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76721-89-6,MFCD00043185
Catalog No.:AA0035MB

76721-89-6 | Thiorphan

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5mg
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25mg
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50mg
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100mg
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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0035MB
Chemical Name:
Thiorphan
CAS Number:
76721-89-6
Molecular Formula:
C12H15NO3S
Molecular Weight:
253.3174
MDL Number:
MFCD00043185
SMILES:
SCC(C(=O)NCC(=O)O)Cc1ccccc1
NSC Number:
727676
Properties
Properties
 
Form:
Solid  
MP:
136-138°C  

Computed Properties
 
Complexity:
265  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
6  
Undefined Atom Stereocenter Count:
1  
XLogP3:
1.3  

Downstream Synthesis Route
76721-89-6   
(2'R)-N-(2thiomethyl-3-phenylpropanoyl)glycine 

[1]CurrentPatentAssignee:GLAXOSMITHKLINEPLC-US6048852,2000,A

N-S-Acetyl-2'-benzyl-3'-mercaptopropionylglycinemethylester 
  76721-89-6 

[1]CurrentPatentAssignee:SOCIETECIVILEBIOPROJET-US4513009,1985,A

dizinc(II)formoftherelatedmetallo-β-lactamase 
  76721-89-6   
dizinc(II)formoftherelatedmetallo-β-lactamasecomplexwithDL-thiorphan 

[1]Bergstrom,Alexander;Bretz,StaceyLowery;Cheng,Zishuo;Crowder,MichaelW.;Fullington,Sarah;Ju,Lin-Cheng;Miller,Callie;Page,RichardC.;Shurina,BenA.;Thomas,Caitlyn;Tierney,DavidL.;Yang,Kundi[JournalofBiologicalInorganicChemistry,2020]

Literature

Title: Dried blood spot on-card derivatization: an alternative form of sample handling to overcome the instability of thiorphan in biological matrix.

Journal: Biomedical chromatography : BMC 20121201

Title: Angiotensin-(1-7) receptor Mas agonist ameliorates progress of atherosclerosis in apoE-knockout mice.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20120201

Title: Routine antenatal anti-D prophylaxis--is the protection adequate?

Journal: Transfusion medicine (Oxford, England) 20111201

Title: The role of neutral endopeptidase in caerulein-induced acute pancreatitis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20111115

Title: Aβ-degrading enzymes: potential for treatment of Alzheimer disease.

Journal: Journal of neuropathology and experimental neurology 20111101

Title: Impaired β-amyloid secretion in Alzheimer's disease pathogenesis.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20111026

Title: Racecadotril for childhood gastroenteritis: an individual patient data meta-analysis.

Journal: Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver 20110901

Title: Grading recommendations in clinical practice guidelines: randomised experimental evaluation of four different systems.

Journal: Archives of disease in childhood 20110801

Title: Collateral sensitivity of multidrug-resistant cells to the orphan drug tiopronin.

Journal: Journal of medicinal chemistry 20110728

Title: Inhibition of insulin degrading enzyme by racecadotril in the brain of Wistar rats.

Journal: Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20110601

Title: Spectrophotometric and spectrofluorimetric methods for determination of Racecadotril.

Journal: Pakistan journal of pharmaceutical sciences 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Control of APN/CD13 and NEP/CD10 on sperm motility.

Journal: Asian journal of andrology 20101101

Title: A nonhuman primate model of Alzheimer's disease generated by intracranial injection of amyloid-β42 and thiorphan.

Journal: Metabolic brain disease 20100901

Title: Remarks and questions on the article 'Prospective randomized double-blind trial of racecadotril compared with loperamide in elderly people with gastroenteritis living in nursing homes'.

Journal: European journal of clinical pharmacology 20100801

Title: Increase of plasma insulin by racecadotril, an inhibitor of enkephalinase, in Wistar rats.

Journal: Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20100401

Title: Prospective randomized double-blind trial of racecadotril compared with loperamide in elderly people with gastroenteritis living in nursing homes.

Journal: European journal of clinical pharmacology 20100201

Title: Diabetes-associated changes and role of N epsilon-(carboxymethyl)lysine in big ET-1-induced coronary vasoconstriction.

