Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C5H10N2O2S |
Molecular Weight | 162.21 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)N[C@@H](CS)C(N)=O
InChI
InChIKey=UJCHIZDEQZMODR-BYPYZUCNSA-N
InChI=1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1
Molecular Formula | C5H10N2O2S |
Molecular Weight | 162.21 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Acetylcysteine amide (NACA) is a novel thiol-containing antioxidant. NACA is a modified form of its parent compound N-acetylcysteine (NAC) that is a precursor of the most abundant endogenous antioxidant, glutathione (GSH). NACA demonstrated the multiple therapeutic abilities, including antioxidant, anti-apoptotic, and anti-inflammatory properties with greater efficacy compared to its parent compound. NACA treatment significantly maintained acute mitochondrial bioenergetics and normalized GSH levels following spinal cord injury. It is a new neuroprotective drug, that might be effective at slowing down nigral neuronal degeneration and illness progression in patients with Parkinson's disease.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23472882 |
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Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23472882 |
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Target ID: GO:0005746 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805071 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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A low molecular weight copper chelator crosses the blood-brain barrier and attenuates experimental autoimmune encephalomyelitis. | 2004 Jun |
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Analysis of gene expression in MOG-induced experimental autoimmune encephalomyelitis after treatment with a novel brain-penetrating antioxidant. | 2005 |
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N-acetylcysteine amide, a novel cell-permeating thiol, restores cellular glutathione and protects human red blood cells from oxidative stress. | 2005 Jan 1 |
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Is brain dehydroepiandrosterone synthesis modulated by free radicals in mice? | 2005 Mar 29 |
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A novel brain-targeted antioxidant (AD4) attenuates haloperidol-induced abnormal movement in rats: implications for tardive dyskinesia. | 2005 Nov-Dec |
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Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12. | 2005 Sep 21 |
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Role of N-acetylcysteine in the management of COPD. | 2006 |
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Low molecular weight thiol amides attenuate MAPK activity and protect primary neurons from Abeta(1-42) toxicity. | 2006 Jan 19 |
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Separation and quantification of N-acetyl-l-cysteine and N-acetyl-cysteine-amide by HPLC with fluorescence detection. | 2006 May |
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Potentiation of lead-induced cell death in PC12 cells by glutamate: protection by N-acetylcysteine amide (NACA), a novel thiol antioxidant. | 2006 Oct 15 |
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A novel antioxidant N-acetylcysteine amide prevents gp120- and Tat-induced oxidative stress in brain endothelial cells. | 2006 Sep |
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A novel thiol compound, N-acetylcysteine amide, attenuates allergic airway disease by regulating activation of NF-kappaB and hypoxia-inducible factor-1alpha. | 2007 Dec 31 |
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[N-acetylcysteine improves lysosomal function and enhances the degradation of photoreceptor outer segments in cultured RPE cells]. | 2007 Jul |
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Advanced glycation end products attenuate cellular insulin sensitivity by increasing the generation of intracellular reactive oxygen species in adipocytes. | 2007 May |
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Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC). | 2008 Apr |
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Endoplasmic reticulum stress and unfolded protein response in Atm-deficient thymocytes and thymic lymphoma cells are attributable to oxidative stress. | 2008 Feb |
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N-acetylcysteine amide (AD4) attenuates oxidative stress in beta-thalassemia blood cells. | 2008 Feb |
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Effects of N-acetylcysteine amide (NACA), a thiol antioxidant on radiation-induced cytotoxicity in Chinese hamster ovary cells. | 2008 May 23 |
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Anti-inflammatory and arthritic effects of thiacremonone, a novel sulfur compound isolated from garlic via inhibition of NF-kappaB. | 2009 |
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N-acetylcysteine amide decreases oxidative stress but not cell death induced by doxorubicin in H9c2 cardiomyocytes. | 2009 Apr 15 |
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N-Acetylcysteine amide protects against methamphetamine-induced oxidative stress and neurotoxicity in immortalized human brain endothelial cells. | 2009 Jun 12 |
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N-acetylcysteineamide (NACA) prevents inflammation and oxidative stress in animals exposed to diesel engine exhaust. | 2009 Jun 22 |
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Attenuation of pulmonary inflammation after exposure to blast overpressure by N-acetylcysteine amide. | 2009 Sep |
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N-acetylcysteine amide protects renal proximal tubular epithelial cells against iohexol-induced apoptosis by blocking p38 MAPK and iNOS signaling. | 2010 |
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HIV proteins (gp120 and Tat) and methamphetamine in oxidative stress-induced damage in the brain: potential role of the thiol antioxidant N-acetylcysteine amide. | 2010 May 15 |
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Effects of N-acetyl-cysteine and N-acetyl-cysteine-amide supplementation on in vitro matured porcine oocytes. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805071
75, 150, 300 or 600 mg/kg body weight at 15min and 6h post-injury
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15733082
Survival of neuroblastoma cells exposed to levodopa (0.06 mM), dopamine (0.06 mM), 6-OHDA (0.06 mM) or MPP+ (1.5 mM) was reduced by 50% (P < 0.01). However, cotreatment with AD4 (0.05–2 mM) raised the survival rates by 20–50% (P < 0.05) in a dose-dependent manner.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:26:39 GMT 2023
by
admin
on
Fri Dec 15 17:26:39 GMT 2023
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Record UNII |
4N69717RKW
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C275
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FDA ORPHAN DRUG |
417513
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FDA ORPHAN DRUG |
771920
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FDA ORPHAN DRUG |
768820
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C487056
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DTXSID30436398
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10176265
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C87651
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SUB181947
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DB14480
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100000168521
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ACETYLCYSTEINAMIDE
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1591923
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4N69717RKW
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38520-57-9
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Related Record | Type | Details | ||
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