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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/17 12:22:29」(JST)

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Acetylcysteine rINN /əˌsɛtəlˈsɪstiːn/, also known as N-acetylcysteine or N-acetyl-L-cysteine (abbreviated NAC), 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.^[7]

Acetylcysteine is a derivative of cysteine; an acetyl group that is attached to the nitrogen atom. This compound is sold as a dietary supplement commonly claiming antioxidant and liver protecting effects. It is used as a cough medicine because it breaks disulfide bonds in mucus and liquefies it, making it easier to cough up. It is also this action of breaking disulfide bonds that makes it useful in thinning the abnormally thick mucus in cystic and pulmonary fibrosis patients.

1 Medical uses
- 1.1 Paracetamol overdose
- 1.2 Mucolytic therapy
- 1.3 Nephroprotective agent
- 1.4 Treatment of cyclophosphamide-induced hemorrhagic cystitis
- 1.5 Microbiological use
- 1.6 Interstitial lung disease
- 1.7 Psychiatry
- 1.8 Polycystic ovary syndrome
2 Adverse effects
3 Mechanism of action
4 Complexing agent
5 Chemistry
6 Dosage forms
7 Research
8 References
9 External links

Medical uses[edit]

Paracetamol overdose[edit]

Main article: Paracetamol poisoning

Intravenous acetylcysteine is indicated for the treatment of paracetamol (acetaminophen) overdose. When paracetamol is taken in large quantities, a minor metabolite called N-acetyl-p-benzoquinone imine (NAPQI) accumulates within the body. It is normally conjugated by glutathione, but when taken in excess, the body's glutathione reserves are not sufficient to inactivate the toxic NAPQI. This metabolite is then free to react with key hepatic enzymes, therefore damaging hepatocytes. This may lead to severe liver damage and even death by fulminant liver failure.

For this indication, acetylcysteine acts to augment the glutathione reserves in the body and, together with glutathione, directly bind to toxic metabolites. These actions serve to protect hepatocytes in the liver from NAPQI toxicity.

Although both IV and oral acetylcysteine are equally effective for this indication, oral administration is poorly tolerated because high oral doses are required due to low oral bioavailability,^[8] because of its very unpleasant taste and odour, and because of adverse effects, particularly nausea and vomiting. Studies conducted by Baker and Dilger^[9] suggest that the prior pharmacokinetic studies of acetylcysteine did not include acetylation as a reason for the low bioavailability of acetylcysteine. In the research conducted by Baker,^[9] it was concluded that oral acetylcysteine was identical in bioavailability to cysteine precursors. However, 3% to 6% of people given intravenous acetylcysteine show a severe, anaphylaxis-like allergic reaction, which may include extreme breathing difficulty (due to bronchospasm), a decrease in blood pressure, rash, angioedema, and sometimes also nausea and vomiting.^[10] Repeated doses of intravenous acetylcysteine will cause these allergic reactions to progressively worsen in these people.

Several studies have found this anaphylaxis-like reaction to occur more often in people given IV acetylcysteine despite serum levels of paracetamol not high enough to be considered toxic.^[11]^[12]^[13]^[14]

In some countries, a specific intravenous formulation does not exist to treat paracetamol overdose. In these cases, the formulation used for inhalation may be used intravenously.

Mucolytic therapy[edit]

Inhaled acetylcysteine is indicated for mucolytic ("mucus-dissolving") therapy as an adjuvant in respiratory conditions with excessive and/or thick mucus production. Such conditions include emphysema, bronchitis, tuberculosis, bronchiectasis, amyloidosis, pneumonia, cystic fibrosis, chronic obstructive pulmonary disease, and pulmonary fibrosis. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. It may be considered ineffective in cystic fibrosis.^[15] However, a recent paper in the Proceedings of the National Academy of Sciences reports that high-dose oral acetylcysteine modulates inflammation in cystic fibrosis and has the potential to counter the intertwined redox and inflammatory imbalances in CF.^[16] Oral acetylcysteine may also be used as a mucolytic in less serious cases.

For this indication, acetylcysteine acts to reduce mucus viscosity by splitting disulfide bonds linking proteins present in the mucus (mucoproteins).

