Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H15NO3S |
| Molecular Weight | 253.317 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CNC(=O)[C@@H](CS)CC1=CC=CC=C1
InChI
InChIKey=LJJKNPQAGWVLDQ-SNVBAGLBSA-N
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)/t10-/m1/s1
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2994 |
|||
Target ID: CHEMBL2642 |
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Target ID: CHEMBL2642 |
3.5 nM [Ki] | ||
Target ID: CHEMBL2994 |
140.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
400 mg 2 times / day multiple, oral (max) Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.1142 |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: Cardiac Failure Congestive Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: Page: p.1142 |
Other AEs: Headache, Dizziness... Other AEs: Headache (16%) Sources: Page: p.1142Dizziness (grade 1-2, 35%) Insomnia (6%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | 16% | 400 mg 2 times / day multiple, oral (max) Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.1142 |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: Cardiac Failure Congestive Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: Page: p.1142 |
| Insomnia | 6% | 400 mg 2 times / day multiple, oral (max) Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.1142 |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: Cardiac Failure Congestive Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: Page: p.1142 |
| Dizziness | grade 1-2, 35% | 400 mg 2 times / day multiple, oral (max) Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.1142 |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: Cardiac Failure Congestive Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: Page: p.1142 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [Activation 11.2202 uM] | ||||
| no | ||||
| no | ||||
| yes [IC50 0.1259 uM] | ||||
| yes [IC50 0.3162 uM] | ||||
| yes [IC50 0.6918 uM] | ||||
| yes [IC50 1.2302 uM] | ||||
| yes [IC50 2.512 uM] |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| The enkephalinase inhibitor thiorphan shows antinociceptive activity in mice. | 1980 Nov 20 |
|
| Thiorphan potentiation of stress-induced analgesia in the mouse. | 1982 Sep 20-27 |
|
| Complete differentiation between enkephalinase and angiotensin-converting enzyme inhibition by retro-thiorphan. | 1983 Jun |
|
| Pharmacological properties of acetorphan, a parenterally active "enkephalinase" inhibitor. | 1986 Jun |
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| Naloxone-reversible antidiarrheal effects of enkephalinase inhibitors. | 1987 Dec 1 |
|
| Attenuation of the morphine withdrawal syndrome by inhibition of catabolism of endogenous enkephalins in the periaqueductal gray matter. | 1992 Apr |
|
| Role of neutral endopeptidase in exercise-induced bronchoconstriction in asthmatic subjects. | 1996 Aug |
|
| The effect of inhaled thiorphan on allergen-induced airway responses in asthmatic subjects. | 1996 May |
|
| Inhibition of opioid-degrading enzymes potentiates delta9-tetrahydrocannabinol-induced antinociception in mice. | 1998 |
|
| Ecadotril. (S)-acetorphan, sinorphan. | 1999 Apr |
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| Perceived benefit after participating in positive or negative/neutral heart failure trials: the patients' perspective. | 2001 Mar |
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| Strategies for access to enantiomerically pure ecadotril, dexecadotril and fasidotril: a review. | 2002 Jun |
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| Effects of chronic neutral endopeptidase inhibition on the progression of left ventricular dysfunction and remodeling in dogs with moderate heart failure. | 2002 May |
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| The effect of acute angiotensin-converting enzyme and neutral endopeptidase 24.11 inhibition on plasma extravasation in the rat. | 2004 Jun |
|
| Mechanism of vasopeptidase inhibitor-induced plasma extravasation: comparison of omapatrilat and the novel neutral endopeptidase 24.11/angiotensin-converting enzyme inhibitor GW796406. | 2005 Dec |
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| Neutral endopeptidase (EC 3.4.24.11) in cirrhotic liver: a new target to treat portal hypertension? | 2005 Nov |
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| Thiorphan, a neutral endopeptidase inhibitor used for diarrhoea, is neuroprotective in newborn mice. | 2006 Dec |
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| Neprilysin participates in skeletal muscle regeneration and is accumulated in abnormal muscle fibres of inclusion body myositis. | 2006 Feb |
|
| Synergy between natriuretic peptides and phosphodiesterase 5 inhibitors ameliorates pulmonary arterial hypertension. | 2008 Oct 15 |
|
| Role of mu- and delta-opioid receptors in the nucleus accumbens in cocaine-seeking behavior. | 2009 Jul |
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| A comprehensive review of the pharmacodynamics, pharmacokinetics, and clinical effects of the neutral endopeptidase inhibitor racecadotril. | 2012 |
Patents
Sample Use Guides
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XJ8Z52GK3X
Created by
admin on Sat Dec 16 20:01:49 UTC 2023 , Edited by admin on Sat Dec 16 20:01:49 UTC 2023
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95909-00-5
Created by
admin on Sat Dec 16 20:01:49 UTC 2023 , Edited by admin on Sat Dec 16 20:01:49 UTC 2023
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4369380
Created by
admin on Sat Dec 16 20:01:49 UTC 2023 , Edited by admin on Sat Dec 16 20:01:49 UTC 2023
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PRIMARY |
ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
