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Wikipedia

Acetylcysteine

January 01, 1970

Acetylcysteine, also known as N-acetylcysteine (NAC), is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders like pneumonia and bronchitis.[7] It has been used to treat lactobezoar in infants. It can be taken intravenously, by mouth, or inhaled as a mist.[7] Some people use it as a dietary supplement.[10][11]

Acetylcysteine
Clinical data
Pronunciation/əˌsiːtəlˈsɪstiːn/ and similar (/əˌsɛtəl-, ˌæsɪtəl-, -tiːn/)
Trade namesACC 200, Acetadote, Fluimucil, Mucomyst, others
Other namesN-acetylcysteine; N-acetyl-L-cysteine; NALC; NAC
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth, intravenous, inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability10% (Oral)[6]
Protein binding50 to 83%[7]
MetabolismLiver[7]
Elimination half-life5.6 hours[5]
ExcretionKidney (30%),[7] faecal (3%)
Identifiers
  • (2R)-2-acetamido-3-sulfanylpropanoic acid[8]
CAS Number
  • 616-91-1 Y
PubChem CID
  • 12035
DrugBank
  • DB06151 Y
ChemSpider
  • 11540 Y
UNII
  • WYQ7N0BPYC
KEGG
  • D00221 Y
ChEBI
  • CHEBI:28939 Y
ChEMBL
  • ChEMBL600 Y
CompTox Dashboard (EPA)
  • DTXSID5020021
ECHA InfoCard100.009.545
Chemical and physical data
FormulaC5H9NO3S
Molar mass163.19 g·mol−1
3D model (JSmol)
  • Interactive image
Specific rotation+5° (c = 3% in water)[9]
Melting point109 to 110 °C (228 to 230 °F) [9]
  • C/C(=N/[C@@H](CS)C(=O)O)/O
  • 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 Y
  • Key:PWKSKIMOESPYIA-BYPYZUCNSA-N Y
  (verify)

Common side effects include nausea and vomiting when taken by mouth.[7] The skin may occasionally become red and itchy with any route of administration.[7] A non-immune type of anaphylaxis may also occur.[7] It appears to be safe in pregnancy.[7] For paracetamol overdose, it works by increasing the level of glutathione, an antioxidant that can neutralise the toxic breakdown products of paracetamol.[7] When inhaled, it acts as a mucolytic by decreasing the thickness of mucus.[12]

Acetylcysteine was initially patented in 1960 and came into medical use in 1968.[13][14][15] It is on the World Health Organization's List of Essential Medicines.[16][17] It is available as a generic medication.[18]

The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids.[19][20]

Uses edit

Medical uses edit

Paracetamol overdose edit

Main article: Paracetamol poisoning

Intravenous and oral formulations of acetylcysteine are available for the treatment of paracetamol (acetaminophen) overdose.[21] 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 deactivate the toxic NAPQI. This metabolite is then free to react with key hepatic enzymes, thereby damaging liver cells. This may lead to severe liver damage and even death by acute liver failure.

In the treatment of paracetamol (acetaminophen) overdose, acetylcysteine acts to maintain or replenish depleted glutathione reserves in the liver and enhance non-toxic metabolism of acetaminophen.[22] These actions serve to protect liver cells from NAPQI toxicity. It is most effective in preventing or lessening hepatic injury when administered within 8–10 hours after overdose.[22] Research suggests that the rate of liver toxicity is approximately 3% when acetylcysteine is administered within 10 hours of overdose.[21]

Although IV and oral acetylcysteine are equally effective for this indication, oral administration is generally poorly tolerated due to the higher dosing required to overcome its low oral bioavailability,[23] its foul taste and odour, and a higher incidence of adverse effects when taken by mouth, particularly nausea and vomiting. Prior pharmacokinetic studies of acetylcysteine did not consider acetylation as a reason for the low bioavailability of acetylcysteine.[24] Oral acetylcysteine is identical in bioavailability to cysteine precursors.[24] 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.[25] 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 intravenous acetylcysteine despite serum levels of paracetamol not high enough to be considered toxic.[26][27][28][29]

