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38520-57-9,MFCD01696115
Catalog No.:AA00365J

38520-57-9 | (R)-2-Acetamido-3-mercaptopropanamide

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100mg
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$68.00   $48.00
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250mg
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$130.00   $91.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00365J
Chemical Name:
(R)-2-Acetamido-3-mercaptopropanamide
CAS Number:
38520-57-9
Molecular Formula:
C5H10N2O2S
Molecular Weight:
162.2101
MDL Number:
MFCD01696115
SMILES:
SC[C@@H](C(=O)N)NC(=O)C
Properties
Properties
 
Form:
Solid  
MP:
146- 149°C  
Solubility:
H2O: ≥20mg/mL  
Storage:
2-8℃;Inert atmosphere;  

Computed Properties
 
Complexity:
149  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
-0.3  

Downstream Synthesis Route

[1]Patent:US6369106,2002,B1

[1]Patent:WO2015/181551,2015,A1.Locationinpatent:Page/Pagecolumn35

[2]AngewandteChemie-InternationalEdition,2008,vol.47,p.2244-2247

[3]Patent:WO2014/11624,2014,A2.Locationinpatent:Paragraph00139;00140

[4]Patent:WO2015/148880,2015,A1.Locationinpatent:Paragraph0024;0025

[5]Patent:WO2016/185200,2016,A1.Locationinpatent:Page/Pagecolumn30;31

[1]CurrentPatentAssignee:XPDHOLDINGS-WO2014/11624,2014,A2Locationinpatent:Paragraph00143;00144

Literature

Title: N-acetylcysteine amide, a promising antidote for acetaminophen toxicity.

Journal: Toxicology letters 20160122

Title: Estrogen Sulfotransferase Is an Oxidative Stress-responsive Gene That Gender-specifically Affects Liver Ischemia/Reperfusion Injury.

Journal: The Journal of biological chemistry 20150605

Title: N-acetylcysteine amide protects against methamphetamine-induced tissue damage in CD-1 mice.

Journal: Human & experimental toxicology 20120901

Title: Characterizing N-acetylcysteine (NAC) and N-acetylcysteine amide (NACA) binding for lead poisoning treatment.

Journal: Journal of colloid and interface science 20120401

Title: Mutations in the mitochondrial methionyl-tRNA synthetase cause a neurodegenerative phenotype in flies and a recessive ataxia (ARSAL) in humans.

Journal: PLoS biology 20120301

Title: Blood-brain barrier abnormalities caused by HIV-1 gp120: mechanistic and therapeutic implications.

Journal: TheScientificWorldJournal 20120101

Title: Protective effects of N-acetylcysteine amide (NACA) on gentamicin-induced apoptosis in LLC-PK1 cells.

Journal: Renal failure 20120101

Title: Glutathione homeostasis and functions: potential targets for medical interventions.

Journal: Journal of amino acids 20120101

Title: Free radical scavenger properties of α-mangostin: thermodynamics and kinetics of HAT and RAF mechanisms.

Journal: The journal of physical chemistry. B 20111103

Title: Effectiveness of sulfur-containing antioxidants in delaying skeletal muscle fatigue.

Journal: Medicine and science in sports and exercise 20110601

Title: Directing dopaminergic fiber growth along a preformed molecular pathway from embryonic ventral mesencephalon transplants in the rat brain.

Journal: Journal of neuroscience research 20110501

Title: N-acetylcysteine amide (NACA) prevents retinal degeneration by up-regulating reduced glutathione production and reversing lipid peroxidation.

Journal: The American journal of pathology 20110501

Title: Highly active antiretroviral therapy drug combination induces oxidative stress and mitochondrial dysfunction in immortalized human blood-brain barrier endothelial cells.

Journal: Free radical biology & medicine 20110401

Title: In vivo inhibition of l-buthionine-(S,R)-sulfoximine-induced cataracts by a novel antioxidant, N-acetylcysteine amide.

Journal: Free radical biology & medicine 20110315

Title: Comparative evaluation of N-acetylcysteine (NAC) and N-acetylcysteine amide (NACA) on glutamate and lead-induced toxicity in CD-1 mice.

Journal: Toxicology letters 20110225

Title: Hypoxia-inducible factor-1 α/platelet derived growth factor axis in HIV-associated pulmonary vascular remodeling.

Journal: Respiratory research 20110101

Title: In vitro acute exposure to DEHP affects oocyte meiotic maturation, energy and oxidative stress parameters in a large animal model.

Journal: PloS one 20110101

Title: The HIV-1 transactivator factor (Tat) induces enterocyte apoptosis through a redox-mediated mechanism.

Journal: PloS one 20110101

Title: Effects of N-acetyl-cysteine and N-acetyl-cysteine-amide supplementation on in vitro matured porcine oocytes.

Journal: Reproduction in domestic animals = Zuchthygiene 20101001

Title: HIV proteins (gp120 and Tat) and methamphetamine in oxidative stress-induced damage in the brain: potential role of the thiol antioxidant N-acetylcysteine amide.

