(2R)-2-acetamido-3-sulfanylpropanoic acid

• ChemBase ID: 4418
• Molecular Formular: C5H9NO3S
• Molecular Mass: 163.19486
• Monoisotopic Mass: 163.03031415
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 616-91-1
• EC Number: 210-498-3
• MDL Number: MFCD00004880
• Beilstein Number: 1724426
• Merck Index: 1488
• PubChem SID: 160967850; 24891402; 99443235; 24891213; 24890942; 24277970
• PubChem CID: 12035

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8175774
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.396545
• LogD (pH = 7.4): -3.9664288
• Log P: -0.7113128
• Molar Refractivity: 37.6674 cm^3
• Polarizability: 14.845324 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.03
• LOG S: -1.51
• Solubility (Water): 5.09e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: ≥10 mg/mL; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble100 mg/mL (with heating); Methanol; Water
• Apperance: powder; White Solid
• Melting Point: 106-108 °C(lit.); 108-111°C; 109-110°C; 109-111°C; 110-112 °C
• Optical Rotation: [α]20/D +5.3±0.5°, c = 2% in H2O; +5.3 (c=2 in water)
• Hydrophobicity(logP): -0.624

Safety Information

• Storage Condition: -20°C; 2-8°C; protect from light; Refrigerator, Under Inert Atmosphere
• Storage Warning: IRRITANT
• RTECS: HA1660000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Respiratory Disease

Product Information

• Purity: >96%; ≥98.5%; ≥99% (TLC); ≥99.0% (T); 95%; 95+%; 98%; 98.0-102.0%; 98+%
• Grade: certified reference material; EP; puriss.; SAJ special grade; Sigma Grade; USP
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Suitability: cell culture tested; suitable for manufacturing use
• Ignition Residue: ≤0.5%
• Impurities: ≤0.002% Phosphorus (P); ≤0.1% Insoluble matter; endotoxin, tested
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.1%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Biological Source: from non-animal source
• Quality Level: GMP-COMPENDIA
• Shipped in: wet ice
• Pharmacopeia Traceability: traceable to BP 907; traceable to PhEur A0150000; traceable to USP 1009005
• Linear Formula: HSCH2CH(NHCOCH3)CO2H

DETAILS

MP Biomedicals - 02100098

Crystalline
Purity: >96%
A mucolytic agent for isolation of mycobacteria from sputum.

DrugBank - DB06151

• 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

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

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

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

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 - 01-0870

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.

Sigma Aldrich - A8199

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 - A7250

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 - A5099

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

Toronto Research Chemicals - A172091

A metabolite of Methyl Isocyanate.

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
• 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).