Lungs edit

Inhaled acetylcysteine has been used for mucolytic ("mucus-dissolving") therapy in addition to other therapies in respiratory conditions with excessive and/or thick mucus production. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. It may be considered ineffective in cystic fibrosis.[30] A 2013 Cochrane review in cystic fibrosis found no evidence of benefit.[31]

Acetylcysteine is used in the treatment of obstructive lung disease as an adjuvant treatment.[32][33][34]

Other uses 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.[35] N-acetylcysteine can be used to protect the liver.[36]

Microbiological use edit

Acetylcysteine can be used in Petroff's method of liquefaction and decontamination of sputum, in preparation for recovery of mycobacterium.[37] It also displays significant antiviral activity against the influenza A viruses.[38]

Acetylcysteine has bactericidal properties and breaks down bacterial biofilms of clinically relevant pathogens including Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Enterobacter cloacae, Staphylococcus epidermidis, and Klebsiella pneumoniae.[39]

Side effects edit

"SNOAC" redirects here. For the gene, see snoaC.

The most commonly reported adverse effects for IV formulations of acetylcysteine are rash, urticaria, and itchiness.[22]

Adverse effects for inhalational formulations of acetylcysteine include nausea, vomiting, stomatitis, fever, rhinorrhea, drowsiness, clamminess, chest tightness, and bronchoconstriction. Although infrequent, bronchospasm has been reported to occur unpredictably in some patients.[40]

Adverse effects for oral formulations of acetylcysteine have been reported to include nausea, vomiting, rash, and fever.[40]

Large doses in a mouse model showed that acetylcysteine could potentially cause damage to the heart and lungs.[41] 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.[41] In humans, a much lower dosages (600 mg per day) have been observed to counteract some age-related decline in the hypoxic ventilatory response as tested by inducing prolonged hypoxia.[42]

Although N-acetylcysteine prevented liver damage in mice when taken before alcohol, when taken four hours after alcohol it made liver damage worse in a dose-dependent fashion.[43]

Pharmacology edit

Pharmacodynamics edit

Acetylcysteine serves as a prodrug to L-cysteine, a precursor to the biologic antioxidant glutathione. Hence administration of acetylcysteine replenishes glutathione stores.[44]

L-cysteine also serves as a precursor to cystine, which in turn serves as a substrate for the cystine-glutamate antiporter on astrocytes; hence there is increasing glutamate release into the extracellular space. This glutamate in turn acts on mGluR2/3 receptors, and at higher doses of acetylcysteine, mGluR5.[50][51] Acetylcysteine may have other biological functions in the brain, such as the modulation of dopamine release and the reduction in inflammatory cytokine formation possibly via inhibiting NF-κB and modulating cytokine synthesis.[48] These properties, along with the reduction of oxidative stress and the re‐establishment of glutamatergic balance, would lead to an increase in growth factors, such as brain‐derived neurotrophic factor (BDNF), and the regulation of neuronal cell death through B‐cell lymphoma 2 expression (BLC-2).[52]

Pharmacokinetics edit

Acetylcysteine is extensively liver metabolized, CYP450 minimal, urine excretion is 22–30% with a half-life of 5.6 hours in adults and 11 hours in newborns.

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.

N-acetyl-L-cysteine is soluble in water and alcohol, and practically insoluble in chloroform and ether.[53]

It is a white to white with light yellow cast powder, and has a pKa of 9.5 at 30 °C.[9]

Society and culture edit

Acetylcysteine was first studied as a drug in 1963. Amazon removed acetylcysteine for sale in the US in 2021, due to claims by the FDA of it being classified as a drug rather than a supplement.[54][55][56][57] In April 2022, the FDA released draft guidance on FDA's policy regarding products labeled as dietary supplements that contain N-acetyl-L-cysteine.[58] Amazon subsequently re-listed NAC products as of August 2022.[59]

