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Identification
NameSalmeterol
Accession NumberDB00938  (APRD00277)
TypeSmall Molecule
GroupsApproved
DescriptionSalmeterol is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease COPD.
Structure
Thumb
Synonyms
GR-33343-X
GR-33343X
Salmaterol
Salmeterol
Salmeterolum
Serevent
Serevent diskus
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Serevent (25mcg/actuation)Aerosol, metered25 mcgOral; Respiratory (inhalation)Glaxosmithkline Inc1998-04-092006-07-12Canada
Serevent Diskhaler Disk (50mcg/dose)Powder50 mcgOral; Respiratory (inhalation)Glaxosmithkline Inc1998-02-11Not applicableCanada
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)Glaxo Smith Kline Llc1997-12-01Not applicableUs
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)Glaxo Smith Kline Llc1997-11-25Not applicableUs
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)Dispensing Solutions, Inc.1997-11-25Not applicableUs
Serevent Diskus (50mcg/dose)Powder50 mcgRespiratory (inhalation)Glaxosmithkline Inc1998-04-01Not applicableCanada
Serevent- Aem 25mcg/aemAerosol, metered25 mcgOral; Respiratory (inhalation)Glaxo Canada Inc1994-12-311998-07-30Canada
Serevent-pwr 50mcg/blister PackPowder50 mcgOral; Respiratory (inhalation)Glaxo Canada Inc1994-12-311998-07-30Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Aeromax DiskusNot Available
ArialNot Available
SalmetedurNot Available
SereventNot Available
Brand mixtures
NameLabellerIngredients
Advair 100 DiskusGlaxosmithkline Inc
Advair 125Glaxosmithkline Inc
Advair 250Glaxosmithkline Inc
Advair 250 DiskusGlaxosmithkline Inc
Advair 500 DiskusGlaxosmithkline Inc
Advair DiskusGlaxo Smith Kline Llc
Advair HFAGlaxo Smith Kline Llc
Advairdiskus DiskusREMEDYREPACK INC.
Salts
Name/CASStructureProperties
Salmeterol xinafoate
ThumbNot applicableDBSALT001372
Categories
UNII2I4BC502BT
CAS number89365-50-4
WeightAverage: 415.5656
Monoisotopic: 415.272258677
Chemical FormulaC25H37NO4
InChI KeyGIIZNNXWQWCKIB-UHFFFAOYSA-N
InChI
InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2
IUPAC Name
4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol
SMILES
OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1
Pharmacology
IndicationFor the treatment of asthma and chronic obstructive pulmonary disease (COPD).
Structured Indications
PharmacodynamicsSalmeterol is a long acting beta2-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 beclometasone. The primary noticable 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 presecribed, inhaled salmeterol decreases the number and severity of asthma attacks. However, it is not for use for relieving an asthma attack that has already started. Inhaled salmeterol works like other beta 2-agonists, causing bronchodilatation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma. Salmeterol is similar in action to formoterol, however 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.
Mechanism of actionSalmeterol's long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the molecule to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
TargetKindPharmacological actionActionsOrganismUniProt ID
Beta-2 adrenergic receptorProteinyes
agonist
HumanP07550 details
Related Articles
AbsorptionBecause of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.
