Nifenazone

Last updated
Nifenazone
Nifenazone.png
Clinical data
ATC code
Identifiers
  • N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)nicotinamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.016.716 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H16N4O2
Molar mass 308.341 g·mol−1
3D model (JSmol)
  • c1ccccc1N2N(C)C(C)=C(C2=O)NC(=O)c3cccnc3
  • InChI=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) Yes check.svgY
  • Key:BRZANEXCSZCZCI-UHFFFAOYSA-N Yes check.svgY

Nifenazone is a drug that has been used as an analgesic for a number of rheumatic conditions. [1]

Contents

Synthesis

Nifenazone synthesis.svg

Nifenazone is the amide formed when ampyrone and the acid chloride of nicotinic acid are combined in a Schotten–Baumann reaction. [2] [3]

See also

Related Research Articles

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In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.

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<span class="mw-page-title-main">Peptide bond</span> Covalent chemical bond between amino acids in a peptide or protein chain

In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 of one alpha-amino acid and N2 of another, along a peptide or protein chain.

A polyamide is a polymer with repeating units linked by amide bonds.

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Oleamide is an organic compound with the formula CH3(CH2)7CH=CH(CH2)7CONH2. It is the amide derived from the fatty acid oleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it is biosynthesized from N-oleoylglycine.

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References

  1. Hart FD, Boardman PL (June 1964). "Trial of Nifenazone ("Thylin")". British Medical Journal. 1 (5397): 1553–4. doi:10.1136/bmj.1.5397.1553. PMC   1814611 . PMID   14133613.
  2. Pongratz A, Zirm L (1957). "Über neue pharmakologisch wirksame Amide und Ester der Nicotinsäure". Monatshefte für Chemie. 88 (3): 330–335. doi:10.1007/BF00901766.
  3. "Nifenazone". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-07-16.