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MedKoo Cat#: 529508 | Name: Nitroaspirin
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Description:

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

Nitroaspirin is a nitric oxide donor potentially for the treatment of peripheral arterial obstructive disease (PAOD).

Chemical Structure

Nitroaspirin
CAS#175033-36-0

Theoretical Analysis

MedKoo Cat#: 529508

Name: Nitroaspirin

CAS#: 175033-36-0

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
5mg USD 190.00
10mg USD 350.00
25mg USD 650.00
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Related CAS #
No Data
Synonym
NCX-4016; NO-ASA; m-NO-ASA; m-NO-aspirin; NCX4016; NOASA; mNOASA; NCX 4016; NO ASA; m NO ASA
IUPAC/Chemical Name
2-((nitrooxy)methyl)phenyl 2-acetoxybenzoate
InChi Key
SGYYAQBLQPNUIL-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H13NO7/c1-11(18)23-15-9-5-3-7-13(15)16(19)24-14-8-4-2-6-12(14)10-22-17(20)21/h2-9H,10H2,1H3
SMILES Code
O=C(OC1=CC=CC=C1CO[N+]([O-])=O)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
>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:
Nitroaspirin (NCX 4016) is a nitric oxide (NO) donor and acts as a direct and irreversible inhibitor of COX-1.
In vitro activity:
The inhibitory effect of NCX-4016 on cell proliferation was associated with G(1) phase cell cycle arrest with increased activity of p53, p21 and p27 proteins. NCX-4016 modulated the Bcl-2 family of proteins, and induced apoptosis by activating Bax and cytochrome c release in a time-dependent manner. Taken together, the results clearly suggested that NCX-4016 causes significant induction of cell cycle arrest and apoptosis in cisplatin-resistant human ovarian cancer cells via down-regulation of EGFR/PI3K/STAT3 signaling and modulation of Bcl-2 family proteins. Reference: Cell Cycle. 2008 Jan 1;7(1):81-8. https://pubmed.ncbi.nlm.nih.gov/18196976/
In vivo activity:
Furthermore, this study was interested in comparing the effects of a conventional NO donor [2,2'-hydroxynitrosohydrazino-bis-etanamine (DETA/NO)] and NCX-4016 at the microvascular level in the hamster cheek pouch visualized by using an intravital fluorescent microscopy technique. Pretreatment with NCX-4016 maintained ROS at normal levels; increased arteriolar diameter, blood flow, and PCL; and decreased leukocyte adhesion (P < 0.05). DETA-NO decreased ROS during 30-min reperfusion; however, later there was a significant increase during reperfusion. Reference: Am J Physiol Gastrointest Liver Physiol. 2004 Mar;286(3):G437-43. https://pubmed.ncbi.nlm.nih.gov/14563672/

