Salmeterol

Brand names: Serevent®

Chemical formula:

Drug Forms:
• Salmeterol Xinafoate Inhalation powder (below)
• Salmeterol Xinafoate Pressurized inhalation, suspension

Español:
• Xinafoato de Salmeterol, Polvo para inhalación
• Xinafoato de Salmeterol, Suspensión para inhalación presurizada

Salmeterol Xinafoate Inhalation powder

What is this medicine?

SALMETEROL (sal ME te role) is a slow-acting bronchodilator. It helps to open up the airways in your lungs to make it easier to breathe. This medicine is used long term to treat asthma and to prevent bronchospasm. Do not use in an acute asthma attack. This medicine is not a replacement for inhaled or oral corticosteroids.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of the following conditions:
•diabetes
•heart disease or irregular heartbeat
•high blood pressure
•pheochromocytoma
•seizures
•thyroid disease
•worsening asthma
•an unusual or allergic reaction to salmeterol, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

This medicine is inhaled through the mouth. Follow the directions on the prescription label. Take your medicine at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your doctor's advice. Make sure that you are using your inhaler correctly. Ask you doctor or health care provider if you have any questions.
 
A special MedGuide will be given to you by the pharmacist with each prescription and refill. Be sure to read this information carefully each time.
 
Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for children as young as 4 years of age for selected conditions, precautions do apply.
 
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

Do not take this medicine with any of the following medications:
•MAOIs like Carbex, Eldepryl, Marplan, Nardil, and Parnate
•procarbazine

This medicine may also interact with the following medications:
•anti-infectives like chloroquine, and pentamidine
•antiviral medicines for HIV or AIDS
•caffeine
•cisapride
•diuretics
•medicines for colds
•medicines for depression, anxiety, or psychotic disturbances
•medicines for fungal infections like ketoconazole and itraconazole
•medicines for weight loss including some herbal products
•methadone
•some antibiotics like clarithromycin, erythromycin, levofloxacin, linezolid, and telithromycin
•some heart medicines
•steroid hormones like dexamethasone, cortisone, hydrocortisone
•theophylline
•thyroid hormones

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or health care professional if your symptoms do not improve. This medicine may increase the possibility of dying from asthma. If your symptoms get worse or if you need your short acting inhalers more often, call your doctor right away. Do not use more than every 12 hours. NEVER use this medicine for an acute asthma attack.

Your diskus device has a dose counter and will tell you when only a few doses are left.

If you are going to have surgery tell your doctor or health care professional that you are using this medicine.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions such as skin rash or itching, hives, swelling of the face, lips or tongue
•chest pain
•difficulty breathing or wheezing that increases or does not go away
•dizziness or fainting
•fever
•irregular heartbeat
•need for more doses of short acting bronchodilators

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•cough
•headache
•fast heart rate
•nervousness, trembling
•sore throat
•stuffy nose
•upset stomach

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 20 and 25 degrees C (68 and 77 degrees F). Do not freeze. Protect from light and moisture. Throw away 6 weeks after you remove from the foil pouch, or after the dose indicator reads 0, whichever comes first. Throw away unopened packages after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

1 : 1 mixture (racemate)
Salmeterol

Systematic (IUPAC) name
(RS)-2-(hydroxymethyl)-4-{1-hydroxy-2-[6-(4-phenylbutoxy) hexylamino]ethyl}phenol
Identifiers
CAS number	89365-50-4
ATC code	R03AC12
PubChem	5152
DrugBank	APRD00277
Chemical data
Formula	C25H37NO4
Mol. mass	415.57
Pharmacokinetic data
Bioavailability	?
Protein binding	96%
Metabolism	hepatic CYP3A4
Half life	5.5 h
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Prescription Only (S4)(AU) POM(UK) ℞-only(US)
Routes	Inhalation
Y(what is this?)  (verify)

Salmeterol is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease (COPD). It is currently available as a metered-dose inhaler (MDI) or a proprietary "disk-styled" inhaler that releases a powdered form of the drug.

