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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Salmeterol (DB00938)

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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

• Asthma
• Chronic Obstructive Pulmonary Disease (COPD)
• Exercise-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

Target	Actions	Organism
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 C_max of 47.897pg/mL, with a T_max 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

• Salmeterol
  • alpha-hydroxysalmeterol
  • Salmeterol O-dealkylated Metabolite

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	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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Food Interactions

No interactions found.

Products

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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
Serevent (25mcg/actuation)	Aerosol, metered	25 mcg / act	Respiratory (inhalation)	Glaxosmithkline Inc	1998-04-09	2006-07-12
Serevent Diskhaler Disk (50mcg/dose)	Powder	50 mcg / act	Respiratory (inhalation)	Glaxosmithkline Inc	1998-02-11	2017-09-20
Serevent Diskus	Powder, metered	50 ug/1	Oral; Respiratory (inhalation)	Dispensing Solutions, Inc.	1997-11-25	Not applicable
Serevent Diskus	Powder, metered	50 ug/1	Oral; Respiratory (inhalation)	GlaxoSmithKline LLC	1997-12-01	2021-12-31
Serevent Diskus	Powder, metered	50 ug/1	Oral; Respiratory (inhalation)	GlaxoSmithKline LLC	1997-11-25	Not applicable
Serevent Diskus (50mcg/dose)	Powder	50 mcg / act	Respiratory (inhalation)	Glaxosmithkline Inc	1998-04-01	Not applicable
Serevent- Aem 25mcg/aem	Aerosol, metered	25 mcg / act	Respiratory (inhalation)	Glaxo Canada Inc	1994-12-31	1998-07-30
Serevent-pwr 50mcg/blister Pack	Powder	50 mcg / pck	Respiratory (inhalation)	Glaxo Canada Inc	1994-12-31	1998-07-30

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
\-	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (250 mcg)			บริษัท แกล็กโซสมิทไคล์น (ประเทศไทย)	2019-07-23	Not applicable
ACTİONFLU 50 MCG/100 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,120 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (100 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/100 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,180 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (100 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/100 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,60 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (100 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/250 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,120 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (250 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/250 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,180 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (250 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/250 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,60 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (250 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/500 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,120 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (500 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/500 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,180 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (500 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ACTİONFLU 50 MCG/500 MCG İNHALOSYON İÇİN TOZ İÇEREN KAPSÜL,60 KAPSÜL	Salmeterol xinafoate (50 mcg) + Fluticasone propionate (500 mcg)	Powder	Respiratory (inhalation)	EXELTIS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
AIRPLUS 25/125 MCG INHALASYON ICIN OLCULU DOZLU AEROSOL 120 DOZ	Salmeterol (25 mcg) + Fluticasone propionate (125 mcg)	Aerosol, metered	Respiratory (inhalation)	TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ.	2020-08-14	Not applicable

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

R03AK12 — Salmeterol and budesonide

• R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
• R03A — ADRENERGICS, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

R03AC12 — Salmeterol

• R03AC — Selective beta-2-adrenoreceptor agonists
• 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
• Long-acting beta-adrenoceptor agonists
• 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)

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]

External Links

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

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	32
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)
Gas	Respiratory (inhalation)
Aerosol, powder	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)	0.500 mg
Aerosol; suspension	Respiratory (inhalation)
Powder	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)
Suspension	Oral; Respiratory (inhalation)
Suspension	Buccal; Respiratory (inhalation)
Aerosol; aerosol, metered	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)
Aerosol	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)	100 mcg
Powder, metered	Respiratory (inhalation)	250 mcg
Powder, metered	Respiratory (inhalation)	500 mcg
Capsule	Respiratory (inhalation)
Aerosol	Respiratory (inhalation)
Aerosol, powder	Respiratory (inhalation)	25 mcg
Powder	Respiratory (inhalation)	50 mcg
Powder, metered	Respiratory (inhalation)	50 MICROGRAMMI
Powder, metered	Respiratory (inhalation)	50 MCG
Gas	Respiratory (inhalation)	25 µg
Aerosol, metered	Respiratory (inhalation)	25 MCG
Aerosol, spray	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)	100 mcg/inhalation
Powder, metered	Respiratory (inhalation)	250 mcg/inhalation
Powder, metered	Respiratory (inhalation)	500 mcg/inhalation
Aerosol, spray	Respiratory (inhalation)	125 mcg
Aerosol, spray	Respiratory (inhalation)	250 mcg
Aerosol, spray	Respiratory (inhalation)	50 mcg
Suspension	Respiratory (inhalation)
Aerosol	Respiratory (inhalation)	21 ug/1
Aerosol; suspension	Respiratory (inhalation)	25 mcg
Powder	Respiratory (inhalation)	50 mcg / act
Powder, metered	Oral; Respiratory (inhalation)	50 ug/1
Powder	Respiratory (inhalation)	50 μg
Aerosol	Respiratory (inhalation)	25 mcg/1dose
Aerosol, metered	Respiratory (inhalation)
Aerosol, metered	Respiratory (inhalation)	25 mcg / act
Powder	Respiratory (inhalation)	50 mcg / pck
Gas	Respiratory (inhalation)	25 UG

