N-Monoacetylcystine | CAS#25779-79-7 | antidote

MedKoo Cat#: 597031 | Name: N-Monoacetylcystine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

N-Monoacetylcystine is an antidote for paracetamol poisoning. It is also an antioxidant, used in the treatment of influenza A virus pandemic. N-Acetyl-L-cystine promotes fertilization by reducing disulfide bonds in zona pellucida of mouse.

Chemical Structure

N-Monoacetylcystine

CAS#25779-79-7

Theoretical Analysis

MedKoo Cat#: 597031

Name: N-Monoacetylcystine

CAS#: 25779-79-7

Chemical Formula: C8H14N2O5S2

Exact Mass: 282.0344

Molecular Weight: 282.33

Elemental Analysis: C, 34.03; H, 5.00; N, 9.92; O, 28.33; S, 22.71

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 340.00
50mg	USD 610.00
100mg	USD 1,080.00

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Synonym

N-Monoacetylcystine; Parvolex; N-Acetylcystine;

IUPAC/Chemical Name

N-acetyl-S-(((S)-2-amino-2-carboxyethyl)thio)-L-cysteine

InChi Key

ZLCOWUKVVFVVKA-RITPCOANSA-N

InChi Code

InChI=1S/C8H14N2O5S2/c1-4(11)10-6(8(14)15)3-17-16-2-5(9)7(12)13/h5-6H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t5-,6+/m1/s1

SMILES Code

N[C@@H](C(O)=O)CSSC[C@@H](C(O)=O)NC(C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

N-Monoacetylcystine is an antidote for paracetamol poisoning.

In vitro activity:

N-acetylcysteine (NAC) significantly reduced only nonmetal hapten-induced cell death as assessed by propidium iodide exclusion. NAC reduced cell death and ATP release, whereas antioxidants and Panx inhibitors did not inhibit cell death but significantly attenuated ATP release. Reference: J Invest Dermatol. 2014 Jul;134(7):1951-1960. https://pubmed.ncbi.nlm.nih.gov/24531690/

In vivo activity:

The current study assessed whether acute NAC (N-acetylcysteine) could reduce ethanol self-administration, ethanol-seeking behavior, motivation, and reacquisition of ethanol self-administration following abstinence in ethanol-dependent rats. In dependent rats, the low dose of NAC (25 mg/kg) reduced ethanol self-administration and motivation to consume ethanol, evaluated in a progressive ratio paradigm. At 50 mg/kg, but not 25 mg/kg, NAC reduced extinction responding and reacquisition of self-administration after 1 month abstinence. Reference: Neuropharmacology. 2019 May 15;150:112-120. https://pubmed.ncbi.nlm.nih.gov/30880122/

Preparing Stock Solutions

The following data is based on the product molecular weight 282.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Onami K, Kimura Y, Ito Y, Yamauchi T, Yamasaki K, Aiba S. Nonmetal haptens induce ATP release from keratinocytes through opening of pannexin hemichannels by reactive oxygen species. J Invest Dermatol. 2014 Jul;134(7):1951-1960. doi: 10.1038/jid.2014.93. Epub 2014 Feb 14. PMID: 24531690. 2. Ade N, Leon F, Pallardy M, Peiffer JL, Kerdine-Romer S, Tissier MH, Bonnet PA, Fabre I, Ourlin JC. HMOX1 and NQO1 genes are upregulated in response to contact sensitizers in dendritic cells and THP-1 cell line: role of the Keap1/Nrf2 pathway. Toxicol Sci. 2009 Feb;107(2):451-60. doi: 10.1093/toxsci/kfn243. Epub 2008 Nov 25. PMID: 19033392. 3. Lebourgeois S, González-Marín MC, Antol J, Naassila M, Vilpoux C. Evaluation of N-acetylcysteine on ethanol self-administration in ethanol-dependent rats. Neuropharmacology. 2019 May 15;150:112-120. doi: 10.1016/j.neuropharm.2019.03.010. Epub 2019 Mar 15. PMID: 30880122. 4. Liu JQ, Lee TF, Chen C, Bagim DL, Cheung PY. N-acetylcysteine improves hemodynamics and reduces oxidative stress in the brains of newborn piglets with hypoxia-reoxygenation injury. J Neurotrauma. 2010 Oct;27(10):1865-73. doi: 10.1089/neu.2010.1325. PMID: 20649480.

In vitro protocol:

In vivo protocol:

1. Lebourgeois S, González-Marín MC, Antol J, Naassila M, Vilpoux C. Evaluation of N-acetylcysteine on ethanol self-administration in ethanol-dependent rats. Neuropharmacology. 2019 May 15;150:112-120. doi: 10.1016/j.neuropharm.2019.03.010. Epub 2019 Mar 15. PMID: 30880122. 2. Liu JQ, Lee TF, Chen C, Bagim DL, Cheung PY. N-acetylcysteine improves hemodynamics and reduces oxidative stress in the brains of newborn piglets with hypoxia-reoxygenation injury. J Neurotrauma. 2010 Oct;27(10):1865-73. doi: 10.1089/neu.2010.1325. PMID: 20649480.