Contents 1 Indications 2 Formulations 3 History and concerns 4 See also 5 Footnotes

Indications

It is a long acting beta-adrenoceptor agonist (LABA), usually only prescribed for severe persistent asthma following previous treatment with a short-acting beta agonist such as salbutamol and is prescribed concurrently with a corticosteroid, such as beclomethasone. The primary noticeable difference of salmeterol to salbutamol is that the duration of action lasts approximately 12 hours in comparison with 4–6 hours of salbutamol.

When used regularly every day as prescribed, inhaled salmeterol decreases the number and severity of asthma attacks. However, like all LABA medications, it is not for use for relieving an asthma attack that has already started.

Inhaled salmeterol works like other beta 2-agonists, causing bronchodialation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma. The long duration of formoterol action occurs by the formoterol molecules initially diffusing into the plasma membrane of the lung cells, and then slowly being released back outside the cell where they can come into contact with the beta-2 adrenoceptors. Formoterol has been demonstrated to have a faster onset of action than salmeterol as a result of a lower lipophilicity, and has also been demonstrated to be more potent—a 12 µg dose of formoterol has been demonstrated to be equivalent to a 50 µg dose of salmeterol.

Formulations

Currently available long-acting beta₂-adrenoceptor agonists include salmeterol, formoterol, bambuterol, and sustained-release oral albuterol. Combinations of inhaled steroids and long-acting bronchodilators are becoming more widespread; the most common combination currently in use is fluticasone/salmeterol (Advair in the United States, Seretide in the UK).

History and concerns

A typical inhaler, of Serevent (salmeterol)

Salmeterol, marketed and manufactured by GlaxoSmithKline, in the 1980s and was released as Serevent in 1990. However, the product is under license from Allen & Hanburys.(UK)

In November 2005, the American FDA released a health advisory[1], alerting the public to findings that show the use of Long-acting β₂-agonists could lead to a worsening of symptoms, and in some cases death.

While the use of inhaled LABAs are still recommended in asthma guidelines for the resulting improved symptom control,^[1] further concerns have been raised, by a large meta-analysis of the pooled results from 19 trials with 33,826 participants, that salmeterol may increase the small risks of asthma deaths and this additional risk is not reduced with the additional use of inhaled steroids (e.g. as with the combination product Fluticasone/salmeterol).^[2] This seems to occur because although LABAs relieve asthma symptoms, they also promote bronchial inflammation and sensitivity without warning.^[3]

See also

• Asthma
• Beta2-adrenergic receptor agonist

Footnotes

1. ^ British Thoracic Society & Scottish Intercollegiate Guidelines Network (SIGN). British Guideline on the Management of Asthma. Guideline No. 63. Edinburgh:SIGN; 2004. (HTML, Full PDF, Summary PDF)
2. ^ Salpeter S, Buckley N, Ormiston T, Salpeter E (2006). "Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths". Ann Intern Med 144 (12): 904–12. PMID 16754916. 
3. ^ Krishna Ramanujan (June 9 2006). "Common asthma inhalers cause up to 80 percent of asthma-related deaths, Cornell and Stanford researchers assert". ChronicalOnline - Cornell University. 

v • d • e Adrenergics Receptor Ligands α α1 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 α2 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 α? Agonists: Anisodamine • Ephedrine • Ergotamine • Indanidine • Mephentermine • Midodrine • Mivazerol • Naphazoline • Phenylpropanolamine • Pseudoephedrine • Rilmenidine • Synephrine • Talipexole • Tetrahydrozoline β β1 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 β2 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 β3 Agonists: Amibegron • Arotinolol • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Labetalol • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) • Solabegron Antagonists: Carvedilol • SR 59230A β? 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 • β-Methylphenethylamine (β-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

v • d • e Drugs for obstructive airway diseases: asthma/COPD (R03) Adrenergics, inhalants Short acting β2-agonists Salbutamol/Levosalbutamol • Fenoterol • Terbutaline • Pirbuterol • Procaterol • Bitolterol • Rimiterol • Carbuterol • Tulobuterol • Reproterol Long acting β2-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 Combination products Budesonide/formoterol • Fluticasone/salmeterol • Ipratropium/salbutamol

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