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Cetraxate

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Cetraxate
Clinical data
AHFS/Drugs.comInternational 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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H23NO4
Molar mass305.374 g·mol−1
3D model (JSmol)
  • O=C(O)CCc2ccc(cc2)OC(=O)C1CCC(CN)CC1

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

Synthesis

[edit]

Cetraxate is aprodrug oftranexamic acid. The latter is ahemostatic agent because it inhibits the activation ofplasminogen toplasmin. The result is to prevent excess loss of blood ingastrointestinal ulcers.The synthesis begins with theesterification of 3-(p-hydroxyphenyl)propionic acid (2) bytrans-4-cyanocyclohexanecarbonyl chloride (1). The product (3) is reduced tocetraxate (4) bycatalytic hydrogenation withhydrogen andRaney nickel.[3][4]

Cetraxate synthesis

References

[edit]
  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.
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Prostaglandins (E)/
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