Nephroprotective agent[edit]

Oral acetylcysteine is used for the prevention of radiocontrast-induced nephropathy (a form of acute renal failure). Some studies show that prior administration of acetylcysteine markedly decreases radiocontrast nephropathy,^[17] whereas others appear to cast doubt on its efficacy.^[18]^[19] Data published in two papers in the New England Journal of Medicine and the Journal of the American Medical Association. conclude:

"Intravenous and oral N-acetylcysteine may prevent contrast-medium–induced nephropathy with a dose-dependent effect in patients treated with primary angioplasty and may improve hospital outcome."^[20]
"Acetylcysteine protects patients with moderate chronic renal insufficiency from contrast-induced deterioration in renal function after coronary angiographic procedures, with minimal adverse effects and at a low cost"^[21]

A clinical trial from 2010, however, found that acetylcysteine is ineffective for the prevention of contrast-induced nephropathy. This trial, involving 2,308 patients, found that acetylcysteine was no better than placebo; whether acetylcysteine or placebo was used, the incidence of nephropathy was the same — 13%.^[22]

Acetylcysteine continues to be commonly used in individuals with renal impairment to prevent the precipitation of acute renal failure.^{[citation needed]}

Treatment of cyclophosphamide-induced hemorrhagic cystitis[edit]

Acetylcysteine has been used for cyclophosphamide-induced hemorrhagic cystitis, although mesna is generally preferred due to the ability of acetylcysteine to diminish the effectiveness of cyclophosphamide. ^[23] ^[24]

Microbiological use[edit]

Acetylcysteine can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis. It also displays significant antiviral activity against the influenza A viruses.^[25]

Interstitial lung disease[edit]

Acetylcysteine is used in the treatment of interstitial lung disease to prevent disease progression.^[26]^[27]^[28]^[29]

Psychiatry[edit]

Acetylcysteine has been successfully tried as a treatment for schizophrenia, acute mood episodes (e.g. depression, mania, hypomania^[30]) as part of bipolar disorder, unipolar depression,^[31] trichotillomania, skin picking, autism, obsessive-compulsive disorder, drug (including nicotine, cannabis, methamphetamine, cocaine, etc.) and gambling addiction.^[32]^[33]

Polycystic ovary syndrome[edit]

In a small prospective trial comparing acetylcysteine to metformin (which is the standard drug treatment for PCOS), both treatments resulted in a significant decrease in body mass index, hirsutism score, fasting insulin, HOMA index, free testosterone and menstrual irregularity compared with baseline values, and both treatments had equal efficacy.^[34]

Adverse effects[edit]

Researchers at the University of Virginia reported in 2007 study using very large doses in a mouse model that acetylcysteine could potentially cause damage to the heart and lungs.^[35] They found that acetylcysteine was metabolized to S-nitroso-N-acetylcysteine (SNOAC), which increased blood pressure in the lungs and right ventricle of the heart (pulmonary artery hypertension) in mice treated with acetylcysteine. The effect was similar to that observed following a 3-week exposure to an oxygen-deprived environment (chronic hypoxia). The authors also found that SNOAC induced a hypoxia-like response in the expression of several important genes both in vitro and in vivo.

The implications of these findings for long-term treatment with acetylcysteine have not yet been investigated. The dose used by Palmer and colleagues was dramatically higher than that used in humans, the equivalent of about 20 grams per day.^[36]^[35] Nonetheless, positive effects on age-diminished control of respiration (the hypoxic ventilatory response) have been observed previously in human subjects at more moderate doses.^[37]

Researchers from Anhui Medical University in China reported in 2006 that although N-acetylcysteine prevented liver damage when taken before alcohol, when taken 4 hours after alcohol it actually made liver damage worse in a dose-dependent fashion.^[38]

Mechanism of action[edit]

Acetylcysteine serves as a prodrug to L-cysteine which is a precursor to the biologic antioxidant, glutathione and hence administration of acetylcysteine replenishes glutathione stores.^[5] L-cysteine also serves as a precursor to cystine which in turn serves as a substrate for the cystine-glutamate antiporter on astrocytes hence increasing glutamate release into the extracellular space. This glutamate in turn acts on mGluR_2/3 receptors, and at higher doses of acetylcysteine, mGluR₅.^[32]^[39] Glutathione also modulates the NMDA receptor by acting at the redox site.^[33]^[40] Acetylcysteine also possesses some anti-inflammatory effects possibly via inhibiting NF-κB and modulating cytokine synthesis.^[33] It may also facilitate dopamine release in certain brain areas.^[33]

Complexing agent[edit]

Acetylcysteine has been used to complex palladium, to help it dissolve in water. This helps to remove palladium from drugs or precursors synthesized by palladium-catalyzed coupling reactions.^[41]

Chemistry[edit]

Acetylcysteine is the N-acetyl derivative of the amino acid L-cysteine, and is a precursor in the formation of the antioxidant glutathione in the body. The thiol (sulfhydryl) group confers antioxidant effects and is able to reduce free radicals.

