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Ataciguat

Alias: HMR-1766 HMR1766 HMR 1766
Cat No.:V6198 Purity: ≥98%
Ataciguat (HMR-1766) is a nitric oxide-independent activator of soluble guanylate cyclase (sGC).
Ataciguat
Ataciguat Chemical Structure CAS No.: 254877-67-3
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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10mg
50mg
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Product Description
Ataciguat (HMR-1766) is a nitric oxide-independent activator of soluble guanylate cyclase (sGC). Ataciguat can activate the heme iron redox form of sGC and stimulate the production of cGMP. Ataciguat has vasodilatory effects.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Ataciguat (1-100 μM) causes the coronary or aortic artery rings to relax [2]. In HUVEC cells, ataciguat (0.1–10 μM; 30 minutes) boosts NO production [2]. High-concentration biliary contractions are induced in the carbachine-precontracted circular sphincter of Oddi (SO) by ataciguat (1 nM-100 μM). [3].
References

[1]. Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase. Mol Pharmacol. 2006 Apr;69(4):1260-8.

[2]. In Endothelial Cells, the Activation or Stimulation of Soluble Guanylyl Cyclase Induces the Nitric Oxide Production by a Mechanism Dependent of Nitric Oxide Synthase Activation. J Pharm Pharm Sci. 2018;21(1):38-45.

[3]. Comparative Relaxant Effects of Ataciguat and Zaprinast on Sheep Sphincter of Oddi. Balkan Med J. 2016 Jul;33(4):453-7.

Additional Infomation
Ataciguat has been investigated for the basic science of Aortic Valve Stenosis.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
574.981
CAS #
254877-67-3
Related CAS #
254877-67-3;254976-06-2 (Sodium);
PubChem CID
213037
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Index of Refraction
1.685
LogP
6.08
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
7
Heavy Atom Count
35
Complexity
944
Defined Atom Stereocenter Count
0
SMILES
O=C(NC1=CC=C(S(=O)(N2CCOCC2)=O)C=C1)C3=CC(Cl)=CC=C3NS(=O)(C4=CC=C(Cl)S4)=O
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)
Chemical Name
5-chloro-2-[(5-chlorothiophen-2-yl)sulfonylamino]-N-(4-morpholin-4-ylsulfonylphenyl)benzamide
Synonyms
HMR-1766 HMR1766 HMR 1766
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~173.46 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02049203 COMPLETED Drug: Ataciguat
Drug: Placebo
Aortic Valve Stenosis Jordan D. Miller, Ph.D. 2014-01 Phase 1
NCT00799656 COMPLETED Drug: ataciguat (HMR1766)
Drug: placebo
Pain Sanofi 2008-11 Phase 2
NCT02481258 COMPLETEDWITH RESULTS Drug: Ataciguat (HMR1766)
Other: Placebo Comparator: Matching Placebo
Aortic Valve Stenosis Mayo Clinic 2015-06 Phase 2
NCT00443287 COMPLETED Drug: ataciguat (HMR1766)
Drug: placebo
Drug: cilostazol
Intermittent Claudication Sanofi 2007-02 Phase 2
Biological Data
  • Relaxation responses induced by ataciguat (10−9–10−4 mol/L) in the presence and absence of ODQ (10−5 mol/L) on isolated sheep SO rings. Relaxations are expressed as the percentage of carbachol (10−6mol/L)-induced pre-contraction and are shown as mean±SD. *Statistically different from agent only (p=0.0012).[3]. Çakmak E, et, al. Comparative Relaxant Effects of Ataciguat and Zaprinast on Sheep Sphincter of Oddi. Balkan Med J. 2016 Jul;33(4):453-7.
  • Relaxation responses induced by ataciguat (10−9–10−4 mol/L) and zaprinast (10−9–10−4 mol/L) on isolated sheep SO rings. Relaxations are expressed as percentage of carbachol (10−6 mol/L)-induced pre-contraction and shown as mean±SD. *Statistically different from zaprinast (p=0.0024).[3]. Çakmak E, et, al. Comparative Relaxant Effects of Ataciguat and Zaprinast on Sheep Sphincter of Oddi. Balkan Med J. 2016 Jul;33(4):453-7.
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