Identification

Name
Salmeterol
Accession Number
DB00938  (APRD00277)
Type
Small Molecule
Groups
Approved
Description

Salmeterol is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease COPD.

Structure
Thumb
Synonyms
  • Salmaterol
  • Salmeterolum
External IDs
GR 33343 X / GR-33343-X / SN408D
Product Ingredients
IngredientUNIICASInChI Key
Salmeterol xinafoate6EW8Q962A594749-08-3XTZNCVSCVHTPAI-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SereventAerosol21 ug/1Respiratory (inhalation)GlaxoSmithKline2006-05-102006-08-29Us
Serevent (25mcg/actuation)Aerosol, metered25 mcgOral; Respiratory (inhalation)Glaxosmithkline Inc1998-04-09Not applicableCanada
Serevent Diskhaler Disk (50mcg/dose)Powder50 mcgOral; Respiratory (inhalation)Glaxosmithkline Inc1998-02-11Not applicableCanada
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)Dispensing Solutions, Inc.1997-11-25Not applicableUs
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)GlaxoSmithKline LLC1997-12-01Not applicableUs
Serevent DiskusPowder, metered50 ug/1Oral; Respiratory (inhalation)GlaxoSmithKline LLC1997-11-25Not applicableUs
Serevent Diskus (50mcg/dose)Powder50 mcgRespiratory (inhalation)Glaxosmithkline Inc1998-04-01Not applicableCanada
Serevent- Aem 25mcg/aemAerosol, metered25 mcgOral; Respiratory (inhalation)Glaxo Canada Inc1994-12-311998-07-30Canada
Serevent-pwr 50mcg/blister PackPowder50 mcgOral; Respiratory (inhalation)Glaxo Canada Inc1994-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advair 100 DiskusSalmeterol (50 mcg) + Fluticasone propionate (100 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc1999-09-24Not applicableCanada
Advair 125Salmeterol (25 mcg) + Fluticasone propionate (125 mcg)Aerosol, meteredRespiratory (inhalation)Glaxosmithkline Inc2001-12-21Not applicableCanada
Advair 250Salmeterol (25 mcg) + Fluticasone propionate (250 mcg)Aerosol, meteredRespiratory (inhalation)Glaxosmithkline Inc2001-12-21Not applicableCanada
Advair 250 DiskusSalmeterol (50 mcg) + Fluticasone propionate (250 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc1999-09-24Not applicableCanada
Advair 500 DiskusSalmeterol (50 mcg) + Fluticasone propionate (500 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc1999-09-24Not applicableCanada
Advair DiskusSalmeterol xinafoate (50 ug/1) + Fluticasone propionate (500 ug/1)PowderRespiratory (inhalation)A-S Medication Solutions2001-03-05Not applicableUs
Advair DiskusSalmeterol xinafoate (50 ug/1) + Fluticasone propionate (250 ug/1)PowderRespiratory (inhalation)Aidarex Pharmaceuticals LLC2001-02-05Not applicableUs
Advair DiskusSalmeterol xinafoate (50 ug/1) + Fluticasone propionate (500 ug/1)PowderRespiratory (inhalation)Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-172016-12-31Us
Advair DiskusSalmeterol xinafoate (50 ug/1) + Fluticasone propionate (100 ug/1)PowderOral; Respiratory (inhalation)Physicians Total Care, Inc.2001-06-21Not applicableUs
Advair DiskusSalmeterol xinafoate (50 ug/1) + Fluticasone propionate (500 ug/1)PowderRespiratory (inhalation)Glaxosmithkline Inc2001-03-052018-01-05Us
International/Other Brands
Aeromax Diskus / Arial / Salmetedur / Serevent
Categories
UNII
2I4BC502BT
CAS number
89365-50-4
Weight
Average: 415.5656
Monoisotopic: 415.272258677
Chemical Formula
C25H37NO4
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

Pharmacology

Indication

For the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Associated Conditions
Pharmacodynamics