Journal: Free radical biology & medicine 20100515

Title: N-acetylcysteine amide protects renal proximal tubular epithelial cells against iohexol-induced apoptosis by blocking p38 MAPK and iNOS signaling.

Journal: American journal of nephrology 20100101

Title: Attenuation of pulmonary inflammation after exposure to blast overpressure by N-acetylcysteine amide.

Journal: Shock (Augusta, Ga.) 20090901

Title: N-acetylcysteineamide (NACA) prevents inflammation and oxidative stress in animals exposed to diesel engine exhaust.

Journal: Toxicology letters 20090622

Title: N-Acetylcysteine amide protects against methamphetamine-induced oxidative stress and neurotoxicity in immortalized human brain endothelial cells.

Journal: Brain research 20090612

Title: N-acetylcysteine amide decreases oxidative stress but not cell death induced by doxorubicin in H9c2 cardiomyocytes.

Journal: BMC pharmacology 20090101

Title: Anti-inflammatory and arthritic effects of thiacremonone, a novel sulfur compound isolated from garlic via inhibition of NF-kappaB.

Journal: Arthritis research & therapy 20090101

Title: Effects of N-acetylcysteine amide (NACA), a thiol antioxidant on radiation-induced cytotoxicity in Chinese hamster ovary cells.

Journal: Life sciences 20080523

Title: Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC).

Journal: Free radical research 20080401

Title: N-acetylcysteine amide (AD4) attenuates oxidative stress in beta-thalassemia blood cells.

Journal: Biochimica et biophysica acta 20080201

Title: Endoplasmic reticulum stress and unfolded protein response in Atm-deficient thymocytes and thymic lymphoma cells are attributable to oxidative stress.

Journal: Neoplasia (New York, N.Y.) 20080201

Title: A novel thiol compound, N-acetylcysteine amide, attenuates allergic airway disease by regulating activation of NF-kappaB and hypoxia-inducible factor-1alpha.

Journal: Experimental & molecular medicine 20071231

Title: [N-acetylcysteine improves lysosomal function and enhances the degradation of photoreceptor outer segments in cultured RPE cells].

Journal: Klinische Monatsblatter fur Augenheilkunde 20070701

Title: Advanced glycation end products attenuate cellular insulin sensitivity by increasing the generation of intracellular reactive oxygen species in adipocytes.

Journal: Diabetes research and clinical practice 20070501

Title: Role of N-acetylcysteine in the management of COPD.

Journal: International journal of chronic obstructive pulmonary disease 20061201

Title: Potentiation of lead-induced cell death in PC12 cells by glutamate: protection by N-acetylcysteine amide (NACA), a novel thiol antioxidant.

Journal: Toxicology and applied pharmacology 20061015

Title: A novel antioxidant N-acetylcysteine amide prevents gp120- and Tat-induced oxidative stress in brain endothelial cells.

Journal: Experimental neurology 20060901

Title: Separation and quantification of N-acetyl-l-cysteine and N-acetyl-cysteine-amide by HPLC with fluorescence detection.

Journal: Biomedical chromatography : BMC 20060501

Title: Low molecular weight thiol amides attenuate MAPK activity and protect primary neurons from Abeta(1-42) toxicity.

Journal: Brain research 20060119

Title: Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12.

Journal: Brain research 20050921

Title: Is brain dehydroepiandrosterone synthesis modulated by free radicals in mice?

Journal: Neuroscience letters 20050329

Title: N-acetylcysteine amide, a novel cell-permeating thiol, restores cellular glutathione and protects human red blood cells from oxidative stress.

Journal: Free radical biology & medicine 20050101

Title: Analysis of gene expression in MOG-induced experimental autoimmune encephalomyelitis after treatment with a novel brain-penetrating antioxidant.

Journal: Journal of molecular neuroscience : MN 20050101

Title: A novel brain-targeted antioxidant (AD4) attenuates haloperidol-induced abnormal movement in rats: implications for tardive dyskinesia.

Journal: Clinical neuropharmacology 20050101

Title: A low molecular weight copper chelator crosses the blood-brain barrier and attenuates experimental autoimmune encephalomyelitis.

Journal: Journal of neurochemistry 20040601

Title: Shi R, et al. N-acetylcysteine amide decreases oxidative stress but not cell death induced by doxorubicin in H9c2 cardiomyocytes. BMC Pharmacol. 2009 Apr 15;9:7.

Title: Pandya JD, et al. N-acetylcysteine amide confers neuroprotection, improves bioenergetics and behavioral outcome following TBI. Exp Neurol. 2014 Jul;257:106-13.

Title: Zhang X, et al. N-Acetylcysteine amide protects against methamphetamine-induced oxidative stress and neurotoxicity in immortalized human brain endothelial cells. Brain Res. 2009 Jun 12;1275:87-95.

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