MedKoo Cat#: 597015 | Name: S-Nitroso-N-acetylcysteine

Description:

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

S-Nitroso-N-acetylcysteine inhibits proliferation and survival of multiple MM cells via S-nitrosylation-dependent inhibition of STAT3 and NF-κB.

Chemical Structure

S-Nitroso-N-acetylcysteine
S-Nitroso-N-acetylcysteine
CAS#56577-02-7

Theoretical Analysis

MedKoo Cat#: 597015

Name: S-Nitroso-N-acetylcysteine

CAS#: 56577-02-7

Chemical Formula: C5H8N2O4S

Exact Mass: 192.0205

Molecular Weight: 192.18

Elemental Analysis: C, 31.25; H, 4.20; N, 14.58; O, 33.30; S, 16.68

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
S-Nitroso-N-acetylcysteine; S-Nitrosoacetylcysteine;
IUPAC/Chemical Name
N-acetyl-S-nitroso-L-cysteine
InChi Key
QTJKCQPXTOYYHJ-BYPYZUCNSA-N
InChi Code
InChI=1S/C5H8N2O4S/c1-3(8)6-4(5(9)10)2-12-7-11/h4H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1
SMILES Code
O=C(O)[C@H](CSN=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

Preparing Stock Solutions

The following data is based on the product molecular weight 192.18 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.

