CAS 616-91-1|acetylcysteine|Parvolex|(2R)-2-acetamido-3-sulfanylpropanoic acid|Mucomyst|N-acetylcysteine|Mucolysin|NAC|Acetadote|ACC|Acetylcysteine|Fluimucil|Lysox|LNAC|N-Acetyl-L-cysteine|N-乙酰基-...

基本信息

化学结构

分子式

C₅H₉NO₃S

分子量

163.19486

精确质量

163.03031415

电荷

0

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

Canonic Smiles

SC[C@@H](C(=O)O)NC(=O)C

Isomeric Smiles

SC[C@H](NC(=O)C)C(=O)O

计算属性

JChem

LogD (pH = 7.4)

-4.10

LogD (pH = 5.5)

-2.40

Log P

-0.71

可自由旋转的化学键

3

质子供体

3

质子受体

3

里宾斯基五规则

true

Acid pKa

3.82

极化表面积

66.40

极化性

15.47

摩尔折射率

37.67

LOG S

-0.69

数据来源

学术数据

数据来源

名称和标识

IUPAC传统名

acetylcysteine

商标名

ParvolexMucomystMucolysinAcetadoteACCFluimucilLysox

IUPAC标准名

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

别名

N-acetylcysteineNACAcetylcysteineLNACN-Acetyl-L-cysteineN-乙酰基-L-半胱氨酸N-AcetylcysteineMercapturic acidN-Acetyl-3-MercaptoalanineN-ACETYL-L-CYSTEINEAcetylcysteineBroncholysinAcetein(R)-Mercapturic AcidN-Acetyl-N-Cysteine1-alpha-Acetamido-beta-mercaptopropionic acidN-acetyl-L-cysteineABrunacN.alpha.-AcetylcysteineFluibioticACCFabrolTixairFluatoxAcetadoteRespaireParvolexExomucAirbronFluimicilAcetilcysteinaFluimicil InfantilSyntemucol(2R)-2-acetamido-3-sulfanylpropanoic acidN-乙酰-L-半胱氨酸N-Acetyl-cysteinemercapturic acidAcetylcysteineN-acetylcysteineN-acetyl-L-(+)-cysteineL-acetylcysteine(2R)-2-acetylamino-3-sulfanylpropanoic acidN-acetyl-L-cysteineN-ACETYL-L-CYSTEINENAC(R)-mercapturic acid(R)-2-acetylamino-3-mercaptopropanoic acidL-alpha-acetamido-beta-mercaptopropionic acid

API名称

Acetylcysteine

国际非专利药品(INN)

acetylcysteinumacetilcisteina

名称和标识

数据登录号

EC号

CAS号

Beilstein号

MDL号

默克索引号

PubChem SID

24890942248914021609678502489121324277970994432358144902

PubChem CID

12035

DrugBank ID

DB06151

BRENDA Ligand数据库

9159198837241552429445538273479907592484480495723317104592209109084

SureChEMBL数据库

SCHEMBL5292

PDB数据库

5nn45icx207l5hpm2j1g2j2p2j58

MetaboLights数据库

MTBLS301MTBLS355MTBLS1861MTBLS106MTBLS926MTBLS186MTBLS3540MTBLS1079MTBLS172MTBLS2017MTBLS145MTBLS682MTBLS135MTBLS180MTBLS1906MTBLS533MTBLS1209MTBLS1221MTBLS2542MTBLS406

ArrayExpress (Gene Expression Altlas)

E-MTAB-4398

PubMed文献链接

17174578241199269711192208197932555348415647642120577171958082311544433150257801065116620267269624310

维基百科标题

Acetylcysteine

Gmelin ID

142554

BKMS React数据库

5242347924841710459445538271090849159148049241590759572339883792209

SABIO-RK数据库

1433914058155

CHEMBL

CHEMBL600

Golm数据库

d346c40a-03a2-480a-981f-10a1ce642cc542ef8dd0-8d1d-458d-a31b-87135057b2855ed0d8d1-a843-4c75-8696-8b7958495bbc

CHEBI ID

CHEBI:21548CHEBI:2418CHEBI:45481CHEBI:28939

ACToR数据库

PDBeChem数据库

KEGG DRUG Database

CompTox数据库

LINCS数据库

MetaCyc数据库

Reaxys Registry

HMDB数据库

Drug Central Database

66

KEGG ID

C06809

数据登录号

化合物性质

药理学性质

作用靶点

Respiratory Disease

化合物性质

分子相关蛋白质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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]

MP Biomedicals

02100098

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

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

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。

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。

PHR1098

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。
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.

A5099

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
按照 cGMP 制造和包装

01-0870

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。

01039

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。
Other Notes
硫醇保护试剂1

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]

TRC

A172091

A metabolite of Methyl Isocyanate.

ChEBI

CHEBI:28939

An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.

描述信息

参考文献

PubChem文献

数据源提供

• 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

• 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

• 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

• 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

• Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. 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).

参考文献

生物活性

PubChem BioAssay

生物活性

化合物信息

ID:4418