Identification

Name
Formoterol
Accession Number
DB00983  (APRD00641)
Type
Small Molecule
Groups
Approved, Investigational
Description

Formoterol is a long-acting (12 hours) beta2-agonist used in the management of asthma and/or chronic obstructive pulmonary disease (COPD). Inhaled formoterol works like other beta2-agonists, causing bronchodilatation through relaxation of the smooth muscle in the airway so as to treat the exacerbation of asthma.

Structure
Thumb
Synonyms
  • 2'-Hydroxy-5'-(1-hydroxy-2-((P-methoxy-alpha-methylphenethyl)amino)ethyl)formanilide
  • 2'-Hydroxy-5'-{1-hydroxy-2-[(P-methoxy-alpha-methylphenethyl)amino]ethyl}formanilide
  • Formoterolum
  • N-[2-Hydroxy-5-(1-hydroxy-2-{[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)phenyl]formamide
Product Ingredients
IngredientUNIICASInChI Key
Formoterol fumarateW34SHF8J2K183814-30-4RATSWNOMCHFQGJ-AYJOUMQSSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ForadilCapsule12 ug/1Respiratory (inhalation)Physicians Total Care, Inc.2004-05-28Not applicableUs
ForadilCapsule12 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2001-02-162017-01-31Us
ForadilCapsule12 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2001-02-162017-01-31Us
Foradil Dry Powder Capsules for InhalationCapsule12 mcgRespiratory (inhalation)Novartis1997-07-08Not applicableCanada
Oxeze TurbuhalerPowder6 mcgRespiratory (inhalation)Astra Zeneca1998-03-12Not applicableCanada
Oxeze TurbuhalerPowder12 mcgRespiratory (inhalation)Astra Zeneca1998-03-12Not applicableCanada
PerforomistSolution20 ug/2mLRespiratory (inhalation)Mylan Specialty L.P.2007-10-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bevespi AerosphereFormoterol fumarate (4.8 ug/1) + Glycopyrronium bromide (9 ug/1)Aerosol, meteredRespiratory (inhalation)AstraZeneca Pharmaceuticals LP2016-10-03Not applicableUs
Bevespi AerosphereFormoterol fumarate (5.8 mcg) + Glycopyrronium bromide (8.3 mcg)Aerosol, meteredRespiratory (inhalation)Astra ZenecaNot applicableNot applicableCanada
Duaklir GenuairFormoterol fumarate (12 μg) + Aclidinium bromide (340 μg)Respiratory (inhalation)Astra Zeneca Ab2014-11-19Not applicableEu
Duaklir GenuairFormoterol fumarate (12 μg) + Aclidinium bromide (340 μg)Respiratory (inhalation)Astra Zeneca Ab2014-11-19Not applicableEu
Duaklir GenuairFormoterol fumarate (12 mcg) + Aclidinium bromide (400 mcg)Powder, meteredRespiratory (inhalation)Astra Zeneca2015-07-09Not applicableCanada
Duaklir GenuairFormoterol fumarate (12 μg) + Aclidinium bromide (340 μg)Respiratory (inhalation)Astra Zeneca Ab2014-11-19Not applicableEu
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (100 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (200 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (200 ug/1)AerosolRespiratory (inhalation)A-S Medication Solutions2010-06-22Not applicableUs
SymbicortFormoterol fumarate (4.5 ug/1) + Budesonide (80 ug/1)AerosolRespiratory (inhalation)Astra Zeneca Lp2007-05-29Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Budesonide/formoterol TevaFormoterol fumarate (4.5 μg / dose) + Budesonide (160 μg / dose)Respiratory (inhalation)Teva Pharma B.V.2014-11-192017-01-31Eu
Budesonide/formoterol TevaFormoterol fumarate (9 μg / dose) + Budesonide (320 μg / dose)Respiratory (inhalation)Teva Pharma B.V.2014-11-192017-01-31Eu
International/Other Brands
Foradile / Oxis Turbuhaler
Categories
UNII
5ZZ84GCW8B
CAS number
73573-87-2
Weight
Average: 344.4049
Monoisotopic: 344.173607266
Chemical Formula
C19H24N2O4
InChI Key
BPZSYCZIITTYBL-UHFFFAOYSA-N
InChI
InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)
IUPAC Name
N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide
SMILES
COC1=CC=C(CC(C)NCC(O)C2=CC(NC=O)=C(O)C=C2)C=C1

