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Thiorphan

From Wikipedia, the free encyclopedia

Chemical compound

Further information:Racecadotril

Pharmaceutical compound

Thiorphan
Clinical data

ATC code	none
Identifiers
IUPAC name (±)-2-[(2-benzyl-3-sulfanyl-propanoyl)amino]acetic acid
CAS Number	76721-89-6^N
PubChemCID	3132
DrugBank	DB08626^N
ChemSpider	3020^Y
UNII	B79L7B5X3Z
KEGG	C01619
ChEMBL	ChEMBL10247^Y
CompTox Dashboard(EPA)	DTXSID70868412
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)^Y Key:LJJKNPQAGWVLDQ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Thiorphan is the activemetabolite of theantidiarrheal racecadotril (acetorphan).^[1] It prevents the degradation ofendogenous enkephalins by acting as anenkephalinase inhibitor.^[1]^[2]

^^a ^bSpillantini 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.
^Matheson AJ, Noble S (April 2000). "Racecadotril".Drugs.59 (4):829–35, discussion 836–7.doi:10.2165/00003495-200059040-00010.PMID 10804038.S2CID 245710392.

v t e Antidiarrheals,intestinal anti-inflammatory andanti-infective agents (A07)
Rehydration	Oral rehydration therapy
Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline
Intestinaladsorbents	Charcoal Bismuth (includingbismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crossesBBB:Diphenoxylate (+atropine) Difenoxin does not cross BBB:Eluxadoline Loperamide^# (+simethicone)
Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone^# Hydrocortisone Prednisone Betamethasone^# Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid Aminosalicylates Sulfasalazine Mesalazine Olsalazine Balsalazide
Antidiarrheal micro-organisms	Escherichia coli Saccharomyces boulardii
Other antidiarrheals	Albumin tannate Bismuth subsalicylate Ceratonia Crofelemer Octreotide Racecadotril Kaopectate
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III