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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
Structure of Thiorphan, (S)-

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

HIDE SMILES / InChI

Molecular Formula C12H15NO3S
Molecular Weight 253.317
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Ecadotril or sinorphan is the S-enantiomer of racemic acetorphan (racecadotril). It inhibits enkephalinase activity. Ecadotril was studied for the treatment of hypertension and heart failure, however, its development was discontinued.

CNS Activity

Curator's Comment: Ecadotril ((S)-acetorphan) is CNS active in animals when administered parenterally. No human data available.

Originator

Curator's Comment: Roques, B. P., Schwartz, J. C. & Lecomte, J. M., inventors. Derives d'acides amines et leur application therapeutique. Fr. Pat. 8008601, Apr. 17, 1980; Eur. Pat. Appl. EP 38,758; Apr. 14, 1981.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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%)
Dizziness (grade 1-2, 35%)
Insomnia (6%)
Sources: Page: p.1142
AEs

AEs

AESignificanceDosePopulation
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Naloxone-reversible antidiarrheal effects of enkephalinase inhibitors.
1987 Dec 1
Perceived benefit after participating in positive or negative/neutral heart failure trials: the patients' perspective.
2001 Mar
Strategies for access to enantiomerically pure ecadotril, dexecadotril and fasidotril: a review.
2002 Jun
Neutral endopeptidase (EC 3.4.24.11) in cirrhotic liver: a new target to treat portal hypertension?
2005 Nov
Role of mu- and delta-opioid receptors in the nucleus accumbens in cocaine-seeking behavior.
2009 Jul
A comprehensive review of the pharmacodynamics, pharmacokinetics, and clinical effects of the neutral endopeptidase inhibitor racecadotril.
2012
Patents

Sample Use Guides

Mice: 300 mg/kg
Route of Administration: Intraperitoneal
In saturation binding studies in various mouse tissues [3H]-thiorphan exhibited an affinity (Kd value) of 0.46–0.77 nM, and the density of [3H]-thiorphan binding sites was well correlated with measured enkephalinase activity in a panel of 11 different mouse tissues.
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:01:49 GMT 2023
Edited
by admin
on Sat Dec 16 20:01:49 GMT 2023
Record UNII
XJ8Z52GK3X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Thiorphan, (S)-
Common Name English
(+)-Thiorphan
Common Name English
Glycine, N-[(2S)-2-(mercaptomethyl)-1-oxo-3-phenylpropyl]-
Systematic Name English
N-[(2S)-2-(Mercaptomethyl)-1-oxo-3-phenylpropyl]glycine
Systematic Name English
LY-171436
Code English
Thiorphan, (+)-
Common Name English
(S)-Thiorphan
Common Name English
LY171436
Code English
Code System Code Type Description
FDA UNII
XJ8Z52GK3X
Created by admin on Sat Dec 16 20:01:49 GMT 2023 , Edited by admin on Sat Dec 16 20:01:49 GMT 2023
PRIMARY
CAS
95909-00-5
Created by admin on Sat Dec 16 20:01:49 GMT 2023 , Edited by admin on Sat Dec 16 20:01:49 GMT 2023
PRIMARY
PUBCHEM
4369380
Created by admin on Sat Dec 16 20:01:49 GMT 2023 , Edited by admin on Sat Dec 16 20:01:49 GMT 2023
PRIMARY
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ACTIVE MOIETY