Salmeterol is a long acting beta2-adrenoceptor agonist (LABA), usually only prescribed for severe persistent asthma following previous treatment with a short-acting beta agonist such as salbutamol and is prescribed concurrently with a corticosteroid, such as beclometasone. The primary noticable difference of salmeterol to salbutamol is that the duration of action lasts approximately 12 hours in comparison with 4-6 hours of salbutamol. When used regularly every day as presecribed, inhaled salmeterol decreases the number and severity of asthma attacks. However, it is not for use for relieving an asthma attack that has already started. Inhaled salmeterol works like other beta 2-agonists, causing bronchodilatation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma. Salmeterol is similar in action to formoterol, however formoterol has been demonstrated to have a faster onset of action than salmeterol as a result of a lower lipophilicity, and has also been demonstrated to be more potent - a 12 µg dose of formoterol has been demonstrated to be equivalent to a 50 µg dose of salmeterol.

Mechanism of action

Salmeterol's long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the molecule to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Human
UBeta-1 adrenergic receptor
agonist
Human
UBeta-3 adrenergic receptor
agonist
Human
Absorption

Because of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.

Volume of distribution
Not Available
Protein binding

96%

Metabolism

Hepatic, metabolized by hydroxylation via CYP3A4

Route of elimination
Not Available
Half life

5.5 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor. By the oral route, no deaths occurred in rats at 1,000 mg/kg (approximately 81,000 times the maximum recommended daily inhalation dose in adults and approximately 38,000 times the maximum recommended daily inhalation dose in children on a mg/m2 basis).

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Salmeterol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Salmeterol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Salmeterol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Salmeterol.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Salmeterol.
6-Deoxyerythronolide BThe metabolism of Salmeterol can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Salmeterol.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Salmeterol.
AbediterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Abediterol.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Salmeterol.
Food Interactions
Not Available

