オルシプレナリン
- 関
- metaproterenol、orciprenaline sulfate
- 関
- Metaproterenol
WordNet
- a bronchodilator (trade name Alupent) used to treat asthma and emphysema and other lung conditions; available in oral or inhalant forms; side effects include tachycardia and shakiness (同)Alupent
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/04/19 20:13:28」(JST)
[Wiki en表示]
Orciprenaline
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Systematic (IUPAC) name |
(RS)-5-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol |
Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a682084 |
Pregnancy cat. |
A (AU) C (US) |
Legal status |
℞-only (US) |
Routes |
Inhalation / tablets |
Pharmacokinetic data |
Bioavailability |
3% if inhaled, 40% if taken orally |
Metabolism |
Gastrointestinal and hepatic |
Half-life |
6 hours |
Identifiers |
CAS number |
586-06-1 Y |
ATC code |
R03AB03 R03CB03
R03CB53 |
PubChem |
CID 4086 |
DrugBank |
DB00816 |
ChemSpider |
3944 Y |
UNII |
53QOG569E0 Y |
KEGG |
D08300 Y |
ChEMBL |
CHEMBL776 Y |
Chemical data |
Formula |
C11H17NO3 |
Mol. mass |
211.258 g/mol |
SMILES
- Oc1cc(cc(O)c1)C(O)CNC(C)C
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InChI
-
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3 Y
Key:LMOINURANNBYCM-UHFFFAOYSA-N Y
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Physical data |
Solubility in water |
9.7 mg/mL (20 °C) |
N (what is this?) (verify)
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Orciprenaline (INN, also known as metaproterenol) is a bronchodilator used in the treatment of asthma. Orciprenaline is a moderately selective beta2-adrenergic receptor agonist that stimulates receptors of the smooth muscle in the lungs, uterus, and vasculature supplying skeletal muscle, with minimal or no effect on alpha-adrenergic receptors. The pharmacologic effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of ATP to cAMP. Increased cAMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from many cells, especially from mast cells.
Possible side effects
- tremor
- nervousness
- dizziness
- weakness
- headache
- nausea
- tachycardia
- Rare side effects that could be life threatening
- increased difficulty breathing
- rapid or increased heart rate
- irregular heartbeat
- chest pain or discomfort
Brand names
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
- 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
- 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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UpToDate Contents
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English Journal
- [Right ventricular outflow tract tachycardia 30 years after surgical correction of tetralogy of Fallot].
- Bellmann B1, Tscholl V, Nagel P, Roser M.
- Herzschrittmachertherapie & Elektrophysiologie.Herzschrittmacherther Elektrophysiol.2015 May 20. [Epub ahead of print]
- This case report describes a 31-year-old man with a sustained wide complex tachycardia with left bundle brunch block morphology after surgical repair of a tetralogy of Fallot. The tachycardia was inducible after orciprenaline administration after ventricular stimulation with one extra beat. In combi
- PMID 25990265
- Enhanced endothelium-dependent relaxation of rat pulmonary artery following β-adrenergic overstimulation: involvement of the NO/cGMP/VASP pathway.
- Davel AP1, Victorio JA2, Delbin MA2, Fukuda LE3, Rossoni LV3.
- Life sciences.Life Sci.2015 Mar 15;125:49-56. doi: 10.1016/j.lfs.2015.01.018. Epub 2015 Jan 29.
- AIMS: The aim of this study was to investigate whether β-adrenoceptor (β-AR) overstimulation induced by in vivo treatment with isoproterenol (ISO) alters vascular reactivity and nitric oxide (NO) production and signaling in pulmonary arteries.MAIN METHODS: Vehicle or ISO (0.3mgkg(-1)day(-1)) was a
- PMID 25640757
- Insights from preclinical ultra high-density electroanatomical sinus node mapping.
- Bollmann A1, Hilbert S2, John S2, Kosiuk J2, Hindricks G2.
- Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology.Europace.2015 Mar;17(3):489-94. doi: 10.1093/europace/euu276. Epub 2014 Oct 27.
- AIMS: Although sinus node modification by catheter ablation is an established therapy for the treatment of inappropriate sinus tachycardia, there is incomplete understanding of sinus node anatomy and function but also limited electroanatomical mapping data. Recently, an automatic, ultra high-resolut
- PMID 25349222
Japanese Journal
- Screening of β-2 agonists and confirmation of fenoterol, orciprenaline, reproterol and terbutaline with gas chromatography-mass spectrometry as tetrahydroisoquinoline derivatives
- HENZE Maria Kristina,OPFERMANN Georg,SPAHN-LANGGUTA Hildegard,SCHANZER Wilhelm
- Journal of chromatography. B, Biomedical sciences and applications 751(1), 93-105, 2001-02-10
- NAID 10012266160
- シロスタゾールにより心拍数の増加と日常生活動作能力の向上を認めた洞機能不全症候群の一例
- 山下 純世,宮川 浩一,稲垣 俊明,土肥 靖明
- 日本老年医学会雑誌 36(8), 561-564, 1999-08-25
- 症例は86歳, 男性. 高血圧症に対しカルシウム拮抗薬の内服治療中であったが徐脈の原因となる薬剤の服用歴はなかった. 平成10年1月, 初診時の12誘導心電図で洞性徐脈と完全右脚+左脚前枝ブロックを認め, 精査治療目的で入院となった. ホルター心電図検査では一日総心拍数の減少 (74,182/日) と2秒以上の心停止 (187/日) を認めた. 電気生理学的検査では修正洞結節機能回復時間の延長(5 …
- NAID 10008485316
- イソフルレン吸入を施行した小児気管支喘息の重積発作の2例
- 田中 秀典,浅井 朋子,武田 紹,影山 里実,藤田 直也,志水 麻実子,岸 真司,石井 睦夫,矢守 信昭,神田 康司,上村 治,側島 久典,岩佐 充二,安藤 恒三郎
- 日本小児アレルギー学会誌 12(3), 281-287, 1998
- 症例1は5才2ヵ月女児. 3ヵ月前から喘息コントロールのため他院に入院していたが, 呼吸不全のため当院に搬送入院, 直ちに人工換気を施行した. 入院3日目皮下気腫を併発, イソフルレンを23時間投与し入院4日目に抜管できた. 症例2は11才女児. フェノテロールエアロゾル, オルシプレリン吸入等で他院で治療されていた. 当院受診時大発作で, 種々の治療により一旦軽快傾向を示したが, 数時間後増悪し …
- NAID 130004370539
Related Links
- Orciprenaline (INN, also known as metaproterenol pronounced: "met a proe ter' e nole") is a bronchodilator used in the treatment of asthma. Orciprenaline is a moderately selective beta2-adrenergic receptor agonist that stimulates receptors of ...
Related Pictures
★リンクテーブル★
[★]
- 英
- orciprenaline、orciprenaline sulfate
- 関
- メタプロテレノール、硫酸オルシプレナリン
[★]
メタプロテレノール
- 関
- orciprenaline
[★]
- 関
- orciprenaline