ニプラジロール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2019/06/11 10:36:38」(JST)
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Nipradilol
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Names
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IUPAC name
[8-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-2H-chromen-3-yl] nitrate
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Identifiers
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CAS Number
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3D model (JSmol)
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ChemSpider
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InChI
InChI=1S/C15H22N2O6/c1-10(2)16-7-12(18)8-21-14-5-3-4-11-6-13(23-17(19)20)9-22-15(11)14/h3-5,10,12-13,16,18H,6-9H2,1-2H3 Key: OMCPLEZZPVJJIS-UHFFFAOYSA-N
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SMILES
CC(C)NCC(COC1=CC=CC2=C1OCC(C2)O[N+](=O)[O-])O
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Properties
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Chemical formula
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C15H22N2O6
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Molar mass
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326.349 g·mol−1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Nipradilol is a beta blocker and nitric oxide donor.[1]
References
- ^ Inoue, K; Kei Noguchi, K; Masumoto, M; Wakakura, G (2011). "Effect of five years of treatment with nipradilol eye drops in patients with normal tension glaucoma". Clinical ophthalmology (Auckland, N.Z.). 5: 1211–6. doi:10.2147/OPTH.S23233. PMC 3180485. PMID 21966188.
Adrenergic receptor modulators |
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α1 |
- Agonists: 6-FNE
- Amidephrine
- Anisodine
- Buspirone
- Cirazoline
- Corbadrine
- Desglymidodrine
- Dexisometheptene
- Dipivefrine
- Dopamine
- Droxidopa (L-DOPS)
- Ephedrine
- Epinephrine
- Etilefrine
- Etilevodopa
- Ethylnorepinephrine
- Indanidine
- Isometheptene
- L-DOPA (levodopa)
- L-Phenylalanine
- L-Tyrosine
- Melevodopa
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine (drug)
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetryzoline
- Tiamenidine
- XP21279
- Xylometazoline
- Antagonists: Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Anisodamine
- Arotinolol
- Atiprosin
- Atypical antipsychotics (e.g., brexpiprazole, clozapine, olanzapine, quetiapine, risperidone)
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- Corynanthine
- Dapiprazole
- Domesticine
- Doxazosin
- Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride)
- Etoperidone
- Eugenodilol
- Fenspiride
- Hydroxyzine
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- mCPP
- Mepiprazole
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Niaprazine
- Nicergoline
- Niguldipine
- Pardoprunox
- Pelanserin
- Perlapine
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
- Piperoxan
- Prazosin
- Quinazosin
- Quinidine
- Ritanserin
- Silodosin
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tiodazosin
- Tolazoline
- Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin)
- Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine)
- Trimazosin
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Urapidil
- WB-4101
- Zolertine
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α2 |
- Agonists: (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Corbadrine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Droxidopa (L-DOPS)
- Etilevodopa
- Ephedrine
- Ergotamine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- L-DOPA (levodopa)
- L-Phenylalanine
- L-Tyrosine
- Lofexidine
- Medetomidine
- Melevodopa
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rezatomidine
- Rilmenidine
- Romifidine
- Talipexole
- Tasipimidine
- Tetrahydrozoline
- Tiamenidine
- Tizanidine
- Tolonidine
- Urapidil
- Vatinoxan
- XP21279
- Xylazine
- Xylometazoline
- Antagonists: 1-PP
- Adimolol
- Amesergide
- Aptazapine
- Atipamezole
- Atypical antipsychotics (e.g., asenapine, brexpiprazole, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine)
- Azapirones (e.g., buspirone, gepirone, ipsapirone, tandospirone)
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- Idazoxan
- mCPP
- Mianserin
- Mirtazapine
- NAN-190
- Olanzapine
- Pardoprunox
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Yohimbine
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β | |
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Nitric oxide signaling modulators |
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Forms |
- Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion)