Volume of distributionNot Available
Protein binding96%
Metabolism

Hepatic, metabolized by hydroxylation via CYP3A4

SubstrateEnzymesProduct
Salmeterol
alpha-hydroxysalmeterolDetails
Route of eliminationNot Available
Half life5.5 hours
ClearanceNot Available
ToxicitySymptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor. By the oral route, no deaths occurred in rats at 1,000 mg/kg (approximately 81,000 times the maximum recommended daily inhalation dose in adults and approximately 38,000 times the maximum recommended daily inhalation dose in children on a mg/m2 basis).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Salmeterol.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Salmeterol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Salmeterol.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Salmeterol.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Salmeterol.Illicit, Withdrawn
AmiodaroneThe serum concentration of Salmeterol can be increased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Salmeterol.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Salmeterol.Approved
AnagrelideSalmeterol may increase the QTc-prolonging activities of Anagrelide.Approved
AprepitantThe serum concentration of Salmeterol can be increased when it is combined with Aprepitant.Approved, Investigational
Arsenic trioxideSalmeterol may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherSalmeterol may increase the QTc-prolonging activities of Artemether.Approved
AsenapineSalmeterol may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirThe serum concentration of Salmeterol can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololAtenolol may decrease the bronchodilatory activities of Salmeterol.Approved
AtomoxetineThe serum concentration of Salmeterol can be increased when it is combined with Atomoxetine.Approved
AtosibanThe risk or severity of adverse effects can be increased when Salmeterol is combined with Atosiban.Approved
AzithromycinSalmeterol may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineSalmeterol may increase the QTc-prolonging activities of Bedaquiline.Approved
BendroflumethiazideSalmeterol may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Salmeterol.Withdrawn
Benzylpenicilloyl PolylysineSalmeterol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Salmeterol can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Salmeterol.Approved
BexaroteneThe serum concentration of Salmeterol can be decreased when it is combined with Bexarotene.Approved, Investigational
BisoprololBisoprolol may decrease the bronchodilatory activities of Salmeterol.Approved
BoceprevirThe serum concentration of Salmeterol can be increased when it is combined with Boceprevir.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Salmeterol.Approved
BortezomibThe serum concentration of Salmeterol can be increased when it is combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Salmeterol can be decreased when it is combined with Bosentan.Approved, Investigational
BromocriptineBromocriptine may increase the hypertensive activities of Salmeterol.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Salmeterol.Investigational
BumetanideSalmeterol may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Salmeterol.Approved
CabergolineCabergoline may increase the hypertensive activities of Salmeterol.Approved
CarbamazepineThe metabolism of Salmeterol can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Salmeterol.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Salmeterol.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Salmeterol.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Salmeterol.Approved, Investigational
CeritinibThe serum concentration of Salmeterol can be increased when it is combined with Ceritinib.Approved
ChloroquineSalmeterol may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorothiazideSalmeterol may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineSalmeterol may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorthalidoneSalmeterol may increase the hypokalemic activities of Chlorthalidone.Approved
CiprofloxacinSalmeterol may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideSalmeterol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramSalmeterol may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinThe serum concentration of Salmeterol can be increased when it is combined with Clarithromycin.Approved
ClemastineThe serum concentration of Salmeterol can be increased when it is combined with Clemastine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Salmeterol.Approved, Vet Approved
ClotrimazoleThe serum concentration of Salmeterol can be increased when it is combined with Clotrimazole.Approved, Vet Approved
ClozapineSalmeterol may increase the QTc-prolonging activities of Clozapine.Approved
CobicistatThe serum concentration of Salmeterol can be increased when it is combined with Cobicistat.Approved
ConivaptanThe serum concentration of Salmeterol can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Salmeterol can be increased when it is combined with Crizotinib.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Salmeterol.Approved
CyclosporineThe serum concentration of Salmeterol can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Salmeterol can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Salmeterol can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Salmeterol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Salmeterol can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Salmeterol can be increased when it is combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Salmeterol.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Salmeterol.Approved
DexamethasoneThe serum concentration of Salmeterol can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe serum concentration of Salmeterol can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Salmeterol can be increased when it is combined with Diltiazem.Approved
DisopyramideSalmeterol may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideSalmeterol may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronSalmeterol may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneSalmeterol may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Salmeterol.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Salmeterol.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Salmeterol.Approved
DoxycyclineThe serum concentration of Salmeterol can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Salmeterol can be increased when it is combined with Dronedarone.Approved
DroperidolSalmeterol may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of Salmeterol.Approved
EfavirenzThe serum concentration of Salmeterol can be decreased when it is combined with Efavirenz.Approved, Investigational
EliglustatSalmeterol may increase the QTc-prolonging activities of Eliglustat.Approved
