U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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=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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
0.51 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1.89 μg/mL
25 mg 1 times / day steady-state, oral
ATACIGUAT plasma
Homo sapiens
12.66 μg/mL
100 mg 1 times / day steady-state, oral
ATACIGUAT plasma
Homo sapiens
22.07 μg/mL
200 mg 1 times / day steady-state, oral
ATACIGUAT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
31.08 μg × h/mL
25 mg 1 times / day steady-state, oral
ATACIGUAT plasma
Homo sapiens
173.54 μg × h/mL
100 mg 1 times / day steady-state, oral
ATACIGUAT plasma
Homo sapiens
245.68 μg × h/mL
200 mg 1 times / day steady-state, oral
ATACIGUAT plasma
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
HFK2RU2LJ9
Record Status Validated (UNII)
Record Version