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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/05/01 00:22:32」(JST)
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Metaraminol
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Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy
category |
- AU: C
- US: C (Risk not ruled out)
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Routes of
administration |
Intravenous Endotracheal |
ATC code |
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Legal status |
Legal status |
- UK: POM (Prescription only)
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Pharmacokinetic data |
Bioavailability |
n/a |
Protein binding |
~45% |
Metabolism |
Hepatic |
Identifiers |
IUPAC name
- (1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
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CAS Number |
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PubChem CID |
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IUPHAR/BPS |
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DrugBank |
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ChemSpider |
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UNII |
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KEGG |
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ChEBI |
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ChEMBL |
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Chemical and physical data |
Formula |
C9H13NO2 |
Molar mass |
167.205 g/mol |
3D model (Jmol) |
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SMILES
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O[C@H](c1cc(O)ccc1)[C@@H](N)C
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InChI
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InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1 Y
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Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N Y
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NY (what is this?) (verify) |
Metaraminol (INN; trade names Aramine, Metaramin, and Pressonex), also known as metaradrine, a stereoisomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine), is a potent sympathomimetic amine used in the prevention and treatment of hypotension, particularly as a complication of anesthesia. It is an α1-adrenergic receptor agonist with some β effect.[1]
Metaraminol is also used in the treatment of priapism. Although not approved for this use, it appears to be effective.[2][3][4]
See also
- Gepefrine
- Phenylpropanolamine
References
- ^ Kee VR. Hemodynamic pharmacology of intravenous vasopressors. Crit Care Nurse. 2003 Aug;23(4):79-82. PMID 12961786
- ^ McDonald M, Santucci R (2004). "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.". Int Braz J Urol. 30 (2): 121–2. doi:10.1590/S1677-55382004000200007. PMID 15703094.
- ^ Koga S, Shiraishi K, Saito Y (1990). "Post-traumatic priapism treated with metaraminol bitartrate: case report.". J Trauma. 30 (12): 1591–3. doi:10.1097/00005373-199012000-00029. PMID 2258979.
- ^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E (1988). "[Metaraminol in therapy of various forms of priapism]". Urologe A. 27 (4): 225–9. PMID 3140463.
Cardiac stimulants excluding cardiac glycosides (C01C)
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|
Adrenergic and
dopaminergic agents |
Adrenergic agonists |
α |
- Metaraminol
- Phenylephrine
- Methoxamine
- Norfenefrine
- Oxedrine
- Midodrine
- Mephentermine
|
|
β |
- Dobutamine
- Arbutamine
- Isoprenaline
- Prenalterol
|
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mixed |
- Amezinium metilsulfate
- Droxidopa
- Epinephrine #
- Norepinephrine
- Etilefrine
|
|
|
Dopamine agonists |
|
|
Both |
- Dopamine #
- Dopexamine
- Ibopamine
- octopamine
|
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Unknown/ungrouped |
- Dimetofrine
- Gepefrine
- Cafedrine
- Theodrenaline
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|
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Phosphodiesterase inhibitors (PDE3I) |
- Amrinone
- Milrinone
- Enoximone
- Bucladesine
|
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Other cardiac stimulants |
- Angiotensinamide
- Xamoterol
- Levosimendan
- Pimobendan
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
Adrenergic receptor modulators
|
|
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., 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
- Nefazodone
- Neldazosin
- Niaprazine
- Nicergoline
- Niguldipine
- Pardoprunox
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- Silodosin
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tiodazosin
- Tolazoline
- Trazodone
- 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
|
|
|
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
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tiamenidine
- Tizanidine
- Tolonidine
- Urapidil
- XP21279
- Xylazine
- Xylometazoline
|
|
- Antagonists
- 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine)
- Azapirones (e.g., buspirone, 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 |
- Agonists
- Abediterol
- Alifedrine
- Amibegron
- Arbutamine
- Arformoterol
- Arotinolol
- BAAM
- Bambuterol
- Befunolol
- Bitolterol
- Broxaterol
- Buphenine
- Carbuterol
- Carmoterol
- Cimaterol
