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targets (1) transporters (1)
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Identification
Name Acetylcysteine
Accession Number DB06151
Type small molecule
Groups approved
Description

Acetylcysteine is the N-acetyl derivative of cysteine. It is used as a mucolytic agent to reduce the viscosity of mucous secretions. It has also been shown to have antiviral effects in patients with HIV due to inhibition of viral stimulation by reactive oxygen intermediates. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • N-acetylcysteine
  • NAC
Brand names
  • ACC
  • Acetadote
  • Fluimucil
  • Lysox
  • Mucolysin
  • Mucomyst
  • Parvolex
Brand name mixtures Not Available
Categories
  • Antiviral Agents
  • Free Radical Scavengers
  • Expectorants
CAS number 616-91-1
Weight Average: 163.195
Monoisotopic: 163.030313849
Chemical Formula C5H9NO3S
InChI Key InChIKey=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
Plain Text
IUPAC Name
(2R)-2-acetamido-3-sulfanylpropanoic acid
SMILES
CC(=O)N[C@@H](CS)C(O)=O
Plain Text
Mass Spec show (8.3 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Thiols
  • Carboxamides and Derivatives
Pharmacology
Indication Acetylcysteine is used mainly as a mucolytic and in the management of paracetamol (acetaminophen) overdose.
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 may protect against acetaminophen overdose-induced hepatotoxicity by maintaining or restoring hepatic concentrations of glutathione. It does this by producing the glutathione precursor cysteine. Glutathione is required to inactivate an intermediate metabolite (N-acetyl-p-benzoquinoneimine) of acetaminophen that is thought to be hepatotoxic. In acetaminophen overdose, 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. When inhaled, cetylcysteine exerts its mucolytic action through its free sulfhydryl group, which opens the disulfide bonds 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.
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
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
Pharmacoeconomics
Manufacturers
  • Cumberland pharmaceuticals inc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Roxane laboratories inc
  • Apothecon inc div bristol myers squibb
  • Dey lp
Packagers
Dosage forms
Form Route Strength
Liquid Respiratory (inhalation)
Solution Respiratory (inhalation)
Prices
Unit description Cost Unit
Mucomyst-10 10% Solution 30ml Vial 25.99 USD vial
Acetylcysteine 20% Solution 10ml Vial 22.99 USD vial
Acetylcysteine 10% Solution 30ml Vial 19.99 USD vial
Mucomyst 20% Solution 30ml Vial 18.99 USD vial
Acetylcysteine 20% Solution 30ml Vial 17.99 USD vial
Acetylcysteine 20% Solution 4ml Vial 16.99 USD vial
Acetylcysteine 10% Solution 10ml Vial 8.66 USD vial
Acetadote 200 mg/ml vial 6.65 USD ml
Acetylcysteine powder 3.07 USD g
N-acetyl-l-cysteine powder 0.84 USD g
Mucomyst 20 % Solution 0.75 USD ml
Acetylcysteine 20 % Solution 0.68 USD ml
Patents Not Available
Properties
State solid
Melting point 109.5 oC
Experimental Properties
Property Value Source
pKa 9.52 Various sources
Predicted Properties
Property Value Source
water solubility 5.09e+00 g/l ALOGPS
logP -0.03 ALOGPS
logP -0.71 ChemAxon Molconvert
logS -1.51 ALOGPS
pKa 10.05 ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 66.40 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 37.67 ChemAxon Molconvert
polarizability 15.34 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  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
  2. Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. Pubmed
  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. 2000;78(1):55-62. Pubmed
  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
  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
  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
External Links
Resource Link
KEGG Drug D00221 Link_out
KEGG Compound C06809 Link_out
PubChem Compound 12035 Link_out
PubChem Substance 99443235 Link_out
ChemSpider 11540 Link_out
ChEBI 28939 Link_out
ChEMBL 28939 Link_out
Therapeutic Targets Database DNC000981 Link_out
PharmGKB PA448033 Link_out
HET SC2 Link_out
Drug Product Database 2091526 Link_out
RxList http://www.rxlist.com/cgi/generic/acetylcysteine.htm Link_out
Drugs.com http://www.drugs.com/cdi/acetylcysteine-solution.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Acetylcysteine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (238.2 KB)
MSDS show (59.9 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. N-acetyl-p-benzoquinoneimine

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
  2. Prescott LF, Critchley JA: The treatment of acetaminophen poisoning. Annu Rev Pharmacol Toxicol. 1983;23:87-101. Pubmed
  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
Transporters

1. Solute carrier organic anion transporter family member 1B1

Actions: inhibitor

Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver

UniProt ID: Q9Y6L6 Link_out
Gene: SLCO1B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Comments
Drug created on January 15, 2008 09:45 / Updated on January 31, 2011 00:21

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.