References

Synthesis Reference

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

US20030162840
General References
  1. Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths. Ann Intern Med. 2006 Jun 20;144(12):904-12. Epub 2006 Jun 5. [PubMed:16754916]
External Links
Human Metabolome Database
HMDB0015073
KEGG Drug
D05792
KEGG Compound
C07241
PubChem Compound
5152
PubChem Substance
46508024
ChemSpider
4968
BindingDB
25771
ChEBI
64064
ChEMBL
CHEMBL1263
Therapeutic Targets Database
DAP000947
PharmGKB
PA451300
IUPHAR
559
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Salmeterol
ATC Codes
R03AK06 — Salmeterol and fluticasoneR03AK12 — Salmeterol and budesonideR03AC12 — 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
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentSpinal Cord Injuries (SCI)1
1CompletedNot AvailableAsthma Bronchial1
1CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Smoke-related Lung Diseases1
1CompletedScreeningPulmonary Disease, Chronic Obstructive1
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)3
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentPulmonary Disease, Chronic Obstructive1
1Not Yet RecruitingOtherBioequivalence1
2Active Not RecruitingTreatmentAsthma Bronchial1
2CompletedTreatmentAbdominal Contour Defects1
2CompletedTreatmentAsthma Bronchial7
2CompletedTreatmentAsthma Bronchial / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentCentral Abdominal Bulging1
2CompletedTreatmentChronic Lung Diseases / Lung Diseases, Obstructive / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)5
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentPeriumbilical Subcutaneous Adipose Tissue Reduction1
2CompletedTreatmentPulmonary Disease, Chronic Obstructive6
2CompletedTreatmentSubmental Fat1
2RecruitingTreatmentAsthma Bronchial1
2WithdrawnNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
3Active Not RecruitingTreatmentAsthma Bronchial1
3Active Not RecruitingTreatmentCentral Abdominal Bulging1
3CompletedPreventionAsthma, Exercise-Induced1
3CompletedTreatmentAsthma Bronchial14
3CompletedTreatmentBronchial Asthma1
3CompletedTreatmentCentral Abdominal Bulging1
3CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema2
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)11
3CompletedTreatmentExercised Induced Asthma1
3CompletedTreatmentPulmonary Disease, Chronic Obstructive8
3Not Yet RecruitingTreatmentAsthma Bronchial1
3RecruitingOtherAsthma Bronchial1
3RecruitingTreatmentAsthma Bronchial5
3RecruitingTreatmentAsthma, Allergic1
3RecruitingTreatmentPulmonary Disease, Chronic Obstructive1
3TerminatedTreatmentPulmonary Disease, Chronic Obstructive2
3Unknown StatusTreatmentPulmonary Disease, Chronic Obstructive2
3WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)3
3WithdrawnTreatmentPulmonary Disease, Chronic Obstructive1
4CompletedNot AvailableAsthma Bronchial1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4CompletedBasic SciencePharmacokinetics in Healthy Young Men1
4CompletedDiagnosticAsthmatic Smokers / Non-asthmatic Smokers1
4CompletedOtherAsthma Bronchial1
4CompletedOtherPulmonary Disease, Chronic Obstructive1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAsthma Bronchial11
4CompletedTreatmentAsthma Bronchial / Bronchial Asthma1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)6
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Depression1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive2
4CompletedTreatmentPulmonary Disease, Chronic Obstructive9
4RecruitingOtherPulmonary Disease, Chronic Obstructive1
4RecruitingTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Chronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentPulmonary Disease, Chronic Obstructive1
4TerminatedTreatmentAsthma Bronchial2
4TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive1
4Unknown StatusTreatmentAsthma Bronchial1
4Unknown StatusTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
4Unknown StatusTreatmentPercentage of Annual Acute Exacerbation / Quality of Life1
4WithdrawnTreatmentAsthma Bronchial1
Not AvailableCompletedNot AvailableAsthma Bronchial3
Not AvailableCompletedNot AvailableAsthma Bronchial / BMI >30 kg/m21
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailablePulmonary Disease, Chronic Obstructive2
Not AvailableCompletedNot AvailableRespiratory Disorders2
Not AvailableCompletedBasic ScienceAsthma, Allergic1
Not AvailableCompletedBasic ScienceBronchodilator Agents / Chronic Obstructive Pulmonary Disease (COPD) / Salmeterol / Salmeterol Effect Against an Acute Alveolar Fluid Clearance Challenge Secondary to Lung Fluid Overload in COPD Patients1
Not AvailableCompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentAsthma Bronchial4
Not AvailableCompletedTreatmentAsthma, Allergic / Mild, Allergic Asthma1
Not AvailableCompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingNot AvailableAsthma Bronchial1
Not AvailableRecruitingTreatmentChronic Lung Diseases / Medication Compliance1
Not AvailableSuspendedTreatmentCystic Fibrosis (CF)1
Not AvailableTerminatedTreatmentAsthma Bronchial1
Not AvailableUnknown StatusTreatmentAsthma Bronchial1
Not AvailableUnknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableWithdrawnNot AvailableChronic Obstructive Pulmonary Disease (COPD) / Sleep disorders and disturbances1