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Am J Crit Care. 2015 Sep;24(5):440-5. doi: 10.4037/ajcc2015335. PubMed PMID: 26330437. 5: Tork S, Kelley SR, Tymitz KM. A novel use of N-acetylcystine for the management of recurrent small bowel pseudo-obstruction in a patient with autoimmune autonomic ganglionopathy. Am Surg. 2015 May;81(5):E226-7. PubMed PMID: 25975318. 6: Azuelos I, Jung B, Picard M, Liang F, Li T, Lemaire C, Giordano C, Hussain S, Petrof BJ. Relationship between Autophagy and Ventilator-induced Diaphragmatic Dysfunction. Anesthesiology. 2015 Jun;122(6):1349-61. doi: 10.1097/ALN.0000000000000656. PubMed PMID: 25828754. 7: Liu H, Gooneratne R, Huang X, Lai R, Wei J, Wang W. A rapid in vivo zebrafish model to elucidate oxidative stress-mediated PCB126-induced apoptosis and developmental toxicity. Free Radic Biol Med. 2015 Jul;84:91-102. doi: 10.1016/j.freeradbiomed.2015.03.002. Epub 2015 Mar 12. PubMed PMID: 25770664. 8: von der Beck D, Löh B, Drakopanagiotakis F, Markart P, Günther A. [Antifibrotic treatment]. 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PubMed PMID: 23928270. 12: Ghanizadeh A, Moghimi-Sarani E. A randomized double blind placebo controlled clinical trial of N-Acetylcysteine added to risperidone for treating autistic disorders. BMC Psychiatry. 2013 Jul 25;13:196. doi: 10.1186/1471-244X-13-196. PubMed PMID: 23886027; PubMed Central PMCID: PMC3737121. 13: Reddell L, Cotton BA. Antioxidants and micronutrient supplementation in trauma patients. Curr Opin Clin Nutr Metab Care. 2012 Mar;15(2):181-7. doi: 10.1097/MCO.0b013e32835076df. Review. PubMed PMID: 22261953; PubMed Central PMCID: PMC3800099. 14: Reichel CM, See RE. Chronic N-acetylcysteine after cocaine self-administration produces enduring reductions in drug-seeking. Neuropsychopharmacology. 2012 Jan;37(1):298. doi: 10.1038/npp.2011.164. PubMed PMID: 22157864; PubMed Central PMCID: PMC3238061. 15: Wang ZH, Chen YX, Zhang CM, Wu L, Yu Z, Cai XL, Guan Y, Zhou ZN, Yang HT. Intermittent hypobaric hypoxia improves postischemic recovery of myocardial contractile function via redox signaling during early reperfusion. Am J Physiol Heart Circ Physiol. 2011 Oct;301(4):H1695-705. doi: 10.1152/ajpheart.00276.2011. Epub 2011 Aug 5. PubMed PMID: 21821784. 16: Liu JQ, Lee TF, Chen C, Bagim DL, Cheung PY. N-acetylcysteine improves hemodynamics and reduces oxidative stress in the brains of newborn piglets with hypoxia-reoxygenation injury. J Neurotrauma. 2010 Oct;27(10):1865-73. doi: 10.1089/neu.2010.1325. PubMed PMID: 20649480. 17: Knackstedt LA, Melendez RI, Kalivas PW. Ceftriaxone restores glutamate homeostasis and prevents relapse to cocaine seeking. Biol Psychiatry. 2010 Jan 1;67(1):81-4. doi: 10.1016/j.biopsych.2009.07.018. PubMed PMID: 19717140; PubMed Central PMCID: PMC2795043. 18: Yang R, Miki K, He X, Killeen ME, Fink MP. Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity. Crit Care. 2009;13(2):R55. doi: 10.1186/cc7782. Epub 2009 Apr 9. PubMed PMID: 19358737; PubMed Central PMCID: PMC2689502. 19: Ade N, Leon F, Pallardy M, Peiffer JL, Kerdine-Romer S, Tissier MH, Bonnet PA, Fabre I, Ourlin JC. HMOX1 and NQO1 genes are upregulated in response to contact sensitizers in dendritic cells and THP-1 cell line: role of the Keap1/Nrf2 pathway. Toxicol Sci. 2009 Feb;107(2):451-60. doi: 10.1093/toxsci/kfn243. Epub 2008 Nov 25. PubMed PMID: 19033392. 20: Zhang G, Wu H, Zhu B, Shimoishi Y, Nakamura Y, Murata Y. Effect of dimethyl sulfides on the induction of apoptosis in human leukemia Jurkat cells and HL-60 cells. Biosci Biotechnol Biochem. 2008 Nov;72(11):2966-72. Epub 2008 Nov 7. PubMed PMID: 18997406.