Journal: Peptides 20100201

Title: Possible role of tau in mediating pathological effects of apoE4 in vivo prior to and following activation of the amyloid cascade.

Journal: Neuro-degenerative diseases 20100101

Title: Amyloid-beta as a positive endogenous regulator of release probability at hippocampal synapses.

Journal: Nature neuroscience 20091201

Title: Stability-indicating methods for the determination of racecadotril in the presence of its degradation products.

Journal: Bioscience trends 20091201

Title: A scrutiny of the biochemical pathways from Ang II to Ang-(3-4) in renal basolateral membranes.

Journal: Regulatory peptides 20091127

Title: Synthesis and enzymatic evaluation of novel partially fluorinated thiol dual ACE/NEP inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20090815

Title: Role of mu- and delta-opioid receptors in the nucleus accumbens in cocaine-seeking behavior.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090701

Title: Use of racecadotril as outpatient treatment for acute gastroenteritis: a prospective, randomized, parallel study.

Journal: The Journal of pediatrics 20090701

Title: Colon in acute intestinal infection.

Journal: Journal of pediatric gastroenterology and nutrition 20090401

Title: Angiotensin metabolism in rat stomach wall: prevalence of angiotensin-(1-7) formation.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20090301

Title: [Changes in the activity of amyloid-degrading metallopeptidases leads to disruption of memory in rats].

Journal: Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova 20090101

Title: [Systematic review of the efficacy of racecadotril in the treatment of acute diarrhoea].

Journal: Anales de pediatria (Barcelona, Spain : 2003) 20081101

Title: Synergy between natriuretic peptides and phosphodiesterase 5 inhibitors ameliorates pulmonary arterial hypertension.

Journal: American journal of respiratory and critical care medicine 20081015

Title: Thiorphan-induced survival and proliferation of rat thymocytes by activation of Akt/survivin pathway and inhibition of caspase-3 activity.

Journal: The Journal of pharmacology and experimental therapeutics 20081001

Title: Acute infectious diarrhoea in children: new insights in antisecretory treatment with racecadotril.

Journal: Acta paediatrica (Oslo, Norway : 1992) 20080801

Title: The characterization of selected drugs with infrared laser desorption/tunable synchrotron vacuum ultraviolet photoionization mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20080801

Title: Expression of enkephalin-degrading enzymes in human semen and implications for sperm motility.

Journal: Fertility and sterility 20080501

Title: Immunocapture-based fluorometric assay for the measurement of neprilysin-specific enzyme activity in brain tissue homogenates and cerebrospinal fluid.

Journal: Journal of neuroscience methods 20080130

Title: A rapid and validated HPLC method to quantify racecadotril metabolite, thiorphan, in human plasma using solid-phase extraction.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080101

Title: Changes in A-type natriuretic peptide and its receptors induced by a neutral endopeptidase inhibitor in a rat model of sepsis.

Journal: Surgery today 20080101

Title: Phosphodiesterase-5A and neutral endopeptidase activities in human adipocytes do not control atrial natriuretic peptide-mediated lipolysis.

Journal: British journal of pharmacology 20071201

Title: Metabolic inactivation of the circadian transmitter, pigment dispersing factor (PDF), by neprilysin-like peptidases in Drosophila.

Journal: The Journal of experimental biology 20071201

Title: [Prevention and treatment of acute diarrhea in infants].

Journal: Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20071101

Title: Characterisation of endothelin converting enzyme-1 shedding from endothelial cells.

Journal: FEBS letters 20070918

Title: Systematic review: racecadotril in the treatment of acute diarrhoea in children.

Journal: Alimentary pharmacology & therapeutics 20070915

Title: Quantitative analysis of racecadotril metabolite in human plasma using a liquid chromatography/tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070601

Title: Decrease of dehydrogenase activity of cerebral glyceraldehyde-3-phosphate dehydrogenase in different animal models of Alzheimer's disease.

Journal: Biochimica et biophysica acta 20070501

Title: Expression of NEP2, a soluble neprilysin-like endopeptidase, during embryogenesis in Drosophila melanogaster.

Journal: Peptides 20070101

Title: [Study of substrate specificity of a new peptide substrate of endothelin converting enzyme].

