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Chemical compound
Further information: Racecadotril
Thiorphan ATC code
(±)-2-[(2-benzyl-3-sulfanyl-propanoyl)amino]acetic acid
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEMBL Formula C 12 H 15 N O 3 S Molar mass 253.32 g·mol−1 3D model (JSmol) Chirality Racemic mixture
C1=CC=C(C=C1)CC(CS)C(=O)NCC(=O)O
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
N Y (what is this?) (verify)
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 [ edit]
^ 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 .
Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
Rehydration Intestinal anti-infectives
Antibiotics
Amphotericin B
Colistin
Fidaxomicin
Kanamycin
Natamycin
Neomycin
Nystatin
Paromomycin
Polymyxin B
Rifaximin
Streptomycin
Vancomycin
Sulfonamides
Phthalylsulfathiazole
Succinylsulfathiazole
Sulfaguanidine
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
Aminosalicylates
Sulfasalazine
Mesalazine
Olsalazine
Balsalazide
Antidiarrheal micro-organisms Other antidiarrheals
Albumin tannate
Bismuth subsalicylate
Ceratonia
Crofelemer
Octreotide
Racecadotril
Kaopectate
# WHO-EM
‡ Withdrawn from market
Clinical trials:
† Phase III
§ Never to phase III
Opioid receptor modulators
MOR DOR KOR
Agonists: 3CS-nalmefene
6'-GNTI
8-CAC
18-MC
14-Methoxymetopon
β-Chlornaltrexamine
β-Funaltrexamine
Adrenorphin (metorphamide)
Akuammicine
Alazocine (SKF-10047)
Allomatrine
Apadoline
Asimadoline
BAM-12P
BAM-18P
BAM-22P
Big dynorphin
Bremazocine
BRL-52537
Butorphan
Butorphanol
BW373U86
Cebranopadol
Ciprefadol
CR665
Cyclazocine
Cyclorphan
Cyprenorphine
Desmetramadol (desmethyltramadol)
Diamorphine (heroin)
Diacetylnalorphine
Difelikefalin
Dihydroetorphine
Dihydromorphine
Dinalbuphine sebacate
Diprenorphine
Dynorphin A
Dynorphin B (rimorphin)
Eluxadoline
Enadoline
Eptazocine
Erinacine E
Ethylketazocine
Etorphine
Fedotozine
Fentanyl
Gemazocine
GR-89696
GR-103545
Hemorphin-4
Herkinorin
HS665
Hydromorphone
HZ-2
Ibogaine
ICI-199,441
ICI-204,448
Ketamine
Ketazocine
Laudanosine
Leumorphin (dynorphin B-29)
Levallorphan
Levomethorphan
Levorphanol
Lexanopadol
Lofentanil
LPK-26
Lufuradom
Matrine
MB-1C-OH
Menthol
Metazocine
Metkefamide
Mianserin
Mirtazapine
Morphine
Moxazocine
MR-2034
N-MPPP
Nalbuphine
NalBzOH
Nalfurafine
Nalmefene
Nalodeine (N-allylnorcodeine)
Nalorphine
Naltriben
Niravoline
Norbuprenorphine
Norbuprenorphine-3-glucuronide
Noribogaine
Norketamine
Oripavine
Oxilorphan
Oxycodone
Pentazocine
Pethidine (meperidine)
Phenazocine
Proxorphan
Racemethorphan
Racemorphan
RB-64
Salvinorin A (salvia)
Salvinorin B ethoxymethyl ether
Salvinorin B methoxymethyl ether
Samidorphan
Spiradoline (U-62,066)
TH-030418
Thienorphine
Tifluadom
Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
U-50488
U-54,494A
U-69,593
Xorphanol
Antagonists: 4′-Hydroxyflavanone
4',7-Dihydroxyflavone
5'-GNTI
6'-GNTI
6β-Naltrexol
6β-Naltrexol-d4
β-Chlornaltrexamine
Buprenorphine/samidorphan
Amentoflavone
ANTI
Apigenin
Arodyne
AT-076
Aticaprant
Axelopran
AZ-MTAB
Binaltorphimine
BU09059
Buprenorphine
Catechin
Catechin gallate
CERC-501 (LY-2456302)
Clocinnamox
CVL-354
Cyclofoxy
Dezocine
DIPPA
EGC
ECG
Epicatechin
Hyperoside
JDTic
LY-255582
LY-2196044
LY-2444296
LY-2459989
LY-2795050
MeJDTic
Methylnaltrexone
ML190
ML350
MR-2266
N-Fluoropropyl-JDTic
Naloxone
Naltrexone
Naltrindole
Naringenin
Norbinaltorphimine
Noribogaine
Pawhuskin A
PF-4455242
RB-64
Quadazocine
Taxifolin
UPHIT
Zyklophin
Unknown/unsorted: Akuammicine
Akuammine
Coronaridine
Cyproterone acetate
Dihydroakuuamine
Ibogamine
Tabernanthine
NOP
Agonists: (Arg14,Lys15)Nociceptin
((pF)Phe4 )Nociceptin(1-13)NH2
(Phe1 Ψ(CH2 -NH)Gly2 )Nociceptin(1-13)NH2
Ac-RYYRWK-NH2
Ac-RYYRIK-NH2
BU08070
Buprenorphine
Cebranopadol
Dihydroetorphine
Etorphine
JNJ-19385899
Levomethorphan
Levorphanol
Lexanopadol
MCOPPB
MT-7716
NNC 63-0532
Nociceptin (orphanin FQ)
Nociceptin (1-11)
Nociceptin (1-13)NH2
Norbuprenorphine
Racemethorphan
Racemorphan
Ro64-6198
Ro65-6570
SCH-221510
SCH-486757
SR-8993
SR-16435
Sunobinop (S-117957)
TH-030418
Antagonists: (Nphe1 )Nociceptin(1-13)NH2
AT-076
BAN-ORL-24
BTRX-246040 (LY-2940094)
J-113,397
JTC-801
NalBzOH
Nociceptin (1-7)
Nocistatin
SB-612,111
SR-16430
Thienorphine
Trap-101
UFP-101
Unsorted
β-Casomorphins
Amidorphin
BAM-20P
Cytochrophin-4
Deprolorphin
Gliadorphin (gluteomorphin)
Gluten exorphins
Hemorphins
Kava constituents
MEAGL
MEAP
NEM
Neoendorphins
Nepetalactone (catnip)
Peptide B
Peptide E
Peptide F
Peptide I
Rubiscolins
Soymorphins
Others
Enkephalinase inhibitors: Amastatin
BL-2401
Candoxatril
D -Phenylalanine
Dexecadotril (retorphan)
Ecadotril (sinorphan)
Kelatorphan
Racecadotril (acetorphan)
RB-101
RB-120
RB-3007
Opiorphan
Selank
Semax
Spinorphin
Thiorphan
Tynorphin
Ubenimex (bestatin)
Propeptides: β-Lipotropin (proendorphin)
Prodynorphin
Proenkephalin
Pronociceptin
Proopiomelanocortin (POMC)
Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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