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. Selvendiran K, Bratasz A, Tong L, Ignarro LJ, Kuppusamy P. NCX-4016, a nitro-derivative of aspirin, inhibits EGFR and STAT3 signaling and modulates Bcl-2 proteins in cisplatin-resistant human ovarian cancer cells and xenografts. Cell Cycle. 2008 Jan 1;7(1):81-8. doi: 10.4161/cc.7.1.5103. Epub 2007 Sep 28. PMID: 18196976; PMCID: PMC2890223. 2. Parinandi NL, Sharma A, Eubank TD, Kaufman BF, Kutala VK, Marsh CB, Ignarro LJ, Kuppusamy P. Nitroaspirin (NCX-4016), an NO donor, is antiangiogenic through induction of loss of redox-dependent viability and cytoskeletal reorganization in endothelial cells. Antioxid Redox Signal. 2007 Nov;9(11):1837-49. doi: 10.1089/ars.2007.1603. PMID: 17760507. 3. Corazzi T, Leone M, Maucci R, Corazzi L, Gresele P. Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). J Pharmacol Exp Ther. 2005 Dec;315(3):1331-7. doi: 10.1124/jpet.105.089896. Epub 2005 Sep 6. PMID: 16144976. 4. Bertuglia S, Giusti A, Del Soldato P. Antioxidant activity of nitro derivative of aspirin against ischemia-reperfusion in hamster cheek pouch microcirculation. Am J Physiol Gastrointest Liver Physiol. 2004 Mar;286(3):G437-43. doi: 10.1152/ajpgi.00339.2003. Epub 2003 Oct 16. PMID: 14563672.
In vitro protocol:
1. Selvendiran K, Bratasz A, Tong L, Ignarro LJ, Kuppusamy P. NCX-4016, a nitro-derivative of aspirin, inhibits EGFR and STAT3 signaling and modulates Bcl-2 proteins in cisplatin-resistant human ovarian cancer cells and xenografts. Cell Cycle. 2008 Jan 1;7(1):81-8. doi: 10.4161/cc.7.1.5103. Epub 2007 Sep 28. PMID: 18196976; PMCID: PMC2890223. 2. Parinandi NL, Sharma A, Eubank TD, Kaufman BF, Kutala VK, Marsh CB, Ignarro LJ, Kuppusamy P. Nitroaspirin (NCX-4016), an NO donor, is antiangiogenic through induction of loss of redox-dependent viability and cytoskeletal reorganization in endothelial cells. Antioxid Redox Signal. 2007 Nov;9(11):1837-49. doi: 10.1089/ars.2007.1603. PMID: 17760507.
In vivo protocol:
1. Corazzi T, Leone M, Maucci R, Corazzi L, Gresele P. Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). J Pharmacol Exp Ther. 2005 Dec;315(3):1331-7. doi: 10.1124/jpet.105.089896. Epub 2005 Sep 6. PMID: 16144976. 2. Bertuglia S, Giusti A, Del Soldato P. Antioxidant activity of nitro derivative of aspirin against ischemia-reperfusion in hamster cheek pouch microcirculation. Am J Physiol Gastrointest Liver Physiol. 2004 Mar;286(3):G437-43. doi: 10.1152/ajpgi.00339.2003. Epub 2003 Oct 16. PMID: 14563672.
1: Momi S, Pitchford SC, Alberti PF, Minuz P, Del Soldato P, Gresele P. Nitroaspirin plus clopidogrel versus aspirin plus clopidogrel against platelet thromboembolism and intimal thickening in mice. Thromb Haemost. 2005 Mar;93(3):535-43. PubMed PMID: 15735806. 2: Parinandi NL, Sharma A, Eubank TD, Kaufman BF, Kutala VK, Marsh CB, Ignarro LJ, Kuppusamy P. Nitroaspirin (NCX-4016), an NO donor, is antiangiogenic through induction of loss of redox-dependent viability and cytoskeletal reorganization in endothelial cells. Antioxid Redox Signal. 2007 Nov;9(11):1837-49. PubMed PMID: 17760507. 3: al-Swayeh OA, Clifford RH, del Soldato P, Moore PK. A comparison of the anti-inflammatory and anti-nociceptive activity of nitroaspirin and aspirin. Br J Pharmacol. 2000 Jan;129(2):343-50. PubMed PMID: 10694241; PubMed Central PMCID: PMC1571848. 4: Carini M, Aldini G, Orioli M, Piccoli A, Rossoni G, Maffei Facino R. Nitric oxide release and distribution following oral and intraperitoneal administration of nitroaspirin (NCX 4016) in the rat. Life Sci. 2004 May 14;74(26):3291-305. PubMed PMID: 15094329. 5: Carini M, Aldini G, Orioli M, Piccoli A, Tocchetti P, Facino RM. Chemiluminescence and LC-MS/MS analyses for the study of nitric oxide release and distribution following oral administration of nitroaspirin (NCX 4016) in healthy volunteers. J Pharm Biomed Anal. 2004 Apr 16;35(2):277-87. PubMed PMID: 15063462. 