Cetraxate
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| IUPAC_name = 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]oxyphenyl]propanoic acid
| image = Cetraxate.svg
| tradename =
| Drugs.com = {{drugs.com|international|cetraxate}}
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = Rx-only
| routes_of_administration = Oral
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 34675-84-8
| ATC_prefix = none
| ATC_suffix =
| ATC_supplemental =
| PubChem = 2680
| DrugBank =
| ChemSpiderID = 2579
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5VPA8CPF0N
| KEGG = D07663
| ChEMBL = 502896
| chemical_formula =
| C=17 | H=23 | N=1 | O=4
| smiles = O=C(O)CCc2ccc(cc2)OC(=O)C1CCC(CN)CC1
}}
Cetraxate (INN) is an oral gastrointestinal medication which has a cytoprotective effect.{{cite journal | vauthors = Kurebayashi Y, Ikeda T, Osada Y | title = Cytoprotective action of cetraxate against HCl.ethanol-induced gastric lesion in rats | journal = Japanese Journal of Pharmacology | volume = 46 | issue = 1 | pages = 17–25 | date = January 1988 | pmid = 3367546 | doi = 10.1254/jjp.46.17 | doi-access = free }}{{cite journal | vauthors = Ishimori A, Yamagata S, Taima T | title = Effect of p-hydroxyphenyl-propionic ester of tranexamic acid hydrochloride (Cetraxate) on peptic ulcer. Multi-center clinical study | journal = Arzneimittel-Forschung | volume = 29 | issue = 10 | pages = 1625–1632 | year = 1979 | pmid = 391240 | url = https://pubmed.ncbi.nlm.nih.gov/391240/ }}{{Unreliable medical source|reason=Animal and clinical studies, also outdated|date=February 2025}}
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.Japan Kokai, 59/134,758 (1984){{cite journal | vauthors = Svahn CM, Merenyi F, Karlson L, Widlund L, Grälls M | title = Tranexamic acid derivatives with enhanced absorption | journal = Journal of Medicinal Chemistry | volume = 29 | issue = 4 | pages = 448–453 | date = April 1986 | pmid = 3959024 | doi = 10.1021/jm00154a004 }}
References
{{reflist}}
{{Drugs for peptic ulcer and GORD}}
Category:Drugs acting on the gastrointestinal system and metabolism
Category:Aminomethyl compounds
{{gastrointestinal-drug-stub}}