Cetraxate

Last updated

Cetraxate
Cetraxate.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]oxyphenyl]propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H23NO4
Molar mass 305.374 g·mol−1
3D model (JSmol)
  • O=C(O)CCc2ccc(cc2)OC(=O)C1CCC(CN)CC1

Cetraxate (INN) is an oral gastrointestinal medication which has a cytoprotective effect. [1] [2] [ unreliable medical source? ]

Synthesis

Cetraxate is a prodrug of tranexamic acid. The latter is a hemostatic agent because it inhibits the activation of plasminogen to plasmin. The result is to prevent excess loss of blood in gastrointestinal ulcers. The synthesis begins with the esterification of 3-(p-hydroxyphenyl)propionic acid (2) by trans-4-cyanocyclohexanecarbonyl chloride (1). The product (3) is reduced to cetraxate (4) by catalytic hydrogenation with hydrogen and Raney nickel. [3] [4]

Cetraxate synthesis Cetraxate synthesis.svg
Cetraxate synthesis

References

  1. Kurebayashi Y, Ikeda T, Osada Y (January 1988). "Cytoprotective action of cetraxate against HCl.ethanol-induced gastric lesion in rats". Japanese Journal of Pharmacology. 46 (1): 17–25. doi: 10.1254/jjp.46.17 . PMID   3367546.
  2. Ishimori A, Yamagata S, Taima T (1979). "Effect of p-hydroxyphenyl-propionic ester of tranexamic acid hydrochloride (Cetraxate) on peptic ulcer. Multi-center clinical study". Arzneimittel-Forschung. 29 (10): 1625–1632. PMID   391240.
  3. Japan Kokai, 59/134,758 (1984)
  4. Svahn CM, Merenyi F, Karlson L, Widlund L, Grälls M (April 1986). "Tranexamic acid derivatives with enhanced absorption". Journal of Medicinal Chemistry. 29 (4): 448–453. doi:10.1021/jm00154a004. PMID   3959024.