Pharmacology

Indication

For use as long-term maintenance treatment of asthma in patients 6 years of age and older with reversible obstructive airways disease, including patients with symptoms of nocturnal asthma, who are using optimal corticosteroid treatment and experiencing regular or frequent breakthrough symptoms requiring use of a short-acting bronchodilator. Not indicated for asthma that can be successfully managed with occasional use of an inhaled, short-acting beta2-adrenergic agonist. Also used for the prevention of exercise-induced bronchospasm, as well as long-term treatment of bronchospasm associated with COPD.

Associated Conditions
Pharmacodynamics

Formoterol is a long-acting selective beta2-adrenergic receptor agonist (beta2-agonist). Inhaled formoterol fumarate acts locally in the lung as a bronchodilator. In vitro studies have shown that formoterol has more than 200-fold greater agonist activity at beta2-receptors than at beta1- receptors. Although beta2-receptors are the predominant adrenergic receptors in bronchial smooth muscle and beta1-receptors are the predominant receptors in the heart, there are also beta2-receptors in the human heart comprising 10%-50% of the total beta-adrenergic receptors. The precise function of these receptors has not been established, but they raise the possibility that even highly selective beta2- agonists may have cardiac effects.

Mechanism of action

The pharmacologic effects of beta2-adrenoceptor agonist drugs, including formoterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3', 5'-adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibits the release of pro-inflammatory mast-cell mediators such as histamine and leukotrienes. Formoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-responsiveness. The relevance of these in vitro and animal findings to humans is unknown.

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

Rapidly absorbed into plasma following administration by oral inhalation. It is likely that the majority of the inhaled formoterol delivered is swallowed and then absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

The binding of formoterol to human plasma proteins in vitro was 61%-64% at concentrations from 0.1 to 100 ng/mL. Binding to human serum albumin in vitro was 31%-38% over a range of 5 to 500 ng/mL. The concentrations of formoterol used to assess the plasma protein binding were higher than those achieved in plasma following inhalation of a single 120 µg dose.

Metabolism

Metabolized primarily by direct glucuronidation at either the phenolic or aliphatic hydroxyl group and O-demethylation followed by glucuronide conjugation at either phenolic hydroxyl groups. Minor pathways involve sulfate conjugation of formoterol and deformylation followed by sulfate conjugation. The most prominent pathway involves direct conjugation at the phenolic hydroxyl group. The second major pathway involves O-demethylation followed by conjugation at the phenolic 2'-hydroxyl group. Four cytochrome P450 isozymes (CYP2D6, CYP2C19, CYP2C9 and CYP2A6) are involved in the O-demethylation of formoterol.

Route of elimination

Following inhalation of a 12 mcg or 24 mcg dose by 16 patients with asthma, about 10% and 15%-18% of the total dose was excreted in the urine as unchanged formoterol and direct conjugates of formoterol, respectively.

Half life

10 hours

Clearance
  • Renal cl=150 mL/min [Healty subjects receiving oral administration of 80 mcg]
Toxicity

An overdosage is likely to lead to effects that are typical of ß2-adrenergic stimulants: nausea, vomiting, headache, tremor, somnolence, palpitations, tachycardia, ventricular arrhythmias, metabolic acidosis, hypokalemia, hyperglycemia.

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

Interactions

Drug Interactions
DrugInteraction
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Formoterol.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of hypokalemia can be increased when 3-isobutyl-1-methyl-7H-xanthine is combined with Formoterol.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Formoterol.
6-O-benzylguanineThe risk or severity of hypokalemia can be increased when 6-O-benzylguanine is combined with Formoterol.
7-DeazaguanineThe risk or severity of hypokalemia can be increased when 7-Deazaguanine is combined with Formoterol.
7,9-DimethylguanineThe risk or severity of hypokalemia can be increased when 7,9-Dimethylguanine is combined with Formoterol.
8-azaguanineThe risk or severity of hypokalemia can be increased when 8-azaguanine is combined with Formoterol.
8-chlorotheophyllineThe risk or severity of hypokalemia can be increased when 8-chlorotheophylline is combined with Formoterol.
9-DeazaguanineThe risk or severity of hypokalemia can be increased when 9-Deazaguanine is combined with Formoterol.
9-MethylguanineThe risk or severity of hypokalemia can be increased when 9-Methylguanine is combined with Formoterol.
Food Interactions
Not Available

