Mabuterol

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Mabuterol

IUPAC name (RS)-1-[4-Amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethanol
Identifiers
CAS number	56341-08-3^N
PubChem	3995
ChemSpider	3857^Y
MeSH	mabuterol
ChEMBL	CHEMBL86749^Y
Jmol-3D images	Image 1
SMILES Clc1cc(cc(c1N)C(F)(F)F)C(O)CNC(C)(C)C
InChI InChI=1S/C13H18ClF3N2O/c1-12(2,3)19-6-10(20)7-4-8(13(15,16)17)11(18)9(14)5-7/h4-5,10,19-20H,6,18H2,1-3H3^Y Key: JSJCTEKTBOKRST-UHFFFAOYSA-N^Y InChI=1/C13H18ClF3N2O/c1-12(2,3)19-6-10(20)7-4-8(13(15,16)17)11(18)9(14)5-7/h4-5,10,19-20H,6,18H2,1-3H3 Key: JSJCTEKTBOKRST-UHFFFAOYAW
Properties
Molecular formula	C₁₃H₁₈ClF₃N₂O
Molar mass	310.74 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Mabuterol is a beta-adrenergic agonist.^[1]

References

^ Akahane K, Furukawa Y, Ogiwara Y, Haniuda M, Chiba S (July 1989). "Beta-adrenoceptor blocking effects of a selective beta 2-agonist, mabuterol, on the isolated, blood-perfused right atrium of the dog". Br. J. Pharmacol. 97 (3): 709–16. PMC 1854580. PMID 2474351. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1854580.

Adrenergics

Receptor ligands

α₁	Agonists: 5-FNE 6-FNE Amidephrine Anisodamine Anisodine Cirazoline Dipivefrine Dopamine Ephedrine Epinephrine (Adrenaline) Etilefrine Ethylnorepinephrine Indanidine Levonordefrin Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine (Noradrenaline) 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 (Thymoxamine) 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 trazodone nefazodone etoperidone, and mepiprazole all antagonize α₁-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.

α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Ephedrine Ergotamine Epinephrine (Adrenaline) Esproquin Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz Levonordefrin Lofexidine Medetomidine Methyldopa Mivazerol Naphazoline Norepinephrine (Noradrenaline) 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 and gepirone (via metabolite 1-PP) antagonize α₂-adrenergic receptors as well.

β	Agonists: 2-FNE 5-FNE Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Cimaterol Clenbuterol Denopamine Deterenol Dipivefrine Dobutamine Dopamine Dopexamine Ephedrine Epinephrine (Adrenaline) Etafedrine Etilefrine Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline (Isoproterenol) Isoxsuprine Labetalol Levonordefrin Levosalbutamol Mabuterol Methoxyphenamine Methyldopa N-Isopropyloctopamine Norepinephrine (Noradrenaline) Orciprenaline Oxyfedrine Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol (Albuterol) Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Xamoterol Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bormetolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Buftiralol Bufuralol Bunitrolol Bunolol Bupranolol Burocrolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Dropranolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esmolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levocicloprolol Levomoprolol Medroxalol Mepindolol Metalol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nafetolol Nebivolol Neraminol Nifenalol Nipradilol Oberadilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Parodilol Penbutolol Penirolol PhQA-33 Pindolol Pirepolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol TA-2005 Talinolol Tazolol Teoprolol Tertatolol Terthianolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Tribendilol Trigevolol Xibenolol Xipranolol

Reuptake inhibitors

NET	Selective norepinephrine reuptake inhibitors: Amedalin Atomoxetine (Tomoxetine) Ciclazindol Daledalin 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 Tramadol Ziprasidone

VMAT	Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Morazone
Phendimetrazine
Phenmetrazine; Oxazolines: 4-Methylaminorex
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
Benzphetamine
BOH
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
Dimethylamphetamine
Dimethylcathinone (Dimethylpropion, metamfepramone)
DMA
DMMA
EBDB
Ephedrine
Ethcathinone
Ethylamphetamine
Ethylone
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
IAP
IMP
L-Deprenyl (Selegiline)
Lisdexamfetamine
Lophophine
MBDB
MDA (Tenamfetamine)
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Mefenorex
Mephedrone
Mephentermine
Methamphetamine (Dextromethamphetamine
Levomethamphetamine)
Methcathinone
Methedrone
Methylone
NAP
Ortetamine
Paredrine
pBA
pCA
Pentorex (Phenpentermine)
Phenethylamine
Pholedrine
Phenpromethamine
Phentermine
Phenylpropanolamine
pIA
Prenylamine
Propylamphetamine
Pseudoephedrine
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
mCPP
MDBZP
MeOPP
pFPP; Others: 2-Amino-1,2-dihydronaphthalene
2-Aminoindane
2-Aminotetralin
2-Benzylpiperidine
4-Benzylpiperidine
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
Indanorex
Isometheptene
Methylhexanamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Enzyme inhibitors

Anabolism

PAH	3,4-Dihydroxystyrene

TH	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD	Benserazide Carbidopa Genistein Methyldopa

DBH	Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	CGS-19281A SKF-64139 SKF-7698

Catabolism

MAO	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: D-Deprenyl Selegiline (L-Deprenyl) Ladostigil Lazabemide Milacemide Mofegiline Pargyline Rasagiline Safinamide * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT	Entacapone Tolcapone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine L-DOPS (Droxidopa)

Cofactors	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⁺)

Others	Activity enhancers: BPAP PPAP; Release blockers: Bethanidine Bretylium Guanadrel Guanazodine Guanclofine Guanethidine Guanoxan; Toxins: Oxidopamine (6-Hydroxydopamine)

List of adrenergic drugs

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Mabuterol

Mabuterol

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