Tolfenamic acid

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Structural formula
Structural formula of tolfenamic acid
General
Non-proprietary name Tolfenamic acid
other names

2 - [(3-chloro-2-methylphenyl) amino] benzoic acid

Molecular formula C 14 H 12 ClNO 2
External identifiers / databases
CAS number 13710-19-5
EC number 237-264-3
ECHA InfoCard 100,033,862
PubChem 610479
ChemSpider 530683
DrugBank DB09216
Wikidata Q59412
Drug information
ATC code

M01 AG02

Drug class

non-steroidal anti-inflammatory drug

properties
Molar mass 261.70  g · mol -1
density
  • 1.397 g cm −3 (20 ° C, white polymorph)
  • 1.400 g cm −3 (20 ° C, yellow polymorph)
Melting point
  • 211.0 ° C (white polymorph)
  • 212.6 ° C (yellow polymorph)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: 301 + 310
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tolfenamic acid is a derivative of anthranilic acid and belongs to the fenamate group. In medicine it is used as a non-steroidal anti - inflammatory (anti-inflammatory agent).

Extraction and presentation

Tolfenamic acid can be synthesized by reacting the potassium salt of 2-bromobenzoic acid with 3-chloro-2-methylaniline at 145 ° C. in NMP in the presence of copper (II) acetate .

Synthesis of tolfenamic acid

properties

Tolfenamic acid occurs in two differently colored polymorphic crystal forms. The yellow crystal form shows a melting point of 212.6 ° C with a heat of fusion of 49 kJ · mol −1 . The white crystal form melts at 211.0 ° C with a heat of fusion of 41 kJ mol −1 . Both crystal forms are monotropic to one another. The yellow polymorph is the thermodynamically more stable form. Both crystal forms form a monoclinic crystal lattice. The space group of the white form is P2 1 / c, that of the yellow form P2 1 / n. They are conformational polymorphs.

Working principle

Tolfenamic acid is an inhibitor of the so-called cyclooxygenase , an enzyme in the synthesis of prostaglandin . As a result of the suppression of this inflammatory substance, it has anti-inflammatory (anti-inflammatory), fever-lowering ( antipyretic ) and analgesic ( analgesic ) effects .

Contraindications

The agent should not be used for damage to the kidneys , liver , heart and for ulcers and bleeding in the gastrointestinal tract . It is also contraindicated for hemophiliacs .

Trade names

Migea, Tolfedine, Clotam (Tobishi Shingaku)

Web links

  • Entry on tolfenamic acid at Vetpharm, accessed on August 11, 2012.

Individual evidence

  1. ↑ a b c d e A. O. Surov, P. Szterner, W. Zielenkiewicz, GL Perlovich: Thermodynamic and structural study of tungstenic acid polymorphs. In: J Pharm Biomed Anal . 50, 2009, pp. 831-840; doi: 10.1016 / j.jpba.2009.06.045 .
  2. ↑ a b Datasheet Tolfenamic acid from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  3. ↑ TOLFENAMIC ACID CRS data sheet (PDF) at EDQM , accessed on July 5, 2009.
  4. ^ A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances -Synthesis, Patens, Applications-. 4th edition. Thieme Chemistry, Stuttgart 2001, ISBN 3-13-115134-X .
  5. ↑ JS Kaltenbronn, RA Scherrer, FW Short, EM Jones, HR Beatty, MM Saka, CV Winder, J. Wax, WR Williamson: Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids. In: drug research. Volume 33, Number 4A, 1983, pp. 621-627. PMID 6683967 .
  6. ↑ KV Anderson, S. Larsen, B. Alhede, N. Gelting, O. Buchardt: Characterization of Two Polymorphic Forms of Tolfenamic Acid, N- (2-Methyl-3-chlorophenyl) anthranilic Acid: Their Crystal Structures and Relative Stabilities. In: J. Chem. Soc., Perkin Trans. 2 . 1989, pp. 1443-1447, doi: 10.1039 / P29890001443 .