Dosage forms[edit]

Acetylcysteine is available in different dosage forms for different indications:

Solution for inhalation (Assist, Mucomyst, Mucosil) – inhaled for mucolytic therapy or ingested for nephroprotective effect (to protect the kidneys)
IV injection (Assist,Parvolex, Acetadote) – treatment of paracetamol/acetaminophen overdose
Oral solution – various indications.
Effervescent Tablets (200 mg) - Reolin (Hochland Pharma Germany), Solmucol (600 mg)(IBSA, Switzerland), Cystaline (Thailand), Mucinac (Cipla India), Siran (MegaPharm, Israel / Temmler Pharma, Germany), Amuco200 (Camox Pharmaceuticals, South Africa), ACC200 (Hexal Pharma, South Africa).
Ocular solution - for mucolytic therapy
Sachet (600 mg) - Bilim Pharmaceuticals, trebon N (Uni-Pharma Greece)
CysNAC (900 mg) – NeuroScience Inc.
PharmaNAC Effervescent Tablets (900 mg) - Bioadvantex Pharma.

The IV injection and inhalation preparations are, in general, prescription only, whereas the oral solution and the effervescent tablets are available over the counter in many countries.

Research[edit]

The following uses have not been well-established or investigated:

Acetylcysteine is being tested in a double blind trial in Systemic Lupus Erythematosus.^[42] The objective is to correct mitochondrial dysfunction.
It may reduce the incidence of chronic obstructive pulmonary disease (COPD) exacerbations.^[43]
In the treatment of AIDS, acetylcysteine has been shown to cause a "marked increase in immunological functions and plasma albumin concentrations".^[44] Albumin concentration are inversely correlated with muscle wasting (cachexia), a condition associated with AIDS.
A human study of 262 primarily elderly individuals indicates that acetylcysteine may decrease influenza symptoms. In the study, 25% of virus-infected subjects who received acetylcysteine treatment developed symptoms whereas 79% in the placebo group developed symptoms.^[45]
Stability studies of carbocisteine in two differet dosage form, tablets and capsules.^[43]
It has been suggested that acetylcysteine may help sufferers of Samter's triad by increasing levels of glutathione allowing faster breakdown of salicylates, though there is no evidence that it is of benefit.^[46]
There are claims that acetylcysteine taken together with vitamin C and B₁ can be used to prevent and relieve symptoms of veisalgia (hangover following ethanol (alcohol) consumption). The claimed mechanism is through scavenging of acetaldehyde, a toxic intermediate in the metabolism of ethanol.^[47]^[48] A 2006 rodent study found that while pretreatment with acetylcysteine protected against ethanol-induced liver damage, post-treatment actually worsened ethanol-induced liver damage.^[38]
It has been shown to help women with PCOS (polycystic ovary syndrome) to reduce insulin problems and possibly improve fertility.^[49]
Small studies have shown acetylcysteine to be of benefit to sufferers of blepharitis.^[50]
It has been shown effective in the treatment of Unverricht-Lundborg disease in an open trial in 4 patients. A marked decrease in myoclonus and some normalization of somatosensory evoked potentials with acetylcysteine treatment has been documented.^[51]
Results of a research study published in the New England Journal of Medicine in November 2011, tested the effect of acetylcysteine in combination with glucocorticoids (combination group) for patients suffering from severe alcoholic hepatitis. The data showed that the combination of acetylcysteine with prednisolone decreased mortality significantly at one month compared to the prednisolone-only group (8% vs 24%, P=0.006). However, the improvement was not as significant at 3 months or 6 months (22% vs 34%, P=0.06) and (27% vs 38%, P=0.07). Factors that were associated with increased 6-month survival included younger age, shorter prothrombin time, lower levels of bilirubin in baseline studies, and decrease in bilirubin on day 14, all (P<0.001). Death due to hepatorenal syndrome occurred less frequently for the combination group at 6 months (9% vs 22%, P=0.02) and infections were also less frequent in the combination group as well (P=0.001). Six-month survival, the primary outcome, was not improved in conclusion.^[52]
Acetylcysteine appears to improve the clinical efficacy of B vitamins in patients with raised homocysteine and memory disorders, including dementia.^[53]

References[edit]

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^ Oner, G; Muderris, II (2011). "Clinical, endocrine and metabolic effects of metformin vs N-acetyl-cysteine in women with polycystic ovary syndrome". European journal of obstetrics, gynecology, and reproductive biology 159 (1): 127–31. doi:10.1016/j.ejogrb.2011.07.005. PMID 21831508.
^ ^a ^b Palmer, Lisa A.; Doctor, Allan; Chhabra, Preeti; Sheram, Mary Lynn; Laubach, Victor E.; Karlinsey, Molly Z.; Forbes, Michael S.; MacDonald, Timothy; Gaston, Benjamin (2007). "S-Nitrosothiols signal hypoxia-mimetic vascular pathology". Journal of Clinical Investigation 117 (9): 2592–601. doi:10.1172/JCI29444. PMC 1952618. PMID 17786245.
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External links[edit]

