Identification
- Name
- Salmeterol
- Accession Number
- DB00938
- Description
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
Structure for Salmeterol (DB00938)
- Weight
- Average: 415.5656
Monoisotopic: 415.272258677 - Chemical Formula
- C25H37NO4
- Synonyms
- Salmaterol
- Salmeterol
- Salmeterolum
- External IDs
- GR 33343 X
- GR-33343-X
- SN408D
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- 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
- Associated Conditions
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans UBeta-1 adrenergic receptor inverse agonistHumans UBeta-3 adrenergic receptor inverse agonistHumans - 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- 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
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Salmeterol can be increased when it is combined with Abametapir. Abatacept The metabolism of Salmeterol can be increased when combined with Abatacept. Acalabrutinib The metabolism of Salmeterol can be decreased when combined with Acalabrutinib. Acebutolol The therapeutic efficacy of Salmeterol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Salmeterol is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Salmeterol is combined with Acemetacin. Acetylcholine The risk or severity of adverse effects can be increased when Salmeterol is combined with Acetylcholine. Acetylsalicylic acid The risk or severity of hypertension can be increased when Salmeterol is combined with Acetylsalicylic acid. Acipimox The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Salmeterol is combined with Acipimox. Aclidinium The risk or severity of Tachycardia can be increased when Salmeterol is combined with Aclidinium. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Salmeterol xinafoate 6EW8Q962A5 94749-08-3 XTZNCVSCVHTPAI-UHFFFAOYSA-N - International/Other Brands
- Aeromax Diskus / Arial / Salmetedur
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Serevent Aerosol 21 ug/1 Respiratory (inhalation) GlaxoSmithKline 2006-05-10 2006-08-29 US 
Serevent (25mcg/actuation) Aerosol, metered Respiratory (inhalation) Glaxosmithkline Inc 1998-04-09 2006-07-12 Canada 
Serevent Diskhaler Disk (50mcg/dose) Powder Respiratory (inhalation) Glaxosmithkline Inc 1998-02-11 2017-09-20 Canada Serevent Diskus Powder, metered 50 ug/1 Oral; Respiratory (inhalation) GlaxoSmithKline LLC 1997-11-25 Not applicable US Serevent Diskus Powder, metered 50 ug/1 Oral; Respiratory (inhalation) Dispensing Solutions, Inc. 1997-11-25 Not applicable US Serevent Diskus Powder, metered 50 ug/1 Oral; Respiratory (inhalation) GlaxoSmithKline LLC 1997-12-01 Not applicable US Serevent Diskus (50mcg/dose) Powder Respiratory (inhalation) Glaxosmithkline Inc 1998-04-01 Not applicable Canada Serevent- Aem 25mcg/aem Aerosol, metered Respiratory (inhalation) Glaxo Canada Inc 1994-12-31 1998-07-30 Canada Serevent-pwr 50mcg/blister Pack Powder Respiratory (inhalation) Glaxo Canada Inc 1994-12-31 1998-07-30 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Advair 100 Diskus Salmeterol (50 mcg) + Fluticasone propionate (100 mcg) Powder Respiratory (inhalation) Glaxosmithkline Inc 1999-09-24 Not applicable Canada Advair 125 Salmeterol (25 mcg) + Fluticasone propionate (125 mcg) Aerosol, metered Respiratory (inhalation) Glaxosmithkline Inc 2001-12-21 Not applicable Canada Advair 250 Salmeterol (25 mcg) + Fluticasone propionate (250 mcg) Aerosol, metered Respiratory (inhalation) Glaxosmithkline Inc 2001-12-21 Not applicable Canada Advair 250 Diskus Salmeterol (50 mcg) + Fluticasone propionate (250 mcg) Powder Respiratory (inhalation) Glaxosmithkline Inc 1999-09-24 Not applicable Canada Advair 500 Diskus Salmeterol (50 mcg) + Fluticasone propionate (500 mcg) Powder Respiratory (inhalation) Glaxosmithkline Inc 1999-09-24 Not applicable Canada Advair Diskus Salmeterol xinafoate (50 ug/1) + Fluticasone propionate (100 ug/1) Powder Oral; Respiratory (inhalation) Physicians Total Care, Inc. 2001-06-21 Not applicable US Advair Diskus Salmeterol xinafoate (50 ug/1) + Fluticasone propionate (100 ug/1) Powder Respiratory (inhalation) Glaxosmithkline Inc 2001-02-28 2018-01-05 US Advair Diskus Salmeterol xinafoate (50 ug/1) + Fluticasone propionate (250 ug/1) Powder Respiratory (inhalation) GlaxoSmithKline LLC 2001-02-05 Not applicable US Advair Diskus Salmeterol xinafoate (50 ug/1) + Fluticasone propionate (500 ug/1) Powder Respiratory (inhalation) Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc 2012-02-17 2016-12-31 US Advair Diskus Salmeterol xinafoate (50 ug/1) + Fluticasone propionate (500 ug/1) Powder Respiratory (inhalation) Glaxo Wellcome Production 2017-12-07 2018-03-13 US
