nifenazone
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| IUPAC_name = N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)nicotinamide
| image = nifenazone.png
| image_class = skin-invert-image
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2139-47-1
| ATC_prefix = M02
| ATC_suffix = AA24
| ATC_supplemental = {{ATC|N02|BB05}}
| PubChem = 4487
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1413176
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8780F0K71U
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01437
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4332
| C=17 | H=16 | N=4 | O=2
| smiles = c1ccccc1N2N(C)C(C)=C(C2=O)NC(=O)c3cccnc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H16N4O2/c1-12-15(19-16(22)13-7-6-10-18-11-13)17(23)21(20(12)2)14-8-4-3-5-9-14/h3-11H,1-2H3,(H,19,22)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BRZANEXCSZCZCI-UHFFFAOYSA-N
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Nifenazone is a drug that has been used as an analgesic for a number of rheumatic conditions.{{cite journal | vauthors = Hart FD, Boardman PL | journal = British Medical Journal | volume = 1 | issue = 5397 | pages = 1553–4 | date = June 1964 | pmid = 14133613 | pmc = 1814611 | doi = 10.1136/bmj.1.5397.1553 | title = Trial of Nifenazone ("Thylin") }}
Synthesis
:File:Nifenazone synthesis.svg
Nifenazone is the amide formed when ampyrone and the acid chloride of nicotinic acid are combined in a Schotten–Baumann reaction.{{cite journal |doi=10.1007/BF00901766 |title=Über neue pharmakologisch wirksame Amide und Ester der Nicotinsäure |date=1957 | vauthors = Pongratz A, Zirm L |journal=Monatshefte für Chemie |volume=88 |issue=3 |pages=330–335 }}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-14-0058 | title = Nifenazone | work = Pharmaceutical Substances |publisher=Georg Thieme Verlag KG |access-date=2024-07-16 }}
See also
References
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{{Anti-inflammatory products}}
{{Topical products for joint and muscular pain}}
{{musculoskeletal-drug-stub}}