- Nitric oxide (NO⋅; nitrogen monoxide)
- Nitrosonium (NO+; nitrosyl cation)
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Targets | sGC |
- Activators/stimulators: Ataciguat
- BAY 41-2272
- BAY 41-8543
- BAY 60-4552
- BI-703704
- Cinaciguat (BAY 58-2667)
- GSK-2181236A
- Praliciguat
- Riociguat (BAY 63-2521)
- Vericiguat
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NO donors (prodrugs) |
- Nitrates: Diethylene glycol dinitrate (DEGDN)
- Erythritol tetranitrate (ETN)
- Ethylene glycol dinitrate (EGDN; nitroglycol)
- Isosorbide mononitrate (ISMN)
- Isosorbide dinitrate (ISDN)
- Itramin tosilate
- Mannitol hexanitrate
- Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
- NCX-466
- NCX-2216
- NCX-4016
- NCX 4040
- NCX-4215
- Nicorandil
- Nipradilol (K-351)
- Nitrate (NO−
3)
- Nitroatorvastatin (NCX-6560)
- Nitroflurbiprofen (HCT-1026)
- Nitrofluvastatin
- Nitroglycerin (glyceryl trinitrate (GTN))
- Nitropravastatin (NCX-6550)
- Pentaerithrityl tetranitrate (PETN)
- Propatylnitrate
- Propylene glycol dinitrate (PGDN)
- Sodium trioxodinitrate (Angeli's salt)
- Tenitramine
- Trolnitrate
- Nitroso compounds/nitrites: Nitrite (NO−
2); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
- Cyclohexyl nitrite
- Ethyl nitrite
- Hexyl nitrite
- Isobutyl nitrite (2-methylpropyl nitrite)
- Isopropyl nitrite
- Methyl nitrite
- n-Butyl nitrite
- Pentyl nitrite
- tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
- S-Nitrosoalbumin (SNALB)
- S-Nitrosated AR545C
- S-Nitroso-N-acetylcysteine (SNAC)
- S-Nitroso-N-acetylpenicillamine (SNAP)
- S-Nitroso-N-valerylpenicillamine (SNVP)
- S-Nitrosocaptopril (SNO-Cap)
- S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
- S-Nitrosodiclofenac
- S-Nitrosoglutathione (GSNO, SNOG)
- SNO-t-PA
- SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A
- Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
- Roussin's red salt
- Sodium nitroprusside (SNP)
- NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
- Diethylenetriamine/NO (DETA/NO)
- GLO/NO
- JS-K
- Methylamine hexamethylene methylamine/NO (MAHMA/NO)
- PROLI/NO
- Spermine/NO (SPER/NO)
- V-PYRRO/NO
- Heterocyclic compounds: Furoxans: Furoxan
- REC15/2739; Sydnonimines: Feprosidnine
- Linsidomine (SIN-1)
- Molsidomine (SIN-10)
- Sydnonimine
- Unsorted: CXL-1427
- FK-409
- FR144220
- FR146881
- N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
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Enzyme (inhibitors) | NOS | nNOS |
- 3-Bromo-7-nitroindazole
- 3-Chloroindazole
- 3-Chloro-5-nitroindazole
- 5-Nitroindazole
- 6-Nitroindazole
- 7-Nitroindazole
- A-84643
- Aminoguanidine (pimagedine)
- ARL-17477
- Indazole
- N5-(1-Iminoethyl)-L-ornithine (L-NIO)
- Nω-Methyl-L-arginine (L-NMA)
- Nω-Propyl-L-arginine (L-NPA)
- Nitroarginine (NNA, NOARG)
- Pentamidine isethionate
- TRIM
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iNOS |
- 1-Amino-2-hydroxyguanidine
- 2-Ethylaminoguanidine
- 2-Iminopiperidine
- 1400W
- AEITU
- Aminoguanidine (pimagedine)
- AMT
- AR-C 102222
- BYK-191023
- Canavanine
- Cindunistat (SD-6010)
- EITU
- IPTU
- MITU
- N5-(1-Iminoethyl)-L-ornithine (L-NIO)
- N6-(1-Iminoethyl)-L-lysine (L-NIL)
- Nω-Methyl-L-arginine (L-NMA)
- Ronopterin (VAS-203)
- TRIM
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eNOS |
- Aminoguanidine (pimagedine)
- N5-(1-Iminoethyl)-L-ornithine (L-NIO)
- Nω-Methyl-L-arginine (L-NMA)
- Nitroarginine (NNA, NOARG)
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Unsorted |
- Asymmetric dimethylarginine (ADMA)
- CKD-712
- Guanidinoethyldisulfide (GED)
- GW-273629
- Indospicine
- KD-7040
- Nitroarginine methyl ester (NAME)
- NCX-456
- NXN-462
- ONO-1714
- VAS-2381
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Arginase |
- ABH
- Nω-Hydroxy-L-arginine (NOHA)
- chlorogenic acid
- korean red ginseng root water extract
- epicatechin
- ornithine
- norvaline
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CAMK | |
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Others |
- Precursors: L-Arginine
- Nω-Hydroxy-L-arginine (NOHA)
- Cofactors: NADPH
- FAD
- FMN
- Heme
- BH4
- CaM
- O2
- Ca2+
- Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
- ETB receptor antagonists (e.g., bosentan)
- L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
- Nebivolol (beta blocker)
- PDE5 inhibitors (e.g., sildenafil)
- Statins (e.g., simvastatin)
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See also: Receptor/signaling modulators |
English Journal
- Nipradilol promotes axon regeneration through S-nitrosylation of PTEN in retinal ganglion cells.