EnzalutamideThe serum concentration of Salmeterol can be decreased when it is combined with Enzalutamide.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Salmeterol.Approved
ErgonovineErgonovine may increase the hypertensive activities of Salmeterol.Approved
ErgotamineErgotamine may increase the hypertensive activities of Salmeterol.Approved
ErythromycinThe serum concentration of Salmeterol can be increased when it is combined with Erythromycin.Approved, Vet Approved
EscitalopramSalmeterol may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Salmeterol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Salmeterol.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Salmeterol.Approved
Etacrynic acidSalmeterol may increase the hypokalemic activities of Etacrynic acid.Approved
EtravirineThe serum concentration of Salmeterol can be decreased when it is combined with Etravirine.Approved
FlecainideSalmeterol may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluconazoleThe serum concentration of Salmeterol can be increased when it is combined with Fluconazole.Approved
FluoxetineSalmeterol may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolSalmeterol may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluvoxamineThe serum concentration of Salmeterol can be increased when it is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Salmeterol can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Salmeterol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Salmeterol can be increased when combined with Fosphenytoin.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Salmeterol.Approved, Vet Approved
FurosemideSalmeterol may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Salmeterol can be increased when it is combined with Fusidic Acid.Approved
Gadobenic acidSalmeterol may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemifloxacinSalmeterol may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GoserelinSalmeterol may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronSalmeterol may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolSalmeterol may increase the QTc-prolonging activities of Haloperidol.Approved
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Salmeterol.Approved
HydrochlorothiazideSalmeterol may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideSalmeterol may increase the hypokalemic activities of Hydroflumethiazide.Approved
IbutilideSalmeterol may increase the QTc-prolonging activities of Ibutilide.Approved
IdelalisibThe serum concentration of Salmeterol can be increased when it is combined with Idelalisib.Approved
IloperidoneSalmeterol may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe serum concentration of Salmeterol can be increased when it is combined with Imatinib.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Salmeterol.Approved
IndapamideSalmeterol may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe serum concentration of Salmeterol can be increased when it is combined with Indinavir.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Salmeterol.Withdrawn
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Salmeterol.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Salmeterol.Withdrawn
IsavuconazoniumThe serum concentration of Salmeterol can be increased when it is combined with Isavuconazonium.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Salmeterol.Approved
IsradipineThe serum concentration of Salmeterol can be increased when it is combined with Isradipine.Approved
ItraconazoleThe serum concentration of Salmeterol can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Salmeterol can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Salmeterol can be increased when it is combined with Ketoconazole.Approved, Investigational
LabetalolLabetalol may decrease the vasoconstricting activities of Salmeterol.Approved
LenvatinibSalmeterol may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideSalmeterol may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinSalmeterol may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Salmeterol.Approved
LopinavirThe serum concentration of Salmeterol can be increased when it is combined with Lopinavir.Approved
LovastatinThe serum concentration of Salmeterol can be increased when it is combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Salmeterol is combined with Loxapine.Approved
LuliconazoleThe serum concentration of Salmeterol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Salmeterol can be increased when combined with Lumacaftor.Approved
LumefantrineSalmeterol may increase the QTc-prolonging activities of Lumefantrine.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Salmeterol.Withdrawn
MethadoneSalmeterol may increase the QTc-prolonging activities of Methadone.Approved
MethyclothiazideSalmeterol may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Salmeterol.Investigational
MetolazoneSalmeterol may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Salmeterol.Approved, Investigational
MifepristoneMifepristone may increase the QTc-prolonging activities of Salmeterol.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Salmeterol.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Salmeterol.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Salmeterol.Approved
MitotaneThe serum concentration of Salmeterol can be decreased when it is combined with Mitotane.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Salmeterol.Approved
ModafinilThe serum concentration of Salmeterol can be decreased when it is combined with Modafinil.Approved, Investigational
MoxifloxacinSalmeterol may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NadololNadolol may decrease the bronchodilatory activities of Salmeterol.Approved
NafcillinThe serum concentration of Salmeterol can be decreased when it is combined with Nafcillin.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Salmeterol.Approved, Investigational
NefazodoneThe serum concentration of Salmeterol can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Salmeterol can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Salmeterol can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Salmeterol can be increased when it is combined with Nevirapine.Approved
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Salmeterol.Withdrawn
NilotinibThe serum concentration of Salmeterol can be increased when it is combined with Nilotinib.Approved, Investigational
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Salmeterol.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Salmeterol.Withdrawn
OfloxacinSalmeterol may increase the QTc-prolonging activities of Ofloxacin.Approved
OlaparibThe serum concentration of Salmeterol can be increased when it is combined with Olaparib.Approved
OndansetronSalmeterol may increase the QTc-prolonging activities of Ondansetron.Approved
