Cetraxate

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

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

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