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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/10/31 15:00:26」(JST)
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Pronethalol
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| Systematic (IUPAC) name |
| 1-(naphthalen-2-yl)-2-(propan-2-ylamino)ethanol |
| Clinical data |
| Pregnancy cat. |
? |
| Legal status |
Withdrawn |
| Routes |
Oral |
| Identifiers |
| CAS number |
51-02-5 |
| ATC code |
None |
| PubChem |
CID 4930 |
| ChemSpider |
4761 |
| UNII |
XBP4RT1IMQ |
| Chemical data |
| Formula |
C15H19NO |
| Mol. mass |
229.32 g/mol |
SMILES
- CC(C)NCC(C1=CC2=CC=CC=C2C=C1)O
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Pronethalol (Alderlin, Nethalide) was an early non-selective beta blocker clinical candidate. It was never used clinically due to carcinogenicity in mice, which was thought to result from formation of a carcinogenic naphthalene epoxide metabolite.[1]
See also
References
- ^ Stapleton MP (1997). "Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology". Tex Heart Inst J 24 (4): 336–42. PMC 325477. PMID 9456487. //www.ncbi.nlm.nih.gov/pmc/articles/PMC325477/.
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Adrenergics
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Receptor ligands
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α1
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- Agonists: 5-FNE
- 6-FNE
- Amidephrine
- Anisodamine
- Anisodine
- Cirazoline
- Dipivefrine
- Dopamine
- Ephedrine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Indanidine
- Levonordefrin
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetrahydrozoline
Antagonists: Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Arotinolol
- Atiprosin
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- CI-926
- Corynanthine
- Dapiprazole
- DL-017
- Domesticine
- Doxazosin
- Eugenodilol
- Fenspiride
- GYKI-12,743
- GYKI-16,084
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- Mephendioxan
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Nicergoline
- Niguldipine
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- RS-97,078
- SGB-1,534
- Silodosin
- SL-89.0591
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tibalosin
- Tiodazosin
- Tipentosin
- Tolazoline
- Trimazosin
- Upidosin
- Urapidil
- Zolertine
- Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.
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α2
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- Agonists: (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Ephedrine
- Ergotamine
- Epinephrine
- Esproquin
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- Levonordefrin
- Lofexidine
- Medetomidine
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tizanidine
- Tolonidine
- Urapidil
- Xylazine
- Xylometazoline
Antagonists: 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- GYKI-12,743
- GYKI-16,084
- Idazoxan
- Mianserin
- Mirtazapine
- MK-912
- NAN-190
- Olanzapine
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269,970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Yohimbine
* Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well.
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β
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Reuptake inhibitors
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NET
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- Selective norepinephrine reuptake inhibitors: Amedalin
- Atomoxetine (Tomoxetine)
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine
- Bupropion (Amfebutamone)
- Fencamine
- Fencamfamine
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Methylphenidate
- Nomifensine
- O-2172
- Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- Sibutramine
- Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- JNJ-7925476
- JZ-IV-10
- Methylnaphthidate
- Naphyrone
- NS-2359
- PRC200-SS
- SEP-225,289
- SEP-227,162
- Tesofensine; Tricyclic antidepressants: Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- melitracen
- Nortriptyline
- Protriptyline
- Trimipramine; Tetracyclic antidepressants: Amoxapine
- Maprotiline
- Mianserin
- Oxaprotiline
- Setiptiline; Others: Cocaine
- CP-39,332
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Nefopam
- Pridefrine
- Tapentadol
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tramadol
- Ziprasidone
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VMAT
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- Ibogaine
- Reserpine
- Tetrabenazine
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Enzyme inhibitors
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Anabolism
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PAH
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TH
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- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
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AAAD
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- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
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DBH
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- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
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PNMT
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- CGS-19281A
- SKF-64139
- SKF-7698
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Catabolism
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MAO
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- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids (Harmine,
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective:
- Ladostigil
- Lazabemide
- Milacemide
- Mofegiline
- Pargyline
- Rasagiline
- Safinamide
- Selegiline (also [[D-Deprenyl]])
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.
