Salmeterol

Identification

Summary

Salmeterol is a long-acting beta-2 adrenergic receptor agonist used to treat asthma and COPD.

Brand Names
Advair, Airduo, Airduo Respiclick, Serevent, Serevent Diskus, Wixela
Generic Name
Salmeterol
DrugBank Accession Number
DB00938
Background

Salmeterol is a long-acting beta-2 adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease COPD.8,9,10,11,12 It has a longer duration of action than the short-acting beta-2 adrenergic receptor agonist, salbutamol.5 Salmeterol was first described in the literature in 1988.6 Salmeterol's structure is similar to salbutamol's with an aralkyloxy-alkyl substitution on the amine.1

Salmeterol was granted FDA approval on 4 February 1994.7

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 415.5656
Monoisotopic: 415.272258677
Chemical Formula
C25H37NO4
Synonyms
  • Salmaterol
  • Salmeterol
  • Salmeterolum
External IDs
  • GR 33343 X
  • GR-33343-X
  • SN408D

Pharmacology

Indication

Salmeterol is indicated in the treatment of asthma with an inhaled corticosteroid, prevention of exercise induced bronchospasm, and the maintenance of airflow obstruction and prevention of exacerbations of chronic obstructive pulmonary disease.8,9,10,11,12

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAsthmaCombination Product in combination with: Fluticasone propionate (DB00588)••••••••••••
Management ofAsthma••••••••••••
Management ofChronic obstructive pulmonary disease••••••••••••
Used in combination to manageChronic obstructive pulmonary diseaseCombination Product in combination with: Fluticasone propionate (DB00588)••••••••••••
Prophylaxis ofExercise-induced bronchospasm••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Salmeterol is a long acting beta-2 adrenergic receptor agonist that binds to both the active and exo sites of the beta-2 adrenergic receptor.1 Salmeterol has a longer duration of action than other beta-2 agonists like salbutamol.5 Patients should be counselled regarding the risks of long acting beta agonist (LABA) monotherapy, hypokalemia, hypoglycemia, and not to take this drug with another LABA.8,9,10,11,12

Mechanism of action

Beta-2 adrenoceptor stimulation causes relaxation of bronchial smooth muscle, bronchodilation, and increased airflow.1

Salmeterol is hypothesized to bind to 2 sites on the beta-2 adrenoceptor.1 The saligenin moiety binds to the active site of the beta-2 adrenoceptor.1 The hydrophilic tail of salmeterol binds to leucine residues in the exo-site of the beta-2 adrenoceptor almost irreversibly, allowing salmeterol to persist in the active site, which is responsible for it's long duration of action.1,3

Another hypothesis is that the lipophilic drug diffuses into lipid bilayer of smooth muscle cells and provides a depot of drug to the cells over a longer period of time.1

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
UBeta-1 adrenergic receptor
inverse agonist
Humans
UBeta-3 adrenergic receptor
inverse agonist
Humans
Absorption

In asthmatic patients, a 50µg dose of inhaled salmeterol powder reaches a Cmax of 47.897pg/mL, with a Tmax of 0.240h, and an AUC of 156.041pg/mL/h.5

Volume of distribution

In asthmatic patients, the volume of distribution of the central compartment is 177L and the volume of distribution of the peripheral compartment is 3160L.5

Protein binding

Salmeterol is 96%8 protein bound in plasma to albumin and alpha-1-acid glycoprotein.1

Metabolism

Salmeterol is predominantly metabolized by CYP3A4 to alpha-hydroxysalmeterol,1 and minorly by an unknown mechanism to an O-dealkylated metabolite.2

Hover over products below to view reaction partners

Route of elimination

Salmeterol is 57.4% eliminated in the feces9 and 23% in the urine.1 Less than 5% of a dose is eliminated in the urine as unchanged salmeterol.1

Half-life

The half life of salmeterol is 5.5h.1

Clearance

The average clearance of salmeterol in a group of asthmatic patients was 392L/h.5 Further data regarding the clearance of salmeterol is not readily available.8,9,10,11,12

