Ataciguat
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MedKoo CAT#: 319566

CAS#: 254877-67-3

Description: Ataciguat, also known as HMR-1766, is a potent guanylate cyclase activator potentially for the treatment of aortic valve stenosis. HMR-1766 is a promising agent for treating diseases associated with increased vascular tone combined with enhanced ROS production. Ataciguat improves vascular function and reduces platelet activation in heart failure.


Chemical Structure

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Ataciguat
CAS# 254877-67-3

Theoretical Analysis

MedKoo Cat#: 319566
Name: Ataciguat
CAS#: 254877-67-3
Chemical Formula: C21H19Cl2N3O6S3
Exact Mass: 574.9813
Molecular Weight: 576.48
Elemental Analysis: C, 43.75; H, 3.32; Cl, 12.30; N, 7.29; O, 16.65; S, 16.68

Price and Availability

Size Price Availability Quantity
5.0mg USD 450.0 2 Weeks
10.0mg USD 770.0 2 Weeks
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Synonym: HMR-1766; HMR 1766; HMR1766; Ataciguat

IUPAC/Chemical Name: 5-Chloro-2-[[(5-chloro-2-thienyl)sulfonyl]amino]-N-[4-(4-morpholinylsulfonyl)phenyl]benzamide

InChi Key: PQHLRGARXNPFCF-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NC1=CC=C(S(=O)(N2CCOCC2)=O)C=C1)C3=CC(Cl)=CC=C3NS(=O)(C4=CC=C(Cl)S4)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 576.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Stasch JP, Schlossmann J, Hocher B. Renal effects of soluble guanylate cyclase stimulators and activators: a review of the preclinical evidence. Curr Opin Pharmacol. 2015 Apr;21:95-104. doi: 10.1016/j.coph.2014.12.014. Epub 2015 Jan 31. Review. PubMed PMID: 25645316.

2: Sharina IG, Sobolevsky M, Papakyriakou A, Rukoyatkina N, Spyroulias GA, Gambaryan S, Martin E. The fibrate gemfibrozil is a NO- and haem-independent activator of soluble guanylyl cyclase: in vitro studies. Br J Pharmacol. 2015 May;172(9):2316-29. doi: 10.1111/bph.13055. Epub 2015 Feb 10. PubMed PMID: 25536881; PubMed Central PMCID: PMC4403096.

3: Inserte J, Hernando V, Ruiz-Meana M, Poncelas-Nozal M, Fernández C, Agulló L, Sartorio C, Vilardosa U, Garcia-Dorado D. Delayed phospholamban phosphorylation in post-conditioned heart favours Ca2+ normalization and contributes to protection. Cardiovasc Res. 2014 Sep 1;103(4):542-53. doi: 10.1093/cvr/cvu163. Epub 2014 Jun 27. PubMed PMID: 25020913.

4: Fraccarollo D, Galuppo P, Motschenbacher S, Ruetten H, Schäfer A, Bauersachs J. Soluble guanylyl cyclase activation improves progressive cardiac remodeling and failure after myocardial infarction. Cardioprotection over ACE inhibition. Basic Res Cardiol. 2014 Jul;109(4):421. doi: 10.1007/s00395-014-0421-1. Epub 2014 Jun 8. PubMed PMID: 24907870.

5: Yadav MR, Rit RK, Sahoo AK. Sulfoximine directed intermolecular o-C-H amidation of arenes with sulfonyl azides. Org Lett. 2013 Apr 5;15(7):1638-41. doi: 10.1021/ol400411v. Epub 2013 Mar 11. PubMed PMID: 23477353.

6: Sharina I, Sobolevsky M, Doursout MF, Gryko D, Martin E. Cobinamides are novel coactivators of nitric oxide receptor that target soluble guanylyl cyclase catalytic domain. J Pharmacol Exp Ther. 2012 Mar;340(3):723-32. doi: 10.1124/jpet.111.186957. Epub 2011 Dec 13. PubMed PMID: 22171090; PubMed Central PMCID: PMC3286313.

7: Haase N, Haase T, Kraehling JR, Behrends S. 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. Biochem Pharmacol. 2010 Dec 1;80(11):1676-83. doi: 10.1016/j.bcp.2010.08.007. Epub 2010 Aug 24. PubMed PMID: 20797390.