References

Synthesis Reference

Jan W. Trofast, Edib Jakupovic, Katarina L. Mansson, "Process for preparing formoterol and related compounds." U.S. Patent US5434304, issued August, 1992.

US5434304
General References
  1. Bartow RA, Brogden RN: Formoterol. An update of its pharmacological properties and therapeutic efficacy in the management of asthma. Drugs. 1998 Feb;55(2):303-22. [PubMed:9506248]
  2. Cheer SM, Scott LJ: Formoterol: a review of its use in chronic obstructive pulmonary disease. Am J Respir Med. 2002;1(4):285-300. [PubMed:14720051]
  3. Steiropoulos P, Tzouvelekis A, Bouros D: Formoterol in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(2):205-15. [PubMed:18686730]
  4. Faulds D, Hollingshead LM, Goa KL: Formoterol. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Drugs. 1991 Jul;42(1):115-37. [PubMed:1718682]
  5. Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [PubMed:17594727]
External Links
Human Metabolome Database
HMDB0015118
KEGG Compound
C07805
PubChem Compound
3410
PubChem Substance
46507099
ChemSpider
3292
BindingDB
86453
ChEBI
63082
ChEMBL
CHEMBL1256786
Therapeutic Targets Database
DAP000247
PharmGKB
PA134687907
IUPHAR
3465
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Formoterol
ATC Codes
R03AK11 — Formoterol and fluticasoneR03AK07 — Formoterol and budesonideR03AL05 — Formoterol and aclidinium bromideR03AK08 — Formoterol and beclometasoneR03AK09 — Formoterol and mometasoneR03AC13 — Formoterol
AHFS Codes
  • 12:12.08.12 — Selective Beta 2-adrenergic Agonists
FDA label
Download (1.48 MB)
MSDS
Download (36.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentAsthma Bronchial5
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
1CompletedTreatmentHealthy Volunteers2
1, 2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedPreventionAcute Respiratory Distress Syndrome (ARDS)1
2CompletedTreatmentAirway Obstruction / Asthma Bronchial1
2CompletedTreatmentAllogeneic Stem Cell Transplantation / Obliterative Bronchiolitis1
2CompletedTreatmentAsthma Bronchial11
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)20
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Chronic Obstructive Pulmonary Disease - COPD1
2CompletedTreatmentExercised Induced Asthma1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentMild Persistent Asthma1
2CompletedTreatmentObstructive Airway Disease1
2CompletedTreatmentPulmonary Disease, Chronic Obstructive2
2CompletedTreatmentStable Asthma1
2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2Unknown StatusTreatmentAsthma Bronchial1
2WithdrawnTreatmentAsthma Bronchial1
2WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedTreatmentAllergies1
2, 3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Lung Diseases, Obstructive / Pulmonary Disease, Chronic Obstructive1
2, 3RecruitingDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedNot AvailableAsthma Bronchial1
3CompletedTreatmentAsthma Bronchial40
3CompletedTreatmentBronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
3CompletedTreatmentCOPD Patients1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)23
3CompletedTreatmentMild or Moderate Asthma1
3CompletedTreatmentPulmonary Disease, Chronic Obstructive6
3RecruitingTreatmentAsthma Bronchial2
3RecruitingTreatmentAsthma Bronchial / Bioequivalence1
3RecruitingTreatmentAsthma, Allergic1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3RecruitingTreatmentSmoking1
3Unknown StatusTreatmentEmphysema / Poor Sleeping Quality1
3Unknown StatusTreatmentPulmonary Disease, Chronic Obstructive1
3WithdrawnPreventionExercise-Induced Bronchoconstriction (EIB)1
4Active Not RecruitingTreatmentPulmonary Disease, Chronic Obstructive2
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2
4CompletedTreatmentAcute Bronchial Obstruction, Asthma1
4CompletedTreatmentAsthma Bronchial10
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)12
4CompletedTreatmentPersistent Asthma1
4CompletedTreatmentPulmonary Disease, Chronic Obstructive3
4Not Yet RecruitingOtherPulmonary Disease, Chronic Obstructive1
4RecruitingNot AvailableAsthma Bronchial1
4RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentBronchial Asthma1
4RecruitingTreatmentBronchiectasis / Chronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentPulmonary Disease,Chronic Obstructive1
4RecruitingTreatmentSevere IgE-mediated Asthma1
4TerminatedTreatmentAsthma Bronchial1
4TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4TerminatedTreatmentExercised Induced Asthma1
4TerminatedTreatmentSafety of Long Acting Beta Agnoists1
4Unknown StatusDiagnosticChronic Obstructive Pulmonary Disease (COPD) / Emphysema / Small Airway Disease1
4Unknown StatusTreatmentBronchial Asthma1
4WithdrawnTreatmentAsthma Bronchial1
4WithdrawnTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableCompletedNot AvailableAsthma Bronchial4
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailablePerception of Physicians & Patients of AMD1
Not AvailableCompletedNot AvailablePulmonary Disease, Chronic Obstructive2
Not AvailableCompletedDiagnosticAsthma Bronchial1
Not AvailableCompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentAsthma Bronchial1
Not AvailableCompletedTreatmentDiabetes, Diabetes Mellitus Type 11
Not AvailableNot Yet RecruitingBasic ScienceHypertrophy / Physical Activity / Physiologic Hypertrophy1
Not AvailableNot Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingNot AvailableAsthma Bronchial1
Not AvailableRecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingPreventionAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Air Pollution1
Not AvailableTerminatedTreatmentAsthma Bronchial1
Not AvailableUnknown StatusNot AvailableAllergic Rhinitis (AR) / Asthma Bronchial1
Not AvailableUnknown StatusTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease1
Not AvailableUnknown StatusTreatmentAsthma Bronchial1

