Nafazatrom

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

MedKoo CAT#: 525722

CAS#: 59040-30-1

Description: Nafazatrom is a pyrazolinone derivative that increases endogenous prostacyclin (PGI2) and has experimental anti-cancer activity. Nafazatrom, a lipoxygenase inhibitor, reduces stimulated Prolactin secretion. Nafazatrom is also an antithrombotic drug that increases prostacycline levels. Nafazatrom also reduces the incidence of accompanying arrhythmias in myocardial injuries.


Price and Availability

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Nafazatrom is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525722
Name: Nafazatrom
CAS#: 59040-30-1
Chemical Formula: C16H16N2O2
Exact Mass: 268.1212
Molecular Weight: 268.3104
Elemental Analysis: C, 71.62; H, 6.01; N, 10.44; O, 11.93


Synonym: Nafazatromum; Nafazatrom

IUPAC/Chemical Name: 3-methyl-1-(2-(naphthalen-2-yloxy)ethyl)-1H-pyrazol-5(4H)-one

InChi Key: ISBUYSPRIJRBKX-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H16N2O2/c1-12-10-16(19)18(17-12)8-9-20-15-7-6-13-4-2-3-5-14(13)11-15/h2-7,11H,8-10H2,1H3

SMILES Code: O=C1N(CCOC2=CC=C3C=CC=CC3=C2)N=C(C)C1


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, not in water

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).

Harmonized System Code:
293490


References

1: Bjøro T, Larsen V, Englund K, Torjesen PA, Haug E. The lipoxygenase inhibitor nafazatrom inhibits stimulated prolactin secretion in cultured rat lactotrophs (GH4C1 cells). Scand J Clin Lab Invest. 1992 Jun;52(4):297-303. PubMed PMID: 1332181.
2: Jones AL, Powles TJ, Forgeson GV, Coombes RC. A clinical study of nafazatrom in advanced human breast cancer. Cancer Chemother Pharmacol. 1991;27(4):326-8. PubMed PMID: 1998990.
3: Massad L, Plotkine M, Boulu RG. Investigations on the role of arachidonic acid metabolism pathways in the antithrombotic activity of nafazatrom and molsidomine. Thromb Res. 1988 Jun 1;50(5):617-25. PubMed PMID: 3137682.
4: Gillis CN, Havill AM, Moalli R. Effect of nafazatrom and indomethacin on pulmonary removal of prostaglandin E1 after endotoxin in rabbits. Br J Pharmacol. 1987 Aug;91(4):721-8. PubMed PMID: 3311263; PubMed Central PMCID: PMC1853588.
5: O'Donnell JF, Blakowski SA, Zacharski LR, Nierenberg DW, Coughlin CT, Fein S, Philipp E, Cornwell GG 3rd. A clinical trial of nafazatrom (Bay g 6575) in advanced cancer. Am J Clin Oncol. 1986 Apr;9(2):152-5. PubMed PMID: 3717082.
6: Maniglia CA, Loulakis PP, Sartorelli AC. Interference with tumor cell-induced degradation of endothelial matrix on the antimetastatic action of nafazatrom. J Natl Cancer Inst. 1986 Apr;76(4):739-44. PubMed PMID: 3457206.
7: Durrant ST, Joosten P, Gordon-Smith EC. Nafazatrom in treatment of thrombotic thrombocytopenic purpura. Lancet. 1985 Oct 12;2(8459):842. PubMed PMID: 2864567.
8: Fiedler VB, Mardin M. Effects of nafazatrom and indomethacin on experimental myocardial ischemia in the anesthetized dog. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):983-9. PubMed PMID: 2413312.
9: Fiedler VB. Failure of nafazatrom to reduce infarct size and arrhythmias in a porcine model of acute coronary occlusion. Eur J Pharmacol. 1985 Aug 15;114(2):189-95. PubMed PMID: 3930268.
10: Bednar M, Smith B, Pinto A, Mullane KM. Nafazatrom-induced salvage of ischemic myocardium in anesthetized dogs is mediated through inhibition of neutrophil function. Circ Res. 1985 Jul;57(1):131-41. PubMed PMID: 2988818.
11: Ensley RD, Rubin LJ. Nafazatrom (Bay g 6575) blunts canine hypoxic pulmonary vasoconstriction: evidence for a prostaglandin-mediated mechanism. Prostaglandins Leukot Med. 1985 Apr;18(1):95-104. PubMed PMID: 3923499.
12: Herrmann KS. Antiaggregatory efficacy and its time-course after application of acetylsalicylic acid, prostacyclin and nafazatrom in vivo. Arch Int Pharmacodyn Ther. 1984 Nov;272(1):150-8. PubMed PMID: 6393886.
13: Shea MJ, Driscoll EM, Romson JL, Pitt B, Lucchesi BR. The beneficial effects of nafazatrom (BAYg6575) on experimental coronary thrombosis. Am Heart J. 1984 Apr;107(4):629-37. PubMed PMID: 6702555.
14: Fiedler VB. Reduction of acute myocardial ischemia in rabbit hearts by nafazatrom. J Cardiovasc Pharmacol. 1984 Mar-Apr;6(2):318-24. PubMed PMID: 6200722.
15: Haas CD, Baker LH, Evans LJ Jr. Phase I and pharmacologic evaluation of nafazatrom in patients with cancer. Invest New Drugs. 1984;2(1):13-7. PubMed PMID: 6469495.
16: Williams HJ, Myatt L, Young KD. Thrombotic thrombocytopenic purpura: treatment with nafazatrom. Clin Lab Haematol. 1984;6(2):199-202. PubMed PMID: 6386286.
17: Deckmyn H, Van Houtte E, Verstraete M, Vermylen J. Manipulation of the local thromboxane and prostacyclin balance in vivo by the antithrombotic compounds dazoxiben, acetylsalicylic acid and nafazatrom. Biochem Pharmacol. 1983 Sep 15;32(18):2757-62. PubMed PMID: 6578796.
18: Fischer S, Struppler M, Weber PC. In vivo and in vitro effects of nafazatrom (Bay g 6575), an antithrombotic compound, on arachidonic acid metabolism in platelets and vascular tissue. Biochem Pharmacol. 1983 Jul 15;32(14):2231-6. PubMed PMID: 6688182.
19: Fiedler VB. The effects of oral nafazatrom (= BAY g 6575) on canine coronary artery thrombosis and myocardial ischemia. Basic Res Cardiol. 1983 May-Jun;78(3):266-80. PubMed PMID: 6615399.
20: Wong PY, Chao PH, McGiff JC. Nafazatrom (Bay g-6575), an antithrombotic and antimetastatic agent, inhibits 15-hydroxyprostaglandin dehydrogenase. J Pharmacol Exp Ther. 1982 Dec;223(3):757-60. PubMed PMID: 6754908.