Tolfenamic acid
2 - [( 3-chloro -2-methylphenyl ) amino ] benzoic acid
M01AG02
Nonsteroidal anti-inflammatory
- 211.0 ° C (white polymorph )
- 212.6 ° C (yellow polymorph )
Risk
- 225 mg · kg -1 ( LD50, rat, oral)
- 280 mg · kg -1 ( LD50, mouse, oral)
Template: Infobox chemical / molecular formula search available
Tolfenamic acid is a derivative of anthranilic acid and belongs to the group of fenamates. In medicine it is used as non-steroidal anti-inflammatory ( anti-inflammatory ).
Production and representation
The synthesis of tolfenamic acid can be effected by the reaction of the potassium salt of 2- bromobenzoic acid with 3-chloro -2-methyl -aniline at 145 ° C in NMP in the presence of copper ( II) acetate.
Properties
Tolfenamic acid occurs in two differently colored polymorphic crystal forms. The yellow crystal form has a melting point of 212.6 ° C with a heat of fusion of 49 kJ · mol -1. The white crystalline form melts at 211.0 ° C with a heat of fusion of 41 kJ · mol -1. Both crystal forms are monotropic each other. The yellow polymorph is the thermodynamically stable form. Both crystal forms form a monoclinic crystal lattice. The space group is in the white form P21 / c, the yellow form P21 / n It is Konformationspolymorphe.
Action principle
Tolfenamic acid is an inhibitor of the so-called cyclooxygenase, an enzyme in the synthesis of prostaglandin. Due to the suppression of this inflammatory substance, it is anti-inflammatory ( anti-inflammatory ), febrifuge ( antipyretic ) and pain-relieving ( analgesic ).
Contraindications
This medication should not be used in damage to the kidneys, liver, heart, and for ulcers and bleeding in the gastrointestinal tract. For hemophiliacs, it is also contraindicated.
Trade names
Migea, Tolfedine, Clotam ( Tobishi Shingaku )