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616-91-1 molecular structure
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(2R)-2-acetamido-3-sulfanylpropanoic acid

ChemBase ID: 4418
Molecular Formular: C5H9NO3S
Molecular Mass: 163.19486
Monoisotopic Mass: 163.03031415
SMILES and InChIs

SMILES:
SC[C@H](NC(=O)C)C(=O)O
Canonical SMILES:
SC[C@@H](C(=O)O)NC(=O)C
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
InChIKey:
PWKSKIMOESPYIA-BYPYZUCNSA-N

Cite this record

CBID:4418 http://www.chembase.cn/molecule-4418.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-2-acetamido-3-sulfanylpropanoic acid
IUPAC Traditional name
acetylcysteine
Brand Name
ACC
Mucomyst
Acetadote
Fluimucil
Parvolex
Lysox
Mucolysin
Synonyms
(2R)-2-acetamido-3-sulfanylpropanoic acid
N-Acetyl-cysteine
ACC
Acetadote
Acetilcysteina
Airbron
Brunac
Exomuc
Fabrol
Fluatox
Fluibiotic
Fluimicil
Fluimicil Infantil
N.alpha.-Acetylcysteine
Parvolex
Respaire
Syntemucol
Tixair
1-alpha-Acetamido-beta-mercaptopropionic acid
Acetein
Acetylcysteine
N-Acetyl-N-Cysteine
N-Acetyl-3-Mercaptoalanine
Broncholysin
Mercapturic acid
(R)-Mercapturic Acid
N-ACETYL-L-CYSTEINE
LNAC
N-Acetyl-L-cysteine
N-acetylcysteine
NAC
Acetylcysteine
N-acetyl-L-cysteine
A
N-Acetylcysteine
N-乙酰-L-半胱氨酸
N-乙酰基-L-半胱氨酸
CAS Number
616-91-1
EC Number
210-498-3
MDL Number
MFCD00004880
Beilstein Number
1724426
Merck Index
1488
PubChem SID
24890942
99443235
24891213
160967850
24891402
24277970
PubChem CID
12035

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.8175774  H Acceptors
H Donor LogD (pH = 5.5) -2.396545 
LogD (pH = 7.4) -3.9664288  Log P -0.7113128 
Molar Refractivity 37.6674 cm3 Polarizability 14.845324 Å3
Polar Surface Area 66.4 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.03  LOG S -1.51 
Solubility (Water) 5.09e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
H2O: ≥10 mg/mL expand Show data source
H2O: soluble0.1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble100 mg/mL (with heating) expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
106-108 °C(lit.) expand Show data source
108-111°C expand Show data source
109-110°C expand Show data source
109-111°C expand Show data source
110-112 °C expand Show data source
Optical Rotation
[α]20/D +5.3±0.5°, c = 2% in H2O expand Show data source
+5.3 (c=2 in water) expand Show data source
Hydrophobicity(logP)
-0.624 expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
protect from light expand Show data source
Refrigerator, Under Inert Atmosphere expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
HA1660000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
R:36/37/38 expand Show data source
Safety Statements
S:20-25-26-37/39 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Respiratory Disease expand Show data source
Purity
>96% expand Show data source
≥98.5% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% (T) expand Show data source
95% expand Show data source
95+% expand Show data source
98% expand Show data source
98.0-102.0% expand Show data source
98+% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
puriss. expand Show data source
SAJ special grade expand Show data source
Sigma Grade expand Show data source
USP expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Packaging
pkg of 1 g expand Show data source
Suitability
cell culture tested expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.5% expand Show data source
Impurities
≤0.002% Phosphorus (P) expand Show data source
≤0.1% Insoluble matter expand Show data source
endotoxin, tested expand Show data source
Cation Traces
Al: ≤0.0005% expand Show data source
Ca: ≤0.0005% expand Show data source
Cu: ≤0.0005% expand Show data source
Fe: ≤0.0005% expand Show data source
K: ≤0.005% expand Show data source
Mg: ≤0.0005% expand Show data source
Na: ≤0.1% expand Show data source
NH4+: ≤0.05% expand Show data source
Pb: ≤0.001% expand Show data source
Zn: ≤0.0005% expand Show data source
Biological Source
from non-animal source expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
Shipped in
wet ice expand Show data source
Pharmacopeia Traceability
traceable to BP 907 expand Show data source
traceable to PhEur A0150000 expand Show data source
traceable to USP 1009005 expand Show data source
Linear Formula
HSCH2CH(NHCOCH3)CO2H expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02100098 external link
Crystalline
Purity: >96%
A mucolytic agent for isolation of mycobacteria from sputum.
DrugBank - DB06151 external link
Item Information
Drug 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]
Indication Acetylcysteine is 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.

