ACETYLCYSTEINAMIDE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805071 | https://www.ncbi.nlm.nih.gov/pubmed/23472882 | https://www.ncbi.nlm.nih.gov/pubmed/15733082

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
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23472882	Inhibitor 8504
Apoptosis 156 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23472882	Inhibitor 8504
mitochondrial respiratory chain 3 Target ID: GO:0005746 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805071	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Retinitis pigmentosa 10 Sources: http://adisinsight.springer.com/drugs/800049761 http://adisinsight.springer.com/trials/700286204 http://adisinsight.springer.com/trials/700286089	Primary	Phase II 1147	Unknown Approved Use Unknown
Spinal cord injury 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805071	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15733082 https://www.ncbi.nlm.nih.gov/pubmed/23472882	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of N-acetyl-cysteine and N-acetyl-cysteine-amide supplementation on in vitro matured porcine oocytes.	2010-10	19220795
HIV proteins (gp120 and Tat) and methamphetamine in oxidative stress-induced damage in the brain: potential role of the thiol antioxidant N-acetylcysteine amide.	2010-05-15	20188164
N-acetylcysteine amide protects renal proximal tubular epithelial cells against iohexol-induced apoptosis by blocking p38 MAPK and iNOS signaling.	2010	20016144
Attenuation of pulmonary inflammation after exposure to blast overpressure by N-acetylcysteine amide.	2009-09	19174737
N-acetylcysteineamide (NACA) prevents inflammation and oxidative stress in animals exposed to diesel engine exhaust.	2009-06-22	19429263
N-Acetylcysteine amide protects against methamphetamine-induced oxidative stress and neurotoxicity in immortalized human brain endothelial cells.	2009-06-12	19374890
N-acetylcysteine amide decreases oxidative stress but not cell death induced by doxorubicin in H9c2 cardiomyocytes.	2009-04-15	19368719
Anti-inflammatory and arthritic effects of thiacremonone, a novel sulfur compound isolated from garlic via inhibition of NF-kappaB.	2009	19788760
Effects of N-acetylcysteine amide (NACA), a thiol antioxidant on radiation-induced cytotoxicity in Chinese hamster ovary cells.	2008-05-23	18448127
Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC).	2008-04	18404536
Endoplasmic reticulum stress and unfolded protein response in Atm-deficient thymocytes and thymic lymphoma cells are attributable to oxidative stress.	2008-02	18283338
N-acetylcysteine amide (AD4) attenuates oxidative stress in beta-thalassemia blood cells.	2008-02	18082636
A novel thiol compound, N-acetylcysteine amide, attenuates allergic airway disease by regulating activation of NF-kappaB and hypoxia-inducible factor-1alpha.	2007-12-31	18160846
[N-acetylcysteine improves lysosomal function and enhances the degradation of photoreceptor outer segments in cultured RPE cells].	2007-07	17657692
Advanced glycation end products attenuate cellular insulin sensitivity by increasing the generation of intracellular reactive oxygen species in adipocytes.	2007-05	17097186
Potentiation of lead-induced cell death in PC12 cells by glutamate: protection by N-acetylcysteine amide (NACA), a novel thiol antioxidant.	2006-10-15	16781745
A novel antioxidant N-acetylcysteine amide prevents gp120- and Tat-induced oxidative stress in brain endothelial cells.	2006-09	16750528
Separation and quantification of N-acetyl-l-cysteine and N-acetyl-cysteine-amide by HPLC with fluorescence detection.	2006-05	16167305
Low molecular weight thiol amides attenuate MAPK activity and protect primary neurons from Abeta(1-42) toxicity.	2006-01-19	16386719
Role of N-acetylcysteine in the management of COPD.	2006	18044098
A novel brain-targeted antioxidant (AD4) attenuates haloperidol-induced abnormal movement in rats: implications for tardive dyskinesia.	2005-12-13	16340385
Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12.	2005-09-21	16120436
Is brain dehydroepiandrosterone synthesis modulated by free radicals in mice?	2005-03-29	15740851
N-acetylcysteine amide, a novel cell-permeating thiol, restores cellular glutathione and protects human red blood cells from oxidative stress.	2005-01-01	15589382
Analysis of gene expression in MOG-induced experimental autoimmune encephalomyelitis after treatment with a novel brain-penetrating antioxidant.	2005	16055951
A low molecular weight copper chelator crosses the blood-brain barrier and attenuates experimental autoimmune encephalomyelitis.	2004-06	15147517

Patents

Sample Use Guides

In Vivo Use Guide

75, 150, 300 or 600 mg/kg body weight at 15min and 6h post-injury

Route of Administration: Intraperitoneal

In Vitro Use Guide

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.

Name

Type

Language

ACETYLCYSTEINE AMIDE

Preferred Name

English

ACETYLCYSTEINAMIDE

Systematic Name

English

PROPANAMIDE, 2-(ACETYLAMINO)-3-MERCAPTO-, (R)-

Systematic Name

English

N-ACETYL CYSTEINE AMIDE

Common Name

English

N-ACETYL-L-CYSTEINAMIDE

Systematic Name

English

PROPANAMIDE, 2-(ACETYLAMINO)-3-MERCAPTO-, (2R)-

Systematic Name

English

N-ACETYLCYSTEINAMIDE

Systematic Name

English

N-ACETYL-CYSTEINE-AMIDE

Common Name

English

NACA

Common Name

English

NAC AMIDE

Common Name

English

N-ACETYLCYSTEINE AMIDE

Common Name

English

N-ACETYL-L-CYSTEINE AMIDE

Common Name

English

AD4

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C275