Alminoprofen

Last updated
Alminoprofen
Alminoprofen.png
Alminoprofen-3D-balls.png
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • 2-{{#parsoidfragment:1}}{4-[(2-Methylprop-2-en-1-yl)amino]phenyl}propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.049.622 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C13H17NO2
Molar mass 219.284 g·mol−1
3D model (JSmol)
  • O=C(O)C(c1ccc(NC/C(=C)C)cc1)C
  • InChI=1S/C13H17NO2/c1-9(2)8-14-12-6-4-11(5-7-12)10(3)13(15)16/h4-7,10,14H,1,8H2,2-3H3,(H,15,16) Yes check.svgY
  • Key:FPHLBGOJWPEVME-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Alminoprofen is a non-steroidal anti-inflammatory drug. [1] [2] the non-proprietary name alminoprofen is derived from the compound's chemical name 2-(4-[{2-methylallyl}amino]phenyl)propanic acid.

Contents

Stereochemistry

Alminoprofen exists as two enantiomers; the stereocenter is located at the benzyl group.

Pharmacology

Although the pharmacology of non-steroidal anti-inflammatory drugs (non-steroidal anti-inflammatory drug) has been extensively studied, their mechanisms of action at the immunological level are not yet fully understood. Alminoprofen is a newer NSAID with a characteristic anti-inflammatory profile mediated through inhibition of cyclooxygenases and phospholipase A2 activity. [3]

Comparison with ibuprofen

The effects of alminoprofen were examined in animal studies and compared with those of ibuprofen. At a dose of 30 mg/kg administered intraduodenally, alminoprofen significantly suppressed passive anaphylactic reaction-induced bronchoconstriction, whereas ibuprofen at the same dose did not. In vitro studies demonstrated that alminoprofen, unlike ibuprofen, inhibits arachidonate-5-lipoxygenase activity, which initiates the biosynthesis of leukotrienes. Alminoprofen inhibited arachidonic acid-induced ear edema in mice and homologous passive cutaneous anaphylaxis in rats at high doses, whereas ibuprofen showed no such effect at comparable doses. [4]

Synthesis

The multistep synthesis of alminoprofen is shown in the following reaction sequence: [5] }} }}

Synthesis of alminoprofen Alminoprofen Synthesis.svg
Synthesis of alminoprofen
Enantiomeric forms (R)-(-)-alminoprofen (top) and (S)-(+)-alminoprofen (bottom) Alminoprofen structural formula enamtiomers.svg
Enantiomeric forms (R)-(-)-alminoprofen (top) and (S)-(+)-alminoprofen (bottom)

The synthesis begins with para-nitrophenylacetic acid as the starting material. The first step is a Mannich reaction with formaldehyde and dimethylamine. The second step is an elimination reaction forming a terminal alkene. In the third step, both the alkene and the nitro group are reduced using palladium on carbon as the catalyst and hydrogen as the reducing agent. The final step is a nucleophilic substitution in which the aryl group [amine]] acts as the nucleophile. The product is a racemate.

Trade names

Minalfen (J) [5]


References

  1. ↑ Raguenes-Nicol C, Russo-Marie F, Domage G, Diab N, Solito E, Dray F, Mace JL, Streichenberger G (February 1999). "Anti-inflammatory mechanism of alminoprofen: action on the phospholipid metabolism pathway". Biochemical Pharmacology. 57 (4): 433–43. doi:10.1016/s0006-2952(98)00312-8. PMID   9933032.
  2. ↑ Céline Raguenes-Nicol, Françoise Russo-Marie, Gisèle Domage, Nadia Diab, Egle Solito (1999-02), "Anti-inflammatory mechanism of alminoprofen: action on the phospholipid metabolism pathway", Biochemical Pharmacology , vol. 57, no. 4, pp. 433–443, doi:10.1016/s0006-2952(98)00312-8 {{citation}}: Check date values in: |date= (help)CS1 maint: multiple names: authors list (link)
  3. ↑ M. Shingu, T. Wada, I. Ezaki, M. Nobunaga (1992), "Pharmacologic modulation by alminoprofen of immunoglobulin and rheumatoid factor production by PWM-stimulated normal human mononuclear cells", Ensho, vol. 12, no. 4, pp. 327–331{{citation}}: CS1 maint: multiple names: authors list (link)
  4. ↑ Kojima E, Tamura N, Higashide Y, Lee B, Yamaura T, Ohnishi H (1990), "Effects of alminoprofen on the allergic reactions", Nihon Yakurigaku zasshi. Folia Pharmacologica Japonica, vol. 96, no. 6, pp. 315–321{{citation}}: CS1 maint: multiple names: authors list (link)
  5. 1 2 A. Kleemann, J. Engel, B. Kutscher, D. Reichert (2014-05-14), Pharmaceutical Substances, 5th Edition: Syntheses, Patents and Applications of the most relevant APIs, Georg Thieme Verlag, p. 44, ISBN   978-3-13-179525-0 {{citation}}: CS1 maint: multiple names: authors list (link)


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