Research edit

While many antioxidants have been researched to treat a large number of diseases by reducing the negative effect of oxidative stress, acetylcysteine is one of the few that has yielded promising results, and is currently already approved for the treatment of paracetamol overdose.[60]

  • In mouse mdx models of Duchenne's muscular dystrophy, treatment with 1–2% acetylcysteine in drinking water significantly reduces muscle damage and improves strength.[60]
  • It is being studied in conditions such as autism, where cysteine and related sulfur amino acids may be depleted due to multifactorial dysfunction of methylation pathways involved in methionine catabolism.[61]
  • Animal studies have also demonstrated its efficacy in reducing the damage associated with moderate traumatic brain or spinal injury, and also ischaemia-induced brain injury. In particular, it has been demonstrated to reduce neuronal losses and to improve cognitive and neurological outcomes associated with these traumatic events.[62]
  • It has been suggested that acetylcysteine may help people with aspirin-exacerbated respiratory disease by increasing levels of glutathione allowing faster breakdown of salicylates, although there is no evidence that it is of benefit.[63]
  • Small studies have shown acetylcysteine to be of benefit to people with blepharitis.[64] It has been shown to reduce ocular soreness caused by Sjögren's syndrome.[65]
  • It has been shown that N-acetylcysteine may protect the human cochlea from subclinical hearing loss caused by loud noises such as impulse noise.[66] In animal models, it reduced age-related hearing loss.
  • It has been shown effective in the treatment of Unverricht-Lundborg disease in an open trial in four patients. A marked decrease in myoclonus and some normalization of somatosensory evoked potentials with acetylcysteine treatment has been documented.[67][68]
  • Addiction to certain addictive drugs (including cocaine, heroin, alcohol, and nicotine) is correlated with a persistent reduction in the expression of excitatory amino acid transporter 2 (EAAT2) in the nucleus accumbens (NAcc);[69] the reduced expression of EAAT2 in this region is implicated in addictive drug-seeking behavior.[69] In particular, the long-term dysregulation of glutamate neurotransmission in the NAcc of long-term, drug-dependent users is associated with an increase in vulnerability to relapse after re-exposure to the addictive drug or its associated drug cues.[69] Drugs that help to normalize the expression of EAAT2 in this region, such as N-acetylcysteine, have been proposed as an adjunct therapy for the treatment of addiction to cocaine, nicotine, alcohol, and other drugs.[69]
  • It has been tested for the reduction of hangover symptoms, though the overall results indicate very limited efficacy.[70][71]
  • A double-blind placebo controlled trial of 262 patients has shown NAC treatment was well-tolerated and resulted in a significant decrease in the frequency of influenza-like episodes, severity, and length of time confined to bed.[72]

Kidney and bladder edit

Evidence for the benefit of acetylcysteine to prevent radiocontrast induced kidney disease is mixed.[73]

Acetylcysteine has been used for cyclophosphamide-induced haemorrhagic cystitis, although mesna is generally preferred due to the ability of acetylcysteine to diminish the effectiveness of cyclophosphamide.[74]

Psychiatry edit

Acetylcysteine has been studied for major psychiatric disorders,[75][52][48][62] including bipolar disorder,[75] major depressive disorder, and schizophrenia.[52][48]

Tentative evidence exists for N-acetylcysteine also in the treatment of Alzheimer's disease, autism, obsessive-compulsive disorder,[76] specific drug addictions (cocaine), drug-induced neuropathy, trichotillomania, excoriation disorder, and a certain form of epilepsy (progressive myoclonic).[52][48][77] Preliminary evidence showed efficacy in anxiety disorder, attention deficit hyperactivity disorder and mild traumatic brain injury although confirmatory studies are required.[77][78][79][80] Tentative evidence also supports use in cannabis use disorder.[81]

It is also being studied for use as a treatment of body-focused repetitive behavior.[82][83]

