DAGLUTRIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H38N2O6
Molecular Weight	534.6432
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)CC2(CCCC2)C(=O)N[C@H]3CCC4=CC=CC=C4N(CC(O)=O)C3=O

InChI

InChIKey=XMQODGUTLZXUGZ-RPBOFIJWSA-N

InChI=1S/C31H38N2O6/c1-2-39-29(37)24(15-14-22-10-4-3-5-11-22)20-31(18-8-9-19-31)30(38)32-25-17-16-23-12-6-7-13-26(23)33(28(25)36)21-27(34)35/h3-7,10-13,24-25H,2,8-9,14-21H2,1H3,(H,32,38)(H,34,35)/t24-,25+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C31H38N2O6
Molecular Weight	534.6432
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12735234
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/25131455 http://adisinsight.springer.com/drugs/800010577

The new chemical entity KC12615 is a potent f neutral endopeptidase inhibitor with additional endothelin-converting enzyme (ECE)–inhibitory activity.2 KC12615 is the hydrolyzed form of the oral prodrug SLV306 (daglutril). In plasma, the compound increases natriuretic peptide levels and prevents the formation of endothelin-1 by inhibiting the degradation of its precursor, big endothelin. It is investigated for use/treatment in congestive heart failure and hypertension.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neprilysin 29 Target ID: CHEMBL1944 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12735234	Inhibitor 8297		4.2 nM [IC50]
Endothelin-converting enzyme 1 4 Target ID: CHEMBL4791 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12735234	Inhibitor 8297		1.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Essential hypertension 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12735234	Primary		Phase II 1132	Unknown Approved Use Unknown
Congestive heart failure 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12735234	Primary		Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15246912 Page: p.238	unhealthy n = 19 Health Status: unhealthy Condition: congestive heart failure Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/15246912 Page: p.238	Sources: https://pubmed.ncbi.nlm.nih.gov/15246912 Page: p.238

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363680379	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363680379	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363680379	yes [IC50 7.5637 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363680379	no

Sourcing

Vendor/Aggregator	ID	URL
AChemBlock	H-8695	http://www.achemblock.com/catalogsearch/result/?q=H-8695
Axon MedChem	1918	https://www.axonmedchem.com/product/1918
MolPort	MolPort-006-170-114	https://www.molport.com/shop/molecule-link/MolPort-006-170-114
MuseChem	I006371	https://www.musechem.com/product/I006371.html
Ryan Scientific	101-93962	https://ryansci.com/products?q=101-93962&list_q=&search_type=exact
eMolecules	49435261	https://orderbb.emolecules.com/search/#?query=49435261

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

150, 300, 600 mg Once Daily or 150-300 mg Twice Daily

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:34:19 UTC 2023` Edited by `admin` on `Fri Dec 15 16:34:19 UTC 2023`
Record UNII	KKV299446X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DAGLUTRIL

Official Name

English

SLV306

Code

English

SLV-306

Code

English

((3S)-3-(1-((2R)-2-ETHOXYCARBONYL-4-PHENYLBUTYL)CYCLOPENTANECARBOXAMIDO)-2-OXO-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-1-YL)ACETIC ACID

Systematic Name

English

daglutril [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783