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
  • Dey pharma lp
Packagers
  • AstraZeneca Inc.
  • Dey Pharma LP
  • Medisca Inc.
  • Novartis AG
  • Physicians Total Care Inc.
  • Schering Corp.
Dosage forms
FormRouteStrength
Powder, meteredRespiratory (inhalation)
CapsuleRespiratory (inhalation)12 ug/1
CapsuleRespiratory (inhalation)12 mcg
PowderRespiratory (inhalation)12 mcg
PowderRespiratory (inhalation)6 mcg
SolutionRespiratory (inhalation)20 ug/2mL
AerosolRespiratory (inhalation)
PowderRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
Prices
Unit descriptionCostUnit
Formoterol fumarate powder1346.4USD g
Foradil Aerolizer 60 12 mcg capsule Box170.72USD box
Foradil aerolizer 12 mcg cap2.83USD each
Foradil 12 mcg Capsule0.88USD capsule
Oxeze Turbuhaler 12 mcg/dose Metered Inhalation Powder0.82USD dose
Oxeze Turbuhaler 6 mcg/dose Metered Inhalation Powder0.61USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6182655No2001-02-062016-12-05Us
US6887459No2005-05-032020-11-28Us
US6488027No2002-12-032019-03-08Us
US6814953No2004-11-092021-06-22Us
US7348362No2008-03-252021-06-22Us
US7462645No2008-12-092021-06-22Us
US6667344No2003-12-232021-06-22Us
US7759328Yes2010-07-202023-07-29Us
US7897646Yes2011-03-012019-03-09Us
US8143239Yes2012-03-272023-07-29Us
US8461211Yes2013-06-112019-03-09Us
US8575137Yes2013-11-052023-07-29Us
US6123924No2000-09-262017-09-26Us
US7967011Yes2011-06-282022-02-11Us
US8616196Yes2013-12-312029-10-07Us
US8387615Yes2013-03-052025-05-10Us
US7587988Yes2009-09-152026-10-10Us
US7367333Yes2008-05-062019-05-11Us
US8528545Yes2013-09-102029-04-16Us
US8875699Yes2014-11-042025-05-10Us
US8623922No2014-01-072021-06-22Us
US6068832No2000-05-302017-08-27Us
US7067502No2006-06-272020-05-21Us
US7566705No2009-07-282020-05-21Us
US9463161No2016-10-112030-05-28Us
US9415009No2016-08-162030-05-28Us
US8808713No2014-08-192030-05-28Us
US8324266No2012-12-042030-05-28Us
US8703806No2014-04-222030-05-28Us
US8815258No2014-08-262031-03-17Us
US9730890No2017-08-152021-06-22Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySlightly (as fumarate salt)Not Available
logP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0416 mg/mLALOGPS
logP1.91ALOGPS
logP1.06ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.61ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.82 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.87 m3·mol-1ChemAxon
Polarizability36.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8991
Blood Brain Barrier-0.8026
Caco-2 permeable-0.6916
P-glycoprotein substrateSubstrate0.747
P-glycoprotein inhibitor INon-inhibitor0.8773
P-glycoprotein inhibitor IINon-inhibitor0.8561
Renal organic cation transporterNon-inhibitor0.8818
CYP450 2C9 substrateNon-substrate0.714
CYP450 2D6 substrateNon-substrate0.7086
CYP450 3A4 substrateSubstrate0.5556
CYP450 1A2 substrateNon-inhibitor0.6609
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8757
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8442
Ames testNon AMES toxic0.7517
CarcinogenicityNon-carcinogens0.8704
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.4047 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9611
hERG inhibition (predictor II)Non-inhibitor0.6602
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Phenoxy compounds / Methoxybenzenes / Anisoles / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds
show 5 more
Substituents
Amphetamine or derivatives / Phenylpropane / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines, secondary alcohol, phenols, formamides, secondary amino compound (CHEBI:63082)