Categories
- ATC Codes
- R03AK06 — Salmeterol and fluticasone
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics, Inhalants
- Agents Causing Muscle Toxicity
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs for Obstructive Airway Diseases
- Ethanolamines
- Ethylamines
- Neurotransmitter Agents
- OCT1 inhibitors
- OCT1 substrates
- OCT2 Inhibitors
- Peripheral Nervous System Agents
- Phenethylamines
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- Sympathomimetic (Adrenergic) Agents
- 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)
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
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
- 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. [PubMed:7905380]
- Prentice B, Jaffe A, Thomas P: Beta2 Receptor Agonists Parnham M. (eds) Compendium of Inflammatory Diseases.
- 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. [PubMed:23131487]
- 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. [PubMed:28374512]
- 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. [PubMed:2904183]
- FDA Approved Drug Products: Serevent Salmeterol Xinafoate Inhaled Metered Aerosol (Discontinued) [Link]
- FDA Approved Drug Products: Wixela Inhub Fluticasone and Salmeterol Inhalation Powder [Link]
- FDA Approved Drug Products: Serevent Diskus Salmeterol Inhalation Powder [Link]
- FDA Approved Drug Products: Airduo Respiclick Fluticasone and Salmeterol Inhalation Powder [Link]
- FDA Approved Drug Products: Advair HFA Fluticasone and Salmeterol Inhalation Aerosol [Link]
- FDA Approved Drug Products: Advair Diskus Fluticasone and Salmeterol Inhalation Powder [Link]
- Cayman Chemical: Salmeterol MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0015073
- KEGG Drug
- D05792
- KEGG Compound
- C07241
- PubChem Compound
- 5152
- PubChem Substance
- 46508024
- ChemSpider
- 4968
- BindingDB
- 25771
- 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
- AHFS Codes
- 12:12.08.12 — Selective Beta 2-adrenergic Agonists
- 12:12.00 — Sympathomimetic (Adrenergic) Agents
- FDA label
- Download (132 KB)
- MSDS
- Download (51 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Asthma 1 4 Completed Basic Science Chronic Obstructive Pulmonary Disease (COPD) 2 4 Completed Basic Science Pharmacokinetics in Healthy Young Men 1 4 Completed Diagnostic Asthmatic Smokers / Non-asthmatic Smokers 1 4 Completed Other Asthma 1 4 Completed Other Chronic Obstructive Pulmonary Disease (COPD) 1 4 Completed Treatment Activity/Exercise Induced Bronchospasm / Bronchospasm 2 4 Completed Treatment Allergic Rhinitis (AR) 1 4 Completed Treatment Asthma 31 4 Completed Treatment Asthma / Bronchial Asthma 1
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
Form Route Strength Powder Oral; Respiratory (inhalation) Powder Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) Aerosol Respiratory (inhalation) 25 mcg Gas Respiratory (inhalation) 125 µg Gas Respiratory (inhalation) 250 µg Aerosol, powder Respiratory (inhalation) 50 mcg Aerosol, powder Respiratory (inhalation) 250 mcg Aerosol, powder Respiratory (inhalation) 500 mcg Powder Respiratory (inhalation) 500 µg Powder Respiratory (inhalation) 500 cg Aerosol, metered Respiratory (inhalation) 25 mcg Powder Respiratory (inhalation) 50 mcg Aerosol; suspension Respiratory (inhalation) 25 mcg Aerosol; suspension Respiratory (inhalation) 50 mcg Gas Respiratory (inhalation) 50 µg Powder Respiratory (inhalation) 100 µg Aerosol, metered Respiratory (inhalation) 125 mcg Powder, metered Respiratory (inhalation) 50 mcg