ECADOTRIL

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H23NO4S
Molecular Weight	385.477
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(=O)SC[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)OCC2=CC=CC=C2

InChI

InChIKey=ODUOJXZPIYUATO-LJQANCHMSA-N

InChI=1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)/t19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H23NO4S
Molecular Weight	385.477
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Angiotensin-converting enzyme 97	Inhibitor 8,297
Neprilysin 29	Inhibitor 8,297
Neprilysin 29	Inhibitor 8,297	3.5 nM [Ki]
Angiotensin-converting enzyme 97	Inhibitor 8,297	140.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Heart failure 103	Primary	Phase II 1,132	Unknown
Pain 614	Primary	Preclinical	Unknown
Asthma 241	Palliative	Phase II 1,132	Unknown
Diarrhea 35	Primary	Preclinical	Unknown

Doses

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Dose	Population	Adverse events
400 mg 2 times / day multiple, oral (max) Highest studied dose	unhealthy, ADULT n = 31	Other AEs: Headache, Dizziness...

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AEs

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AE	Significance	Dose	Population
Headache	16%	400 mg 2 times / day multiple, oral (max) Highest studied dose	unhealthy, ADULT n = 31
Insomnia	6%	400 mg 2 times / day multiple, oral (max) Highest studied dose	unhealthy, ADULT n = 31
Dizziness	grade 1-2, 35%	400 mg 2 times / day multiple, oral (max) Highest studied dose	unhealthy, ADULT n = 31

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 activator 80 inducer 781	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60 CYP2C19 1,478 CYP1A2 1,524

Drug as perpetrator

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Target	Modality	Activity
CYP3A4 1,925	inducer 1,573	inconclusive [Activation 11.2202 uM]
CYP19A1 60	inhibitor 3,277	no
CYP3A4 1,925	activator 214	no
CYP2C19 1,553	inhibitor 3,277	yes [IC50 0.1259 uM]
CYP2D6 1,891	inhibitor 3,277	yes [IC50 0.3162 uM]

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Naloxone-reversible antidiarrheal effects of enkephalinase inhibitors.	1987 Dec 1	3481337
A comprehensive review of the pharmacodynamics, pharmacokinetics, and clinical effects of the neutral endopeptidase inhibitor racecadotril.	2012	22661949

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Patents

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
Record UNII	6XSR933SRK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ECADOTRIL

Official Name

English

BAY Y 7432

Code

English

BAY-Y-7432

Code

English

ECADOTRIL [USAN]

Common Name

English

N-[(S)-α-(Mercaptomethyl)hydrocinnamoyl]glycine, benzyl ester, acetate (ester)

Common Name

English

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Classification Tree

Code System

Code

Enzyme Inhibitor

NCI_THESAURUS

C783

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Code System

Code

Type

Description

PUBCHEM

60561

PRIMARY

WIKIPEDIA

Ecadotril

PRIMARY

EVMPD

SUB06442MIG

PRIMARY

FDA UNII

6XSR933SRK

PRIMARY

EPA CompTox

DTXSID40861036

PRIMARY

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Related Record

Type

Details


					XJ8Z52GK3X

Thiorphan, (S)-

METABOLITE ACTIVE -> PRODRUG

Amount:

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Related Record

Type

Details


					XJ8Z52GK3X

Thiorphan, (S)-

ACTIVE MOIETY

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Drug as perpetrator