Cetraxate

Cetraxate

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]oxyphenyl]propanoic acid
CAS Number	34675-84-8
PubChem CID	2680
ChemSpider	2579
UNII	5VPA8CPF0N
KEGG	D07663
ChEMBL	ChEMBL502896
CompTox Dashboard (EPA)	DTXSID2040658
Chemical and physical data
Formula	C17H23NO4
Molar mass	305.374 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(O)CCc2ccc(cc2)OC(=O)C1CCC(CN)CC1

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

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

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.