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    Ripasudil

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    PharmaCompass
    $ API Ref.Price (USD/KG) : 156,772Xls

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    2D Structure
    Also known as: 223645-67-8, K-115 free base, K115 free base, Ripasudil [inn], Ripasudil free base, K-115 (free base)
    Molecular Formula
    C15H18FN3O2S
    Molecular Weight
    323.4  g/mol
    InChI Key
    QSKQVZWVLOIIEV-NSHDSACASA-N
    FDA UNII
    11978226XX
    Ripasudil, as hydrochloride hydrate (K-115), is a specifc Rho-associated coiled-coil containing protein kinase (ROCK) inhibitor used for the treatment of glaucoma and ocular hypertension. It was first approved for treatment in Japan in September 2014. This medication is available in the form of a 0.4% eye drop solution under the brand name Glanatec. Ripasudil is a well tolerated medication that is used when other drugs have been proven to be non-effective or cannot be administered.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline
    2.1.2 InChI
    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
    2.1.3 InChI Key
    QSKQVZWVLOIIEV-NSHDSACASA-N
    2.1.4 Canonical SMILES
    CC1CNCCCN1S(=O)(=O)C2=CC=CC3=CN=CC(=C32)F
    2.1.5 Isomeric SMILES
    C[C@H]1CNCCCN1S(=O)(=O)C2=CC=CC3=CN=CC(=C32)F
    2.2 Other Identifiers
    2.2.1 UNII
    11978226XX
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Glanatec

    2. K-115

    3. K115 Compound

    2.3.2 Depositor-Supplied Synonyms

    1. 223645-67-8

    2. K-115 Free Base

    3. K115 Free Base

    4. Ripasudil [inn]

    5. Ripasudil Free Base

    6. K-115 (free Base)

    7. Chembl3426621

    8. 4-fluoro-5-[[(2s)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline

    9. 11978226xx

    10. (s)-4-fluoro-5-((2-methyl-1,4-diazepan-1-yl)sulfonyl)isoquinoline

    11. 1h-1,4-diazepine, 1-((4-fluoro-5-isoquinolinyl)sulfonyl)hexahydro-2-methyl-, (2s)-

    12. Isoquinoline, 4-fluoro-5-(((2s)-hexahydro-2-methyl-1h-1,4-diazepin-1-yl)sulfonyl)-

    13. Unii-11978226xx

    14. K 115 Free Base

    15. Ripasudil [mi]

    16. Ripasudil [who-dd]

    17. Schembl31542

    18. Gtpl10423

    19. Chebi:136046

    20. Dtxsid001025609

    21. Bcp11083

    22. Ex-a3647

    23. Zinc3940873

    24. Bdbm50087135

    25. Hy-15685a

    26. Mfcd28291829

    27. Nsc800869

    28. Cs-3402

    29. Db13165

    30. Nsc-800869

    31. Ncgc00496843-01

    32. Ac-36873

    33. As-35170

    34. K-115 (ripasudil Hydrochloride Dihydrate)

    35. Q21098890

    36. (s)-(-)-1-(4-fluoro-5-isoquinolinesulfonyl)-2-methyl-1,4-homopiperazine

    37. 4-fluoro-5-[[(2s)-2beta-methylhexahydro-1h-1,4-diazepine-1-yl]sulfonyl]isoquinoline

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 323.4 g/mol
    Molecular Formula C15H18FN3O2S
    XLogP31.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass323.11037616 g/mol
    Monoisotopic Mass323.11037616 g/mol
    Topological Polar Surface Area70.7 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity482
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Ripasudil has been proven to be effective in the twice daily treatment of glaucoma and ocular hypertension. It is currently in studies to be approved for both diabetic retinopathy and diabetic macular oedema.

    Treatment of corneal dystrophy

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ripasudil has high intraocular permeability and works by decreasing intraocular pressure (IOP) in a dose-dependent manner and increasing flow facility. The maximum reduction of IOP occurs after 1 to 2 hours.

    5.2 ATC Code

    S - Sensory organs

    S01 - Ophthalmologicals

    S01E - Antiglaucoma preparations and miotics

    S01EX - Other antiglaucoma preparations

    S01EX07 - Ripasudil

    5.3 Absorption, Distribution and Excretion

    Route of Elimination

    Riapsudil is cleared by the kidneys at a rate of 7.112L/h.

    Clearance

    Ripasudil has a renal clearance of 7.112 L/h.

    5.4 Biological Half-Life

    The half life of Ripasudil is 0.455 hrs.

    5.5 Mechanism of Action

    Ripasudil is a highly selective and potent Rho-associated coiled/coil-containing kinase protein (ROCK) inhibitor. Rho-kinase (ROCK) is an effector protein of Rho which binds with Rho to form a Rho/Rho-kinase complex. This complex then regulates many physiological functions including smooth muscle contractions, chemotaxis, neural growth and gene expression. ROCK comes in 2 isoforms: ROCK-1 and ROCK-2 and these two isoforms are distributed widely in our tissues including ocular tissues such as the iris, retina, trabecular meshwork and ciliary muscles. Atypical regulation of ROCK levels is involved in the pathogenesis of diseases such as glaucoma, ocular hypertension, cataracts and other retinal disorders. Ripasudil acts as very highly selective and potent inhibitor with an IC50 of Ripasudil with ROCK-1 of 0.051 umol/L and with ROCK-2 of 0.019 umol/L. ROCK inhibitors have efficacy in reducing IOP by acting on the trabecular meshwork in the eye directly to increase conventional outflow through the Schlemms canal. Ripasudil will inhibit ROCK and induce cytoskeletal changes including the retraction and rounding of cell bodies and cause disruption of actin bundles in this trabecular meshwork. This can reduce the compaction of trabecular meshwork tissue and eventually result in increased aqueous outflow in the eye and reduced resistance to fluid flow. Thus, Ripasudil is effective by inducing cytoskeletal changes which are depending on ROCK inhibition. Ripasudil decreases IOP by increasing outflow facility along with modulating the behavior of trabecular meshwork cells and Schlemms canal endothelial (SCE) cell permeability along with a disruption of the tight junction. When Ripasudil is used in combination with prostaglandin analogues it results in increased uveoscleral outflow and when used in combination with beta blockers it results in reduced aqueous production.