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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/09/08 23:15:44」(JST)
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Practolol
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Systematic (IUPAC) name |
(RS)-N-{4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}acetamide |
Clinical data |
Legal status |
?
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Identifiers |
CAS number |
6673-35-4 Y |
ATC code |
C07AB01 |
PubChem |
CID 4883 |
IUPHAR ligand |
555 |
DrugBank |
DB01297 |
ChemSpider |
4715 Y |
UNII |
SUG9176GRW Y |
KEGG |
D05587 N |
ChEBI |
CHEBI:258351 Y |
ChEMBL |
CHEMBL6995 Y |
Chemical data |
Formula |
C14H22N2O3 |
Mol. mass |
266.336 g/mol |
SMILES
- O=C(Nc1ccc(OCC(O)CNC(C)C)cc1)C
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InChI
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InChI=1S/C14H22N2O3/c1-10(2)15-8-13(18)9-19-14-6-4-12(5-7-14)16-11(3)17/h4-7,10,13,15,18H,8-9H2,1-3H3,(H,16,17) Y
Key:DURULFYMVIFBIR-UHFFFAOYSA-N Y
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N (what is this?) (verify) |
Practolol (Eraldin, Dalzic, Praktol, Cardiol, Pralon, Cordialina, Eraldina, Teranol) is a selective beta blocker that has been used in the emergency treatment of cardiac arrhythmias. Practolol is no longer used as it is highly toxic despite the similarity of its chemical formula to propranolol. After its introduction, keratoconjunctivitis sicca, conjunctival scarring, fibrosis, metaplasia, and shrinkage developed in 27 patients as an adverse reaction to practolol. Rashes, nasal and mucosal ulceration, fibrous or plastic peritonitis, pleurisy, cochlear damage, and secretory otitis media also occurred in some cases. Three patients suffered profound visual loss though most retained good vision. Symptoms and signs improved on withdrawal of the drug, but reduction of tear secretion persisted in most patients. (British Medical Journal, March 15, 1975)
Contents
- 1 Side effects
- 2 Ban
- 3 References
- 4 External links
Side effects
Side effects are similar to those of other beta blockers, such as bronchoconstriction, cardiac failure, cold extremities, fatigue and depression, hypoglycaemia.[1]
Furthermore, chronic use of practolol may cause oculomucocutaneous syndrome,[1] a severe syndrome whose signs include conjunctivitis sicca and psoriasiform rashes, otitis and sclerosing serositis. This syndrome has not been observed with other such beta blockers.[2]
Ban
This drug has been withdrawn from the market in India due to Oculomucocutaneous Syndrome.[3]
References
- ^ a b Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5.
- ^ rxmed.com > Nadolol Retrieved on July, 2010.
- ^ "Drugs banned in India". Central Drugs Standard Control Organization, Dte.GHS, Ministry of Health and Family Welfare, Government of India. Retrieved 2013-09-17.
External links
- Scientific information / studies
- Guinea Pig study from 1975
- Liver effect study from 1981
- Study of uses during surgery
- Molecular structure
- General information
Beta blockers (C07)
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Beta, nonselective |
- Alprenolol
- Bopindolol
- Bupranolol
- Carteolol
- Cloranolol
- Mepindolol
- Nadolol
- Oxprenolol
- Penbutolol
- Pindolol
- Propranolol
- Sotalol
- Tertatolol
- Timolol
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Beta1 selective |
- Acebutolol
- Atenolol
- Betaxolol
- Bevantolol
- Bisoprolol
- Celiprolol
- Epanolol
- Esmolol
- Metoprolol
- Nebivolol
- Practolol
- S-atenolol
- Talinolol
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Alpha + beta |
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Other/ungrouped |
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anat (a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot
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noco/syva/cong/lyvd/tumr, sysi/epon, injr
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proc, drug (C2s+n/3/4/5/7/8/9)
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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
- Hydroxyzine
- 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
- Fencamine
- Fencamfamine
- Hydroxybupropion
- 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
- Liafensine
- Methylnaphthidate
- Naphyrone
- NS-2359
- Perafensine
- 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
- Ethanol
- 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
- Brofaromine
- Cimoxatone
- Clorgiline
- Eprobemide
- 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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UpToDate Contents
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English Journal
- Preclinical characterization of a novel radiolabeled analog of practolol for the molecular imaging of myocardial β-adrenoceptor density.