Adverse Effects
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Toxicity

Patients experiencing an overdose have presented with metabolic acidosis, hyperlactatemia, anxiety, palpitations, chest pain, sinus tachycardia, ST depression, hypokalemia, hypophosphatemia.4 Though patients may also present with seizures, angina, hypertension or hypotension, arrhythmia, headache, tremor, muscle cramps, dry mouth, nausea, dizziness, fatigue, malaise, insomnia, and hyperglycemia.9 Patients should be given symptomatic and supportive treatment which may include intravenous fluids, potassium supplementation, a cardioselective beta-blocker, and cardiac monitoring.4,9

Data regarding the LD50 of salmeterol is not readily available.13

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Salmeterol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Salmeterol can be increased when combined with Abatacept.
AcalabrutinibThe metabolism of Salmeterol can be decreased when combined with Acalabrutinib.
AcebutololThe therapeutic efficacy of Salmeterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Salmeterol is combined with Aceclofenac.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Salmeterol xinafoate6EW8Q962A594749-08-3XTZNCVSCVHTPAI-UHFFFAOYSA-N
International/Other Brands
Aeromax Diskus / Arial / Salmetedur
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SereventAerosol21 ug/1Respiratory (inhalation)GlaxoSmithKline2006-05-102006-08-29US flag
Serevent (25mcg/actuation)Aerosol, metered25 mcg / actRespiratory (inhalation)Glaxosmithkline Inc1998-04-092006-07-12Canada flag
Serevent Diskhaler Disk (50mcg/dose)Powder50 mcg / actRespiratory (inhalation)Glaxosmithkline Inc1998-02-112017-09-20Canada flag
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)Dispensing Solutions, Inc.1997-11-25Not applicableUS flag
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)GlaxoSmithKline LLC1997-12-012021-12-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
\-Salmeterol xinafoate (50 mcg) + Fluticasone propionate (250 mcg)บริษัท แกล็กโซสมิทไคล์น (ประเทศไทย)2019-07-23Not applicableThailand flag
ACTİONFLU 50 MCG/100 MCG İNHALASYON İÇİN TOZ İÇEREN KAPSÜL,120 KAPSÜLSalmeterol xinafoate (50 mcg) + Fluticasone propionate (100 mcg)PowderRespiratory (inhalation)EXELTIS İLAÇ SAN. VE TİC. A.Ş.2015-07-062022-12-21Turkey flag
ACTİONFLU 50 MCG/100 MCG İNHALASYON İÇİN TOZ İÇEREN KAPSÜL,180 KAPSÜLSalmeterol xinafoate (50 mcg) + Fluticasone propionate (100 mcg)PowderRespiratory (inhalation)EXELTIS İLAÇ SAN. VE TİC. A.Ş.2015-07-062022-12-21Turkey flag
ACTİONFLU 50 MCG/100 MCG İNHALASYON İÇİN TOZ İÇEREN KAPSÜL,60 KAPSÜLSalmeterol xinafoate (50 mcg) + Fluticasone propionate (100 mcg)PowderRespiratory (inhalation)EXELTIS İLAÇ SAN. VE TİC. A.Ş.2015-07-062022-12-21Turkey flag
ACTİONFLU 50 MCG/250 MCG İNHALASYON İÇİN TOZ İÇEREN KAPSÜL,120 KAPSÜLSalmeterol xinafoate (50 mcg) + Fluticasone propionate (250 mcg)PowderRespiratory (inhalation)EXELTIS İLAÇ SAN. VE TİC. A.Ş.2015-07-062022-12-21Turkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AIRPLUS 25/125 MCG INHALASYON ICIN OLCULU DOZLU AEROSOL 120 DOZSalmeterol (25 mcg) + Fluticasone propionate (125 mcg)Aerosol, meteredRespiratory (inhalation)TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ.2018-02-20Not applicableTurkey flag