Suspension Respiratory (inhalation) 0.15625 g Suspension Oral; Respiratory (inhalation) 125 mcg Suspension Oral; Respiratory (inhalation) 250 mcg Suspension Buccal; Respiratory (inhalation) 250 cg Aerosol Respiratory (inhalation) 0.0625 g Aerosol, powder Respiratory (inhalation) 250 ug Aerosol, powder Respiratory (inhalation) 500 ug Capsule Respiratory (inhalation) Aerosol; aerosol, metered Respiratory (inhalation) 125 mcg Powder, metered Respiratory (inhalation) Aerosol Respiratory (inhalation) 250 mcg Capsule Respiratory (inhalation) 50 mcg Suspension Respiratory (inhalation) 0.23 g Suspension Respiratory (inhalation) 0.46 g Suspension Respiratory (inhalation) 25 mcg Aerosol Respiratory (inhalation) 125 mcg Aerosol Respiratory (inhalation) 50 mcg Powder Respiratory (inhalation) 250 µg Powder Respiratory (inhalation) 25 mcg Aerosol, powder Respiratory (inhalation) 25 mcg Gas Respiratory (inhalation) 25 µg Powder, metered Respiratory (inhalation) 500 mcg Aerosol, metered Respiratory (inhalation) 25 MICROGRAMMI Powder Respiratory (inhalation) 10.9 mcg Aerosol, spray Respiratory (inhalation) 25 mcg Aerosol, spray Respiratory (inhalation) 125 mcg Suspension Respiratory (inhalation) 50 mcg Suspension Respiratory (inhalation) 125 cg Powder Respiratory (inhalation) 72.5 mcg Powder Respiratory (inhalation) 250 cg Aerosol, metered Respiratory (inhalation) 50 mcg Powder Respiratory (inhalation) 100 cg Suspension Respiratory (inhalation) 250 cg Aerosol Respiratory (inhalation) 21 ug/1 Powder, metered Respiratory (inhalation) 50 MICROGRAMMI Powder Respiratory (inhalation) Powder, metered Oral; Respiratory (inhalation) 50 ug/1 Powder Respiratory (inhalation) 50 µg Aerosol Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) 25 Mikrogramm Aerosol, metered Respiratory (inhalation) Aerosol, spray Respiratory (inhalation) 250 mcg Suspension Respiratory (inhalation) 125 mcg Aerosol Respiratory (inhalation) 0.33333 % w/w Suspension Respiratory (inhalation) 250 mcg Aerosol Respiratory (inhalation) 0.16667 % w/w Aerosol Respiratory (inhalation) 50 cg Suspension Respiratory (inhalation) 0.34098 % v/v Suspension Respiratory (inhalation) 0.17094 % w/w Suspension Respiratory (inhalation) 50 cg Gas Respiratory (inhalation) 25 UG Powder Respiratory (inhalation) 9 mcg Gas Respiratory (inhalation) 125 mcg Powder Respiratory (inhalation) 250 mcg Gas Respiratory (inhalation) 250 mcg Powder Respiratory (inhalation) 500 mcg Gas Respiratory (inhalation) 50 mcg Powder Respiratory (inhalation) 100 mcg Aerosol Respiratory (inhalation) - Prices
Unit description Cost Unit Serevent Diskus 60 50 mcg/dose Powder Inhaler 182.81USD inhaler Serevent Diskhaler Device 6.15USD device Serevent 50 mcg/dose Disk 4.21USD disk Serevent diskus 50 mcg 3.71USD each Serevent Diskus 50 mcg/dose Metered Inhalation Powder 1.05USD dose DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5590645 No 1997-01-07 2011-03-01 US CA2165830 No 2005-04-26 2014-06-30 Canada CA1335999 No 1995-06-20 2012-06-20 Canada US5873360 Yes 1999-02-23 2016-08-23 US US6446627 No 2002-09-10 2017-12-18 US US6743413 Yes 2004-06-01 2021-12-01 US US6938796 Yes 2005-09-06 2018-07-16 US US6997349 Yes 2006-02-14 2018-07-16 US US6431168 Yes 2002-08-13 2018-12-08 US US7107986 Yes 2006-09-19 2018-12-06 US US7500444 Yes 2009-03-10 2026-08-26 US US6315173 Yes 2001-11-13 2018-06-23 US US7143908 Yes 2006-12-05 2018-07-16 US US6170717 Yes 2001-01-09 2018-06-23 US US7350676 Yes 2008-04-01 2019-02-24 US US7832351 Yes 2010-11-16 2023-12-19 US US6161724 Yes 2000-12-19 2018-07-16 US US6510969 Yes 2003-01-28 2018-06-23 US US6966467 Yes 2005-11-22 2018-06-23 US US6435372 Yes 2002-08-20 2018-07-16 US US6871646 No 2005-03-29 2021-06-23 US US8978966 No 2015-03-17 2032-01-13 US US6701917 No 2004-03-09 2021-06-23 US US7540282 No 2009-06-02 2023-05-06 US US6748947 No 2004-06-15 2021-06-23 US US8006690 No 2011-08-30 2021-06-23 US US6718972 No 2004-04-13 2021-06-23 US US9216260 No 2015-12-22 2031-06-28 US US8651103 No 2014-02-18 2028-03-26 US US9463288 No 2016-10-11 2025-05-19 US US8714149 No 2014-05-06 2032-02-25 US US9616024 No 2017-04-11 2024-09-01 US