Ripasudil

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ripasudil are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ripasudil?

The molecule Ripasudil presents a molecular formula of C15H18FN3O2S and its IUPAC name is 4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline.

Ripasudil (INN) is a Rho-associated protein kinase (ROCK) inhibitor developed by Kowa Company, Ltd. (Japan). It is being investigated for the treatment of glaucoma and ocular hypertension..

Ripasudil has been shown to lower intraocular pressure (IOP) in animal models of glaucoma and ocular hypertension, and is thought to work by inhibiting the RhoA/ROCK pathway. This pathway participes in the regulation of actin cytoskeleton organization and is upregulated in trabecular meshwork cells in glaucoma. Inhibition of ROCK is thought to improve outflow of aqueous humor and reduce IOP..

Ripasudil is being investigated in a Phase III clinical trial for the treatment of glaucoma and ocular hypertension in Japan..

Kowa is also investigating ripasudil for the treatment of diabetic retinopathy..

3D structure

Cartesian coordinates

Geometry of Ripasudil in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Ripasudil QSKQVZWVLOIIEV-NSHDSACASA-N chemical compound 2D structure molecule svg
Ripasudil

 

Molecule descriptors

 
IUPAC name4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline
InChI codeInChI=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
InChI KeyQSKQVZWVLOIIEV-NSHDSACASA-N
SMILESC[C@H]1CNCCCN1S(=O)(=O)c1cccc2cncc(F)c12

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (S)-(-)-1-(4-fluoro-5-isoquinolinesulfonyl)-2-methyl-1,4-homopiperazine
  • (S)-4-Fluoro-5-((2-methyl-1,4-diazepan-1-yl)sulfonyl)isoquinoline
  • 11978226XX
  • 1H-1,4-Diazepine, 1-((4-fluoro-5-isoquinolinyl)sulfonyl)hexahydro-2-methyl-, (2S)-
  • 223645-67-8
  • 4-Fluoro-5-[[(2S)-2beta-methylhexahydro-1H-1,4-diazepine-1-yl]sulfonyl]isoquinoline
  • 4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline
  • AC-36873
  • AS-35170
  • BCP11083
  • BDBM50087135
  • CS-3402
  • DB13165
  • EX-A3647
  • GTPL10423
  • HY-15685A
  • Isoquinoline, 4-fluoro-5-(((2S)-hexahydro-2-methyl-1H-1,4-diazepin-1-yl)sulfonyl)-
  • K 115 free base
  • K-115 (free base)
  • K-115 (ripasudil hydrochloride dihydrate)
  • K-115 free base
  • MFCD28291829
  • NCGC00496843-01
  • NSC-800869
  • NSC800869
  • Q21098890
  • Ripasudil
  • Ripasudil free base
  • k115 Free base

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3940873
  • UNII-11978226XX
  • DTXSID001025609
  • CHEMBL3426621
  • CHEBI:136046
  • SCHEMBL31542

Physico-Chemical properties

IUPAC name4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline
Molecular formulaC15H18FN3O2S
Molecular weight323.386
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity90.24
LogP3.1
Topological polar surface area70.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.