Recalculate based on batch purity %
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
1: Bouressam ML, Meyer B, Boudier A, Clarot I, Leroy P, Genoni A, Ruiz-Lopez M, Giummelly P, Liminana P, Salgues V, Kouach M, Perrin-Sarrado C, Lartaud I, Dupuis F. In vivo and in silico evaluation of a new nitric oxide donor, S,S'-dinitrosobucillamine. Nitric Oxide. 2017 Dec 1;71:32-43. doi: 10.1016/j.niox.2017.10.004. Epub 2017 Oct 16. PubMed PMID: 29051112. 2: Kim J, Choi S, Saxena N, Singh AK, Singh I, Won JS. Regulation of STAT3 and NF-κB activations by S-nitrosylation in multiple myeloma. Free Radic Biol Med. 2017 May;106:245-253. doi: 10.1016/j.freeradbiomed.2017.02.039. Epub 2017 Feb 21. PubMed PMID: 28232202; PubMed Central PMCID: PMC5826580. 3: Meyer B, Genoni A, Boudier A, Leroy P, Ruiz-Lopez MF. Structure and Stability Studies of Pharmacologically Relevant S-Nitrosothiols: A Theoretical Approach. J Phys Chem A. 2016 Jun 23;120(24):4191-200. doi: 10.1021/acs.jpca.6b02230. Epub 2016 Jun 9. PubMed PMID: 27249061. 4: de Souza GF, de Oliveira MG. Intratablet S-nitrosation: A New Approach for the Oral Administration of S-nitrosothiols as Nitric Oxide Donors. J Pharm Sci. 2016 Jan;105(1):359-61. doi: 10.1016/j.xphs.2015.10.011. Epub 2015 Dec 18. PubMed PMID: 26852866. 5: de Souza GF, Taladriz-Blanco P, Velloso LA, de Oliveira MG. Nitric oxide released from luminal s-nitroso-N-acetylcysteine increases gastric mucosal blood flow. Molecules. 2015 Mar 4;20(3):4109-23. doi: 10.3390/molecules20034109. PubMed PMID: 25749680. 6: Tenopoulou M, Chen J, Bastin J, Bennett MJ, Ischiropoulos H, Doulias PT. Strategies for correcting very long chain acyl-CoA dehydrogenase deficiency. J Biol Chem. 2015 Apr 17;290(16):10486-94. doi: 10.1074/jbc.M114.635102. Epub 2015 Mar 3. PubMed PMID: 25737446; PubMed Central PMCID: PMC4400356. 7: Lutz A, Sfara V, Alzogaray RA. Repellence produced by monoterpenes on Rhodnius prolixus (Hemiptera: Reduviidae) decreases after continuous exposure to these compounds. J Insect Sci. 2014 Jan 1;14. pii: 254. doi: 10.1093/jisesa/ieu116. Print 2014. PubMed PMID: 25525113; PubMed Central PMCID: PMC5634126. 8: Hanff E, Böhmer A, Jordan J, Tsikas D. Stable-isotope dilution LC-MS/MS measurement of nitrite in human plasma after its conversion to S-nitrosoglutathione. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Nov 1;970:44-52. doi: 10.1016/j.jchromb.2014.08.041. Epub 2014 Sep 6. PubMed PMID: 25237784. 9: Yang X, Chen B, Liu T, Chen X. Reversal of myofibroblast differentiation: a review. Eur J Pharmacol. 2014 Jul 5;734:83-90. doi: 10.1016/j.ejphar.2014.04.007. Epub 2014 Apr 15. Review. PubMed PMID: 24742377. 10: Dahboul F, Perrin-Sarrado C, Boudier A, Lartaud I, Schneider R, Leroy P. S,S'-dinitrosobucillamine, a new nitric oxide donor, induces a better vasorelaxation than other S-nitrosothiols. Eur J Pharmacol. 2014 May 5;730:171-9. doi: 10.1016/j.ejphar.2014.02.034. Epub 2014 Mar 10. PubMed PMID: 24625595. 11: Wanschel AC, Caceres VM, Moretti AI, Bruni-Cardoso A, de Carvalho HF, de Souza HP, Laurindo FR, Spadari RC, Krieger MH. Cardioprotective mechanism of S-nitroso-N-acetylcysteine via S-nitrosated betadrenoceptor-2 in the LDLr-/- mice. Nitric Oxide. 2014 Jan 30;36:58-66. doi: 10.1016/j.niox.2013.12.003. Epub 2013 Dec 12. PubMed PMID: 24333561. 12: Mazo DF, de Oliveira MG, Pereira IV, Cogliati B, Stefano JT, de Souza GF, Rabelo F, Lima FR, Ferreira Alves VA, Carrilho FJ, de Oliveira CP. S-nitroso-N-acetylcysteine attenuates liver fibrosis in experimental nonalcoholic steatohepatitis. Drug Des Devel Ther. 2013 Jun 28;7:553-63. doi: 10.2147/DDDT.S43930. Print 2013. Erratum in: Drug Des Devel Ther. 2013;7:971-2. PubMed PMID: 23843692; PubMed Central PMCID: PMC3702228. 13: Cariello AJ, Souza GF, Lowen MS, Oliveira MG, Höfling-Lima AL. Assessment of ocular surface toxicity after topical instillation of nitric oxide donors. Arq Bras Oftalmol. 2013 Jan-Feb;76(1):38-41. PubMed PMID: 23812526. 14: Cariello AJ, Bispo PJ, de Souza GF, Pignatari AC, de Oliveira MG, Hofling-Lima AL. Bactericidal effect of S-nitrosothiols against clinical isolates from keratitis. Clin Ophthalmol. 2012;6:1907-14. doi: 10.2147/OPTH.S34830. Epub 2012 Nov 20. PubMed PMID: 23204833; PubMed Central PMCID: PMC3508747. 15: Nacharaju P, Tuckman-Vernon C, Maier KE, Chouake J, Friedman A, Cabrales P, Friedman JM. A nanoparticle delivery vehicle for S-nitroso-N-acetyl cysteine: sustained vascular response. Nitric Oxide. 2012 Oct 15;27(3):150-60. doi: 10.1016/j.niox.2012.06.003. Epub 2012 Jun 15. PubMed PMID: 22705913; PubMed Central PMCID: PMC4156139. 16: Camacho VR, de Fraga RS, Cerski CT, de Oliveira JR, Álvares-da-Silva MR. Relationship between ischemia/reperfusion injury and the stimulus of fibrogenesis in an experimental model: comparison among different preservation solutions. Transplant Proc. 2011 Dec;43(10):3634-7. doi: 10.1016/j.transproceed.2011.08.114. Erratum in: Transplant Proc. 2012 Jun;44(5):1464. Oliveira, J R [corrected to de Oliveira, J R]; Fraga, R S [corrected to de Fraga, R S]; Alvares-Dasilva, M R [corrected to Álvares-da-Silva, M R]; Oliveira, J R [removed]; Souza, G F [removed]. PubMed PMID: 22172818. 17: Hornyák I, Marosi K, Kiss L, Gróf P, Lacza Z. Increased stability of S-nitrosothiol solutions via pH modulations. Free Radic Res. 2012 Feb;46(2):214-25. doi: 10.3109/10715762.2011.647692. Epub 2012 Jan 12. PubMed PMID: 22149535. 18: Stefano JT, Cogliati B, Santos F, Lima VM, Mazo DC, Matte U, Alvares-da-Silva MR, Silveira TR, Carrilho FJ, Oliveira CP. S-Nitroso-N-acetylcysteine induces de-differentiation of activated hepatic stellate cells and promotes antifibrotic effects in vitro. Nitric Oxide. 2011 Oct 30;25(3):360-5. doi: 10.1016/j.niox.2011.07.001. Epub 2011 Jul 27. PubMed PMID: 21820071. 19: Moran EE, Timerghazin QK, Kwong E, English AM. Kinetics and mechanism of S-nitrosothiol acid-catalyzed hydrolysis: sulfur activation promotes facile NO+ release. J Phys Chem B. 2011 Mar 31;115(12):3112-26. doi: 10.1021/jp1035597. Epub 2011 Mar 8. PubMed PMID: 21384833. 20: Scherer de Fraga R, Camacho VR, Souza GF, Cerski CT, de Oliveira JR, de Oliveira MG, Álvares-da-Silva MR. S-nitroso-N-acetylcysteine: a promising drug for early ischemia/reperfusion injury in rat liver. Transplant Proc. 2010 Dec;42(10):4491-5. doi: 10.1016/j.transproceed.2010.09.152. PubMed PMID: 21168722.