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. Handley DA, Senanayake CH, Dutczak W, Benovic JL, Walle T, Penn RB, Wilkinson HS, Tanoury GJ, Andersson RG, Johansson F, Morley J: Biological actions of formoterol isomers. Pulm Pharmacol Ther. 2002;15(2):135-45. [PubMed:12090787]
  2. Scola AM, Chong LK, Suvarna SK, Chess-Williams R, Peachell PT: Desensitisation of mast cell beta2-adrenoceptor-mediated responses by salmeterol and formoterol. Br J Pharmacol. 2004 Jan;141(1):163-71. Epub 2003 Dec 8. [PubMed:14662724]
  3. Ryall JG, Sillence MN, Lynch GS: Systemic administration of beta2-adrenoceptor agonists, formoterol and salmeterol, elicit skeletal muscle hypertrophy in rats at micromolar doses. Br J Pharmacol. 2006 Mar;147(6):587-95. [PubMed:16432501]
  4. Lofdahl CG, Svedmyr N: Formoterol fumarate, a new beta 2-adrenoceptor agonist. Acute studies of selectivity and duration of effect after inhaled and oral administration. Allergy. 1989 May;44(4):264-71. [PubMed:2544117]
  5. Kompa AR, Molenaar P, Summers RJ: Beta-adrenoceptor regulation and functional responses in the guinea-pig following chronic administration of the long-acting beta 2-adrenoceptor agonist formoterol. Naunyn Schmiedebergs Arch Pharmacol. 1995 Jun;351(6):576-88. [PubMed:7675115]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Bartow RA, Brogden RN: Formoterol. An update of its pharmacological properties and therapeutic efficacy in the management of asthma. Drugs. 1998 Feb;55(2):303-22. [PubMed:9506248]
  8. Cheer SM, Scott LJ: Formoterol: a review of its use in chronic obstructive pulmonary disease. Am J Respir Med. 2002;1(4):285-300. [PubMed:14720051]
  9. Steiropoulos P, Tzouvelekis A, Bouros D: Formoterol in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(2):205-15. [PubMed:18686730]
  10. Faulds D, Hollingshead LM, Goa KL: Formoterol. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Drugs. 1991 Jul;42(1):115-37. [PubMed:1718682]
  11. Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [PubMed:17594727]
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
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Formoterol FDA [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]
  3. Formoterol FDA Label [File]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 13:19