Ataciguat - CAS 254877-67-3
Catalog number:
254877-67-3
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C21H19Cl2N3O6S3
Molecular Weight:
576.5
COA:
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Targets:
Guanylate Cyclase
Description:
Ataciguat, formerly referred to as HMR-1766, a novel anthranilic acid derivative, is a potent guanylate cyclase activator. Ataciguat has potential to treat diseases associated with increased vascular tone combined with enhanced ROS production.
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Purity:
>98%
Appearance:
Solid powder
Synonyms:
5-Chloro-2-[[(5-chloro-2-thienyl)sulfonyl]amino]-N-[4-(4-morpholinylsulfonyl)phenyl]benzamide;Ataciguat;HMR 1766
MSDS:
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Application:
Ataciguat, formerly referred to as HMR-1766, a novel anthranilic acid derivative, belongs to a new structural class of sGC activators capable of activating the oxidized form of sGC. Ataciguat has been shown to improve endothelial function and to reduce p
InChIKey:
PQHLRGARXNPFCF-UHFFFAOYSA-N
InChI:
1S/C21H19Cl2N3O6S3/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/h1-8,13,25H,9-12H2,(H,24,27)
Canonical SMILES:
C1COCCN1S(=O)(=O)C2=CC=C(C=C2)NC(=O)C3=C(C=CC(=C3)Cl)NS(=O)(=O)C4=CC=C(S4)Cl
1.Sulfoximine directed intermolecular o-C-H amidation of arenes with sulfonyl azides.
Yadav MR1, Rit RK, Sahoo AK. Org Lett. 2013 Apr 5;15(7):1638-41. doi: 10.1021/ol400411v. Epub 2013 Mar 11.
The Ru(II)-catalyzed intermolecular o-C-H amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method is successfully employed for the synthesis of HMR 1766.
2.The soluble guanylate cyclase activator HMR1766 reverses hypoxia-induced experimental pulmonary hypertension in mice.
Weissmann N1, Hackemack S, Dahal BK, Pullamsetti SS, Savai R, Mittal M, Fuchs B, Medebach T, Dumitrascu R, Eickels Mv, Ghofrani HA, Seeger W, Grimminger F, Schermuly RT. Am J Physiol Lung Cell Mol Physiol. 2009 Oct;297(4):L658-65. doi: 10.1152/ajplung.00189.2009. Epub 2009 Jul 17.
Severe pulmonary hypertension (PH) is a disabling disease with high mortality, characterized by pulmonary vascular remodeling and right heart hypertrophy. In mice with PH induced by chronic hypoxia, we examined the acute and chronic effects of the soluble guanylate cyclase (sGC) activator HMR1766 on hemodynamics and pulmonary vascular remodeling. In isolated perfused mouse lungs from control animals, HMR1766 dose-dependently inhibited the pressor response of acute hypoxia. This dose-response curve was shifted leftward when the effects of HMR1766 were investigated in isolated lungs from chronic hypoxic animals for 21 days at 10% oxygen. Mice exposed for 21 or 35 days to chronic hypoxia developed PH, right heart hypertrophy, and pulmonary vascular remodeling. Treatment with HMR1766 (10 mg x kg(-1) x day(-1)), after full establishment of PH from day 21 to day 35, significantly reduced PH, as measured continuously by telemetry. In addition, right ventricular (RV) hypertrophy and structural remodeling of the lung vasculature were reduced.
3.Cobinamides are novel coactivators of nitric oxide receptor that target soluble guanylyl cyclase catalytic domain.
Sharina I1, Sobolevsky M, Doursout MF, Gryko D, Martin E. J Pharmacol Exp Ther. 2012 Mar;340(3):723-32. doi: 10.1124/jpet.111.186957. Epub 2011 Dec 13.
Soluble guanylyl cyclase (sGC), a ubiquitously expressed heme-containing receptor for nitric oxide (NO), is a key mediator of NO-dependent processes. In addition to NO, a number of synthetic compounds that target the heme-binding region of sGC and activate it in a NO-independent fashion have been described. We report here that dicyanocobinamide (CN2-Cbi), a naturally occurring intermediate of vitamin B(12) synthesis, acts as a sGC coactivator both in vitro and in intact cells. Heme depletion or heme oxidation does not affect CN2-Cbi-dependent activation. Deletion mutagenesis demonstrates that CN2-Cbi targets a new regulatory site and functions though a novel mechanism of sGC activation. Unlike all known sGC regulators that target the N-terminal regulatory regions, CN2-Cbi directly targets the catalytic domain of sGC, resembling the effect of forskolin on adenylyl cyclases. CN2-Cbi synergistically enhances sGC activation by NO-independent regulators 3-(4-amino-5-cyclopropylpyrimidine-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (BAY41-2272), 4-[((4-carboxybutyl){2-[(4-phenethylbenzyl)oxy]phenethyl}amino) methyl [benzoic]-acid (cinaciguat or BAY58-2667), and 5-chloro-2-(5-chloro-thiophene-2-sulfonylamino-N-(4-(morpholine-4-sulfonyl)-phenyl)-benzamide sodium salt (ataciguat or HMR-1766).
4.Renal effects of soluble guanylate cyclase stimulators and activators: a review of the preclinical evidence.
Stasch JP1, Schlossmann J2, Hocher B3. Curr Opin Pharmacol. 2015 Apr;21:95-104. doi: 10.1016/j.coph.2014.12.014. Epub 2015 Jan 31.
Direct stimulation of soluble guanylate cyclase (sGC) is emerging as a potential new approach for the treatment of renal disorders. sGC catalyzes the formation of cyclic guanosine monophosphate (cGMP), deficiency of which is implicated in the pathogenesis of chronic kidney disease (CKD). Therefore, new classes of drugs - sGC stimulators and activators - are being investigated in preclinical models under conditions where nitric oxide is deficient. In preclinical models with different etiologies of CKD, the sGC stimulators BAY 41-2272, BAY 41-8543, BAY 60-4552, riociguat and vericiguat and the sGC activators cinaciguat, ataciguat, BI 703704 and GSK2181236A have shown consistently renoprotective effects. Clinical trials are required to confirm these findings in humans, and to ascertain whether these agents could provide a future alternative to guideline-recommended treatments.
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CAS 254877-67-3 Ataciguat

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