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
Biotransformation Hepatic. Deacetylated by the liver to cysteine and subsequently metabolized.
Absorption Bioavailability is 6–10% following oral administration and less than 3% following topical administration.
Half Life 5.6 hours (adults), 11 hours (neonates)
Protein Binding 83%
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]
Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. [Pubmed]
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]
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]
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]
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
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1623 external link
Research Area: Metabolic disease
Biological Activity:
Acetylcysteine is a pharmaceutical drug and nutritional supplement used primarily as a mucolytic agent and in the management of paracetamol(acetaminophen) overdose. Other uses include sulfate repletion in conditions, such as autism, where cysteine and related sulfur amino acids may be depleted.It is used as an antidote for acetaminophen overdose to prevent life-threatening liver damage. It is most effective if given within 8 to 10 hours after ingestion, but it can be used anytime up to 24 hours after an overdose. If acetaminophen overdose is suspected, but the exact time of ingestion is unknown, acetylcysteine may still be given. [1]
Sigma Aldrich - A9165 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
抗氧化剂和溶粘液剂。增加细胞库的自由基捕获剂。据报道,N-乙酰半胱氨酸可防止神经细胞凋亡,但会诱导平滑肌细胞凋亡。抑制 HIV 复制。可作为微粒体谷胱甘肽转移酶的底物。
Sigma Aldrich - 01039 external link
Biochem/physiol Actions
Antioxidant and mucolytic agent. Increases cellular pools of free radical scavengers. Reported to prevent apoptosis in neuronal cells but induce apoptosis in smooth muscle cells. Inhibits HIV replication. May serve as a substrate for microsomal glutathione transferase.
Other Notes
Thiol protecting reagent1
Sigma Aldrich - PHR1098 external link
Biochem/physiol Actions
Antioxidant and mucolytic agent. Increases cellular pools of free radical scavengers. Reported to prevent apoptosis in neuronal cells but induce apoptosis in smooth muscle cells. Inhibits HIV replication. May serve as a substrate for microsomal glutathione transferase.
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Sigma Aldrich - A7250 external link
Biochem/physiol Actions
抗氧化剂和溶粘液剂。增加细胞库的自由基捕获剂。据报道,N-乙酰半胱氨酸可防止神经细胞凋亡,但会诱导平滑肌细胞凋亡。抑制 HIV 复制。可作为微粒体谷胱甘肽转移酶的底物。
包装
1 kg in poly bottle
5, 10, 25, 50, 100, 500 g in poly bottle
Sigma Aldrich - A8199 external link
Biochem/physiol Actions
抗氧化剂和溶粘液剂。增加细胞库的自由基捕获剂。据报道,N-乙酰半胱氨酸可防止神经细胞凋亡,但会诱导平滑肌细胞凋亡。抑制 HIV 复制。可作为微粒体谷胱甘肽转移酶的底物。
Sigma Aldrich - A5099 external link
Biochem/physiol Actions
Antioxidant and mucolytic agent. Increases cellular pools of free radical scavengers. Reported to prevent apoptosis in neuronal cells but induce apoptosis in smooth muscle cells. Inhibits HIV replication. May serve as a substrate for microsomal glutathione transferase.
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - 01-0870 external link
Biochem/physiol Actions
Antioxidant and mucolytic agent. Increases cellular pools of free radical scavengers. Reported to prevent apoptosis in neuronal cells but induce apoptosis in smooth muscle cells. Inhibits HIV replication. May serve as a substrate for microsomal glutathione transferase.
Toronto Research Chemicals - A172091 external link
A metabolite of Methyl Isocyanate.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. Pubmed
  • • 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
  • • 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
  • • 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
  • • 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
  • • Slatter, J. G., et al.: Chem. Res. Toxicol., 4, 157 (1991)
  • • Catalyzes the addition of ammonia to nitriles to form amidines in high yield: Tetrahedron Lett., 40, 7067 (1999).
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PATENTS

PATENTS

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INTERNET

INTERNET

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