U.S. National Library of Medicine: Drug Information Portal - Acetylcysteine

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1. 成人におけるアセトアミノフェン（パラセタモール）中毒：治療 acetaminophen paracetamol poisoning in adults treatment
2. 造影剤誘発性腎症の予防 prevention of contrast induced nephropathy
3. アルコール性肝炎：自然経過およびマネージメント alcoholic hepatitis natural history and management
4. 特発性肺線維症の治療 treatment of idiopathic pulmonary fibrosis
5. 小児および思春期の患者におけるアセトアミノフェン（パラセタモール）中毒の臨床症状および診断 clinical manifestations and diagnosis of acetaminophen paracetamol poisoning in children and adolescents

English Journal

The sphingolipid degradation product trans-2-hexadecenal induces cytoskeletal reorganization and apoptosis in a JNK-dependent manner.

Kumar A, Byun HS, Bittman R, Saba JD.SourceCenter for Cancer Research, Children's Hospital Oakland Research Institute, 5700 Martin Luther King Jr. Way, Oakland, CA 94609, USA.
Cellular signalling.2011 Jul;23(7):1144-52. Epub 2011 Mar 6.
The bioactive signaling molecule d-erythro-sphingosine-1-phosphate (S1P) is irreversibly degraded by the enzyme S1P lyase (SPL). The reaction of SPL with C18-S1P generates ethanolamine phosphate and a long-chain fatty aldehyde, trans-2-hexadecenal. Modulation of SPL expression in cells and organisms
PMID 21385609

The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells.

Hour MJ, Yang JS, Chen TL, Chen KT, Kuo SC, Chung JG, Lu CC, Chen CY, Chuang YH.SourceSchool of Pharmacy, China Medical University, Taichung 404, Taiwan.
European journal of medicinal chemistry.2011 Jul;46(7):2709-21. Epub 2011 Apr 3.
We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associat
PMID 21514013

Japanese Journal

Protective effects of exogenous glutathione and related thiol compounds against drug-induced liver injury

Masubuchi Yasuhiro,Nakayama Junpei,Sadakata Yuka
Biological & pharmaceutical bulletin 34(3), 366-370, 2011-03
NAID 40018702791

N-Acetylcysteine Suppresses the Progression of Ventricular Remodeling in Acute Myocarditis : – Studies in an Experimental Autoimmune Myocarditis (EAM) Model –

Niwano Shinichi,Niwano Hiroe,Sasaki Sae,Fukaya Hidehira,Yuge Masaru,Imaki Ryuta,Machida Yoji,Izumi Tohru
Circulation Journal 75(3), 662-671, 2011
… Because the reactive oxygen species (ROS) has been speculated to play a role in the promotion of such remodeling, the effect of N-acetylcysteine (NAC) on the progression of ventricular remodeling was evaluated. …
NAID 130000406041

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★リンクテーブル★

リンク元	「アセチルシステイン」
拡張検索	「N-acetylcysteine」

「アセチルシステイン」

Systematic (IUPAC) name
	(2R)-2-acetamido-3-sulfanylpropanoic acid
Clinical data
Trade names	Acetadote, Fluimucil, Mucomyst, Parvolex
AHFS/Drugs.com	monograph
Licence data	US Daily Med:link
Pregnancy cat.	B2 (AU) B (US)
Legal status	Pharmacy Only (S2) (AU) ℞-only (US)
Routes	Oral, injection, inhalation
Pharmacokinetic data
Bioavailability	4-10% (Oral)
Protein binding	80-83%
Metabolism	Hepatic
Half-life	5.6 hours
Excretion	Renal (22%), faecal (3%)
Identifiers
CAS number	7218-04-4
ATC code	R05CB01 S01XA08 V03AB23
PubChem	CID 581
DrugBank	DB06151
ChemSpider	561
UNII	WYQ7N0BPYC
KEGG	D00221
ChEBI	CHEBI:28939
ChEMBL	CHEMBL600
Chemical data
Formula	C5H9NO3S
Mol. mass	163.195
	SMILES CC(=O)NC(CS)C(O)=O;
	InChI InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9) ; Key:PWKSKIMOESPYIA-UHFFFAOYSA-N ;
Physical data
Melt. point	106 °C (223 °F)
Boiling point	108 °C (226 °F)
Solubility in water	5.1 mg/mL (20 °C)
(what is this?) (verify)

