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Details

Stereochemistry RACEMIC
Molecular Formula C12H15NO3S
Molecular Weight 253.317
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIORPHAN

SMILES

OC(=O)CNC(=O)C(CS)CC1=CC=CC=C1

InChI

InChIKey=LJJKNPQAGWVLDQ-UHFFFAOYSA-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)

HIDE SMILES / InChI
Molecular Formula C12H15NO3S
Molecular Weight 253.317
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

CNS Active
3913
Curator's Comment: Ecadotril ((S)-acetorphan) is CNS active in animals when administered parenterally. No human data available.

Originator

Bioprojet
5
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
 3.5 nM [Ki]
Inhibitor
8297
 140.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Preclinical
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
Page: p.1142
Other AEs: Headache, Dizziness...
Other AEs:
Headache (16%)
Dizziness (grade 1-2, 35%)
Insomnia (6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
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:
https://pubmed.ncbi.nlm.nih.gov/10577446
Page: p.1142
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

activator
80

inducer
781
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
60

CYP2C19
1478

CYP1A2
1524
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1925
 inconclusive [Activation 11.2202 uM]
CYP19A1
60
 no
CYP3A4
1925
 no
CYP2C19
1553
 yes [IC50 0.1259 uM]
CYP2D6
1891
 yes [IC50 0.3162 uM]
CYP3A4
1925
 yes [IC50 0.6918 uM]
CYP2C9
1819
 yes [IC50 1.2302 uM]
CYP1A2
1692
 yes [IC50 2.512 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY438197
https://www.001chemical.com/chem/76721-89-6
3B Scientific (Wuhan) Corp
3B3-046115
http://www.3bsc.com/index/pro_info.php?id=82714
AA Blocks
AA0035MB
https://www.aablocks.com/goods/Goods/detail?id=AA0035MB
AHH Chemical co.,ltd
MT-50654
http://www.ahhchemical.com/product/MT-50654.html
Acadechem
ACDS-070932
http://www.acadechemical.com/product/145631
Achemica
ACMC-20eo1l
http://www.achemica.com/prodinfo/?id=146524
Alfa Chemistry
AP76721896-A
https://reagents.alfa-chemistry.com/product/dl-thiorphan-cas-76721-89-6-16206.html
Alfa Chemistry
AP76721896-B
https://reagents.alfa-chemistry.com/product/dl-thiorphan-cas-76721-89-6-cas-76721-89-6-16207.html
Alichem
19139315
http://www.alichem.com/en/products/76721-89-6.html
Alsachim
668
http://www.alsachim.com/product-C2805-glo.bal-view.html
Ambinter
Amb17620621
http://www.ambinter.com/reference/17620621
Angel Pharmatech
AG202385
http://www.angelpharmatech.com/76721-89-6.html
Angene
AGN-PC-0WAFEB
http://www.angenechemical.com/productshow/AGN-PC-0WAFEB.html
Aurora Fine Chemicals LLC
A17.877.461
http://online.aurorafinechemicals.com/info?ID=A17.877.461
BLD Pharm
BD126637
http://www.bldpharm.com/products/76721-89-6.html
BOC Sciences
76721-89-6
https://aapep.bocsci.com/product/thiorphan-cas-76721-89-6-133335.html
Calbiochem
598510
http://www.emdbiosciences.com/product/598510
ChemMol
99145742
http://www.chemmol.com/chemmol/99145742.html
ChemShuttle
178241
http://www.chemshuttle.com/catalogsearch/result/?q=76721-89-6&cat=
Chemspace
CSSB00000088100
https://chem-space.com/CSSB00000088100
Clearsynth
CS-O-07004
https://www.clearsynth.com/en/CSO07004.html
Clearsynth
CS-T-44255
https://www.clearsynth.com/en/CST44255.html
Combi-Blocks
QM-5257
http://www.combi-blocks.com/cgi-bin/find.cgi?QM-5257
EMD Millipore
598510
http://www.emdbiosciences.com/product/598510
Finetech
FT-0675192
http://www.finetechnology-ind.com/prod/detail/pub/76721-89-6.html
Glentham Life Sciences
GL2922
http://www.glentham.com/products/product/GL2922/
Hairui
HR110100
http://www.hairuichem.com/en/product/76721-89-6.html
MolPort
MolPort-003-850-539
https://www.molport.com/shop/molecule-link/MolPort-003-850-539
Molcore
MC438197
https://www.molcore.com/product/76721-89-6
MuseChem
R004764
https://www.musechem.com/product/R004764.html
Nextpeptide
NP15651
http://www.nextpeptide.com/76721-89-6.html
Sigma-Aldrich
T6031_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/t6031?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech
S055275
http://www.sinfoobiotech.com/product/1058673
Smolecule
S591191
https://www.smolecule.com/products/s591191
THE BioTek
bt-249162
https://www.thebiotek.com/product/peptides/bt-249162
Watanabe Chemical Ind.
L00255
https://www.watanabechem.co.jp/en/search/details.php?code=L00255
abcr GmbH
AB348980
http://www.abcr.com/shop/en/AB348980
eNovation Chemicals
D583125
https://www.enovationchem.com/ProductDetails.asp?ProductID=D583125
PubMed

