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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/03/23 23:52:11」(JST)
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Denopamine
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Systematic (IUPAC) name |
4-[(1S)-2-[2-(3,4-dimethoxyphenyl)ethylamino]-1-hydroxyethyl]phenol |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
℞ Prescription only |
Routes |
Oral |
Identifiers |
CAS number |
71771-90-9 |
ATC code |
None |
PubChem |
CID 71754 |
IUPHAR ligand |
534 |
ChemSpider |
64795 |
UNII |
V5F60UPD8P Y |
KEGG |
D02614 |
Chemical data |
Formula |
C18H23NO4 |
Mol. mass |
317.37 g/mol |
SMILES
- O(c1ccc(cc1OC)CCNC[C@@H](O)c2ccc(O)cc2)C
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Denopamine (INN) is a cardiotonic drug which acts as a Beta-1 adrenergic receptor agonist.[1] It is used in the treatment of angina[2] and may also have potential uses in the treatment of congestive heart failure[3] and for clearing pulmonary oedema.[4]
References
- ^ Ishide T. Denopamine, a selective beta1-receptor agonist and a new coronary vasodilator. Current Medical Research and Opinion. 2002;18(7):407-13. PMID 12487507
- ^ Nakajima D, Negoro N, Nakaboh A, Nakakoji T, Hoshiga M, Nariyama J, Ishihara T, Hanafusa T. Effectiveness of low dose denopamine, a beta1-adrenoceptor agonist, in a patient with vasospastic angina refractory to intensive medical treatment. International Journal of Cardiology. 2006 Apr 4;108(2):281-3. PMID 15913812
- ^ Nishio R, Matsumori A, Shioi T, Wang W, Yamada T, Ono K, Sasayama S. Denopamine, a beta1-adrenergic agonist, prolongs survival in a murine model of congestive heart failure induced by viral myocarditis: suppression of tumor necrosis factor-alpha production in the heart. Journal of the American College of Cardiology. 1998 Sep;32(3):808-15. doi:10.1016/S0735-1097(98)00314-3 PMID 9741531
- ^ Sakuma T, Hida M, Nambu Y, Osanai K, Toga H, Takahashi K, Ohya N, Inoue M, Watanabe Y. Beta1-adrenergic agonist is a potent stimulator of alveolar fluid clearance in hyperoxic rat lungs. Japanese Journal of Pharmacology. 2001 Feb;85(2):161-6. doi:10.1254/jjp.85.161 PMID 11286398
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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English Journal
- Efficacy and limitations of oral inotropic agents for the treatment of chronic heart failure.
- Murai K, Seino Y, Kimata N, Inami T, Murakami D, Abe J, Yodogawa K, Maruyama M, Takano M, Ohba T, Ibuki C, Mizuno K.SourceDepartment of Cardiology, Nippon Medical School.
- International heart journal.Int Heart J.2013;54(2):75-81.
- The heart failure guideline in Japan has stated the necessity of investigating the role of oral inotropic agents in patients with chronic heart failure (CHF), which are clinically available only in Japan. A total of 1,846 consecutive patients with heart failure (mean: 69.5 years old, 1,279 males) tr
- PMID 23676366
- The mechanism of beta-adrenergic preconditioning: roles for adenosine and ROS during triggering and mediation.
- Salie R, Moolman JA, Lochner A.SourceDivision Medical Physiology, Department Biomedical Sciences, Faculty of Health Sciences, University of Stellenbosch, Tygerberg, Republic of South Africa.
- Basic research in cardiology.Basic Res Cardiol.2012 Sep;107(5):281. doi: 10.1007/s00395-012-0281-5. Epub 2012 Jul 15.
- The aim of this study was to investigate the mechanism of beta-adrenergic preconditioning (BPC). The roles of adenosine and its receptor subtypes, the generation of oxygen free radicals (ROS) and activation of the K(ATP) channels as well as the phosphoinositide-3-kinase (PI(3)K)/PKB/Akt and extracel
- PMID 22797560
Japanese Journal
- 23) Denopamineにて治療継続がてきた低血圧を有する冠攣縮狭心症の一例(第91回日本循環器学会四国地方会)
- 横矢 隆宏,佐藤 真一,原田 健
- Circulation journal : official journal of the Japanese Circulation Society 72(Supplement_II), 908, 2008-04-20
- NAID 110006913959
- 少量の denopamine が心室細動の抑制に有効であった Brugada 症候群の一例(第125回日本循環器学会東海地方会)
- 松岡 宏治,藤井 英太郎,大久保 節也,笠井 篤信,大道 近也,内田 文也,中野 赳
- Circulation journal : official journal of the Japanese Circulation Society 69(Supplement_III), 956, 2005-10-20
- NAID 110004051170
Related Links
- デノパミン(Denopamine)の検索ならお薬検索QLife(キューライフ)。お医者さんが処方する処方薬と、薬局で買える市販薬(OTC)、の効果と副作用、写真、添付文書、保管方法等を掲載。商品名だけでなく一般名や剤形、色などからも検索 ...
- Sigma-Aldrich offers Sigma-D7815, R(−)-Denopamine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... ANALYTICAL / CHROMATOGRAPHY » Analytical Standards Gas ...
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