- Koriyama Y1, Kamiya M, Arai K, Sugitani K, Ogai K, Kato S.
- Advances in experimental medicine and biology.Adv Exp Med Biol.2014;801:751-7. doi: 10.1007/978-1-4614-3209-8_94.
- Nipradilol (Nip) is registered as an anti-glaucoma agent. More recently, a protective effect of Nip has been demonstrated in retinal ganglion cells (RGCs) mediated by S-nitrosylation of antioxidative-related Keap1 protein due to its nitric oxide (NO)-donating effect. It also has been reported that N
- PMID 24664767
- Protective action of nipradilol mediated through S-nitrosylation of Keap1 and HO-1 induction in retinal ganglion cells.
- Koriyama Y1, Kamiya M, Takadera T, Arai K, Sugitani K, Ogai K, Kato S.
- Neurochemistry international.Neurochem Int.2012 Dec;61(7):1242-53. doi: 10.1016/j.neuint.2012.09.004. Epub 2012 Sep 17.
- Nipradilol (Nip), which has α1- and β-adrenoceptor antagonist and nitric oxide (NO)-donating properties, has clinically been used as an anti-glaucomatous agent in Japan. NO mediates cellular signaling pathways that regulate physiological functions. The major signaling mechanisms mediated by NO are
- PMID 22995787
- Risk factors for progression of normal-tension glaucoma under β-blocker monotherapy.
- Araie M1, Shirato S, Yamazaki Y, Matsumoto C, Kitazawa Y, Ohashi Y; Nipradilol‐Timolol Study Group.
- Acta ophthalmologica.Acta Ophthalmol.2012 Aug;90(5):e337-43. doi: 10.1111/j.1755-3768.2012.02425.x. Epub 2012 May 2.
- PURPOSE: To prospectively study prognostic factors for normal-tension glaucoma (NTG) under treatment with topical β-blocker.METHODS: One hundred and forty-six eyes of 146 patients with NTG with a mean untreated intraocular pressure (IOP) of 14 mmHg, mild to moderate visual field damage and mean sph
- PMID 22551324
Japanese Journal
- Protective action of nipradilol mediated through S-nitrosylation of Keap1 and HO-1 induction in retinal ganglion cells
- Koriyama Yoshiki,Kamiya Marie,Takadera Tsuneo,Arai Kunizo,Sugitani Kayo,Ogai Kazuhiro,Kato Satoru
- Neurochemistry International 61(7), 1242-1253, 2012-12
- … Nipradilol (Nip), which has α1- and β-adrenoceptor antagonist and nitric oxide (NO)-donating properties, has clinically been used as an anti-glaucomatous agent in Japan. … However, denitro-nipradilol, which does not have NO-donating properties, was not protective against oxidative stress. …
- NAID 120004966623
- Application of target organ dose model: route-to-route and chemical-to-chemical extrapolation of dose
- FOO Swee Cheng,SIN Ivan Siang-Meng
- 日本毒性学会学術年会 39.2(0), AP-3, 2012
- … Applying nipradilol toxicity data to route-to-route extrapolation, (LD50/Wbr-bi)route-i=(Ai,j)(LD50/Wbr-bi)route-j, the relative availability between routes are Aip,iv=3.88, Aig,iv=12.55. …
- NAID 130005009188
- Target organ dose model for extrapolating animal toxicity data to human
- FOO Swee-Cheng,SIN Siang-Meng
- 日本毒性学会学術年会 39.2(0), AP-12, 2012
- … Fitting toxicity data of nipradilol (target organ: respiratory system) yields br values of (1) 0.15 for ig; …
- NAID 130005009055
Related Links
- Araie M, Shirato S, Yamazaki Y, Matsumoto C, Kitazawa Y, Ohashi Y; Nipradilol‐Timolol Study Group. Acta Ophthalmol 2012 Aug;90(5):e337-43. Epub 2012 May 2 doi ... Araie M, Shirato S, Yamazaki Y, Matsumoto C, Kitazawa Y ...
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