Nitroaspirin
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MedKoo CAT#: 529508

CAS#: 175033-36-0

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


Price and Availability

Size Price Shipping out time Quantity
5mg USD 190 2 Weeks
10mg USD 350 2 Weeks
25mg USD 650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-11-23. Prices are subject to change without notice.

Nitroaspirin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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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


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


Technical Data

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


References

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.