Wikipedia - Terbutaline


Terbutaline
Systematic (IUPAC) name
5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
Identifiers
CAS number	23031-25-6
ATC code	R03AC03 R03CC03
PubChem	5403
DrugBank	APRD00589
ChemSpider	5210
Chemical data
Formula	C₁₂H₁₉N O₃
Mol. mass	225.284 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	GI tract (oral), liver; CYP450: unknown
Half life	3-4h
Excretion	urine 90% (60% unchanged), bile/faeces
Therapeutic considerations
Pregnancy cat.	B
Legal status	POM(UK)
Routes	SQ, Oral, Inhaled
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Terbutaline (trade names Brethine, Bricanyl, or Brethaire) is a ß₂-adrenergic receptor agonist, used as a fast-acting bronchodilator (often used as a short-term asthma treatment) and as a tocolytic to delay premature labour. The inhaled form of terbutaline starts working within 15 minutes and can last up to 6 hours.

Terbutaline as a treatment for premature labour is an off-label use not approved by the FDA. It is a pregnancy category 'B' medication and is routinely prescribed to stop contractions. Terbutaline is currently on the World Anti-Doping Agency's list of prohibited drugs for Olympic athletes, except when administered by inhalation and a Therapeutic Use Exemption (TUE) has been obtained in advance.Orally disintegrating tablets by sublimation technique of Terbutaline sulphate have been developed.^{^[1]}

[edit] Side effects

Maternal - tachycardia, nervousness, tremors, headache, hyperglycemia, hypokalemia, and rarely, pulmonary edema.^[2]
Fatal - tachycardia and hypoglycemia^{[citation needed]}.

[edit] References

1. Ashok Kumar, Anuj G. Agrawal. (2009) "Formulation, development and evaluation of orally disintegrating tablets by sublimation technique.". International Journal of PharmTech Research 1 (4), 997-999. http://sphinxsai.com/PTVOL4/pdf_vol4/PT=5%20%20(997-99).pdf

^ [1]
^ Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. pp. 7. ISBN 1-59541-101-1.

Adrenergics

Receptor
Ligands

a₁	Agonists: Amidephrine • Cirazoline • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Isoprenaline • Levonordefrin • Metaraminol • Methoxamine • Methyldopa • Norepinephrine (Noradrenaline) • Oxymetazoline • Phenylephrine Antagonists: Alfuzosin • Arotinolol • Carvedilol • Doxazosin • Indoramin • L-765,314 • Labetalol • Moxisylyte • Nantenine • Phentolamine • Phenoxybenzamine • Prazosin • Silodosin • Tamsulosin • Terazosin • Tolazoline • Trimazosin • Urapidil

a₂	Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • Amitraz • Apraclonidine • Brimonidine • Clonidine • Detomidine • Dexmedetomidine • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Guanabenz • Guanfacine • Guanethidine • Guanoxabenz • Levonordefrin • Lofexidine • Medetomidine • Methyldopa • Norepinephrine (Noradrenaline) • Octopamine • Romifidine • Tizanidine • Tolonidine • Xylazine • Xylometazoline Antagonists: 1-PP • Atipamezole • BRL-44408 • Buspirone • Cirazoline • Efaroxan • Gepirone • Idazoxan • Ipsapirone • Mianserin • Mirtazapine • NAN-190 • Phentolamine • Phenoxybenzamine • Rauwolscine • SB-269,970 • Setiptiline • Spiroxatrine • Tandospirone • Tolazoline • Yohimbine

a_?	Agonists: Anisodamine • Ephedrine • Ergotamine • Indanidine • Mephentermine • Midodrine • Mivazerol • Naphazoline • Phenylpropanolamine • Pseudoephedrine • Rilmenidine • Synephrine • Talipexole • Tetrahydrozoline

ß₁	Agonists: Denopamine • Dobutamine • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) Antagonists: Acebutolol • Alprenolol • Amosulalol • Arotinolol • Atenolol • Bupranolol • Carvedilol • Celiprolol • Betaxolol • Bisoprolol • Dichloroisoprenaline • Esmolol • Labetalol • Metipranolol • Metoprolol • Nadolol • Nebivolol • Oxprenolol • Penbutolol • Pindolol • Practolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol • Xamoterol