Addiction edit

Evidence to date does not support the efficacy for N-acetylcysteine in treating addictions to gambling, methamphetamine, or nicotine.[77] Based upon limited evidence, NAC appears to normalize glutamate neurotransmission in the nucleus accumbens and other brain structures, in part by upregulating the expression of excitatory amino acid transporter 2 (EAAT2), a.k.a. glutamate transporter 1 (GLT1), in individuals with addiction.[69] While NAC has been demonstrated to modulate glutamate neurotransmission in adult humans who are addicted to cocaine, NAC does not appear to modulate glutamate neurotransmission in healthy adult humans.[69] NAC has been hypothesized to exert beneficial effects through its modulation of glutamate and dopamine neurotransmission as well as its antioxidant properties.[48]

Bipolar disorder edit

In bipolar disorder, N-acetylcysteine has been repurposed as an augmentation strategy for depressive episodes in light of the possible role of inflammation in the pathogenesis of mood disorders. Nonetheless, meta-analytic evidence shows that add-on N-acetylcysteine was more effective than placebo only in reducing depression scales scores (low quality evidence), without positive effects on response and remission outcomes, limiting its possible role in clinical practice to date.[75][84]

COVID-19 edit

Acetylcysteine is being considered as a possible treatment for COVID-19.[85][86][87]

A combination of guanfacine and N-acetylcysteine has been found to lift the "brain fog" of eight patients with long COVID, according to researchers.[88]

A combination of glycine and N-acetylcysteine is suspected to have potential to safely replenish depleted glutathione levels in COVID-19 patients.[89]

