Thiorphan

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 ;
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) ; Key:LJJKNPQAGWVLDQ-UHFFFAOYSA-N ;
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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]

References

^ ^a ^b 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.
^ 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.

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[pmid3015640-1] 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. S2CID 245710392.

[1]

[2]

v t e Antidiarrheals, intestinal anti-inflammatory and anti-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
Intestinal adsorbents	Charcoal Bismuth (including bismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: 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