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
CA2165830	No	2005-04-26	2014-06-30
CA1335999	No	1995-06-20	2012-06-20
US5873360	Yes	1999-02-23	2016-08-23
US6446627	No	2002-09-10	2017-12-18
US6743413	Yes	2004-06-01	2021-12-01
US6938796	Yes	2005-09-06	2018-07-16
US6997349	Yes	2006-02-14	2018-07-16
US6431168	Yes	2002-08-13	2018-12-08
US7107986	Yes	2006-09-19	2018-12-06
US7500444	Yes	2009-03-10	2026-08-26
US6315173	Yes	2001-11-13	2018-06-23
US7143908	Yes	2006-12-05	2018-07-16
US6170717	Yes	2001-01-09	2018-06-23
US7350676	Yes	2008-04-01	2019-02-24
US7832351	Yes	2010-11-16	2023-12-19
US6161724	Yes	2000-12-19	2018-07-16
US6510969	Yes	2003-01-28	2018-06-23
US6966467	Yes	2005-11-22	2018-06-23
US6435372	Yes	2002-08-20	2018-07-16
US6871646	No	2005-03-29	2021-06-23
US8978966	Yes	2015-03-17	2032-07-13
US6701917	No	2004-03-09	2021-06-23
US7540282	Yes	2009-06-02	2023-11-06
US6748947	No	2004-06-15	2021-06-23
US8006690	No	2011-08-30	2021-06-23
US6718972	No	2004-04-13	2021-06-23
US9216260	Yes	2015-12-22	2031-12-28
US8651103	Yes	2014-02-18	2028-09-26
US9463288	Yes	2016-10-11	2025-11-19
US8714149	Yes	2014-05-06	2032-08-25
US9616024	Yes	2017-04-11	2025-03-01
US9066957	Yes	2015-06-30	2035-04-06
US9415008	Yes	2016-08-16	2035-04-06
US9731087	Yes	2017-08-15	2031-11-18
US9861771	No	2018-01-09	2020-10-11
US9987229	Yes	2018-06-05	2025-03-01
US10022510	Yes	2018-07-17	2031-11-18
US10124131	Yes	2018-11-13	2031-11-18
US9782550	Yes	2017-10-10	2036-02-28
US9782551	Yes	2017-10-10	2036-02-28
US10195375	Yes	2019-02-05	2031-08-14
US10569034	Yes	2020-02-25	2037-02-16
US10561808	Yes	2020-02-18	2032-07-01
US10765820	Yes	2020-09-08	2025-11-19
US10918816	Yes	2021-02-16	2036-06-14
US11000653	Yes	2021-05-11	2039-06-18
US11173259	Yes	2021-11-16	2041-01-06
US11266796	Yes	2021-08-22	2041-08-22
US11344685	Yes	2020-03-26	2040-03-26
US11351317	Yes	2018-08-10	2038-08-10
US11357935	No	2018-09-24	2038-09-24

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0001900000-3c44a8f19551abbbb83a
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-001j-0029000000-43896c08fd5ce2a060e8
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-001i-4972000000-23117c7d5dc844d67897
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0006-6910000000-2afb08aff0a51fff0532
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0006-9800000000-5575125dd87cfbd258a8
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00kb-0229500000-3598d6091893d5b1aa38

Targets

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Details1. Beta-2 adrenergic receptor

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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	251.19	N/A	N/A	A29229
EC 50 (nM)	794.33	N/A	N/A	A29221 / A29223 / A29225 / A29226 / A29227
IC 50 (nM)	501.19	N/A	N/A	A29226 / A29228
Kd (nM)	4169	7.4	37	A15307
Ki (nM)	1600	N/A	N/A	A15544
Ki (nM)	2300	N/A	N/A	A29222
Ki (nM)	801	N/A	N/A	A29224

Details

Binding Properties2. Beta-1 adrenergic receptor

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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1258.93	N/A	N/A	A29221 / A29223 / A29225 / A29227
Kd (nM)	1862	7.4	37	A15307
Ki (nM)	7180	N/A	N/A	A15544

Details

Binding Properties3. Beta-3 adrenergic receptor

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]

×

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Drug created at June 13, 2005 13:24 / Updated at September 27, 2022 08:31