Sci Sports Exerc. 2014 Jun;46(6):1114-23. doi: 10.1249/MSS.0000000000000222. [Article]
  11. Sadowska AM: N-Acetylcysteine mucolysis in the management of chronic obstructive pulmonary disease. Ther Adv Respir Dis. 2012 Jun;6(3):127-35. doi: 10.1177/1753465812437563. Epub 2012 Feb 23. [Article]
  12. Harada D, Anraku M, Fukuda H, Naito S, Harada K, Suenaga A, Otagiri M: Kinetic studies of covalent binding between N-acetyl-L-cysteine and human serum albumin through a mixed-disulfide using an N-methylpyridinium polymer-based column. Drug Metab Pharmacokinet. 2004 Aug;19(4):297-302. doi: 10.2133/dmpk.19.297. [Article]
  13. Serjeant EP, Dempsey B (1979). Ionisation constants of organic acids in aqueous solution (1st ed.). Oxford ; New York : Pergamon Press. [ISBN:9780080223391]
  14. Dailymed: Acetylcysteine Respiratory Inhalant [Link]
  15. Dailymed: Acetylcysteine Intravenous Injection, Solution [Link]
  16. Health Canada Approved Drug Products: Acetylcysteine USP Solution for Intravenous Injection, Respiratory Inhalation, or Oral Administration [Link]
  17. FDA Approved Drug Products: Cetylev (Acetylcysteine) Oral Effervescent Tablets for Solution [Link]
  18. FDA Approved Drug Products: Mucomyst (Acetylcysteine) Oral and Respiratory Solution (Discontinued) [Link]
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
PDB Entries
207l / 2j1g / 2j2p / 2j58 / 5hpm / 5icx / 5nn4
FDA label
Download (238 KB)
MSDS
Download (59.9 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedPreventionDrug-Induced Nephropathy1somestatusstop reasonjust information to hide
4CompletedBasic ScienceDependence, Cocaine1somestatusstop reasonjust information to hide
4CompletedDiagnosticAnatomic renal artery stenosis / Chronic Kidney Disease (CKD) / Lung Cancer / Pulmonary Embolism1somestatusstop reasonjust information to hide
4CompletedDiagnosticGastric Mucosal Lesion1somestatusstop reasonjust information to hide
4CompletedDiagnosticInsulin Resistance Syndrome X / Pancreatic Beta Cell Function1somestatusstop reasonjust information to hide

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
SolutionOral3.000 g
SyrupOral200 MG/10ML
SolutionOral200 mg/10mL
Tablet, effervescentOral200 mg
GranuleOral200000 g
Tablet, effervescentOral60000000 mg
Injection, solutionIntravenous200 mg/1mL
SolutionOral2000 mg
PowderOral200 mg
PowderOral100 mg
GranuleOral0.2 g
GranuleOral200 mg
Powder200 MG/10ML
Powder, for solutionOral200 MG
Powder
PowderOral600 MG
GranuleOral60000000 mg
Powder, for solutionOral2 g
Tablet, effervescentOral600 mg/1
Tablet, solubleOral100 mg
Tablet, solubleOral600 mg
CapsuleOral200 mg
InhalantOral; Respiratory (inhalation)100 mg/1mL
InhalantOral; Respiratory (inhalation)200 mg/1mL
InhalantRespiratory (inhalation)100 mg/1mL
InhalantRespiratory (inhalation)200 mg/1mL
InjectionIntravenous200 mg/mL
InjectionIntravenous200 mg/1mL
Injection, solutionIntravenous6 g/30mL
SolutionIntravenous200 mg / mL
SolutionIntravenous; Oral; Respiratory (inhalation)200 mg / mL
Granule, effervescentOral100 mg
Tablet, solubleOral
Granule, effervescentOral200 mg
GranuleOral6.666 g
Granule, for solutionOral400 MG
SprayIntravenous300 MG/3ML
SolutionIntravenous
Injection, solutionIntravenous
SolutionParenteral
InjectionIntravenous0.5 g/l
InjectionIntravenous0.25 g/1000ml
SyrupOral4 %
PowderOral1200 mg
PowderOral900 mg
PowderOral
Powder600 mg
Tablet, effervescentOral1200 mg
Tablet, effervescentOral900 mg
Powder, for solutionOral900 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
Solution / dropsOphthalmic
Solution / dropsOphthalmic50 mg/ml
Tablet, effervescentOral2.5 g/1
Tablet, effervescentOral500 mg/1
Tablet, effervescentOral400 mg
Powder1200 mg
InjectionIntravenous300 mg/3ml