　　[★]

英: acetylcysteine
同: ≒N-アセチルシステイン NAC , N-acetyl-L-cysteine
商: (去痰薬)アセテイン、(海外の去痰薬)ムコミスト、; エルネオパ、サテリット、ネオパレン、ビーフリード、ミキシッド、ムコフィリン
関: メルカプツール酸

[show details]

N-アセチルシステイン : 約 317,000 件
アセチルシステイン : 約 81,500 件

用途

アセトアミノフェン中毒の解毒薬
去痰薬

添付文書

アセトアミノフェン中毒の解毒薬

アセチルシステイン内用液17.6%「センジュ」

http://www.info.pmda.go.jp/go/pack/3929006S1022_1_08/3929006S1022_1_08?view=body

去痰薬

ムコフィリン吸入液20％

http://www.info.pmda.go.jp/go/pack/2233700G2034_1_01/2233700G2034_1_01?view=body

アミノ酸の補液

ビーフリード輸液（500mL袋）／*ビーフリード輸液（1000mL袋）

http://www.info.pmda.go.jp/go/pack/3259529G1030_1_02/3259529G1030_1_02?view=body

「N-acetylcysteine」

　　[★] アセチルシステイン

同: Mucomyst, Acetadote

[1] "L-Cysteine, N-acetyl- - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 9 January 2012.

[DMO-2] "ACETYLCYSTEINE solution [Fresenius Kabi USA, LLC]". DailyMed. Fresenius Kabi USA, LLC. September 2013. Retrieved 8 November 2013.

[DMI-3] "ACETADOTE (acetylcysteine) injection, solution [Cumberland Pharmaceuticals Inc.]". DailyMed. Cumberland Pharmaceuticals Inc. June 2013. Retrieved 8 November 2013.

[MD-4] "Acetylcysteine". Martindale: The Complete Drug Reference (The Royal Pharmaceutical Society of Great Britain). 16 November 2012. Retrieved 8 November 2013.

[TGA-5] ^ ^a ^b ^c ^d ^e ^f "PRODUCT INFORMATION ACETADOTE® CONCENTRATED INJECTION" (PDF). TGA eBusiness Services. Phebra Pty Ltd. 16 January 2013. Retrieved 8 November 2013.

[PK-6] Borgström, L; Kågedal, B; Paulsen, O (1986). "Pharmacokinetics of N-acetylcysteine in man". European Journal of Clinical Pharmacology 31 (2): 217–222. PMID 3803419.

[pm1-7] Geier, David A.; Geier, Mark R. (2006). "A Clinical and Laboratory Evaluation of Methionine Cycle-Transsulfuration and Androgen Pathway Markers in Children with Autistic Disorders". Hormone Research 66 (4): 182–8. doi:10.1159/000094467. PMID 16825783.

[8] Borgström, L.; Kågedal, B.; Paulsen, O. (1986). "Pharmacokinetics of N-acetylcysteine in man". European Journal of Clinical Pharmacology 31 (2): 217–222. doi:10.1007/BF00606662. PMID 3803419.

[dilger-9] Dilger, R. N.; Baker, D. H. (2007). "Oral N-acetyl-L-cysteine is a safe and effective precursor of cysteine". Journal of Animal Science 85 (7): 1712–8. doi:10.2527/jas.2006-835. PMID 17371789.

[10] Kanter, M. Z. (2006). "Comparison of oral and i.v. Acetylcysteine in the treatment of acetaminophen poisoning". American Journal of Health-System Pharmacy 63 (19): 1821–7. doi:10.2146/ajhp060050. PMID 16990628.

[11] Dawson, AH; Henry, DA; McEwen, J (1989). "Adverse reactions to N-acetylcysteine during treatment for paracetamol poisoning". The Medical journal of Australia 150 (6): 329–31. PMID 2716644.

[12] Bailey, B; McGuigan, M (1998). "Management of Anaphylactoid Reactions to Intravenous -Acetylcysteine". Annals of Emergency Medicine 31 (6): 710–5. doi:10.1016/S0196-0644(98)70229-X. PMID 9624310.

[13] Schmidt, L. E.; Dalhoff, K (2008). "Risk factors in the development of adverse reactions to N-acetylcysteine in patients with paracetamol poisoning". British Journal of Clinical Pharmacology 51 (1): 87–91. doi:10.1046/j.1365-2125.2001.01305.x. PMC 2014432. PMID 11167669.

[14] Lynch, R; Robertson, R (2004). "Anaphylactoid reactions to intravenous N-acetylcysteine: a prospective case controlled study". Accident and Emergency Nursing 12 (1): 10–5. doi:10.1016/j.aaen.2003.07.001. PMID 14700565.

