netarsudil   Click here for help

GtoPdb Ligand ID: 9322

Synonyms: AR-11324 | AR11324 | ester 60 [PMID: 27072905] | Rhokiinsa® | Rhopressa®
Approved drug
netarsudil is an approved drug (FDA (2017), EMA (2019))
Compound class: Synthetic organic
Comment: Netarsudil (AR-11324) is a combination Rho-associated protein kinase (Rho or ROCK) and norepinephrine transporter (NET) inhibitor [2,5]. Netarsudil is the S-enantiomeric, 2,4-dimethyl benzoate ester of compound 29 (Ki 0.2nM) described in [5]. Esterification improves bioavailability and corneal penetrating ability of the compound. It is an ocular hypotensive medication.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 94.31
Molecular weight 453.21
XLogP 4.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NCC(C(=O)Nc1ccc2c(c1)ccnc2)c1ccc(cc1)COC(=O)c1ccc(cc1C)C
Isomeric SMILES NC[C@@H](C(=O)Nc1ccc2c(c1)ccnc2)c1ccc(cc1)COC(=O)c1ccc(cc1C)C
InChI InChI=1S/C28H27N3O3/c1-18-3-10-25(19(2)13-18)28(33)34-17-20-4-6-21(7-5-20)26(15-29)27(32)31-24-9-8-23-16-30-12-11-22(23)14-24/h3-14,16,26H,15,17,29H2,1-2H3,(H,31,32)/t26-/m1/s1
InChI Key OURRXQUGYQRVML-AREMUKBSSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2017), EMA (2019))
IUPAC Name Click here for help
[4-[(2S)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate
International Nonproprietary Names Click here for help
INN number INN
10160 netarsudil
Synonyms Click here for help
AR-11324 | AR11324 | ester 60 [PMID: 27072905] | Rhokiinsa® | Rhopressa®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9686545
Reactome Reaction Reactome logo R-HSA-9680443
Other databases
CAS Registry No. 1254032-66-0 (source: WHO INN record)
DrugCentral Ligand 5269
GtoPdb PubChem SID 318164841
PubChem CID 66599893
Search Google for chemical match using the InChIKey OURRXQUGYQRVML-AREMUKBSSA-N
Search Google for chemicals with the same backbone OURRXQUGYQRVML
Search PubMed clinical trials netarsudil
Search PubMed titles netarsudil
Search PubMed titles/abstracts netarsudil
Search UniChem for chemical match using the InChIKey OURRXQUGYQRVML-AREMUKBSSA-N
Search UniChem for chemicals with the same backbone OURRXQUGYQRVML