Capsule, coatedOral200 mg
Tablet; tablet, film coatedOral
Tablet, effervescentOral
SyrupOral2 g
SolutionOral20 MG/ML
SyrupOral200 mg/5ml
SyrupOral
Powder, for solutionOral
SolutionOral2 g
AerosolRespiratory (inhalation)100 mg/ml
GranuleOral100 mg
Injection, solutionIntravenous300 MG/3ML
Solution300 MG/3ML
SolutionIntravesical
SprayIntravenous
SyrupOral
SolutionOral10 g
SolutionOral100 mg
Injection, solution, concentrateParenteral
GranuleOral
Tablet, effervescentOral600 mg
PowderOral2 g
SolutionOral200 mg
GranuleOral100 MG/5ML
SyrupOral600 MG/15ML
SolutionIntramuscular; Intravenous; Respiratory (inhalation)300 mg
SolutionIntravenous; Respiratory (inhalation)0.1 g
Powder, for solutionOral0.1 g
PowderOral0.2 g
PowderOral0.6 g
GranuleOral6.6667 g
SyrupOral4 g
Granule, for solutionOral
TabletOral
CapsuleOral600 mg
Injection, solutionIntravenous
Solution200 mg/1ml
Injection, solutionIntravenous5 g/25ml
InjectionIntravenous5 g/25ml
PowderOral
SolutionOral
Tablet, solubleOral200 mg
Powder, for solutionOral
Injection, solutionIntravenous200 mg/mL
Tablet, coatedOral
TabletOral
SolutionOral2.000 g
SolutionNasal300.000 mg
CapsuleOral
Powder900 mg
Tablet, effervescentOral200.00 mg
Tablet, effervescentOral600.00 mg
Solution
PowderOral6.6666 mg
GranuleOral0.6 g
Powder, for solutionOral1200 mg
Powder, for solutionOral100 mg
Powder, for solutionOral600 mg
Tablet, effervescentOral
SyrupOral150 ml
Powder200 mg
SyrupOral100 ml
GranuleOral40 g
Powder, for solutionOral3 g
Powder, for suspensionOral4 g
SolutionOral; Respiratory (inhalation)100 mg/1mL
SolutionOral; Respiratory (inhalation)200 mg/1mL
LiquidIntravenous; Oral; Respiratory (inhalation)200 mg / mL
Granule, effervescentOral400 mg
SyrupOral20 mg/ml
Tablet, effervescentOral200.000 mg
SolutionRespiratory (inhalation)400.000 mg
Powder, for solutionOral4 g
Powder, for solutionOral0.2 g
AerosolRespiratory (inhalation)
GranuleOral5 g
GranuleOral10 g
GranuleOral30 g
GranuleOral0.1 g
SolutionIntravenous; Respiratory (inhalation)300 mg
GranuleOral2 g
SyrupOral3 g
AerosolRespiratory (inhalation)100 MG
Tablet, effervescentOral100 MG
Tablet, for solution; tablet, for suspensionOral200 MG
PowderParenteral600 MG
Tablet, for solution; tablet, for suspensionOral600 MG
PowderParenteral200 MG
Tablet, film coatedOral
GranuleOral200 mg/5ml
LiquidIntravenous200 mg / mL
PowderOral6.67 g
SprayNasal
SolutionIntrasinal; Nasal10 mg
SuspensionNasal; Respiratory (inhalation)10 mg
Granule, for solutionOral100 MG
Granule, for solutionOral200 MG
Granule, for solutionOral600 MG
SyrupOral100 MG/5ML
TabletOral100 MG
TabletOral200 MG
TabletOral600 MG
Granule, for suspensionOral100 mg
EmulsionParenteral
InjectionIntramuscular400 mg/2mL
GranuleOral6666.66 mg
GranuleOral600 mg
Powder, for solutionOral200000 g
SyrupOral4000 mg
Powder600 mg/1sachet
Powder, for solutionOral100 mg/1sachet
Powder100 mg/1sachet
Powder, for suspensionOral100 mg/1sachet
Powder, for suspensionOral200 mg/1sachet
Powder200 mg/1sachet
Solution100 mg/1ml
GranuleOral100 mg/1sachet
GranuleOral200 mg/1sachet
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

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)-2Chemaxon
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-MSsplash10-0006-9300000000-13c710ac0e0547e1ec40
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/MSsplash10-00xr-2900000000-60e89f4337958a291881
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0170-5900000000-33796c76191cea982b62
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-284e542ffa8d44d7df1f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ei-9200000000-b2798bcc4a18b51efa38
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-7647cc4886b018fe281a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05dl-9000000000-74dbe8bfd485b914c399