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January 01, 1970
acetylcysteine, also, known, acetylcysteine, medication, that, used, treat, paracetamol, overdose, loosen, thick, mucus, individuals, with, chronic, bronchopulmonary, disorders, like, pneumonia, bronchitis, been, used, treat, lactobezoar, infants, taken, intra. Acetylcysteine also known as N acetylcysteine NAC is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders like pneumonia and bronchitis 7 It has been used to treat lactobezoar in infants It can be taken intravenously by mouth or inhaled as a mist 7 Some people use it as a dietary supplement 10 11 AcetylcysteineClinical dataPronunciation e ˌ s iː t el ˈ s ɪ s t iː n and similar e ˌ s ɛ t el ˌ ae s ɪ t el t iː n Trade namesACC 200 Acetadote Fluimucil Mucomyst othersOther namesN acetylcysteine N acetyl L cysteine NALC NACAHFS Drugs comMonographLicense dataUS DailyMed AcetylcysteinePregnancycategoryAU B2Routes ofadministrationBy mouth intravenous inhalationATC codeR05CB01 WHO S01XA08 WHO V03AB23 WHO Legal statusLegal statusAU S4 Prescription only 1 2 3 UK POM Prescription only 4 US only 5 Pharmacokinetic dataBioavailability10 Oral 6 Protein binding50 to 83 7 MetabolismLiver 7 Elimination half life5 6 hours 5 ExcretionKidney 30 7 faecal 3 IdentifiersIUPAC name 2R 2 acetamido 3 sulfanylpropanoic acid 8 CAS Number616 91 1 YPubChem CID12035DrugBankDB06151 YChemSpider11540 YUNIIWYQ7N0BPYCKEGGD00221 YChEBICHEBI 28939 YChEMBLChEMBL600 YCompTox Dashboard EPA DTXSID5020021ECHA InfoCard100 009 545Chemical and physical dataFormulaC 5H 9N O 3SMolar mass163 19 g mol 13D model JSmol Interactive imageSpecific rotation 5 c 3 in water 9 Melting point109 to 110 C 228 to 230 F 9 SMILES C C N C H CS C O O OInChI 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 YKey PWKSKIMOESPYIA BYPYZUCNSA N Y verify Common side effects include nausea and vomiting when taken by mouth 7 The skin may occasionally become red and itchy with any route of administration 7 A non immune type of anaphylaxis may also occur 7 It appears to be safe in pregnancy 7 For paracetamol overdose it works by increasing the level of glutathione an antioxidant that can neutralise the toxic breakdown products of paracetamol 7 When inhaled it acts as a mucolytic by decreasing the thickness of mucus 12 Acetylcysteine was initially patented in 1960 and came into medical use in 1968 13 14 15 It is on the World Health Organization s List of Essential Medicines 16 17 It is available as a generic medication 18 The sulfur containing amino acids cysteine and methionine are more easily oxidized than the other amino acids 19 20 Contents 1 Uses 1 1 Medical uses 1 1 1 Paracetamol overdose 1 1 2 Lungs 1 2 Other uses 1 2 1 Microbiological use 2 Side effects 3 Pharmacology 3 1 Pharmacodynamics 3 2 Pharmacokinetics 4 Chemistry 5 Society and culture 6 Research 6 1 Kidney and bladder 6 2 Psychiatry 6 2 1 Addiction 6 2 2 Bipolar disorder 6 3 COVID 19 7 ReferencesUses editMedical uses edit Paracetamol overdose edit Main article Paracetamol poisoning Intravenous and oral formulations of acetylcysteine are available for the treatment of paracetamol acetaminophen overdose 21 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 deactivate the toxic NAPQI This metabolite is then free to react with key hepatic enzymes thereby damaging liver cells This may lead to severe liver damage and even death by acute liver failure In the treatment of paracetamol acetaminophen overdose acetylcysteine acts to maintain or replenish depleted glutathione reserves in the liver and enhance non toxic metabolism of acetaminophen 22 These actions serve to protect liver cells from NAPQI toxicity It is most effective in preventing or lessening hepatic injury when administered within 8 10 hours after overdose 22 Research suggests that the rate of liver toxicity is approximately 3 when acetylcysteine is administered within 10 hours of overdose 21 Although IV and oral acetylcysteine are equally effective for this indication oral administration is generally poorly tolerated due to the higher dosing required to overcome its low oral bioavailability 23 its foul taste and odour and a higher incidence of adverse effects when taken by mouth particularly nausea and vomiting Prior pharmacokinetic studies of acetylcysteine did not consider acetylation as a reason for the low bioavailability of acetylcysteine 24 Oral acetylcysteine is identical in bioavailability to cysteine precursors 24 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 25 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 intravenous acetylcysteine despite serum levels of paracetamol not high enough to be considered toxic 26 27 28 29 Lungs edit Inhaled acetylcysteine has been used for mucolytic mucus dissolving therapy in addition to other therapies in respiratory conditions with excessive and or thick mucus production It is also used post operatively as a diagnostic aid and in tracheotomy care It may be considered ineffective in cystic fibrosis 30 A 2013 Cochrane review in cystic fibrosis found no evidence of benefit 31 Acetylcysteine is used in the treatment of obstructive lung disease as an adjuvant treatment 32 33 34 Other uses 