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COMT
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- Entacapone
- Nitecapone
- Tolcapone
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Others
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Precursors
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- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
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Cofactors
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- Ferrous Iron (Fe2+)
- S-Adenosyl-L-Methionine
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal Phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
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Others
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- Activity enhancers: BPAP
- PPAP; Release blockers: Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanclofine
- Guanethidine
- Guanoxan; Toxins: 6-OHDA
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List of adrenergic drugs
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English Journal
- Minor enantiomer recycling: application to enantioselective syntheses of beta blockers.
- Wen YQ1, Hertzberg R, Gonzalez I, Moberg C.
- Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2014 Mar 24;20(13):3806-12. doi: 10.1002/chem.201303890. Epub 2014 Feb 26.
- Continuous recycling of the minor product enantiomer obtained from the acetylcyanation of prochiral aldehydes provided access to highly enantiomerically enriched products. Cyanohydrin derivatives, which under normal conditions are obtained with modest or poor enantiomeric ratios, were formed with hi
- PMID 24574310
- Comparison of some properties of pronethalol and propranolol. 1965.
- Black JW, Duncan WA, Shanks RG.
- British journal of pharmacology.Br J Pharmacol.2010 Jul;160 Suppl 1:S28-42; discussion S26-7. doi: 10.1111/j.1476-5381.2010.00850.x.
- PMID 20590649
- The role of beta-blockers as a cornerstone of cardiovascular therapy.
- Hollenberg NK1.
- American journal of hypertension.Am J Hypertens.2005 Dec;18(12 Pt 2):165S-168S.
- The beta-adrenergic blockade as a therapeutic approach first emerged in the 1950s. During the past five decades, the total number of indications that have been suggested, and the remarkable number approved by regulatory agencies, places beta-blockade far ahead of all competing treatments, not only i
- PMID 16373194
Japanese Journal
- Development of a chiral non-aqueous capillary electrophoretic system using the partial filling technique with UV and mass spectrometric detection
- LODEN Henrik,HEDELAND Ylva,HEDELAND Mikael,BONDESSON Ulf,PETTERSSON Curt
- Journal of chromatography. A : including electrophoresis and other separation methods 986(1), 143-152, 2003-01-31
- NAID 10011849662
- 和漢薬作用に関する薬学的基礎研究(第12報)漢薬麝香のβ-アドレナリン増強活性因子の薬理学的探索とその臓器選択的活性
- 木村 正康,脇 功巳,稲垣 甚一郎
- 藥學雜誌 98(4), 466-472, 1978-04-25
- … was not due to the inhibition of catechol-O-methyl transferase (COMT) from the following facts : Parallelism between the COMT-inhibition activity and the β-adrenergic potentiation activity was not observed among the lots of musk tested, a purified musk fraction was a weaker inhibitor of COMT activity than the crude, and musk induced a potentiation of isoproterenol (IsP) to the same extent even in the high doses by which the inhibitory effect of pronethalol was surmounted. …
- NAID 110003652767
- INHIBITION OF ADRENALINE-INDUCED FIBRINOLYSIS BY ALPHA-ADRENERGIC BLOCKING AGENTS IN THE RAT
- Sasaki Yasuhiko,Takeyama Shigeyuki
- The Japanese Journal of Pharmacology 24(5), 737-745, 1974
- … No inhibitory effect was observed with β-blockers, dichloroisoproterenol, pronethalol and practolol, even at a dose of 10 mg/kg, although propranolol at a dose of 3 mg/kg did exert an inhibitory effect. …
- NAID 130000838464
Related Links
- Nomenclature Name of the Clinical Form Pronetalol; alderlin; n-alderlin; nethalide; pronetal; pronethalol; AY 6204; ICI 38,174; 2-Isopropylamino-1-naphthalen-2-yl-ethanol; 2-Isopropylamino-1-naphthalen-2-yl-ethanol; 2 isopropylamino 1 ...
- Structure, properties, spectra, suppliers and links for: PRONETHALOL, 51-02-5. ... Predicted data is generated using the US Environmental Protection Agency’s EPISuite Log Octanol-Water Partition Coef (SRC): Log Kow ...
Related Pictures
★リンクテーブル★
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- 英
- pronetalol, pronethalol
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