Thiorphan

Thiorphan is the active metabolite of the antidiarrheal racecadotril (acetorphan).[1] It prevents the degradation of endogenous enkephalins by acting as an enkephalinase inhibitor.[1][2]

Thiorphan

Clinical data
ATC code	none
Identifiers
IUPAC name (±)-2-[(2-benzyl-3-sulfanyl-propanoyl)amino]acetic acid
CAS Number	76721-89-6
PubChem CID	3132
DrugBank	DB08626
ChemSpider	3020
UNII	B79L7B5X3Z
KEGG	C01619
ChEMBL	ChEMBL10247
Chemical and physical data
Formula	C12H15NO3S
Molar mass	253.32 g·mol^−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES C1=CC=C(C=C1)CC(CS)C(=O)NCC(=O)O
InChI InChI=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) Key:LJJKNPQAGWVLDQ-UHFFFAOYSA-N
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References

1. Spillantini MG, Geppetti P, Fanciullacci M, Michelacci S, Lecomte JM, Sicuteri F (June 1986). "In vivo 'enkephalinase' inhibition by acetorphan in human plasma and CSF". European Journal of Pharmacology. 125 (1): 147–50. doi:10.1016/0014-2999(86)90094-4. PMID 3015640.
2. Matheson AJ, Noble S (April 2000). "Racecadotril". Drugs. 59 (4): 829–35, discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038.