PubMed

TitleDatePubMed
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
Ecadotril. (S)-acetorphan, sinorphan.
1999 Apr
Mechanism of vasopeptidase inhibitor-induced plasma extravasation: comparison of omapatrilat and the novel neutral endopeptidase 24.11/angiotensin-converting enzyme inhibitor GW796406.
2005 Dec
Neprilysin participates in skeletal muscle regeneration and is accumulated in abnormal muscle fibres of inclusion body myositis.
2006 Feb
A comprehensive review of the pharmacodynamics, pharmacokinetics, and clinical effects of the neutral endopeptidase inhibitor racecadotril.
2012
Patents

Patents

JPH09249557A
3
WO2009077386A1
3

Sample Use Guides

In Vivo Use Guide
Mice: 300 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
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 01:47:31 GMT 2023
Edited
by admin
on Sat Dec 16 01:47:31 GMT 2023
Record UNII
B79L7B5X3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIORPHAN
Common Name English
RACECADOTRIL IMPURITY B [EP IMPURITY]
Common Name English
DL-THIORPHAN
Common Name English
N-((RS)-2-BENZYL-3-MERCAPTOPROPANOYL)-GLYCINE
Systematic Name English
NSC-727676
Code English
GLYCINE, N-(2-(MERCAPTOMETHYL)-1-OXO-3-PHENYLPROPYL)-
Systematic Name English
(((2RS)-2-BENZYL-3-SULFANYLPROPANOYL)AMINO)ACETIC ACID
Systematic Name English
(±)-THIORPHAN
Common Name English
GLYCINE, N-(2-(MERCAPTOMETHYL)-1-OXO-3-PHENYLPROPYL)-, (+-)-
Systematic Name English
Code System Code Type Description
NSC
727676
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID70868412
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
CAS
76721-89-6
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
SMS_ID
100000085216
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
MESH
D015244
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
EVMPD
SUB21843
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
FDA UNII
B79L7B5X3Z
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
DRUG BANK
DB08626
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
WIKIPEDIA
THIORPHAN
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
PUBCHEM
3132
Created by admin on Sat Dec 16 01:47:31 GMT 2023 , Edited by admin on Sat Dec 16 01:47:31 GMT 2023
PRIMARY
Related Record Type Details
Structure of Thiorphan, (S)-
ENANTIOMER -> RACEMATE
Structure of Thiorphan, (R)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of RACECADOTRIL
PRODRUG -> METABOLITE ACTIVE
bulk of its inhibitory actions on enkephalinase.
MAJOR
PLASMA
Related Record Type Details
Structure of RACECADOTRIL
PARENT -> IMPURITY
Related Record Type Details
Structure of THIORPHAN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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