U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18FN3O2S
Molecular Weight 323.3874
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIPASUDIL

SMILES

C[C@@]1([H])CNCCCN1S(=O)(=O)c2cccc3cncc(c32)F

InChI

InChIKey=QSKQVZWVLOIIEV-NSHDSACASA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25414122 | http://dwti.co.jp/english/business-outline/product-pipeline/glanatec

Ripasudil (K-115) is a selective Rho-associated coiled coil-containing protein kinase (ROCK) inhibitor. This compound, which was originally discovered by D. Western Therapeutics Institute, Inc., reduces intraocular pressure (IOP) by directly acting on the trabecular meshwork, thereby increasing conventional outflow through the Schlemm's canal. As a result of this mechanism of action, ripasudil may offer additive effects in the treatment of glaucoma and ocular hypertension when used in combination with agents such as prostaglandin analogues (which increase uveoscleral outflow) and β blockers (which reduce aqueous production). GLANATEC® (Ripasudil hydrochloride hydrate) ophthalmic solution 0.4% is launched in Japan for the treatment of glaucoma and ocular hypertension.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
51.0 nM [IC50]
19.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GLANATEC

Approved Use

GLANATEC® (Ripasudil hydrochloride hydrate) ophthalmic solution 0.4% inhibits Rho kinase and promotes drainage of aqueous humor from main outflow. It consequently decreases intraocular pressure. It is usually used to treat glaucoma and ocular hypertension when other medicines for glaucoma have insufficient effect or can not be used.

Launch Date

1.41730565E12
Primary
GLANATEC

Approved Use

GLANATEC® (Ripasudil hydrochloride hydrate) ophthalmic solution 0.4% inhibits Rho kinase and promotes drainage of aqueous humor from main outflow. It consequently decreases intraocular pressure. It is usually used to treat glaucoma and ocular hypertension when other medicines for glaucoma have insufficient effect or can not be used.

Launch Date

1.41730565E12
PubMed

PubMed

TitleDatePubMed
Effects of K-115, a rho-kinase inhibitor, on aqueous humor dynamics in rabbits.
2014 Aug
Ripasudil: first global approval.
2014 Dec
Vascular Normalization by ROCK Inhibitor: Therapeutic Potential of Ripasudil (K-115) Eye Drop in Retinal Angiogenesis and Hypoxia.
2016 Apr 1
Ocular Penetration and Pharmacokinetics of Ripasudil Following Topical Administration to Rabbits.
2016 Sep
Ocular hypotensive effects of a Rho-associated protein kinase inhibitor in rabbits.
2017
Efficacy of the Additional Use of Ripasudil, a Rho-Kinase Inhibitor, in Patients With Glaucoma Inadequately Controlled Under Maximum Medical Therapy.
2017 Feb
Efficacy of Ripasudil as a Second-line Medication in Addition to a Prostaglandin Analog in Patients with Exfoliation Glaucoma: A Pilot Study.
2017 Jun
Time Course of Conjunctival Hyperemia Induced by a Rho-kinase Inhibitor Anti-glaucoma Eye Drop: Ripasudil 0.4.
2017 May
Efficacy and safety of adding ripasudil to existing treatment regimens for reducing intraocular pressure.
2018 Feb
Patents

Sample Use Guides

GLANATEC® (Ripasudil hydrochloride hydrate) ophthalmic solution 0.4% one drop twice daily
Route of Administration: Topical
Ripasudil but not fasudil significantly reduced VEGF-induced MYPT-1 phosphorylation in human retinal microvascular endothelial cells (HRMECs) at 30 μmol/L. Ripasudil significantly inhibited VEGF-induced HRMECs migration and proliferation.
Name Type Language
RIPASUDIL
INN   WHO-DD  
INN  
Official Name English
1H-1,4-DIAZEPINE, 1-((4-FLUORO-5-ISOQUINOLINYL)SULFONYL)HEXAHYDRO-2-METHYL-, (2S)-
Systematic Name English
RIPASUDIL [INN]
Common Name English
ISOQUINOLINE, 4-FLUORO-5-(((2S)-HEXAHYDRO-2-METHYL-1H-1,4-DIAZEPIN-1-YL)SULFONYL)-
Systematic Name English
RIPASUDIL [WHO-DD]
Common Name English
RIPASUDIL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1404
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
NCI_THESAURUS C29705
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
Code System Code Type Description
FDA UNII
11978226XX
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
CAS
223645-67-8
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
EVMPD
SUB185276
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
NCI_THESAURUS
C152226
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
DRUG BANK
DB13165
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
DRUG CENTRAL
4938
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
MERCK INDEX
M11878
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
PUBCHEM
9863672
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY
INN
9691
Created by admin on Sat Jun 26 04:43:08 UTC 2021 , Edited by admin on Sat Jun 26 04:43:08 UTC 2021
PRIMARY