thiorphan

{{short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{further|Racecadotril}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470608964

| IUPAC_name = (±)-2-[(2-benzyl-3-sulfanyl-propanoyl)amino]acetic acid

| image = Thiorphan2DCSD.svg

| width = 200px

| chirality = Racemic mixture

| drug_name =

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 76721-89-6

| ATC_prefix = none

| ATC_suffix =

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LJJKNPQAGWVLDQ-UHFFFAOYSA-N

| PubChem = 3132

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB08626

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = B79L7B5X3Z

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3020

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 10247

| KEGG = C01619

| C=12 | H=15 | N=1 | O=3 | S=1

| smiles = C1=CC=C(C=C1)CC(CS)C(=O)NCC(=O)O

}}

Thiorphan is the active metabolite of the antidiarrheal racecadotril (acetorphan).{{cite journal | vauthors = Spillantini MG, Geppetti P, Fanciullacci M, Michelacci S, Lecomte JM, Sicuteri F | title = In vivo 'enkephalinase' inhibition by acetorphan in human plasma and CSF | journal = European Journal of Pharmacology | volume = 125 | issue = 1 | pages = 147–50 |date=June 1986 | pmid = 3015640 | doi = 10.1016/0014-2999(86)90094-4}} It prevents the degradation of endogenous enkephalins by acting as an enkephalinase inhibitor.{{cite journal | journal = Drugs | pmid = 10804038 | volume=59 | issue=4 | title = Racecadotril |date=April 2000 | pages=829–35; discussion 836–7 |vauthors=Matheson AJ, Noble S | doi=10.2165/00003495-200059040-00010| s2cid = 245710392 }}