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Ripasudil

Product NameRipasudil
CAS223645-67-8
MFC15H18FN3O2S
MW323.39
EINECS
MOL File223645-67-8.mol

Chemical Properties

Boiling point	497.2±55.0 °C(Predicted)
Density	1.293±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
solubility	Soluble in DMSO
form	powder
pka	9.70±0.40(Predicted)
color	white to beige
Water Solubility	H2O: 2mg/mL, clear
InChI	1S/C15H18FN3O2S/c1-11-8-17-6-3-7-19(11)22(20,21)14-5-2-4-12-9-18-10-13(16)15(12)14/h2,4-5,9-11,17H,3,6-8H2,1H3/t11-/m0/s1
InChIKey	QSKQVZWVLOIIEV-NSHDSACASA-N
SMILES	Fc1c2c(cnc1)cccc2[S](=O)(=O)N3[C@H](CNCCC3)C

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Ripasudil (Glanatec TM, Kowa Pharmaceutical), a close derivative of fasudil, is another Rho kinase inhibitor approved in Japan at the end of 2014 for the treatment of glaucoma and ocular hypertensionwhen other therapeutic agents are not effective or cannot be administered. Additionally, ripasudil has been tested in diabetic retinopathy clinical trials and shown to promote corneal endothelial cell proliferation, endothelium regeneration, and wound healing.

Uses

Ripasudil free base (K-115 free base) is a specific inhibitor of ROCK, with IC50s of 19 and 51 nM for ROCK2 and ROCK1, respectively.

Definition

ChEBI: Ripasudil is a member of isoquinolines.

in vivo

Ripasudil (K-115) reduces intraocular pressure (IOP) in a concentration-dependent manner at concentrations between 0.1% and 0.4% in monkey eyes and 0.0625% to 0.5% in rabbit eyes, respectively^[1]. Ripasudil (K-115; 1 mg/kg, p.o. daily) shows a neuroprotective effect on retinal ganglion cells (RGCs) after nerve crush (NC). Ripasudil also inhibits the oxidative stress induced by axonal injury in mice. Ripasudil suppresses the time-dependent production of ROS in RGCs after NC injury^[3].

IC 50

ROCK2: 19 nM (IC₅₀); ROCK1: 51 nM (IC₅₀); CaMKIIa: 370 nM (IC₅₀); PKACa: 2.1 μM (IC₅₀); PKC: 27 μM (IC₅₀)

References

[1] Isobe T, et al. Effects of K-115, a rho-kinase inhibitor, on aqueous humor dynamics in rabbits. Curr Eye Res. 2014 Aug;39(8):813-22. DOI:10.3109/02713683.2013.874444
[2] Kaneko Y, et al. Effects of K-115 (Ripasudil), a novel ROCK inhibitor, on trabecular meshwork and Schlemm's canal endothelial cells. Sci Rep. 2016 Jan 19;6:19640. DOI:10.1038/srep19640
[3] Yamamoto K, et al. The novel Rho kinase (ROCK) inhibitor K-115: a new candidate drug for neuroprotective treatment in glaucoma. Invest Ophthalmol Vis Sci. 2014 Oct 2;55(11):7126-36. DOI:10.1167/iovs.13-13842

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