8: Schäfer A, Fraccarollo D, Werner L, Bauersachs J. Guanylyl cyclase activator ataciguat improves vascular function and reduces platelet activation in heart failure. Pharmacol Res. 2010 Nov;62(5):432-8. doi: 10.1016/j.phrs.2010.06.008. Epub 2010 Jun 22. PubMed PMID: 20600916.

9: Schäfer A, Galuppo P, Fraccarollo D, Vogt C, Widder JD, Pfrang J, Tas P, Barbosa-Sicard E, Ruetten H, Ertl G, Fleming I, Bauersachs J. Increased cytochrome P4502E1 expression and altered hydroxyeicosatetraenoic acid formation mediate diabetic vascular dysfunction: rescue by guanylyl-cyclase activation. Diabetes. 2010 Aug;59(8):2001-9. doi: 10.2337/db09-1668. Epub 2010 Jun 3. PubMed PMID: 20522591; PubMed Central PMCID: PMC2911073.

10: Weissmann N, 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. The soluble guanylate cyclase activator HMR1766 reverses hypoxia-induced experimental pulmonary hypertension in mice. Am J Physiol Lung Cell Mol Physiol. 2009 Oct;297(4):L658-65. doi: 10.1152/ajplung.00189.2009. Epub 2009 Jul 17. PubMed PMID: 19617308.

11: Hoffmann LS, Schmidt PM, Keim Y, Schaefer S, Schmidt HH, Stasch JP. Distinct molecular requirements for activation or stabilization of soluble guanylyl cyclase upon haem oxidation-induced degradation. Br J Pharmacol. 2009 Jul;157(5):781-95. doi: 10.1111/j.1476-5381.2009.00263.x. Epub 2009 May 18. PubMed PMID: 19466990; PubMed Central PMCID: PMC2721263.

12: Kasseckert SA, Schäfer C, Kluger A, Gligorievski D, Tillmann J, Schlüter KD, Noll T, Sauer H, Piper HM, Abdallah Y. Stimulation of cGMP signalling protects coronary endothelium against reperfusion-induced intercellular gap formation. Cardiovasc Res. 2009 Jul 15;83(2):381-7. doi: 10.1093/cvr/cvp065. Epub 2009 Feb 21. PubMed PMID: 19234300.

13: Schmidt HH, Schmidt PM, Stasch JP. NO- and haem-independent soluble guanylate cyclase activators. Handb Exp Pharmacol. 2009;(191):309-39. doi: 10.1007/978-3-540-68964-5_14. Review. PubMed PMID: 19089335.

14: Zhou Z, Pyriochou A, Kotanidou A, Dalkas G, van Eickels M, Spyroulias G, Roussos C, Papapetropoulos A. Soluble guanylyl cyclase activation by HMR-1766 (ataciguat) in cells exposed to oxidative stress. Am J Physiol Heart Circ Physiol. 2008 Oct;295(4):H1763-71. doi: 10.1152/ajpheart.51.2008. Epub 2008 Aug 29. PubMed PMID: 18757489.

15: Benz K, Orth SR, Simonaviciene A, Linz W, Schindler U, Rütten H, Amann K. Blood pressure-independent effect of long-term treatment with the soluble heme-independent guanylyl cyclase activator HMR1766 on progression in a model of noninflammatory chronic renal damage. Kidney Blood Press Res. 2007;30(4):224-33. Epub 2007 Jun 15. PubMed PMID: 17575468.

16: Oberwittler H, Hirschfeld-Warneken A, Wesch R, Willerich H, Teichert L, Lehr KH, Ding R, Haefeli WE, Mikus G. Significant pharmacokinetic and pharmacodynamic interaction of warfarin with the NO-independent sGC activator HMR1766. J Clin Pharmacol. 2007 Jan;47(1):70-7. PubMed PMID: 17192504.

17: Schäfer A, Flierl U, Kobsar A, Eigenthaler M, Ertl G, Bauersachs J. Soluble guanylyl cyclase activation with HMR1766 attenuates platelet activation in diabetic rats. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2813-8. Epub 2006 Oct 5. PubMed PMID: 17023677.

18: Schindler U, Strobel H, Schönafinger K, Linz W, Löhn M, Martorana PA, Rütten H, Schindler PW, Busch AE, Sohn M, Töpfer A, Pistorius A, Jannek C, Mülsch A. Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase. Mol Pharmacol. 2006 Apr;69(4):1260-8. Epub 2005 Dec 6. PubMed PMID: 16332991.