Ataciguat Sodium

Investigational

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=CC=C(Cl)C=C2C(=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	Na
Molecular Weight	22.98976928
Charge	1
Count

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

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

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 36 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 1447		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 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1.89 μg/mL CLINICAL TRIAL https://www.clinicaltrialsregister.eu/ctr-search/trial/2006-004275-35/results	25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATACIGUAT plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
12.66 μg/mL CLINICAL TRIAL https://www.clinicaltrialsregister.eu/ctr-search/trial/2006-004275-35/results	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATACIGUAT plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
22.07 μg/mL CLINICAL TRIAL https://www.sanofi.com/assets/dotcom/content-app/clinical-studies/pharma/DFI6174_summary.pdf	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATACIGUAT plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
31.08 μg × h/mL CLINICAL TRIAL https://www.clinicaltrialsregister.eu/ctr-search/trial/2006-004275-35/results	25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATACIGUAT plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
173.54 μg × h/mL CLINICAL TRIAL https://www.clinicaltrialsregister.eu/ctr-search/trial/2006-004275-35/results	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATACIGUAT plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
245.68 μg × h/mL CLINICAL TRIAL https://www.sanofi.com/assets/dotcom/content-app/clinical-studies/pharma/DFI6174_summary.pdf	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATACIGUAT plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206754	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466340	yes [IC50 15.4871 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466340	yes [IC50 2.1876 uM]
CYP2C9 2497	inhibitor 4027 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 2052	substrate 4014 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
eMolecules	10604938	https://orderbb.emolecules.com/search/#?query=10604938
mcule	MCULE-9000169331	https://mcule.com/MCULE-9000169331/
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

PubMed

Title	Date	PubMed
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.	2010-12-01	20797390
Guanylyl cyclase activator ataciguat improves vascular function and reduces platelet activation in heart failure.	2010-11	20600916
Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase.	2006-04	16332991

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 `Wed Apr 02 13:51:23 GMT 2025` Edited by `admin` on `Wed Apr 02 13:51:23 GMT 2025`
Record UNII	HFK2RU2LJ9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Ataciguat Sodium

Common Name

English

Ataciguat Sodium [WHO-DD]

Preferred 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

Code System Code Type Description

PUBCHEM

23694739

Created by admin on Wed Apr 02 13:51:23 GMT 2025 , Edited by admin on Wed Apr 02 13:51:23 GMT 2025

PRIMARY

CAS

254976-06-2

Created by admin on Wed Apr 02 13:51:23 GMT 2025 , Edited by admin on Wed Apr 02 13:51:23 GMT 2025

PRIMARY

FDA UNII

HFK2RU2LJ9

Created by admin on Wed Apr 02 13:51:23 GMT 2025 , Edited by admin on Wed Apr 02 13:51:23 GMT 2025

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

Cmax

AUC

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

C_max

Drug as perpetrator