[15] Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.

[16] Tirouvanziam, R.; Conrad, CK; Bottiglieri, T; Herzenberg, LA; Moss, RB; Herzenberg, LA (2006). "High-dose oral N-acetylcysteine, a glutathione prodrug, modulates inflammation in cystic fibrosis". Proceedings of the National Academy of Sciences 103 (12): 4628–33. doi:10.1073/pnas.0511304103. PMC 1450222. PMID 16537378.

[17] Tepel, Martin; Van Der Giet, Marcus; Schwarzfeld, Carola; Laufer, Ulf; Liermann, Dieter; Zidek, Walter (2000). "Prevention of Radiographic-Contrast-Agent–Induced Reductions in Renal Function by Acetylcysteine". New England Journal of Medicine 343 (3): 180–4. doi:10.1056/NEJM200007203430304. PMID 10900277.

[18] Hoffmann, U.; Fischereder, M; Krüger, B; Drobnik, W; Krämer, BK (2004). "The Value of N-Acetylcysteine in the Prevention of Radiocontrast Agent-Induced Nephropathy Seems Questionable". Journal of the American Society of Nephrology 15 (2): 407–10. doi:10.1097/01.ASN.0000106780.14856.55. PMID 14747387.

[19] Miner, S; Dzavik, V; Nguyen-Ho, P; Richardson, R; Mitchell, J; Atchison, D; Seidelin, P; Daly, P; Ross, J et al. (2004). "N-acetylcysteine reduces contrast-associated nephropathy but not clinical events during long-term follow-up". American Heart Journal 148 (4): 690–5. doi:10.1016/j.ahj.2004.05.015. PMID 15459602.

[20] Marenzi, Giancarlo; Assanelli, Emilio; Marana, Ivana; Lauri, Gianfranco; Campodonico, Jeness; Grazi, Marco; De Metrio, Monica; Galli, Stefano; Fabbiocchi, Franco et al. (2006). "N-Acetylcysteine and Contrast-Induced Nephropathy in Primary Angioplasty". New England Journal of Medicine 354 (26): 2773–82. doi:10.1056/NEJMoa054209. PMID 16807414.

[21] Kay, J.; Chow, WH; Chan, TM; Lo, SK; Kwok, OH; Yip, A; Fan, K; Lee, CH; Lam, WF (2003). "Acetylcysteine for Prevention of Acute Deterioration of Renal Function Following Elective Coronary Angiography and Intervention: A Randomized Controlled Trial". JAMA 289 (5): 553–8. doi:10.1001/jama.289.5.553. PMID 12578487.

[22] Act, Investigators (September 2011). "Acetylcysteine for prevention of renal outcomes in patients undergoing coronary and peripheral vascular angiography: main results from the randomized Acetylcysteine for Contrast-induced nephropathy Trial (ACT)". Circulation 124 (11): 1250–9. doi:10.1161/CIRCULATIONAHA.111.038943. PMID 21859972. Cite uses deprecated parameters (help)

[23] Palma PC, Villaça Júnior CJ, Netto Júnior NR, PC; Villaça Júnior, CJ; Netto Júnior, NR (1986). "N-acetylcysteine in the prevention of cyclophosphamide induced haemorrhagic cystitis". Int Surg 71 (1): 36–37. PMID 3522468.

[24] Hemorrhagic Cystitis Treatment & Management http://emedicine.medscape.com/article/2056130-treatment#aw2aab6b5b4

[25] Geiler, Janina; Michaelis, Martin; Naczk, Patrizia; Leutz, Anke; Langer, Klaus; Doerr, Hans-Wilhelm; Cinatl Jr, Jindrich (2010). "N-acetyl-l-cysteine (NAC) inhibits virus replication and expression of pro-inflammatory molecules in A549 cells infected with highly pathogenic H5N1 influenza a virus". Biochemical Pharmacology 79 (3): 413–20. doi:10.1016/j.bcp.2009.08.025. PMID 19732754.

[26] Kasielski, M; Nowak, D (2001). "Long-term administration of N-acetylcysteine decreases hydrogen peroxide exhalation in subjects with chronic obstructive pulmonary disease". Respiratory Medicine 95 (6): 448–56. doi:10.1053/rmed.2001.1066. PMID 11421501.

[27] Grandjean, E; Berthet, P; Ruffmann, R; Leuenberger, P (2000). "Efficacy of oral long-term -acetylcysteine in chronic bronchopulmonary disease: A meta-analysis of published double-blind, placebo-controlled clinical trials". Clinical Therapeutics 22 (2): 209–21. doi:10.1016/S0149-2918(00)88479-9. PMID 10743980.