Journal: Biomeditsinskaia khimiia 20070101

Title: Inhibition of neutral endopeptidase by thiorphan does not modify coronary vascular responses to angiotensin I, angiotensin II and bradykinin in the isolated guinea pig heart.

Journal: Pharmacological reports : PR 20070101

Title: Thiorphan, a neutral endopeptidase inhibitor used for diarrhoea, is neuroprotective in newborn mice.

Journal: Brain : a journal of neurology 20061201

Title: Structural studies of racecadotril and its process impurities by NMR and mass spectroscopy.

Journal: Die Pharmazie 20061201

Title: P2Y receptor-mediated excitation in the posterior hypothalamus.

Journal: The European journal of neuroscience 20060901

Title: Current status of anti-diarrheal and anti-secretory drugs in the management of acute childhood diarrhea.

Journal: Indian journal of pediatrics 20060801

Title: Hypersensitivity to racecadotril: a case report.

Journal: European journal of pediatrics 20060601

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Inhibition of neprilysin by infusion of thiorphan into the hippocampus causes an accumulation of amyloid Beta and impairment of learning and memory.

Journal: The Journal of pharmacology and experimental therapeutics 20060401

Title: Inhibition of neprilysin by thiorphan (i.c.v.) causes an accumulation of amyloid beta and impairment of learning and memory.

Journal: Behavioural brain research 20060315

Title: Neprilysin participates in skeletal muscle regeneration and is accumulated in abnormal muscle fibres of inclusion body myositis.

Journal: Journal of neurochemistry 20060201

Title: The effects of substance P on the biomechanic properties of ruptured rat Achilles' tendon.

Journal: Archives of physical medicine and rehabilitation 20060201

Title: Thiorphan, tiopronin, and related analogs as substrates and inhibitors of peptidylglycine alpha-amidating monooxygenase (PAM).

Journal: FEBS letters 20060123

Title: Neutral endopeptidase (EC 3.4.24.11) in cirrhotic liver: a new target to treat portal hypertension?

Journal: Journal of hepatology 20051101

Title: NEP inhibitors enhance C-type natriuretic peptide-induced relaxation in porcine isolated coronary artery.

Journal: Vascular pharmacology 20051001

Title: Exogenously administered substance P and neutral endopeptidase inhibitors stimulate fibroblast proliferation, angiogenesis and collagen organization during Achilles tendon healing.

Journal: Foot & ankle international 20051001

Title: Ascorbic acid decreases neutral endopeptidase activity in cultured osteoblastic cells.

Journal: Regulatory peptides 20050815

Title: Endothelin-1 (1-31) is an intermediate in the production of endothelin-1 after big endothelin-1 administration in vivo.

Journal: Hypertension (Dallas, Tex. : 1979) 20050701

Title: Racecadotril in acute diarrhea.

Journal: Indian pediatrics 20050501

Title: A blind, randomized comparison of racecadotril and loperamide for stopping acute diarrhea in adults.

Journal: World journal of gastroenterology 20050314

Title: Neutral endopeptidase inhibition augments vascular actions of bradykinin in patients treated with angiotensin-converting enzyme inhibition.

Journal: Hypertension (Dallas, Tex. : 1979) 20041201

Title: Racecadotril-is there enough evidence to recommend it for treatment of acute diarrhea?

Journal: Indian pediatrics 20041201

Title: Raacecadotril.

Journal: Indian pediatrics 20041201

Title: Further evidence on the anxiogenic-like effect of substance P evaluated in the elevated plus-maze in rats.

Journal: Behavioural brain research 20041005

Title: Angiotensin II-induced relaxation of anococcygeus smooth muscle via desensitization of AT1 receptor, and activation of AT2 receptor associated with nitric-oxide synthase pathway.

Journal: The Journal of pharmacology and experimental therapeutics 20041001

Title: Chronic morphine treatment reduces recovery from opioid desensitization.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040901

Title: Cardiac length dependence of force and force redevelopment kinetics with altered cross-bridge cycling.

Journal: Biophysical journal 20040901

Title: The effect of acute angiotensin-converting enzyme and neutral endopeptidase 24.11 inhibition on plasma extravasation in the rat.

