Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H27N3O3 |
Molecular Weight | 453.5323 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(C)=C(C=C1)C(=O)OCC2=CC=C(C=C2)[C@@H](CN)C(=O)NC3=CC=C4C=NC=CC4=C3
InChI
InChIKey=OURRXQUGYQRVML-AREMUKBSSA-N
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
Molecular Formula | C28H27N3O3 |
Molecular Weight | 453.5323 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2973 |
1.0 nM [Ki] | ||
Target ID: CHEMBL3231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28609185 |
1.0 nM [Ki] | ||
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27072905 |
|||
Target ID: CHEMBL3616 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27072905 |
|||
Target ID: CHEMBL2996 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27072905 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Rhopressa Approved UseRHOPRESSA® (netarsudil ophthalmic solution) 0.02% is a Rho kinase
inhibitor indicated for the reduction of elevated intraocular pressure in
patients with open-angle glaucoma or ocular hypertension. Launch Date2017 |
|||
Primary | Rhopressa Approved UseRHOPRESSA® (netarsudil ophthalmic solution) 0.02% is a Rho kinase
inhibitor indicated for the reduction of elevated intraocular pressure in
patients with open-angle glaucoma or ocular hypertension. Launch Date2017 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.51 ng/mL |
0.53 mg/kg 1 times / day multiple, intravenous dose: 0.53 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
NETARSUDIL METABOLITE AR-13503 unknown | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3004 ng × h/mL |
12.5 mg/kg single, intravenous dose: 12.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NETARSUDIL METABOLITE AR-13503 plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.5 h |
unknown, unknown |
NETARSUDIL METABOLITE AR-13503 plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.02 % 2 times / day multiple, ophthalmic Highest studied dose Dose: 0.02 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.02 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
|
0.02 % 1 times / day multiple, ophthalmic Recommended Dose: 0.02 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.02 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Conjunctival hyperemia, Eye disorders NEC... Other AEs: Conjunctival hyperemia (53%) Sources: Eye disorders NEC (20%) Ocular signs and symptoms NEC (5 - 10) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Eye disorders NEC | 20% | 0.02 % 1 times / day multiple, ophthalmic Recommended Dose: 0.02 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.02 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Ocular signs and symptoms NEC | 5 - 10 | 0.02 % 1 times / day multiple, ophthalmic Recommended Dose: 0.02 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.02 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Conjunctival hyperemia | 53% | 0.02 % 1 times / day multiple, ophthalmic Recommended Dose: 0.02 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.02 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208254Orig1s000ClinPharmR.pdf#page=15 Page: 15.0 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
Netarsudil Increases Outflow Facility in Human Eyes Through Multiple Mechanisms. | 2016 Nov 1 |
|
Visualization of conventional outflow tissue responses to netarsudil in living mouse eyes. | 2016 Sep 15 |
|
Two Phase 3 Clinical Trials Comparing the Safety and Efficacy of Netarsudil to Timolol in Patients With Elevated Intraocular Pressure: Rho Kinase Elevated IOP Treatment Trial 1 and 2 (ROCKET-1 and ROCKET-2). | 2018 Feb |
|
Discovery and Preclinical Development of Netarsudil, a Novel Ocular Hypotensive Agent for the Treatment of Glaucoma. | 2018 Jan/Feb |
Patents
Sample Use Guides
RHOPRESSA® (netarsudil ophthalmic solution) 0.02%, for topical ophthalmic use. One drop into the affected eye(s) once daily in the evening.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28609185
Curator's Comment: At 10 uM, Netarsudil (AR-13324) inhibits NET by 96% and SERT by 94%. In a kinase screening panel 0.5 uM AR-13324 inhibited 11 kinases by >90%. https://www.ncbi.nlm.nih.gov/pubmed/27072905
Netarsudil inhibited kinases ROCK1 and ROCK2 with a Ki of 1 nM each, disrupted actin stress fibers and focal adhesions in TM cells with IC50s of 79 and 16 nM, respectively, and blocked the profibrotic effects of TGF-β2 in HTM cells.
Substance Class |
Chemical
Created
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Related Record | Type | Details | ||
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OFF-TARGET->INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Ki
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Ki
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
MAJOR
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Related Record | Type | Details | ||
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ACTIVE MOIETY |