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Salmeterol.Investigational
OsimertinibThe serum concentration of Salmeterol can be increased when it is combined with Osimertinib.Approved
OxprenololOxprenolol may decrease the bronchodilatory activities of Salmeterol.Approved
PalbociclibThe serum concentration of Salmeterol can be increased when it is combined with Palbociclib.Approved
PaliperidoneSalmeterol may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatSalmeterol may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Salmeterol.Approved
PazopanibSalmeterol may increase the QTc-prolonging activities of Pazopanib.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Salmeterol.Approved, Investigational
PentamidineSalmeterol may increase the QTc-prolonging activities of Pentamidine.Approved
PentobarbitalThe metabolism of Salmeterol can be increased when combined with Pentobarbital.Approved, Vet Approved
PerflutrenSalmeterol may increase the QTc-prolonging activities of Perflutren.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Salmeterol.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Salmeterol.Withdrawn
PhenobarbitalThe metabolism of Salmeterol can be increased when combined with Phenobarbital.Approved
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Salmeterol.Withdrawn
PhenytoinThe metabolism of Salmeterol can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideSalmeterol may increase the QTc-prolonging activities of Pimozide.Approved
PindololPindolol may decrease the bronchodilatory activities of Salmeterol.Approved
PiretanideSalmeterol may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Salmeterol.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Salmeterol.Withdrawn
PolythiazideSalmeterol may increase the hypokalemic activities of Polythiazide.Approved
PosaconazoleThe serum concentration of Salmeterol can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Salmeterol.Approved
PrimaquineSalmeterol may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe metabolism of Salmeterol can be increased when combined with Primidone.Approved, Vet Approved
ProcainamideSalmeterol may increase the QTc-prolonging activities of Procainamide.Approved
PromazineSalmeterol may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenoneSalmeterol may increase the QTc-prolonging activities of Propafenone.Approved
PropranololPropranolol may decrease the bronchodilatory activities of Salmeterol.Approved, Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Salmeterol.Approved
QuetiapineSalmeterol may increase the QTc-prolonging activities of Quetiapine.Approved
QuinethazoneSalmeterol may increase the hypokalemic activities of Quinethazone.Approved
QuinidineSalmeterol may increase the QTc-prolonging activities of Quinidine.Approved
QuinineSalmeterol may increase the QTc-prolonging activities of Quinine.Approved
RanolazineThe serum concentration of Salmeterol can be increased when it is combined with Ranolazine.Approved, Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Salmeterol.Approved
RifabutinThe metabolism of Salmeterol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Salmeterol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Salmeterol can be increased when combined with Rifapentine.Approved
RitonavirThe serum concentration of Salmeterol can be increased when it is combined with Ritonavir.Approved, Investigational
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Salmeterol.Withdrawn
SaquinavirThe serum concentration of Salmeterol can be increased when it is combined with Saquinavir.Approved, Investigational
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Salmeterol.Approved, Investigational, Vet Approved
SildenafilThe serum concentration of Salmeterol can be increased when it is combined with Sildenafil.Approved, Investigational
SilodosinSilodosin may decrease the vasoconstricting activities of Salmeterol.Approved
SiltuximabThe serum concentration of Salmeterol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Salmeterol can be increased when it is combined with Simeprevir.Approved
SotalolSotalol may decrease the bronchodilatory activities of Salmeterol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Salmeterol.Approved
St. John's WortThe serum concentration of Salmeterol can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Salmeterol can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe serum concentration of Salmeterol can be increased when it is combined with Sulfisoxazole.Approved, Vet Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Salmeterol.Approved, Investigational
TelaprevirThe serum concentration of Salmeterol can be increased when it is combined with Telaprevir.Approved
TelavancinSalmeterol may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinThe serum concentration of Salmeterol can be increased when it is combined with Telithromycin.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Salmeterol.Approved
TetrabenazineSalmeterol may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThioridazineSalmeterol may increase the QTc-prolonging activities of Thioridazine.Approved
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Salmeterol.Approved
TiclopidineThe serum concentration of Salmeterol can be increased when it is combined with Ticlopidine.Approved
TimololTimolol may decrease the bronchodilatory activities of Salmeterol.Approved
TipranavirThe serum concentration of Salmeterol can be increased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Salmeterol can be decreased when it is combined with Tocilizumab.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Salmeterol.Approved
TorasemideSalmeterol may increase the hypokalemic activities of Torasemide.Approved
ToremifeneSalmeterol may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Salmeterol.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Salmeterol.Approved
TrichlormethiazideSalmeterol may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Salmeterol.Experimental
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Salmeterol.Approved
VandetanibSalmeterol may increase the QTc-prolonging activities of Vandetanib.Approved
VemurafenibSalmeterol may increase the QTc-prolonging activities of Vemurafenib.Approved
VenlafaxineThe serum concentration of Salmeterol can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Salmeterol can be increased when it is combined with Verapamil.Approved
VoriconazoleThe serum concentration of Salmeterol can be increased when it is combined with Voriconazole.Approved, Investigational
ZiprasidoneThe serum concentration of Salmeterol can be increased when it is combined with Ziprasidone.Approved
ZuclopenthixolSalmeterol may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food InteractionsNot Available
References
Synthesis Reference

Panayiotis Procopiou, “Novel process for preparing salmeterol.” U.S. Patent US20030162840, issued August 28, 2003.