Categories

ATC Codes
R03AK06 — Salmeterol and fluticasoneR03AK12 — Salmeterol and budesonideR03AC12 — Salmeterol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzyl alcohols
Direct Parent
Benzyl alcohols
Alternative Parents
Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Benzyl alcohol / Dialkyl ether / Ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, phenols, secondary amino compound, ether, primary alcohol (CHEBI:64064)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2I4BC502BT
CAS number
89365-50-4
InChI Key
GIIZNNXWQWCKIB-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

References

Synthesis Reference

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

US20030162840
General References
  1. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]
  2. Manchee GR, Barrow A, Kulkarni S, Palmer E, Oxford J, Colthup PV, Maconochie JG, Tarbit MH: Disposition of salmeterol xinafoate in laboratory animals and humans. Drug Metab Dispos. 1993 Nov-Dec;21(6):1022-8. [Article]
  3. Prentice B, Jaffe A, Thomas P: Beta2 Receptor Agonists Parnham M. (eds) Compendium of Inflammatory Diseases. [Article]
  4. Manara A, Hantson P, Vanpee D, Thys F: Lactic acidosis following intentional overdose by inhalation of salmeterol and fluticasone. CJEM. 2012 Nov;14(6):378-81. doi: 10.2310/8000.2012.110581. [Article]
  5. Soulele K, Macheras P, Karalis V: Pharmacokinetic analysis of inhaled salmeterol in asthma patients: Evidence from two dry powder inhalers. Biopharm Drug Dispos. 2017 Oct;38(7):407-419. doi: 10.1002/bdd.2077. Epub 2017 Jul 12. [Article]
  6. Ullman A, Svedmyr N: Salmeterol, a new long acting inhaled beta 2 adrenoceptor agonist: comparison with salbutamol in adult asthmatic patients. Thorax. 1988 Sep;43(9):674-8. doi: 10.1136/thx.43.9.674. [Article]
  7. FDA Approved Drug Products: Serevent Salmeterol Xinafoate Inhaled Metered Aerosol (Discontinued) [Link]
  8. FDA Approved Drug Products: Wixela Inhub Fluticasone and Salmeterol Inhalation Powder [Link]
  9. FDA Approved Drug Products: Serevent Diskus Salmeterol Inhalation Powder [Link]
  10. FDA Approved Drug Products: Airduo Respiclick Fluticasone and Salmeterol Inhalation Powder [Link]
  11. FDA Approved Drug Products: Advair HFA Fluticasone and Salmeterol Inhalation Aerosol [Link]
  12. FDA Approved Drug Products: Advair Diskus Fluticasone and Salmeterol Inhalation Powder [Link]
  13. Cayman Chemical: Salmeterol MSDS [Link]
Human Metabolome Database
HMDB0015073
KEGG Drug
D05792
KEGG Compound
C07241
PubChem Compound
5152
PubChem Substance
46508024
ChemSpider
4968
BindingDB
25771
RxNav
36117
ChEBI
64064
ChEMBL
CHEMBL1263
Therapeutic Targets Database
DAP000947
PharmGKB
PA451300
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Salmeterol
FDA label
Download (132 KB)
MSDS
Download (51 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingHealth Services ResearchAsthma1
4CompletedNot AvailableAsthma1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2
4CompletedBasic SciencePharmacokinetics in Healthy Young Men1
4CompletedDiagnosticAsthmatic Smokers / Non-asthmatic Smokers1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Glaxo group ltd dba glaxosmithkline
Packagers
  • A-S Medication Solutions LLC
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • GlaxoSmithKline Inc.
  • Lake Erie Medical and Surgical Supply
  • Rebel Distributors Corp.
Dosage Forms
FormRouteStrength
PowderOral; Respiratory (inhalation)
PowderRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
GasRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)0.500 mg
Aerosol; suspensionRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
PowderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
