N-Acetylcysteine amide

Names

[ Name ]:
N-Acetylcysteine amide

[Synonym ]:
Nac amide
acetylcysteinamide
Acetylcysteine amide
(R)- 2-(Acetylamino)-3-mercapto-Propanamide AD4 N-Acetyl-L-cysteinamide NACA acetylcysteinamide
N-Acetyl-L-cysteine amide
N-Acetylcysteine amide
NACA
N-Acetyl-L-cysteinamide

Biological Activity

[Description]:

N-Acetylcysteine amide is a cell membranes and blood brain barrier permeant thiol antioxidant and neuroprotective agent.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[In Vitro]

N-Acetylcysteine amide shows no obvious effect on the viability of H9c2 cells treated with doxorubicin (DOX) at < 1 mM, but causes significant cytotoxicity at 10-20 mM. N-Acetylcysteine amide (750 μM) reduces the ROS levle and lipid peroxidation induced by DOX, and restores GSH/GSSG ratio and activities of antioxidant enzymes, such as catalase (CAT), gluthathione peroxidase (GPx), gluthathione reductase (GR)[1]. N-Acetylcysteine amide (1 mM) protects the human brain microvascular endothelial (HBMVEC) from methamphetamine (METH)- induced cell death[3].

[In Vivo]

N-Acetylcysteine amide has increased CNS bioavailability. N-Acetylcysteine amide (150 mg/kg, i.p.) improves cortical sparing and functional outcome, reduces oxidative stress, improves mitochondrial bioenergetics, and maintains mitochondrial glutathione content following traumatic brain injury (TBI) in rats[2].

[Cell Assay]

To choose a sublethal concentration of N-Acetylcysteine amide and N-acetylcysteine for the study on their ability to protect cells from doxorubicin (DOX)-induced toxicity, H9c2 cells are exposed with N-Acetylcysteine amide or N-acetylcysteine at 0.25 mM, 0.50 mM, 0.75 mM, 1 mM, 2 mM, 5 mM, 10 mM, and 20 mM for 24 h. Untreated cells are used as the control for each experiment[1].

[Animal admin]

Rats[2] In order to assess mitochondrial respiration and glutathione content following traumatic brain injury (TBI), rats are randomly divided into three groups (n = 5 animals/group). (I.) N-Acetylcysteine amide group receives multiple bolus IP injections of N-Acetylcysteine amide (150 mg/kg) immediately after 5 minutes and then every 6 hours up to 24 hrs post-injury. (II.) Vehicle group receives equivalent v/v saline at 5 minutes and every 6 hours (6, 12, 18, 24 hrs) up to 24 hrs post-injury. (III.) Sham injured group animals do not receive any drug treatment. At 25 hrs post-injury, all animals are euthanized and mitochondria are isolated from the ipsilateral cortical hemisphere (6 mm punch) to carry out measurements of mitochondrial respiration and glutathione content[2].

[References]

[1]. 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.

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

[3]. 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.

[Related Small Molecules]

Chemical & Physical Properties

[ Molecular Formula ]:
C₅H₁₀N₂O₂S

[ Molecular Weight ]:
162.21000

[ Exact Mass ]:
162.04600

[ PSA ]:
115.47000

[ LogP ]:
0.89620

[ Storage condition ]:
-20℃

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2930909090

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Related Compounds

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