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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 of Ataciguat Sodium

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
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.

Approval Year

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes [IC50 15.4871 uM]
yes [IC50 2.1876 uM]
yes
yes (co-administration study)
Comment: Coadministration under SS condition increased (S)-warfarin AUCinf by 221%
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase.
2006 Apr
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
Guanylyl cyclase activator ataciguat improves vascular function and reduces platelet activation in heart failure.
2010 Nov
Patents

Patents

Sample Use Guides

200mg taken daily for 12 months
Route of Administration: Oral
Ataciguat (1 ul/L) was used to activate sGC in cultured coronary endothelial monolayers and isolated saline-perfused rat hearts.
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