[28] Stey, C.; Steurer, J.; Bachmann, S.; Medici, T.C.; Tramèr, M.R (2000). "The effect of oral N-acetylcysteine in chronic bronchitis: a quantitative systematic review". European Respiratory Journal 16 (2): 253–62. doi:10.1034/j.1399-3003.2000.16b12.x. PMID 10968500.

[29] Poole, P.; Black, PN (2001). "Oral mucolytic drugs for exacerbations of chronic obstructive pulmonary disease: systematic review". BMJ 322 (7297): 1271–4. doi:10.1136/bmj.322.7297.1271. PMC 31920. PMID 11375228.

[30] Magalhães, PV; Dean, OM; Bush, AI; Copolov, DL; Malhi, GS; Kohlmann, K; Jeavons, S; Schapkaitz, I; Anderson-Hunt, M; Berk, M (June 2013). "A preliminary investigation on the efficacy of N-acetyl cysteine for mania or hypomania". The Australian and New Zealand Journal of Psychiatry 47 (6). doi:10.1177/0004867413481631. PMID 23493756.

[31] "N-acetylcysteine (NAC) Also Effective in Unipolar Depression". Bipolar Network News. 14 November 2012. Retrieved 8 November 2013.

[BM2008-32] Dodd, S; Dean, O; Copolov, DL; Malhi, GS; Berk, M (December 2008). "N-acetylcysteine for antioxidant therapy: pharmacology and clinical utility". Expert Opinion on Biological Therapy 8 (12): 1955–1962. doi:10.1517/14728220802517901. PMID 18990082.

[BM2013-33] Berk, M; Malhi, GS; Gray, LJ; Dean, OM (March 2013). "The promise of N-acetylcysteine in neuropsychiatry". Trends in Pharmacological Sciences 34 (3): 167–177. doi:10.1016/j.tips.2013.01.001. PMID 23369637.

[34] Oner, G; Muderris, II (2011). "Clinical, endocrine and metabolic effects of metformin vs N-acetyl-cysteine in women with polycystic ovary syndrome". European journal of obstetrics, gynecology, and reproductive biology 159 (1): 127–31. doi:10.1016/j.ejogrb.2011.07.005. PMID 21831508.

[palmer-35] Palmer, Lisa A.; Doctor, Allan; Chhabra, Preeti; Sheram, Mary Lynn; Laubach, Victor E.; Karlinsey, Molly Z.; Forbes, Michael S.; MacDonald, Timothy; Gaston, Benjamin (2007). "S-Nitrosothiols signal hypoxia-mimetic vascular pathology". Journal of Clinical Investigation 117 (9): 2592–601. doi:10.1172/JCI29444. PMC 1952618. PMID 17786245.

[36] "The Overlooked Compound That Saves Lives". Retrieved 8 July 2013. Julius Goepp, MD. Published in Life Extension, May 2010, quote: ". . . the doses they used correspond to a human dose of about 20 grams (20,000 mg) per day."

[37] Hildebrandt, W.; Alexander, S; Bärtsch, P; Dröge, W (2002). "Effect of N-acetyl-cysteine on the hypoxic ventilatory response and erythropoietin production: linkage between plasma thiol redox state and O2 chemosensitivity". Blood 99 (5): 1552–5. doi:10.1182/blood.V99.5.1552. PMID 11861267.

[:0-38] Wang, A; Wang, J; Wang, H; Chen, Y; Zhao, L; Wang, L; Wei, W; Xu, D (2006). "A dual effect of N-acetylcysteine on acute ethanol-induced liver damage in mice". Hepatology Research 34 (3): 199–206. doi:10.1016/j.hepres.2005.12.005. PMID 16439183.

[NAc2012-39] Kupchik, YM; Moussawi, K; Tang, XC; Wang, X; Kalivas, BC; Kolokithas, R; Ogburn, KB; Kalivas, PW (June 2012). "The effect of N-acetylcysteine in the nucleus accumbens on neurotransmission and relapse to cocaine". Biological Psychiatry 71 (11): 978–986. doi:10.1016/j.biopsych.2011.10.024. PMC 3340445. PMID 22137594.

[DOI2008-40] Lavoie, S; Murray, MM; Deppen, P; Knyazeva, MG; Berk, M; Boulat, O; Bovet, P; Bush, AI; Conus, P; Copolov, D; Fornari, E; Meuli, R; Solida, A; Vianin, P; Cuénod, M; Buclin, T; Do, KQ (August 2008). "Glutathione Precursor, N-Acetyl-Cysteine, Improves Mismatch Negativity in Schizophrenia Patients". Neuropsychopharmacology 33 (9). doi:10.1038/sj.npp.1301624. PMID 18004285.

