| Version |
2.5 |
| Creation Date |
2008-01-15 16:45:58 |
| Update Date |
2009-04-16 16:48:29 |
| Primary Accession Number |
DB06151 |
| Secondary Accession Number |
Not Available |
| Name |
Acetylcysteine |
| Drug Type |
|
| Description |
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] |
| Synonyms |
- N-acetylcysteine
- NAC
|
| Brand Names |
- ACC
- Acetadote
- Fluimucil
- Lysox
- Mucolysin
- Mucomyst
- Parvolex
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
(2R)-2-acetamido-3-sulfanylpropanoic acid |
| Chemical Formula |
C5H9NO3S |
| Chemical Structure |
 |
| CAS Registry Number |
616-91-1 |
| InChI Identifier |
InChI=1/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1/f/h6,8H |
| InChI Key |
PWKSKIMOESPYIA-JVBVHTJODB |
| KEGG Drug |
D00221  |
| KEGG Compound |
C06809 |
| PubChem Compound |
12035 |
| PubChem Substance |
11371394 |
| ChEBI ID |
28939 |
| PharmGKB ID |
PA448033 |
| HET ID |
SC2 |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02091526 |
| RxList Link |
http://www.rxlist.com/cgi/generic/acetylcysteine.htm |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Acetylcysteine |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
|
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
163.1950 |
| Monoisotopic Molecular Weight |
163.0303 |
| State |
Solid |
| Melting Point |
109.5 oC |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
5.09e+00 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
| Predicted LogP |
-0.03
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-1.51
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
9.52 |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download |
| SDF File |
Show | Download |
| PDB File |
Show | Download |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
CC(=O)N[C@@H](CS)C(O)=O |
| Canonical SMILES |
CC(=O)NC(CS)C(O)=O |
| Drug Category |
- Antiviral Agents
- Expectorants
- Free Radical Scavengers
|
| ATC Codes |
Not Available |
| AHFS Codes |
Not Available |
| Indication |
Used mainly as a mucolytic and in the management of paracetamol (acetaminophen) overdose. |
| Pharmacology |
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. Glutathione is required to inactivate an intermediate metabolite 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. Inhalation - Acetylcysteine 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. |
| Absorption |
Bioavailability is 6–10% following oral administration and less than 3% following topical administration. |
| 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. |
| Protein Binding |
83% |
| Biotransformation |
Hepatic. Deacetylated by the liver to cysteine and subsequently metabolized. |
| Half Life |
5.6 hours (adults), 11 hours (neonates) |
| Dosage Forms |
| Form |
Route |
| Liquid |
Respiratory (inhalation) |
| Solution |
Respiratory (inhalation) |
|
| Patient Information |
Not Available |
| Contraindications |
Show |
| Interactions |
Show |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| General References |
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. [PubMed ]
- Wikipedia
- RxList
|
| Organisms Affected |
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