AerosolBuccal0.480 mg
SuspensionOral; Respiratory (inhalation)
SuspensionBuccal; Respiratory (inhalation)
Aerosol, powderRespiratory (inhalation)
CapsuleRespiratory (inhalation)
Aerosol; aerosol, meteredRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
Drug delivery systemBuccal
AerosolRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)100 mcg
Powder, meteredRespiratory (inhalation)250 mcg
Powder, meteredRespiratory (inhalation)500 mcg
AerosolRespiratory (inhalation)
AerosolBuccal0.4539 mg
Aerosol, powderRespiratory (inhalation)25 mcg
PowderRespiratory (inhalation)50 mcg
Powder, meteredRespiratory (inhalation)50 MICROGRAMMI
Powder, meteredRespiratory (inhalation)50 MCG
GasRespiratory (inhalation)25 µg
Aerosol, meteredRespiratory (inhalation)25 MCG
Aerosol, sprayRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)100 mcg/inhalation
Powder, meteredRespiratory (inhalation)250 mcg/inhalation
Powder, meteredRespiratory (inhalation)500 mcg/inhalation
AerosolBuccal
Aerosol, sprayRespiratory (inhalation)125 mcg
Aerosol, sprayRespiratory (inhalation)250 mcg
Aerosol, sprayRespiratory (inhalation)50 mcg
SuspensionRespiratory (inhalation)
AerosolBuccal0.330 mg
AerosolRespiratory (inhalation)21 ug/1
Aerosol; suspensionRespiratory (inhalation)25 mcg
PowderRespiratory (inhalation)50 mcg / act
Powder, meteredOral; Respiratory (inhalation)50 ug/1
PowderRespiratory (inhalation)50 µg
AerosolRespiratory (inhalation)25 mcg/1dose
Aerosol, meteredRespiratory (inhalation)25 Mikrogramm
PowderRespiratory (inhalation)25 mcg
Aerosol, meteredRespiratory (inhalation)25 mcg / act
PowderRespiratory (inhalation)50 mcg / pck
PowderBuccal0.0725 mg
GasRespiratory (inhalation)25 UG
PowderBuccal
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)Region
US5590645No1997-01-072011-03-01US flag
CA2165830No2005-04-262014-06-30Canada flag
CA1335999No1995-06-202012-06-20Canada flag
US5873360Yes1999-02-232016-08-23US flag
US6446627No2002-09-102017-12-18US flag
US6743413Yes2004-06-012021-12-01US flag
US6938796Yes2005-09-062018-07-16US flag
US6997349Yes2006-02-142018-07-16US flag
US6431168Yes2002-08-132018-12-08US flag
US7107986Yes2006-09-192018-12-06US flag
US7500444Yes2009-03-102026-08-26US flag
US6315173Yes2001-11-132018-06-23US flag
US7143908Yes2006-12-052018-07-16US flag
US6170717Yes2001-01-092018-06-23US flag
US7350676Yes2008-04-012019-02-24US flag
US7832351Yes2010-11-162023-12-19US flag
US6161724Yes2000-12-192018-07-16US flag
US6510969Yes2003-01-282018-06-23US flag
US6966467Yes2005-11-222018-06-23US flag
US6435372Yes2002-08-202018-07-16US flag
US6871646No2005-03-292021-06-23US flag
US8978966Yes2015-03-172032-07-13US flag
US6701917No2004-03-092021-06-23US flag
US7540282Yes2009-06-022023-11-06US flag
US6748947No2004-06-152021-06-23US flag
US8006690No2011-08-302021-06-23US flag
US6718972No2004-04-132021-06-23US flag
US9216260Yes2015-12-222031-12-28US flag
US8651103Yes2014-02-182028-09-26US flag
US9463288Yes2016-10-112025-11-19US flag
US8714149Yes2014-05-062032-08-25US flag
US9616024Yes2017-04-112025-03-01US flag
US9066957Yes2015-06-302035-04-06US flag
US9415008Yes2016-08-162035-04-06US flag
US9731087Yes2017-08-152031-11-18US flag
US9861771No2018-01-092020-10-11US flag
US9987229Yes2018-06-052025-03-01US flag
US10022510Yes2018-07-172031-11-18US flag
US10124131Yes2018-11-132031-11-18US flag
US9782550Yes2017-10-102036-02-28US flag
US9782551Yes2017-10-102036-02-28US flag
US10195375Yes2019-02-052031-08-14US flag
US10569034Yes2020-02-252037-02-16US flag
US10561808Yes2020-02-182032-07-01US flag
US10765820Yes2020-09-082025-11-19US flag
US10918816Yes2021-02-162036-06-14US flag
US11000653Yes2021-05-112039-06-18US flag
US11173259Yes2021-11-162041-01-06US flag
US11266796Yes2021-08-222041-08-22US flag