US20030162840
General References
  1. Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths. Ann Intern Med. 2006 Jun 20;144(12):904-12. Epub 2006 Jun 5. [PubMed:16754916 ]
External Links
ATC CodesR03AK06R03AK12R03AC12
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelDownload (132 KB)
MSDSDownload (51 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8516
Blood Brain Barrier-0.8862
Caco-2 permeable-0.6968
P-glycoprotein substrateSubstrate0.7767
P-glycoprotein inhibitor IInhibitor0.539
P-glycoprotein inhibitor IIInhibitor0.7663
Renal organic cation transporterNon-inhibitor0.6106
CYP450 2C9 substrateNon-substrate0.8
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5937
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9099
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.6121
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8618
Ames testNon AMES toxic0.807
CarcinogenicityNon-carcinogens0.9378
BiodegradationReady biodegradable0.5587
Rat acute toxicity2.0830 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.741
hERG inhibition (predictor II)Inhibitor0.7149
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Glaxo group ltd dba glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)
PowderOral; Respiratory (inhalation)
PowderRespiratory (inhalation)
PowderOral; Respiratory (inhalation)50 mcg
Powder, meteredOral; Respiratory (inhalation)50 ug/1
PowderRespiratory (inhalation)50 mcg
Aerosol, meteredOral; Respiratory (inhalation)25 mcg
Prices
Unit descriptionCostUnit
Serevent Diskus 60 50 mcg/dose Powder Inhaler182.81USD inhaler
Serevent Diskhaler Device6.15USD device
Serevent 50 mcg/dose Disk4.21USD disk
Serevent diskus 50 mcg3.71USD each
Serevent Diskus 50 mcg/dose Metered Inhalation Powder1.05USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1335999 No1995-06-202012-06-20Canada
CA2165830 No2005-04-262014-06-30Canada
US5590645 No1994-03-012011-03-01Us
US5873360 Yes1996-08-232016-08-23Us
US6161724 Yes1998-07-162018-07-16Us
US6170717 Yes1998-06-232018-06-23Us
US6315173 Yes1998-06-232018-06-23Us
US6431168 Yes1998-12-082018-12-08Us
US6435372 Yes1998-07-162018-07-16Us
US6510969 Yes1998-06-232018-06-23Us
US6743413 Yes2001-12-012021-12-01Us
US6938796 Yes1998-07-162018-07-16Us
US6966467 Yes1998-06-232018-06-23Us
US6997349 Yes1998-07-162018-07-16Us
US7107986 Yes1998-12-082018-12-08Us
US7143908 Yes1998-07-162018-07-16Us
US7350676 Yes1999-02-242019-02-24Us
US7500444 Yes2006-08-262026-08-26Us
US7832351 Yes2003-12-192023-12-19Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point75.5-76.5 °CNot Available
water solubilitySparingly solubleNot Available
logP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00226 mg/mLALOGPS
logP3.82ALOGPS
logP3.61ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area81.95 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity122.39 m3·mol-1ChemAxon
Polarizability50.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative Parents
Substituents
  • Benzyl alcohol
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Rong Y, Arbabian M, Thiriot DS, Seibold A, Clark RB, Ruoho AE: Probing the salmeterol binding site on the beta 2-adrenergic receptor using a novel photoaffinity ligand, [(125)I]iodoazidosalmeterol. Biochemistry. 1999 Aug 31;38(35):11278-86. [PubMed:10471277 ]
  2. Finney PA, Donnelly LE, Belvisi MG, Chuang TT, Birrell M, Harris A, Mak JC, Scorer C, Barnes PJ, Adcock IM, Giembycz MA: Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). Br J Pharmacol. 2001 Mar;132(6):1261-70. [PubMed:11250877 ]
  3. Green SA, Rathz DA, Schuster AJ, Liggett SB: The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s). Eur J Pharmacol. 2001 Jun 15;421(3):141-7. [PubMed:11516429 ]
  4. Meliton AY, Munoz NM, Liu J, Lambertino AT, Boetticher E, Myo S, Myou S, Zhu X, Johnson M, Leff AR: Blockade of LTC4 synthesis caused by additive inhibition of gIV-PLA2 phosphorylation: Effect of salmeterol and PDE4 inhibition in human eosinophils. J Allergy Clin Immunol. 2003 Aug;112(2):404-10. [PubMed:12897749 ]
  5. Brogden RN, Faulds D: Salmeterol xinafoate: a review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Allergol Immunopathol (Madr). 1992 Mar-Apr;20(2):72-84. [PubMed:1359777 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on December 03, 2016 04:02