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 35 N acetylcysteine can be used to protect the liver 36 Microbiological use edit Acetylcysteine can be used in Petroff s method of liquefaction and decontamination of sputum in preparation for recovery of mycobacterium 37 It also displays significant antiviral activity against the influenza A viruses 38 Acetylcysteine has bactericidal properties and breaks down bacterial biofilms of clinically relevant pathogens including Pseudomonas aeruginosa Staphylococcus aureus Enterococcus faecalis Enterobacter cloacae Staphylococcus epidermidis and Klebsiella pneumoniae 39 Side effects edit SNOAC redirects here For the gene see snoaC The most commonly reported adverse effects for IV formulations of acetylcysteine are rash urticaria and itchiness 22 Adverse effects for inhalational formulations of acetylcysteine include nausea vomiting stomatitis fever rhinorrhea drowsiness clamminess chest tightness and bronchoconstriction Although infrequent bronchospasm has been reported to occur unpredictably in some patients 40 Adverse effects for oral formulations of acetylcysteine have been reported to include nausea vomiting rash and fever 40 Large doses in a mouse model showed that acetylcysteine could potentially cause damage to the heart and lungs 41 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 41 In humans a much lower dosages 600 mg per day have been observed to counteract some age related decline in the hypoxic ventilatory response as tested by inducing prolonged hypoxia 42 Although N acetylcysteine prevented liver damage in mice when taken before alcohol when taken four hours after alcohol it made liver damage worse in a dose dependent fashion 43 Pharmacology editPharmacodynamics edit Acetylcysteine serves as a prodrug to L cysteine a precursor to the biologic antioxidant glutathione Hence administration of acetylcysteine replenishes glutathione stores 44 Glutathione along with oxidized glutathione GSSG and S nitrosoglutathione GSNO have been found to bind to the glutamate recognition site of the NMDA and AMPA receptors via their g glutamyl moieties and may be endogenous neuromodulators 45 46 At millimolar concentrations they may also modulate the redox state of the NMDA receptor complex 46 In addition glutathione has been found to bind to and activate ionotropic receptors that are different from any other excitatory amino acid receptor and which may constitute glutathione receptors potentially making it a neurotransmitter 47 As such since N acetylcysteine is a prodrug of glutathione it may modulate all of the aforementioned receptors as well Glutathione also modulates the NMDA receptor by acting at the redox site 48 49 L cysteine also serves as a precursor to cystine which in turn serves as a substrate for the cystine glutamate antiporter on astrocytes hence there is increasing glutamate release into the extracellular space This glutamate in turn acts on mGluR2 3 receptors and at higher doses of acetylcysteine mGluR5 50 51 Acetylcysteine may have other biological functions in the brain such as the modulation of dopamine release and the reduction in inflammatory cytokine formation possibly via inhibiting NF kB and modulating cytokine synthesis 48 These properties along with the reduction of oxidative stress and the re establishment of glutamatergic balance would lead to an increase in growth factors such as brain derived neurotrophic factor BDNF and the regulation of neuronal cell death through B cell lymphoma 2 expression BLC 2 52 Pharmacokinetics edit Acetylcysteine is extensively liver metabolized CYP450 minimal urine excretion is 22 30 with a half life of 5 6 hours in adults and 11 hours in newborns Chemistry editAcetylcysteine 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 N acetyl L cysteine is soluble in water and alcohol and practically insoluble in chloroform and ether 53 It is a white to white with light yellow cast powder and has a pKa of 9 5 at 30 C 9 Society and culture editAcetylcysteine was first studied as a drug in 1963 Amazon removed acetylcysteine for sale in the US in 2021 due to claims by the FDA of it being classified as a drug rather than a supplement 54 55 56 57 In April 2022 the FDA released draft guidance on FDA s policy regarding products labeled as dietary supplements that contain N acetyl L cysteine 58 Amazon subsequently re listed NAC products as of August 2022 59 Research editWhile many antioxidants have been researched to treat a large number of diseases by reducing the negative effect of oxidative stress acetylcysteine is one of the few that has yielded promising results and is currently already approved for the treatment of paracetamol overdose 60 In mouse mdx models of Duchenne s muscular dystrophy treatment with 1 2 acetylcysteine in drinking water significantly reduces muscle damage and improves strength 60 It is being studied in conditions such as autism where cysteine and related sulfur amino acids may be depleted due to multifactorial dysfunction of methylation pathways involved in methionine catabolism 61 Animal studies have also demonstrated its efficacy in reducing the damage associated with moderate traumatic brain or spinal injury and also