US11344685Yes2020-03-262040-03-26US flag
US11351317Yes2018-08-102038-08-10US flag
US11357935Yes2019-03-242039-03-24US flag
US11439777Yes2020-11-242040-11-24US flag
US11464923Yes2020-12-192040-12-19US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75.5-76.5 °CChemSpider
boiling point (°C)603ChemSpider
water solubilitySparingly solubleFDA Label
logP4.2Prentice, Jaffe, and Thomas, 2016
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fl4-1931000000-aebe04422bbfbd21a187
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0001900000-3c44a8f19551abbbb83a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001j-0029000000-43896c08fd5ce2a060e8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-4972000000-23117c7d5dc844d67897
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-6910000000-2afb08aff0a51fff0532
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-9800000000-5575125dd87cfbd258a8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kb-0229500000-3598d6091893d5b1aa38
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ls-0129200000-dee4cff926f60e2ea3a6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0803900000-fb59998314743426cd8a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0498100000-0ec7c3665cb63769d571
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01bi-1907000000-18bb0de5ec6bcb85e651
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9812100000-cedf3662055382068f71
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0296-4917000000-6394eb212902df7aa772
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-210.3203598
predicted
DarkChem Lite v0.1.0
[M-H]-199.08626
predicted
DeepCCS 1.0 (2019)
[M+H]+210.7013598
predicted
DarkChem Lite v0.1.0
[M+H]+201.50056
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.9158598
predicted
DarkChem Lite v0.1.0
[M+Na]+208.66173
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]
  8. Coleman RA, Johnson M, Nials AT, Vardey CJ: Exosites: their current status, and their relevance to the duration of action of long-acting beta 2-adrenoceptor agonists. Trends Pharmacol Sci. 1996 Sep;17(9):324-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inverse 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. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Approved Drug Products: Wixela Inhub Fluticasone and Salmeterol Inhalation Powder [Link]
  5. FDA Approved Drug Products: Serevent Diskus Salmeterol Inhalation Powder [Link]
  6. FDA Approved Drug Products: Airduo Respiclick Fluticasone and Salmeterol Inhalation Powder [Link]
  7. FDA Approved Drug Products: Advair Diskus Fluticasone and Salmeterol Inhalation Powder [Link]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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. [Article]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Salomon JJ, Hagos Y, Petzke S, Kuhne A, Gausterer JC, Hosoya K, Ehrhardt C: Beta-2 Adrenergic Agonists Are Substrates and Inhibitors of Human Organic Cation Transporter 1. Mol Pharm. 2015 Aug 3;12(8):2633-41. doi: 10.1021/mp500854e. Epub 2015 Mar 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Salomon JJ, Hagos Y, Petzke S, Kuhne A, Gausterer JC, Hosoya K, Ehrhardt C: Beta-2 Adrenergic Agonists Are Substrates and Inhibitors of Human Organic Cation Transporter 1. Mol Pharm. 2015 Aug 3;12(8):2633-41. doi: 10.1021/mp500854e. Epub 2015 Mar 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Salomon JJ, Hagos Y, Petzke S, Kuhne A, Gausterer JC, Hosoya K, Ehrhardt C: Beta-2 Adrenergic Agonists Are Substrates and Inhibitors of Human Organic Cation Transporter 1. Mol Pharm. 2015 Aug 3;12(8):2633-41. doi: 10.1021/mp500854e. Epub 2015 Mar 18. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48