US9066957 No 2015-06-30 2034-10-06 US US9415008 No 2016-08-16 2034-10-06 US US9731087 No 2017-08-15 2031-05-18 US US9861771 No 2018-01-09 2020-10-11 US US9987229 No 2018-06-05 2024-09-01 US US10022510 No 2018-07-17 2031-05-18 US US10124131 No 2018-11-13 2031-05-18 US US9782550 No 2017-10-10 2035-08-28 US US9782551 No 2017-10-10 2035-08-28 US US10195375 No 2019-02-05 2031-02-14 US US10569034 No 2016-08-16 2036-08-16 US US10561808 No 2012-01-01 2032-01-01 US US10765820 No 2005-05-19 2025-05-19 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 75.5-76.5 °C ChemSpider boiling point (°C) 603 ChemSpider water solubility Sparingly soluble FDA Label logP 4.2 Prentice, Jaffe, and Thomas, 2016 - Predicted Properties
Property Value Source Water Solubility 0.00226 mg/mL ALOGPS logP 3.82 ALOGPS logP 3.61 ChemAxon logS -5.3 ALOGPS pKa (Strongest Acidic) 10.12 ChemAxon pKa (Strongest Basic) 9.4 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 81.95 Å2 ChemAxon Rotatable Bond Count 16 ChemAxon Refractivity 122.39 m3·mol-1 ChemAxon Polarizability 50.6 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8516 Blood Brain Barrier - 0.8862 Caco-2 permeable - 0.6968 P-glycoprotein substrate Substrate 0.7767 P-glycoprotein inhibitor I Inhibitor 0.539 P-glycoprotein inhibitor II Inhibitor 0.7663 Renal organic cation transporter Non-inhibitor 0.6106 CYP450 2C9 substrate Non-substrate 0.8 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5937 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.9099 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.6121 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8618 Ames test Non AMES toxic 0.807 Carcinogenicity Non-carcinogens 0.9378 Biodegradation Ready biodegradable 0.5587 Rat acute toxicity 2.0830 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.741 hERG inhibition (predictor II) Inhibitor 0.7149
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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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
- 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]
- 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]
- 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]
- 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]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
- 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
- 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. [PubMed:14730417]
- 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
- 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. [PubMed:14730417]
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
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Flockhart Table of Drug Interactions [Link]
- FDA Approved Drug Products: Wixela Inhub Fluticasone and Salmeterol Inhalation Powder [Link]
- FDA Approved Drug Products: Serevent Diskus Salmeterol Inhalation Powder [Link]
- FDA Approved Drug Products: Airduo Respiclick Fluticasone and Salmeterol Inhalation Powder [Link]
- 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
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
- 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
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
- 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
- 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]
- 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. [PubMed:26721703]
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
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
- 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
- Cazzola M, Testi R, Matera MG: Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30. doi: 10.2165/00003088-200241010-00003. [PubMed:11825095]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [PubMed:25751092]
- 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
- 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. [PubMed:25751092]
- 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
- 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. [PubMed:25751092]
Drug created on June 13, 2005 13:24 / Updated on February 24, 2021 19:34