Ataciguat Sodium

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H18Cl2N3O6S3.Na
Molecular Weight	598.475
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].ClC1=CC=C(S1)S(=O)(=O)[N-]C2=C(C=C(Cl)C=C2)C(=O)NC3=CC=C(C=C3)S(=O)(=O)N4CCOCC4

InChI

InChIKey=OPLFZLANTJVJDX-UHFFFAOYSA-M

InChI=1S/C21H19Cl2N3O6S3.Na/c22-14-1-6-18(25-34(28,29)20-8-7-19(23)33-20)17(13-14)21(27)24-15-2-4-16(5-3-15)35(30,31)26-9-11-32-12-10-26;/h1-8,13H,9-12H2,(H2,24,25,27);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C21H18Cl2N3O6S3
Molecular Weight	575.485
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://adisinsight.springer.com/drugs/800014027 | https://ncats.nih.gov/files/HMR1766.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19089335

Ataciguat is a novel anthranilic acid derivative that belongs to a new structural class of sGC activators which are capable of activating the oxidized form of sGC. Ataciguat, a nitric oxide-independent soluble guanylate cyclase activator, is being developed by Sanofi (previously sanofi-aventis), in collaboration with Mayo Clinic and National Center for Advancing Translational Sciences. Ataciguat is in phase II clinical trials for the treatment of aortic valve stenosis. It had been used to treat neuropathic pain and peripheral arterial disease, but this research has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Soluble guanylate cyclase 34 Target ID: CHEMBL2111348 Sources: http://adisinsight.springer.com/drugs/800014027 \| https://www.ncbi.nlm.nih.gov/pubmed/20797390 \| https://www.ncbi.nlm.nih.gov/pubmed/16332991 \| https://www.ncbi.nlm.nih.gov/pubmed/19089335	Activator 1430		0.51 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Aortic valve stenosis 6 Sources: https://clinicaltrials.gov/ct2/show/NCT02481258 http://adisinsight.springer.com/drugs/800014027	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60	P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206754	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466340	yes [IC50 15.4871 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466340	yes [IC50 2.1876 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17192504/	yes	yes (co-administration study) Comment: Coadministration under SS condition increased (S)-warfarin AUCinf by 221% Sources: https://pubmed.ncbi.nlm.nih.gov/17192504/

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144206754	no

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00C36T	https://www.1pchem.com/search?query=1P00C36T
AK Scientific	3142AL	https://aksci.com/item_detail.php?cat=3142AL
ApexBio Technology	C4216	https://www.apexbt.com/catalogsearch/result/?q=C4216
AstaTech	42167	http://astatechinc.com/CPSResult.php?CRNO=42167
BLD Pharm	BD294317	http://www.bldpharm.com/search/Search.html?keyword=BD294317
BOC Sciences	254877-67-3	http://www.bocsci.com/description.asp?cas=254877-67-3
Cayman Chemical	16371	http://www.caymanchem.com/app/template/Product.vm/catalog/16371
MolPort	MolPort-006-392-391	https://www.molport.com/shop/molecule-link/MolPort-006-392-391
MuseChem	R009251	https://www.musechem.com/product/R009251.html
Toronto Research Chemicals	A790040	https://www.trc-canada.com/product-detail/?CatNum=A790040
Toronto Research Chemicals	D289997	https://www.trc-canada.com/product-detail/?CatNum=D289997
eMolecules	10604938	https://orderbb.emolecules.com/search/#?query=10604938
mcule	MCULE-9000169331	https://mcule.com/MCULE-9000169331/

PubMed

Title	Date	PubMed
Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase.	2006 Apr	16332991
Direct fusion of subunits of heterodimeric nitric oxide sensitive guanylyl cyclase leads to functional enzymes with preserved biochemical properties: evidence for isoform specific activation by ciguates.	2010 Dec 1	20797390
Guanylyl cyclase activator ataciguat improves vascular function and reduces platelet activation in heart failure.	2010 Nov	20600916

Patents

Sample Use Guides

In Vivo Use Guide

200mg taken daily for 12 months

Route of Administration: Oral

In Vitro Use Guide

Ataciguat (1 ul/L) was used to activate sGC in cultured coronary endothelial monolayers and isolated saline-perfused rat hearts.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:10:27 GMT 2023` Edited by `admin` on `Sat Dec 16 19:10:27 GMT 2023`
Record UNII	HFK2RU2LJ9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Ataciguat Sodium

Common Name

English

Benzamide, 5-chloro-2-[[(5-chloro-2-thienyl)sulfonyl]amino]-N-[4-(4-morpholinylsulfonyl)phenyl]-, sodium salt (1:1)

Systematic Name

English

5-Chloro-2-[[(5-chlorothien-2-yl)sulfonyl]amino]-N-[4-[(morpholin-4-yl)sulfonyl]phenyl]benzamide sodium salt

Systematic Name

English

Ataciguat Sodium [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

23694739

Created by admin on Sat Dec 16 19:10:27 GMT 2023 , Edited by admin on Sat Dec 16 19:10:27 GMT 2023

PRIMARY

CAS

254976-06-2

Created by admin on Sat Dec 16 19:10:27 GMT 2023 , Edited by admin on Sat Dec 16 19:10:27 GMT 2023

PRIMARY

FDA UNII

HFK2RU2LJ9

Created by admin on Sat Dec 16 19:10:27 GMT 2023 , Edited by admin on Sat Dec 16 19:10:27 GMT 2023

PRIMARY

Related Record Type Details


					QP166M390Q

Ataciguat

PARENT -> SALT/SOLVATE

Amount:

Details

SMILES

InChI

DescriptionSources: http://adisinsight.springer.com/drugs/800014027 | https://ncats.nih.gov/files/HMR1766.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19089335

Originator

Approval Year

Targets

Conditions

Approved Use

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://adisinsight.springer.com/drugs/800014027 | https://ncats.nih.gov/files/HMR1766.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19089335

Drug as perpetrator