ischaemia induced brain injury In particular it has been demonstrated to reduce neuronal losses and to improve cognitive and neurological outcomes associated with these traumatic events 62 It has been suggested that acetylcysteine may help people with aspirin exacerbated respiratory disease by increasing levels of glutathione allowing faster breakdown of salicylates although there is no evidence that it is of benefit 63 Small studies have shown acetylcysteine to be of benefit to people with blepharitis 64 It has been shown to reduce ocular soreness caused by Sjogren s syndrome 65 It has been shown that N acetylcysteine may protect the human cochlea from subclinical hearing loss caused by loud noises such as impulse noise 66 In animal models it reduced age related hearing loss It has been shown effective in the treatment of Unverricht Lundborg disease in an open trial in four patients A marked decrease in myoclonus and some normalization of somatosensory evoked potentials with acetylcysteine treatment has been documented 67 68 Addiction to certain addictive drugs including cocaine heroin alcohol and nicotine is correlated with a persistent reduction in the expression of excitatory amino acid transporter 2 EAAT2 in the nucleus accumbens NAcc 69 the reduced expression of EAAT2 in this region is implicated in addictive drug seeking behavior 69 In particular the long term dysregulation of glutamate neurotransmission in the NAcc of long term drug dependent users is associated with an increase in vulnerability to relapse after re exposure to the addictive drug or its associated drug cues 69 Drugs that help to normalize the expression of EAAT2 in this region such as N acetylcysteine have been proposed as an adjunct therapy for the treatment of addiction to cocaine nicotine alcohol and other drugs 69 It has been tested for the reduction of hangover symptoms though the overall results indicate very limited efficacy 70 71 A double blind placebo controlled trial of 262 patients has shown NAC treatment was well tolerated and resulted in a significant decrease in the frequency of influenza like episodes severity and length of time confined to bed 72 Kidney and bladder edit Evidence for the benefit of acetylcysteine to prevent radiocontrast induced kidney disease is mixed 73 Acetylcysteine has been used for cyclophosphamide induced haemorrhagic cystitis although mesna is generally preferred due to the ability of acetylcysteine to diminish the effectiveness of cyclophosphamide 74 Psychiatry edit Acetylcysteine has been studied for major psychiatric disorders 75 52 48 62 including bipolar disorder 75 major depressive disorder and schizophrenia 52 48 Tentative evidence exists for N acetylcysteine also in the treatment of Alzheimer s disease autism obsessive compulsive disorder 76 specific drug addictions cocaine drug induced neuropathy trichotillomania excoriation disorder and a certain form of epilepsy progressive myoclonic 52 48 77 Preliminary evidence showed efficacy in anxiety disorder attention deficit hyperactivity disorder and mild traumatic brain injury although confirmatory studies are required 77 78 79 80 Tentative evidence also supports use in cannabis use disorder 81 It is also being studied for use as a treatment of body focused repetitive behavior 82 83 Addiction edit Evidence to date does not support the efficacy for N acetylcysteine in treating addictions to gambling methamphetamine or nicotine 77 Based upon limited evidence NAC appears to normalize glutamate neurotransmission in the nucleus accumbens and other brain structures in part by upregulating the expression of excitatory amino acid transporter 2 EAAT2 a k a glutamate transporter 1 GLT1 in individuals with addiction 69 While NAC has been demonstrated to modulate glutamate neurotransmission in adult humans who are addicted to cocaine NAC does not appear to modulate glutamate neurotransmission in healthy adult humans 69 NAC has been hypothesized to exert beneficial effects through its modulation of glutamate and dopamine neurotransmission as well as its antioxidant properties 48 Bipolar disorder edit In bipolar disorder N acetylcysteine has been repurposed as an augmentation strategy for depressive episodes in light of the possible role of inflammation in the pathogenesis of mood disorders Nonetheless meta analytic evidence shows that add on N acetylcysteine was more effective than placebo only in reducing depression scales scores low quality evidence without positive effects on response and remission outcomes limiting its possible role in clinical practice to date 75 84 COVID 19 edit Acetylcysteine is being considered as a possible treatment for COVID 19 85 86 87 A combination of guanfacine and N acetylcysteine has been found to lift the brain fog of eight patients with long COVID according to researchers 88 A combination of glycine and N acetylcysteine is suspected to have potential to safely replenish depleted glutathione levels in COVID 19 patients 89 References edit DBL ACETYLCYSTEINE injection concentrate acetylcysteine 2 g 10 mL injection ampoule TGA eBS Product and Consumer Medicine Information Licence Acetylcysteine 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