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5.31230

Troponin Activator, CK-2017357

Name: Troponin Activator, CK-2017357
Brand: MM

Synonym(s):

Troponin Activator, CK-2017357, 6-Ethynyl-1-(3-pentanyl)-1H-imidazo[4,5-b]pyrazin-2-ol, 6-Ethynyl-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2-ol, Fast Skeletal Troponin Activator, CK2017357, Tirasemtiv, CK-357, Tirasemtiv, CK-357, 6-Ethynyl-1-(3-pentanyl)-1H-imidazo[4,5-b]pyrazin-2-ol, 6-Ethynyl-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2-ol, Fast Skeletal Troponin Activator, CK2017357

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₄N₄O

CAS Number:

1005491-05-3

Molecular Weight:

230.27

MDL number:

MFCD28023588

UNSPSC Code:

12352200

NACRES:

NA.77

Form:

powder

Assay:

≥98% (HPLC)

Solubility:

DMSO: 25 mg/mL

Color:

beige

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Properties

assay

≥98% (HPLC)

Quality Segment

100

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

beige

solubility

DMSO: 25 mg/mL

storage temp.

2-8°C

SMILES string

[n]1(c2nc(cnc2[nH][c]1=O)C#C)C(CC)CC

InChI

1S/C12H14N4O/c1-4-8-7-13-10-11(14-8)16(12(17)15-10)9(5-2)6-3/h1,7,9H,5-6H2,2-3H3,(H,13,15,17)

InChI key

RSQGZEAXODVTOL-UHFFFAOYSA-N

Description

General description

An orally bioavailable, non-toxic imidazopyrazinol compound that directly and selectively binds to the troponin complex in fast skeletal muscle (K_d = 40 nM) and sensitizes it to calcium. Its binding site is believed to be between two or more troponin subunits. Exhibits very modest affinity for slow skeletal muscle troponin (K_d = 3.8 µM) and has no measurable affinity for cardiac muscle troponin. Effectively stimulates myosin ATPase activity in fast skeletal muscle (EC₅₀ = 390 nM), but has significantly reduced effect on mixed fiber type (EC₅₀ = 770 nM in bovine rectus abdominis muscle). Slows the first order rate constant for Ca²⁺ release by about 70% (from 14.7 s^-1 to 4.0 s^-1) and shifts the plot of myosin ATPase relationship to calcium leftwards in fast skeletal muscles without increasing the maximum recorded force or the shape of the curve. Shown to improve muscle function in a rodent model of neuromuscular disease where neural input is diminished.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
troponin complex

Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C).

Other Notes

Gordon, P., et al. 2013. Expert Opin. Phamacother.14, 1907.
Miciak, J.J., et al. 2013. Muscle Nerve.48, 279.
Russell, A.J., et al. 2012. Nat. Med.18, 452.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)