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
PowderRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
PowderOral; Respiratory (inhalation)
Powder, meteredRespiratory (inhalation)
AerosolRespiratory (inhalation)21 ug/1
PowderOral; Respiratory (inhalation)50 mcg
Powder, meteredOral; Respiratory (inhalation)50 ug/1
PowderRespiratory (inhalation)50 mcg
Aerosol, meteredOral; Respiratory (inhalation)25 mcg
Prices
Unit descriptionCostUnit
Serevent Diskus 60 50 mcg/dose Powder Inhaler182.81USD inhaler
Serevent Diskhaler Device6.15USD device
Serevent 50 mcg/dose Disk4.21USD disk
Serevent diskus 50 mcg3.71USD each
Serevent Diskus 50 mcg/dose Metered Inhalation Powder1.05USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5590645No1997-01-072011-03-01Us
CA2165830No2005-04-262014-06-30Canada
CA1335999No1995-06-202012-06-20Canada
US5873360Yes1999-02-232016-08-23Us
US6446627No2002-09-102017-12-18Us
US6743413Yes2004-06-012021-12-01Us
US6938796Yes2005-09-062018-07-16Us
US6997349Yes2006-02-142018-07-16Us
US6431168Yes2002-08-132018-12-08Us
US7107986Yes2006-09-192018-12-06Us
US7500444Yes2009-03-102026-08-26Us
US6315173Yes2001-11-132018-06-23Us
US7143908Yes2006-12-052018-07-16Us
US6170717Yes2001-01-092018-06-23Us
US7350676Yes2008-04-012019-02-24Us
US7832351Yes2010-11-162023-12-19Us
US6161724Yes2000-12-192018-07-16Us
US6510969Yes2003-01-282018-06-23Us
US6966467Yes2005-11-222018-06-23Us
US6435372Yes2002-08-202018-07-16Us
US6871646No2005-03-292021-06-23Us
US8978966No2015-03-172032-01-13Us
US6701917No2004-03-092021-06-23Us
US7540282No2009-06-022023-05-06Us
US6748947No2004-06-152021-06-23Us
US8006690No2011-08-302021-06-23Us
US6718972No2004-04-132021-06-23Us
US9216260No2015-12-222031-06-28Us
US8651103No2014-02-182028-03-26Us
US9463288No2016-10-112025-05-19Us
US8714149No2014-05-062032-02-25Us
US9616024No2017-04-112024-09-01Us
US9066957No2015-06-302034-10-06Us
US9415008No2016-08-162034-10-06Us
US9731087No2017-08-152031-05-18Us
US9861771No2018-01-092020-10-11Us
US9987229No2004-09-012024-09-01Us
US10022510No2011-05-182031-05-18Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75.5-76.5 °CNot Available
water solubilitySparingly solubleNot Available
logP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00226 mg/mLALOGPS
logP3.82ALOGPS
logP3.61ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area81.95 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity122.39 m3·mol-1ChemAxon
Polarizability50.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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
Benzyl alcohol / Phenol / Aralkylamine / 1-hydroxy-2-unsubstituted benzenoid / Secondary alcohol / 1,2-aminoalcohol / Dialkyl ether / Secondary aliphatic amine / Ether / Secondary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, phenols, secondary amino compound, ether, primary alcohol (CHEBI:64064)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
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. [PubMed:10471277]
  2. Finney PA, Donnelly LE, Belvisi MG, Chuang TT, Birrell M, Harris A, Mak JC, Scorer C, Barnes PJ, Adcock IM, Giembycz MA: Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). Br J Pharmacol. 2001 Mar;132(6):1261-70. [PubMed:11250877]
  3. Green SA, Rathz DA, Schuster AJ, Liggett SB: The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s). Eur J Pharmacol. 2001 Jun 15;421(3):141-7. [PubMed:11516429]
  4. Meliton AY, Munoz NM, Liu J, Lambertino AT, Boetticher E, Myo S, Myou S, Zhu X, Johnson M, Leff AR: Blockade of LTC4 synthesis caused by additive inhibition of gIV-PLA2 phosphorylation: Effect of salmeterol and PDE4 inhibition in human eosinophils. J Allergy Clin Immunol. 2003 Aug;112(2):404-10. [PubMed:12897749]
  5. Brogden RN, Faulds D: Salmeterol xinafoate: a review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Allergol Immunopathol (Madr). 1992 Mar-Apr;20(2):72-84. [PubMed:1359777]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. [PubMed:14730417]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. 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. [PubMed:14730417]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally 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. [PubMed:15601807]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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]

Drug created on June 13, 2005 07:24 / Updated on December 12, 2018 07:10