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-131.8274557
predicted
DarkChem Lite v0.1.0
[M-H]-131.8400557
predicted
DarkChem Lite v0.1.0
[M-H]-127.70276
predicted
DeepCCS 1.0 (2019)
[M+H]+132.0941557
predicted
DarkChem Lite v0.1.0
[M+H]+132.5999557
predicted
DarkChem Lite v0.1.0
[M+H]+131.5301
predicted
DeepCCS 1.0 (2019)
[M+Na]+131.7661557
predicted
DarkChem Lite v0.1.0
[M+Na]+131.6540557
predicted
DarkChem Lite v0.1.0
[M+Na]+140.41031
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
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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. [Article]
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. [Article]
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. [Article]
  2. Prescott LF, Critchley JA: The treatment of acetaminophen poisoning. Annu Rev Pharmacol Toxicol. 1983;23:87-101. [Article]
  3. Marzullo L: An update of N-acetylcysteine treatment for acute acetaminophen toxicity in children. Curr Opin Pediatr. 2005 Apr;17(2):239-45. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
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. [Article]
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. [Article]
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. [Article]
  2. Wright DJ, Gray LJ, Finkelstein DI, Crouch PJ, Pow D, Pang TY, Li S, Smith ZM, Francis PS, Renoir T, Hannan AJ: N-acetylcysteine modulates glutamatergic dysfunction and depressive behavior in Huntington's disease. Hum Mol Genet. 2016 Jul 15;25(14):2923-2933. doi: 10.1093/hmg/ddw144. Epub 2016 May 14. [Article]
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. [Article]
  2. Wright DJ, Gray LJ, Finkelstein DI, Crouch PJ, Pow D, Pang TY, Li S, Smith ZM, Francis PS, Renoir T, Hannan AJ: N-acetylcysteine modulates glutamatergic dysfunction and depressive behavior in Huntington's disease. Hum Mol Genet. 2016 Jul 15;25(14):2923-2933. doi: 10.1093/hmg/ddw144. Epub 2016 May 14. [Article]
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. [Article]
  2. Wright DJ, Gray LJ, Finkelstein DI, Crouch PJ, Pow D, Pang TY, Li S, Smith ZM, Francis PS, Renoir T, Hannan AJ: N-acetylcysteine modulates glutamatergic dysfunction and depressive behavior in Huntington's disease. Hum Mol Genet. 2016 Jul 15;25(14):2923-2933. doi: 10.1093/hmg/ddw144. Epub 2016 May 14. [Article]
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. [Article]
  2. Wright DJ, Gray LJ, Finkelstein DI, Crouch PJ, Pow D, Pang TY, Li S, Smith ZM, Francis PS, Renoir T, Hannan AJ: N-acetylcysteine modulates glutamatergic dysfunction and depressive behavior in Huntington's disease. Hum Mol Genet. 2016 Jul 15;25(14):2923-2933. doi: 10.1093/hmg/ddw144. Epub 2016 May 14. [Article]
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. [Article]
  2. Wright DJ, Gray LJ, Finkelstein DI, Crouch PJ, Pow D, Pang TY, Li S, Smith ZM, Francis PS, Renoir T, Hannan AJ: N-acetylcysteine modulates glutamatergic dysfunction and depressive behavior in Huntington's disease. Hum Mol Genet. 2016 Jul 15;25(14):2923-2933. doi: 10.1093/hmg/ddw144. Epub 2016 May 14. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Harada D, Anraku M, Fukuda H, Naito S, Harada K, Suenaga A, Otagiri M: Kinetic studies of covalent binding between N-acetyl-L-cysteine and human serum albumin through a mixed-disulfide using an N-methylpyridinium polymer-based column. Drug Metab Pharmacokinet. 2004 Aug;19(4):297-302. doi: 10.2133/dmpk.19.297. [Article]

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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]

Drug created at January 15, 2008 16:45 / Updated at July 18, 2024 09:22