- Carbonnelle E1, Josserand V, Riou LM, Ormezzano O, Broisat A, Perret P, Barone-Rochette G, Fagret D, Ghezzi C.
- Journal of nuclear cardiology : official publication of the American Society of Nuclear Cardiology.J Nucl Cardiol.2014 Oct;21(5):984-92. doi: 10.1007/s12350-014-9913-5. Epub 2014 May 30.
- BACKGROUND: The great clinical potential of myocardial β-AR imaging has been shown by recent studies evaluating the β-AR-specific, non-selective agent [(11)C]-CGP12177 in the setting of idiopathic-dilated cardiomyopathy, and myocardial infarction. However, the short half-life of (11)C hampers the
- PMID 24875578
- Importance of sphingosine kinase (SphK) as a target in developing cancer therapeutics and recent developments in the synthesis of novel SphK inhibitors.
- Plano D1, Amin S, Sharma AK.
- Journal of medicinal chemistry.J Med Chem.2014 Jul 10;57(13):5509-24. doi: 10.1021/jm4011687. Epub 2014 Feb 11.
- Sphingosine kinase (SphK) is an oncogenic lipid kinase that regulates the sphingolipid metabolic pathway that has been shown to play a role in numerous hyperproliferative/inflammatory diseases. The SphK isoforms (SphK1 and SphK2) catalyze the conversion of the proapoptotic substrate d-erythrosphingo
- PMID 24471412
- Sclerosing peritonitis occurring in association with juvenile granulosa cell tumour - a cause of concern.
- K A1, S V1, C G2, Khera A3.
- Journal of clinical and diagnostic research : JCDR.J Clin Diagn Res.2014 Mar;8(3):123-4. doi: 10.7860/JCDR/2014/6825.4131. Epub 2014 Mar 15.
- Sclerosing Peritonitis (SP) is characterized by fibrous thickening and adhesions of the peritoneum and it is encountered frequently in association with peritoneal dialysis, practolol and anticonvulsant therapy. Rarely does it present as a gynaecological complication, most commonly in conjunction wit
- PMID 24783102
Japanese Journal
- Potentiation by Higenamine of the Aconitine-Induced Positive Chronotropic Effect in Isolated Right Atria of Mice : The Effects of Cholera Toxin, Forskolin and Pertussis Toxin
- KIMURA Ikuko,ISLAM Md. Amirul,KIMURA Masayasu
- Biological & pharmaceutical bulletin 19(8), 1032-1037, 1996-08-15
- … Practolol (1 nM), a selective β_1-adrenergic antagonist, but not butoxamine (1 μM), a β_2-adrenergic antagonist, blocked the potentiation by higenamine (5 nM) of the aconitine-induced positive chronotropic effect and, at high concentrations (30 and 300 nM) also shifted the aconitine concentration-response curves to the right. …
- NAID 110003641315
- Positive Chronotropic and Inotropic Effects of Higenamine and Its Enhancing Action on the Aconitine-Induced Tachyarrhythmia in Isolated Murine Atria
- Kimura Ikuko,Makino Mitsuhiro,Takamura Yusaku,Islam Md. Amirul,Kimura Masayasu
- The Japanese Journal of Pharmacology 66(1), 75-80, 1994
- … The positive chronotropic effect of higenamine was antagonized by propranolol (30-300 nM) and practolol (10 nM 3 μM), but not by butoxamine (1 μM), indicating that it was a β1-adrenoceptor-mediated action. …
- NAID 130000840644
Related Links
- Practololとは?goo Wikipedia (ウィキペディア) 。出典:Wikipedia(ウィキペディア)フリー百科事典。 Practololとは - goo Wikipedia (ウィキペディア) gooトップ サイトマップ スタートページに設定 RSS ヘルプ メニューへスキップ 本文へ ...
- PRACTOLOL Practolol is a selective Beta blocker that has been used in the emergency treatment of Cardiac arrhythmias.. Practolol is no longer used as it is…
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