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MedKoo Cat#: 574815 | Name: NCX-4040
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Description:

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

NCX-4040 is an NO-donating aspirin and anti-inflammatory that blocks inflammatory mediator production in isolated human monocytes, decreases COX-2 expression, and disrupts proteasome-mediated degradation of iκB-α. NCX-4040 also acts as an antiproliferative in HCT116 colon cancer cells and sensitizes drug-resistant ovarian tumor cells to cisplatin.

Chemical Structure

NCX-4040
NCX-4040
CAS# 287118-97-2

Theoretical Analysis

MedKoo Cat#: 574815

Name: NCX-4040

CAS#: 287118-97-2

Chemical Formula: C16H13NO7

Exact Mass: 331.0692

Molecular Weight: 331.28

Elemental Analysis: C, 58.01; H, 3.96; N, 4.23; O, 33.81

Price and Availability

Size Price Availability Quantity
10mg USD 355.00 2 Weeks
50mg USD 1,195.00 2 Weeks
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Related CAS #
No Data
Synonym
NCX-4040; NCX4040; NCX 4040; NO-aspirin
IUPAC/Chemical Name
2-(Acetyloxy)benzoic acid 4-[(nitrooxy)methyl]phenyl ester
InChi Key
CTHNKWFUDCMLIQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H13NO7/c1-11(18)23-15-5-3-2-4-14(15)16(19)24-13-8-6-12(7-9-13)10-22-17(20)21/h2-9H,10H2,1H3
SMILES Code
O=C(OC1=CC=C(CO[N+]([O-])=O)C=C1)C2=CC=CC=C2OC(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
>3 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:
NCX4040 (NO-Aspirin), a non-steroidal anti-inflammatory drug (NSAID), is a nitric oxide (NO) releasing form of Aspirin.
In vitro activity:
Data revealed that NCX4040 is more potent than its parent compound aspirin or NO releasing compound DETA NONOate. NCX4040 significantly induced hydrogen peroxide formation with ensuing oxidative stress and mitochondrial depolarization resulting in lipid peroxidation, cell cycle arrest, inhibition of colony growth and induction of apoptosis in PC3 cells. Moreover, NCX4040 inhibited migration potential of PC3 cells by depolymerizing F-actin and promoting anoikis. Reference: Free Radic Biol Med. 2019 Nov 1;143:494-509. https://pubmed.ncbi.nlm.nih.gov/31446057/
In vivo activity:
In the in vivo experiments, tumor-bearing mice were treated with NCX 4040, five times a week, for six consecutive weeks. In in vivo studies, both NCX 4040 and its parental compound were administered per os. NCX 4040 induced a 40% reduction in tumor weight. Conversely, aspirin did not influence tumor growth at all. Reference: J Transl Med. 2005 Feb 3;3(1):7. https://pubmed.ncbi.nlm.nih.gov/15691389/
Solvent mg/mL mM
Solubility
DMSO 100.0 301.86
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 331.28 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
Formulation protocol:
1. Chinnapaka S, Zheng G, Chen A, Munirathinam G. Nitro aspirin (NCX4040) induces apoptosis in PC3 metastatic prostate cancer cells via hydrogen peroxide (H2O2)-mediated oxidative stress. Free Radic Biol Med. 2019 Nov 1;143:494-509. doi: 10.1016/j.freeradbiomed.2019.08.025. Epub 2019 Aug 22. PMID: 31446057; PMCID: PMC6848783. 2. Ricciotti E, Dovizio M, Di Francesco L, Anzellotti P, Salvatore T, Di Francesco A, Sciulli MG, Pistritto G, Monopoli A, Patrignani P. NCX 4040, a nitric oxide-donating aspirin, exerts anti-inflammatory effects through inhibition of I kappa B-alpha degradation in human monocytes. J Immunol. 2010 Feb 15;184(4):2140-7. doi: 10.4049/jimmunol.0903107. Epub 2010 Jan 11. PMID: 20065114. 3. Tesei A, Ulivi P, Fabbri F, Rosetti M, Leonetti C, Scarsella M, Zupi G, Amadori D, Bolla M, Zoli W. In vitro and in vivo evaluation of NCX 4040 cytotoxic activity in human colon cancer cell lines. J Transl Med. 2005 Feb 3;3(1):7. doi: 10.1186/1479-5876-3-7. PMID: 15691389; PMCID: PMC549525.
In vitro protocol:
1. Chinnapaka S, Zheng G, Chen A, Munirathinam G. Nitro aspirin (NCX4040) induces apoptosis in PC3 metastatic prostate cancer cells via hydrogen peroxide (H2O2)-mediated oxidative stress. Free Radic Biol Med. 2019 Nov 1;143:494-509. doi: 10.1016/j.freeradbiomed.2019.08.025. Epub 2019 Aug 22. PMID: 31446057; PMCID: PMC6848783. 2. Ricciotti E, Dovizio M, Di Francesco L, Anzellotti P, Salvatore T, Di Francesco A, Sciulli MG, Pistritto G, Monopoli A, Patrignani P. NCX 4040, a nitric oxide-donating aspirin, exerts anti-inflammatory effects through inhibition of I kappa B-alpha degradation in human monocytes. J Immunol. 2010 Feb 15;184(4):2140-7. doi: 10.4049/jimmunol.0903107. Epub 2010 Jan 11. PMID: 20065114.
In vivo protocol:
1. Tesei A, Ulivi P, Fabbri F, Rosetti M, Leonetti C, Scarsella M, Zupi G, Amadori D, Bolla M, Zoli W. In vitro and in vivo evaluation of NCX 4040 cytotoxic activity in human colon cancer cell lines. J Transl Med. 2005 Feb 3;3(1):7. doi: 10.1186/1479-5876-3-7. PMID: 15691389; PMCID: PMC549525.
1. Ricciotti et al (2010) NCX 4040, a nitric oxide-donating aspirin, exerts anti-inflammatory effects through inhibition of I kappa B-alpha degradation in human monocytes. J.Immunol. 184 2140 PMID: 20065114 2. Yamakawa et al (2008) Growth inhibition of human colon cancer cell line HCT116 by bis[2-(acylamino)phenyl] disulfide and its action mechanism. Biol.Pharm.Bull. 31 916 PMID: 18451518 3. Bratasz et al (2008) NCX-4040, a nitric oxide-releasing aspirin, sensitizes drug-resistant human ovarian xenograft tumors to cisp. by depletion of cellular thiols. J.Transl.Med. 6 9 PMID: 18302761 4. Gao et al (2008) Immunomodulatory activity of synthetic triterpenoids: inhibition of lymphocyte proliferation, cell-mediated cytotoxicity, and cytokine gene expression through suppression of NF-κB. Immunopharmacol.Immunotoxicol. 30 581 PMID: 18608528

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Ro 31-1118