- Clenbuterol
- Corbadrine
- Denopamine
- Dipivefrine
- Dobutamine
- Dopamine
- Dopexamine
- Droxidopa (L-DOPS)
- Ephedrine
- Epinephrine
- Etafedrine
- Etilefrine
- Etilevodopa
- Ethylnorepinephrine
- Fenoterol
- Formoterol
- Hexoprenaline
- Higenamine
- Indacaterol
- Isoetarine
- Isoprenaline
- Isoxsuprine
- L-DOPA (levodopa)
- L-Phenylalanine
- L-Tyrosine
- Levosalbutamol
- Mabuterol
- Melevodopa
- Methoxyphenamine
- Methyldopa
- Mirabegron
- Norepinephrine
- Orciprenaline
- Oxyfedrine
- PF-610355
- Phenylpropanolamine
- Pirbuterol
- Prenalterol
- Ractopamine
- Procaterol
- Pseudoephedrine
- Reproterol
- Rimiterol
- Ritodrine
- Salbutamol
- Salmeterol
- Solabegron
- Terbutaline
- Tretoquinol
- Tulobuterol
- Vilanterol
- Xamoterol
- XP21279
- Zilpaterol
- Zinterol
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|
- Antagonists
- Acebutolol
- Adaprolol
- Adimolol
- Afurolol
- Alprenolol
- Alprenoxime
- Amosulalol
- Ancarolol
- Arnolol
- Arotinolol
- Atenolol
- Befunolol
- Betaxolol
- Bevantolol
- Bisoprolol
- Bopindolol
- Bornaprolol
- Brefonalol
- Bucindolol
- Bucumolol
- Bufetolol
- Bufuralol
- Bunitrolol
- Bunolol
- Bupranolol
- Butaxamine
- Butidrine
- Butofilolol
- Capsinolol
- Carazolol
- Carpindolol
- Carteolol
- Carvedilol
- Celiprolol
- Cetamolol
- Cicloprolol
- Cinamolol
- Cloranolol
- Cyanopindolol
- Dalbraminol
- Dexpropranolol
- Diacetolol
- Dichloroisoprenaline
- Dihydroalprenolol
- Dilevalol
- Diprafenone
- Draquinolol
- Ecastolol
- Epanolol
- Ericolol
- Ersentilide
- Esatenolol
- Esprolol
- Eugenodilol
- Exaprolol
- Falintolol
- Flestolol
- Flusoxolol
- Hydroxycarteolol
- Hydroxytertatolol
- ICI-118,551
- Idropranolol
- Indenolol
- Indopanolol
- Iodocyanopindolol
- Iprocrolol
- Isoxaprolol
- Isamoltane
- Labetalol
- Landiolol
- Levobetaxolol
- Levobunolol
- Levomoprolol
- Medroxalol
- Mepindolol
- Metipranolol
- Metoprolol
- Moprolol
- Nadolol
- Nadoxolol
- Nebivolol
- Nifenalol
- Nipradilol
- Oxprenolol
- Pacrinolol
- Pafenolol
- Pamatolol
- Pargolol
- Penbutolol
- Pindolol
- Practolol
- Primidolol
- Procinolol
- Pronethalol
- Propafenone
- Propranolol
- Ridazolol
- Ronactolol
- Soquinolol
- Sotalol
- Spirendolol
- SR 59230A
- Sulfinalol
- Talinolol
- Tazolol
- Tertatolol
- Tienoxolol
- Tilisolol
- Timolol
- Tiprenolol
- Tolamolol
- Toliprolol
- Xibenolol
- Xipranolol
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|
|
- See also: Receptor/signaling modulators
- Dopaminergics
- Melatonergics
- Serotonergics
- Monoamine reuptake/release modulators
- Monoamine metabolism modulators
- Monoamine neurotoxins
|
UpToDate Contents
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- Renal medullary hypoxia may contribute to cardiac surgery-associated acute kidney injury (AKI). However, the effects of cardiopulmonary bypass (CPB) on medullary oxygenation are poorly understood. Here we tested whether CPB causes medullary hypoxia and whether medullary oxygenation during CPB can be
- PMID 31005272
- Metaraminol use during spinal anaesthesia for caesarean section: a meta-analysis of randomised controlled trials.
- Chao E, Sun HL, Huang SW, Liao JH, Ma PL, Chen HC.
- International journal of obstetric anesthesia. 2019 Jan;().
- During caesarean section, the use of a vasopressor is often required to achieve haemodynamic stability of the parturient. Metaraminol is a vasopressor used in this context in some countries. However, the differences between metaraminol and other vasopressors remain unclear. A search of the PubMed, C
- PMID 30772119
- Optimization of the Automated Synthesis of [11C]mHED-Administered and Apparent Molar Activities.
- Vraka C, Pichler V, Berroterán-Infante N, Wollenweber T, Pillinger A, Hohensinner M, Fetty L, Beitzke D, Li X, Philippe C, Pallitsch K, Mitterhauser M, Hacker M, Wadsak W.
- Pharmaceuticals (Basel, Switzerland). 2019 Jan;12(1).
- The tracer -Hydroxyephedrine ([[11C]HED) is one of the most applied PET tracers for cardiac imaging, whose radiosynthesis was already reported in 1990. While not stated in the literature, separation difficulties and an adequate formulation of the product are well known challenges in its production.
- PMID 30646635
Japanese Journal
- Pharmacokinetic study of three cardiovascular drugs by high-performance liquid chromatography using pre-column derivatization with 9,10-anthraquinone-2-sulfonyl chloride
- LIU Han,FENG Fang,MA Ming,CUI Shuangjin,XIE Darong,XU Sizhi
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 858(1), 42-48, 2007-10-15
- NAID 10025809878
- Water Intake Reduces the Noradrenaline Release in the Median Preoptic Nucleus Area Caused by Angiotensin II Injected into the Subfornical Oragn in the Rat
- 田中 淳一,宮久保 浩子,川上 綾子,林 泰資
- 鳴門教育大学研究紀要 22, 288-296, 2007-00-00
- … Intravenous infusions of metaraminol (5μg), on the other hand, slightly suppressed the release of NA in the MnPO area that accompanied an elevation in M.A.P. …
- NAID 110006191956
- A Japanese Case of Familial Mediterranean Fever with Family History Demonstrating a Mutation in MEFV
- Yoshida Ken-ichi,Kanaoka Shigeru,Kajimura Masayoshi [他],KATAOKA Hideki,TAKAHIRA Kenichiro,OSAWA Satoshi,SANO Munetaka,HISHIDA Akira
- Internal medicine 42(8), 761-764, 2003-08-01
- … The metaraminol provocative test was positive. …
- NAID 130000766865
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