Journal: The Journal of pharmacology and experimental therapeutics 20040601

Title: [The new class of drugs-- metalloprotease inhibitors -- in the treatment of heart failure].

Journal: Klinicheskaia meditsina 20040101

Title: Thiorphan-induced neprilysin inhibition raises amyloid beta levels in rabbit cortex and cerebrospinal fluid.

Journal: Neuroscience letters 20031030

Title: Efficacy and tolerability of racecadotril in the treatment of cholera in adults: a double blind, randomised, controlled clinical trial.

Journal: Gut 20031001

Title: Effects of the neutral endopeptidase inhibitor thiorphan on cardiovascular and renal function in cirrhotic rats.

Journal: British journal of pharmacology 20030501

Title: Methionine enkephalin suppresses metabolic activity of a leukemic cell line (NALM-1) and enhances CD10 expression.

Journal: International immunopharmacology 20030501

Title: Thiorphan enhances bradykinin-induced vascular relaxation in hypoxic/hyperkalaemic porcine coronary artery.

Journal: The Journal of pharmacy and pharmacology 20030301

Title: Racecadotril versus loperamide: antidiarrheal research revisited.

Journal: Digestive diseases and sciences 20030201

Title: Effect of neutral endopeptidase inhibition on vascular response induced by exogenous angiotensin I in the isolated rat lung.

Journal: Polish journal of pharmacology 20030101

Title: Pharmacological potentiation of natriuretic peptide limits polymorphonuclear neutrophil-vascular cell interactions.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20021101

Title: Effects of neutral endopeptidase 24.11 inhibition on myocardial infarct size and ischemic preconditioning in rabbits.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20021001

Title: Hormonal, renal, hemodynamic responses to acute neutral endopeptidase inhibition in heart transplant patients.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20020801

Title: Characterization of PgPepO, a bacterial homologue of endothelin-converting enzyme-1.

Journal: Clinical science (London, England : 1979) 20020801

Title: Endothelin-1 (1-31) induces a thiorphan-sensitive release of eicosanoids via ET(B) receptors in the guinea pig perfused lung.

Journal: Clinical science (London, England : 1979) 20020801

Title: [Effect of racecadotril in the management of acute diarrhea in infants and children].

Journal: Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20020801

Title: Involvement of proteases in the action of IFN-gamma on WISH cells.

Journal: Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research 20020801

Title: Racecadotril (acetorphan) in the treatment of acute watery diarrhoea in children.

Journal: Journal of the Indian Medical Association 20020801

Title: Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation.

Journal: Placenta 20020701

Title: A multinational comparison of racecadotril and loperamide in the treatment of acute watery diarrhoea in adults.

Journal: Scandinavian journal of gastroenterology 20020601

Title: Strategies for access to enantiomerically pure ecadotril, dexecadotril and fasidotril: a review.

Journal: Mini reviews in medicinal chemistry 20020601

Title: Role of ACE and NEP in bradykinin-induced relaxation and contraction response of isolated porcine basilar artery.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20020501

Title: Effects of chronic neutral endopeptidase inhibition on the progression of left ventricular dysfunction and remodeling in dogs with moderate heart failure.

Journal: Cardiovascular drugs and therapy 20020501

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Intestinal metabolism and absorption of cholecystokinin analogs in rats.

Journal: Biochemical and biophysical research communications 20020405

Title: Beta-amyloid deposition in the brains of rats chronically infused with thiorphan or lipopolysaccharide: the role of ascorbic acid in the vehicle.

Journal: Neuroscience letters 20020405

Title: Toward an optimal joint recognition of the S1' subsites of endothelin converting enzyme-1 (ECE-1), angiotensin converting enzyme (ACE), and neutral endopeptidase (NEP).

Journal: Journal of medicinal chemistry 20020328

Title: Endogenous opioids in dopaminergic cell body regions modulate amphetamine-induced increases in extracellular dopamine levels in the terminal regions.

Journal: The Journal of pharmacology and experimental therapeutics 20020301

Title: Neutral endopeptidase knockout induces hyperalgesia in a model of visceral pain, an effect related to bradykinin and nitric oxide.