[41] Garrett, Christine E.; Prasad, Kapa (2004). "The Art of Meeting Palladium Specifications in Active Pharmaceutical Ingredients Produced by Pd-Catalyzed Reactions". Advanced Synthesis & Catalysis 346 (8): 889–900. doi:10.1002/adsc.200404071.

[42] ClinicalTrials.gov NCT00775476 Treatment of Systemic Lupus Erythematosus (SLE) with N-Aetyl Cysteine (NAC)

[Pela1999-43] Pela, R.; Calcagni, A.M.; Subiaco, S.; Isidori, P.; Tubaldi, A.; Sanguinetti, C.M. (1999). "N-Acetylcysteine Reduces the Exacerbation Rate in Patients with Moderate to Severe COPD". Respiration 66 (6): 495–500. doi:10.1159/000029447. PMID 10575333.

[44] Breitkreutz, Raoul; Pittack, Nicole; Nebe, Carl Thomas; Schuster, Dieter; Brust, Jürgen; Beichert, Matthias; Hack, Volker; Daniel, Volker; Edler, Lutz et al. (2000). "Improvement of immune functions in HIV infection by sulfur supplementation: Two randomized trials". Journal of Molecular Medicine 78 (1): 55–62. doi:10.1007/s001090050382. PMID 10759030.

[45] De Flora, S.; Grassi, C.; Carati, L. (1997). "Attenuation of influenza-like symptomatology and improvement of cell-mediated immunity with long-term N-acetylcysteine treatment". European Respiratory Journal 10 (7): 1535–41. doi:10.1183/09031936.97.10071535. PMID 9230243.

[46] Bachert, C.; Hörmann, K.; Mösges, R.; Rasp, G.; Riechelmann, H.; Müller, R.; Luckhaupt, H.; Stuck, B. A.; Rudack, C. (2003). "An update on the diagnosis and treatment of sinusitis and nasal polyposis". Allergy 58 (3): 176–91. doi:10.1034/j.1398-9995.2003.02172.x. PMID 12653791.

[47] Fowkes, Steven (13 December 1996). "Living with alcohol". Smart Drug News 5. Retrieved 2012-03-02.

[48] Ozaras, R.; Tahan, V.; Aydin, S.; Uzun, H.; Kaya, S.; Senturk, H. (2003). "N-acetylcysteine attenuates alcohol-induced oxidative stress in the rat". World journal of gastroenterology : WJG 9 (1): 125–128. PMID 12508366. edit

[49] Fulghesu, A; Ciampelli, M; Muzj, G; Belosi, C; Selvaggi, L; Ayala, GF; Lanzone, A (2002). "N-acetyl-cysteine treatment improves insulin sensitivity in women with polycystic ovary syndrome". Fertility and Sterility 77 (6): 1128–35. doi:10.1016/S0015-0282(02)03133-3. PMID 12057717.

[50] Aitio, Mirja-Liisa (2006). "N-acetylcysteine - passe-partout or much ado about nothing?". British Journal of Clinical Pharmacology 61 (1): 5–15. doi:10.1111/j.1365-2125.2005.02523.x. PMC 1884975. PMID 16390346. and has been shown to reduce ocular soreness caused by Sjogren's syndrome.Williamson, J; Doig, W M; Forrester, J V; Tham, M H; Wilson, T; Whaley, K; Dick, W C (1974). "Management of the dry eye in Sjogren's syndrome". British Journal of Ophthalmology 58 (9): 798–805. doi:10.1136/bjo.58.9.798. PMC 1215027. PMID 4433493.

[51] ttp://emedicine.medscape.com/article/1153370-overview

[NEJM.2011-52] Nguyen-Khac, E; Khac E.N., Thevenot T., Piquet M.A., Benferhat S., Goria O., Chatelain D., Tramier B., Dewaele F., Ghrib S., Rudler M., Carbonell N., Tossou H., Bental A., Chabert B.B., Dupas J.L. (11 October 2011). "Glucocorticoids plus N-Acetylcysteine in Severe Alcoholic Hepatitis". The New England Journal of Medicine (Massachusetts Medical Society) 365 (19): 1781–9. doi:10.1056/NEJMoa1101214. ISSN 0028-4793. PMID 22070475. Cite uses deprecated parameters (help)

[53] McCaddon, A. (1999). "Homocysteine and cognitive impairment; a case series in a General Practice setting". Nutr J. 5 (6): 2398–406. doi:10.1186/1475-2891-5-6. PMC 1395322. PMID 16480506.

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acetylcysteine