ß₂	Agonists: Arformoterol • Bambuterol • Bitolterol • Carbuterol • Clenbuterol • Dopamine • Dopexamine • Epinephrine (Adrenaline) • Etilefrine • Fenoterol • Formoterol • Hexoprenaline • Indacaterol • Levonordefrin • Levosalbutamol • Methyldopa • Norepinephrine (Noradrenaline) • Orciprenaline • Pirbuterol • Procaterol • Reproterol • Rimiterol • Ritodrine • Salbutamol (Albuterol) • Salmeterol • Terbutaline • Tulobuterol Antagonists: Alprenolol • Amosulalol • Arotinolol • Bupranolol • Butaxamine • Carvedilol • Dichloroisoprenaline • ICI 118551 • Labetalol • Metipranolol • Nadolol • Oxprenolol • Penbutolol • Pindolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol

ß₃	Agonists: Amibegron • Arotinolol • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Labetalol • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) • Solabegron Antagonists: Carvedilol • SR 59230A

ß_?	Agonists: Arbutamine • BAAM • Befunolol • Broxaterol • Buphenine • Cimaterol • Ephedrine • Higenamine • Isoetarine • Isoxsuprine • Mabuterol • Methoxyphenamine • Oxyfedrine • Prenalterol • Pseudoephedrine • Ractopamine • Tretoquinol • Zilpaterol • Zinterol

Reuptake
Inhibitors

Plasmalemmal

NET Inhibitors	Norepinephrine Reuptake Inhibitors: Atomoxetine (Tomoxetine) • Ciclazindol • Mazindol • Nisoxetine • Reboxetine • Tandamine • Tapentadol • Viloxazine; Norepinephrine-Dopamine Reuptake Inhibitors: Amineptine • Bupropion (Amfebutamone) • Fencamine • Fencamfamine • Lefetamine • LR-5182 • Manifaxine • Methylphenidate • Nomifensine • O-2172 • Radafaxine; Serotonin-Norepinephrine Reuptake Inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Sibutramine • Tramadol • 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 • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline; Others: Cocaine • Nefazodone • Nefopam • Ziprasidone

TRPC6 Activators	Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Ibogaine • Reserpine • Tetrabenazine

Releasing
Agents

Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Amfepentorex • ß-Methylphenethylamine (ß-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ephedrine (EPH) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Indanorex • Indanylamphetamine (IAP) • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Mephentermine • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) • Methedrone • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) • Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone • Naphthylamphetamine (NAP) • Ortetamine • Oxaflozane • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine (PMEA) • Paramethoxymethamphetamine (PMMA) • Paredrine (Norpholedrine, Oxamphetamine) • Phendimetrazine • Phenethylamine (PEA) • Phenmetrazine • Pholedrine • Phenpentermine • Phenpromethamine • Phentermine • Phenylpropanolamine (PPA) • Propylamphetamine • Pseudoephedrine (PSE) • Tiflorex (Flutiorex) • Tyramine (TRA) • Xylopropamine • Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine) • Parafluorophenylpiperazine (pFPP; Fluoperazine); Others: 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 2-Benzylpiperidine (2-BP) • 4-Benzylpiperidine (4-BP) • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Isometheptene • Methylhexanamine • Octodrine • Phthalimidopropiophenone • Propylhexedrine (PHX) • Tuaminoheptane (Tuamine)

Enzyme
Inhibitors

Anabolism

PAH Inhibitors	3,4-Dihydroxystyrene

TH Inhibitors	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

AAAD Inhibitors	Benserazide • Carbidopa

DBH Inhibitors	Disulfiram • Nepicastat • Tropolone

PNMT Inhibitors	CGS-19281A • SKF-64139 • SKF-7698

Catabolism

MAO Inhibitors	Nonselective: Etryptamine • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metryptamine • Nialamide • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids (Harmine, Harmaline, Tetrahydroharmine, etc) • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT Inhibitors	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: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Release Blockers: Bretylium • Guanethidine

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short acting ß₂-agonists	Salbutamol/Levosalbutamol • Fenoterol • Terbutaline • Pirbuterol • Procaterol • Bitolterol • Rimiterol • Carbuterol • Tulobuterol • Reproterol

Long acting ß₂-agonists (LABA)	Arformoterol • Bambuterol • Clenbuterol • Formoterol • Salmeterol Ultra LABA: Indacaterol

other	Epinephrine • Hexoprenaline • Isoprenaline (Isoproterenol) • Orciprenaline (Metaproterenol)

Glucocorticoids

Beclometasone • Budesonide • Ciclesonide • Fluticasone • Mometasone

Anticholinergics/
muscarinic antagonist

Ipratropium • Tiotropium

Mast cell stabilizers

Cromoglicate • Nedocromil

Xanthines

Doxofylline • Theobromine • Theophylline/Aminophylline

Eicosanoid inhibition

Leukotriene antagonists	Montelukast • Pranlukast • Zafirlukast

Lipoxygenase inhibitor	Zileuton

Thromboxane receptor antagonists	Ramatroban • Seratrodast