Journal: Journal of molecular neuroscience : MN 20020101

Title: Interaction between neuropeptide FF and opioids in the ventral tegmental area in the behavioral response to novelty.

Journal: Neuroscience 20020101

Title: The treatment of acute diarrhea in the third millennium: a pediatrician's perspective.

Journal: Acta gastro-enterologica Belgica 20020101

Title: Neutral endopeptidase inhibition in diabetic wound repair.

Journal: Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society 20020101

Title: Soluble recombinant neprilysin induces aggrecanase-mediated cleavage of aggrecan in cartilage explant cultures.

Journal: Archives of biochemistry and biophysics 20011215

Title: [Role of delta opioid receptors and their ligands in the development of adaptive heart protection against arrhythmogenesis].

Journal: Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20011201

Title: The neuropeptide FF analogue, 1DMe, acts as a functional opioid autoreceptor antagonist in the rat spinal cord.

Journal: European journal of pharmacology 20011102

Title: A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.

Journal: British journal of pharmacology 20010901

Title: Effect of neutral endopeptidase inhibition on the actions of adrenomedullin and endothelin-1 in resistance arteries from patients with chronic heart failure.

Journal: Hypertension (Dallas, Tex. : 1979) 20010901

Title: Adrenomedullin (ADM) in the human forearm vascular bed: effect of neutral endopeptidase inhibition and comparison with proadrenomedullin NH2-terminal 20 peptide (PAMP).

Journal: British journal of clinical pharmacology 20010801

Title: Neprilysin degrades both amyloid beta peptides 1-40 and 1-42 most rapidly and efficiently among thiorphan- and phosphoramidon-sensitive endopeptidases.

Journal: The Journal of biological chemistry 20010615

Title: Interactions of human matrix metalloproteinase 7 (matrilysin) with the inhibitors thiorphan and R-94138.

Journal: Journal of biochemistry 20010301

Title: Efficacy and tolerability of racecadotril in acute diarrhea in children.

Journal: Gastroenterology 20010301

Title: [Anti-arrhythmia effects of enkephalinase inhibitors].

Journal: Eksperimental'naia i klinicheskaia farmakologiia 20010101

Title: Characterization of delta-opioid receptors and effect of enkephalins on IRD 98 rat epithelial intestinal cell line.

Journal: Pflugers Archiv : European journal of physiology 20000301

Title: Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action.

Journal: Journal of medicinal chemistry 20000210

Title: In vitro metabolism of an insect neuropeptide by neural membrane preparations from Lymantria dispar.

Journal: Peptides 19960101

Title: Jurkat T cells express a functional neutral endopeptidase activity (CALLA) involved in T cell activation.

Journal: The EMBO journal 19921101

Title: Effects of acetorphan, an enkephalinase inhibitor, on experimental and acute diarrhoea.

Journal: Gut 19920601

Title: Feedback inhibition of met-enkephalin release from the rat spinal cord in vivo.

Journal: Synapse (New York, N.Y.) 19920501

Title: Effect of resiniferatoxin on the isolated rabbit iris sphincter muscle: comparison with capsaicin and bradykinin.

Journal: European journal of pharmacology 19920324

Title: Opioid control of the in vitro release of cholecystokinin-like material from the rat substantia nigra.

Journal: Journal of neurochemistry 19920301

Title: Inhibition of apomorphine-induced yawning and penile erection by neurotensin.

Journal: Peptides 19910101

Title: Naloxone-reversible antidiarrheal effects of enkephalinase inhibitors.

Journal: European journal of pharmacology 19871201

Title: Pharmacological properties of acetorphan, a parenterally active 'enkephalinase' inhibitor.

Journal: The Journal of pharmacology and experimental therapeutics 19860601

Title: Angiotensin-converting enzyme inhibitors potentiate the analgesic activity of [Met]-enkephalin-Arg6-Phe7 by inhibiting its degradation in mouse brain.

Journal: Molecular pharmacology 19851201

Title: Thiorphan and analogs: lack of correlation between potency to inhibit 'enkephalinase A' in vitro and analgesic potency in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 19850801

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Tags:76721-89-6 Molecular Formula|76721-89-6 MDL|76721-89-6 SMILES|76721-89-6 Thiorphan