Name | Nepafenac |
Synonyms | Nevanac AL 6515 AHR 9434 Nepafenac Nepafenac - WS nepafenac,Nevance 2-Amino-3-benzoylbenzeneacetamide 2-(2-amino-3-benzoylphenyl)acetamide 2-(2-amino-3-benzoyl-phenyl)acetamide |
CAS | 78281-72-8 |
EINECS | 200-001-8 |
InChI | InChI=1/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18) |
InChIKey | QEFAQIPZVLVERP-UHFFFAOYSA-N |
Molecular Formula | C15H14N2O2 |
Molar Mass | 254.28 |
Density | 1.249g/cm3 |
Melting Point | 177-181°C |
Boling Point | 562.5°C at 760 mmHg |
Flash Point | 294°C |
Water Solubility | 0.014 mg/mL in water |
Solubility | DMSO 51 mg/mL Water <1 mg/mL Ethanol 4 mg/mL |
Vapor Presure | 1.11E-12mmHg at 25°C |
Appearance | powder |
Color | faint yellow to dark yellow |
Merck | 14,6469 |
Storage Condition | room temp |
Sensitive | Sensitive to heat |
Refractive Index | 1.641 |
MDL | MFCD08067732 |
In vivo study | Nepafenac showed significantly greater ocular bioavailability, and amfenac had greater COX-2 inhibitory activity than either ketorolac or bromfenac. Nepafenac showed weak COX-1 inhibitory activity with an IC50 of 64.3 mM. In rabbits, Nepafenac inhibited prostaglandin synthesis in the IRIS/ciliary body (85-95%) and retina/choroid (55%). Nepafenac(0.5%) resulted in a 65% reduction in retinal edema, which was associated with a 62% inhibition of blood-retinal barrier breakdown. Nepafenac(0.5%) significantly inhibited (46%) blood-retinal barrier disruption, accompanied by almost complete inhibition of PGE2 synthesis (96%). Nepafenac significantly inhibits retinal prostaglandin E(2), superoxide, cyclooxygenase-2, and leukostasis in the retinal microvasculature of insulin-deficient diabetic rats, does not affect vascular endothelial growth factor (VEGF) and nitric oxide (NO). In diabetic rats, Nepafenac significantly inhibited the number of transferase-mediated dUTP Nick end-labeled positive capillary cells, acellular capillaries, and pericytes. In mice, Nepafenac resulted in significantly reduced choroidal neovascularization and ischemia-Induced Retinal neovascularization compared to controls. Nepafenac also attenuated ischemia-induced increases in retinal VEGF mRNA expression. In ocular and metastatic animal models, Nepafenac delays the progression of malignancy, as well as the reduction in the weight of uveal melanoma. |
Hazard Symbols | N - Dangerous for the environment |
Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
UN IDs | UN 3077 9 / PGIII |
WGK Germany | 3 |
RTECS | CY1480710 |