6: Ambrosini MV, Mariucci G, Rambotti MG, Tantucci M, Covarelli C, De Angelis L, Del Soldato P. Ultrastructural investigations on protective effects of NCX 4016 (nitroaspirin) on macrovascular endothelium in diabetic Wistar rats. J Submicrosc Cytol Pathol. 2005 Aug;37(2):205-13. PubMed PMID: 16335593. 7: Corazzi T, Leone M, Maucci R, Corazzi L, Gresele P. Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). J Pharmacol Exp Ther. 2005 Dec;315(3):1331-7. PubMed PMID: 16144976. 8: De Santo C, Serafini P, Marigo I, Dolcetti L, Bolla M, Del Soldato P, Melani C, Guiducci C, Colombo MP, Iezzi M, Musiani P, Zanovello P, Bronte V. Nitroaspirin corrects immune dysfunction in tumor-bearing hosts and promotes tumor eradication by cancer vaccination. Proc Natl Acad Sci U S A. 2005 Mar 15;102(11):4185-90. PubMed PMID: 15753302; PubMed Central PMCID: PMC554823. 9: Carini M, Aldini G, Stefani R, Orioli M, Facino RM. Nitrosylhemoglobin, an unequivocal index of nitric oxide release from nitroaspirin: in vitro and in vivo studies in the rat by ESR spectroscopy. J Pharm Biomed Anal. 2001 Nov;26(4):509-18. PubMed PMID: 11516901. 10: Varma SD, Hegde KR. Susceptibility of the ocular lens to nitric oxide: implications in cataractogenesis. J Ocul Pharmacol Ther. 2007 Apr;23(2):188-95. PubMed PMID: 17444807. 11: Gresele P, Momi S, Mezzasoma AM. NCX4016: a novel antithrombotic agent. Dig Liver Dis. 2003 May;35 Suppl 2:S20-6. PubMed PMID: 12846440. 12: Paranjpe A, Srivenugopal KS. Degradation of NF-κB, p53 and other regulatory redox-sensitive proteins by thiol-conjugating and -nitrosylating drugs in human tumor cells. Carcinogenesis. 2013 May;34(5):990-1000. doi: 10.1093/carcin/bgt032. PubMed PMID: 23354308; PubMed Central PMCID: PMC3643424. 13: Gresele P, Migliacci R, Procacci A, De Monte P, Bonizzoni E. Prevention by NCX 4016, a nitric oxide-donating aspirin, but not by aspirin, of the acute endothelial dysfunction induced by exercise in patients with intermittent claudication. Thromb Haemost. 2007 Mar;97(3):444-50. PubMed PMID: 17334512. 14: Pomponi M, Di Gioia A, Bria P, Pomponi MF. Fatty aspirin: a new perspective in the prevention of dementia of Alzheimer's type? Curr Alzheimer Res. 2008 Oct;5(5):422-31. PubMed PMID: 18855583. 15: Gilmer JF, Murphy MA, Shannon JA, Breen CG, Ryder SA, Clancy JM. Single oral dose study of two isosorbide-based aspirin prodrugs in the dog. J Pharm Pharmacol. 2003 Oct;55(10):1351-7. PubMed PMID: 14607016. 16: Santanam N, Parthasarathy S. Aspirin is a substrate for paraoxonase-like activity: implications in atherosclerosis. Atherosclerosis. 2007 Apr;191(2):272-5. PubMed PMID: 16793048. 17: Nath N, Chattopadhyay M, Rodes DB, Nazarenko A, Kodela R, Kashfi K. Nitric Oxide-Releasing Aspirin Suppresses NF-κB Signaling in Estrogen Receptor Negative Breast Cancer Cells in Vitro and in Vivo. Molecules. 2015 Jul 9;20(7):12481-99. doi: 10.3390/molecules200712481. PubMed PMID: 26184135. 18: Ulu N, Iskit AB, Sökmensüer C, Güç MO. The effects of aspirin, flurbiprofen, and NO-donating acetylsalicylic acid (NCX 4016) on mice models of endotoxic and septic shock. Turk J Med Sci. 2015;45(4):812-9. PubMed PMID: 26422851. 19: Gresele P, Migliacci R, Arosio E, Bonizzoni E, Minuz P, Violi F; NCX 4016-X-208 Study Group.. Effect on walking distance and atherosclerosis progression of a nitric oxide-donating agent in intermittent claudication. J Vasc Surg. 2012 Dec;56(6):1622-8, 1628.e1-5. doi: 10.1016/j.jvs.2012.05.064. PubMed PMID: 22963812. 20: Rao CV, Mohammed A, Janakiram NB, Li Q, Ritchie RL, Lightfoot S, Vibhudutta A, Steele VE. Inhibition of pancreatic intraepithelial neoplasia progression to carcinoma by nitric oxide-releasing aspirin in p48(Cre/+)-LSL-Kras(G12D/+) mice. Neoplasia. 2012 Sep;14(9):778-87. PubMed PMID: 23019409; PubMed Central PMCID: PMC3459273.

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