Identification

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

Formoterol is an inhaled beta2-agonist used in the management of COPD and asthma that was first approved for use in the United States in 2001.10 It acts on bronchial smooth muscle to dilate and relax airways, and is administered as a racemic mixture of its active (R;R)- and inactive (S;S)-enantiomers.2 A major clinical advantage of formoterol over other inhaled beta-agonists is its rapid onset of action (2-3 minutes), which is at least as fast as salbutamol, combined with a long duration of action (12 hours) - for this reason, treatment guidelines for asthma recommend its use as both a reliever and maintenance medication.18 It is available as a single-entity product10,16 and in several formulations in combination with both inhaled corticosteroids13,15 and long-acting muscarinic antagonists.12,11

Structure
Thumb
Synonyms
  • 2'-hydroxy-5'-(1-hydroxy-2-((p-methoxy-α-methylphenethyl)amino)ethyl)formanilide
  • 2'-hydroxy-5'-{1-hydroxy-2-[(p-methoxy-α-methylphenethyl)amino]ethyl}formanilide
  • Formoterol
  • 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
Budesonide/formoterol TevaRespiratory (inhalation)Teva Pharma B.V.2014-11-192017-01-31Eu
Budesonide/formoterol TevaRespiratory (inhalation)Teva Pharma B.V.2014-11-192017-01-31Eu
Duaklir GenuairRespiratory (inhalation)Astra Zeneca Ab2014-11-18Not applicableEu
Duaklir GenuairRespiratory (inhalation)Astra Zeneca Ab2014-11-18Not applicableEu
Duaklir GenuairRespiratory (inhalation)Astra Zeneca Ab2014-11-18Not applicableEu
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 InhalationCapsuleRespiratory (inhalation)Novartis1997-07-08Not applicableCanada
Oxeze TurbuhalerPowderRespiratory (inhalation)Astra Zeneca1998-03-12Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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
Budesonide and Formoterol Fumarate DihydrateFormoterol fumarate (4.5 ug/1) + Budesonide (80 ug/1)AerosolRespiratory (inhalation)AstraZeneca Pharmaceuticals LP2020-01-03Not applicableUs
Budesonide and Formoterol Fumarate DihydrateFormoterol fumarate (4.5 ug/1) + Budesonide (160 ug/1)AerosolRespiratory (inhalation)AstraZeneca Pharmaceuticals LP2020-01-03Not applicableUs
Duaklir GenuairFormoterol fumarate (12 mcg) + Aclidinium bromide (400 mcg)Powder, meteredRespiratory (inhalation)Astra Zeneca2015-07-09Not applicableCanada
Duaklir PressairFormoterol fumarate (12 ug/1) + Aclidinium bromide (400 ug/1)Powder, meteredRespiratory (inhalation)Circassia Pharmaceuticals Inc.2019-10-11Not applicableUs
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (50 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2019-08-12Not 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
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (100 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
International/Other Brands
Foradil / 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

Formoterol is indicated in various formulations for the treatment of asthma and COPD. For the treatment of COPD, formoterol is available as a single-entity inhalation solution,10 in combination with the long-acting muscarinic antagonists (LAMAs) aclidinium12 and glycopyrronium,11 and in combination with the corticosteroid budesonide.15 For the treatment of asthma, formoterol is available in combination with mometasone furoate for patients 5 years and older13 and with budesonide for patients 6 years and older.15 Formoterol may also be used on an as-needed basis for prophylaxis against exercise-induced bronchospasm.14

Associated Conditions
Pharmacodynamics

Formoterol works locally in the lungs as a bronchodilator, relaxing smooth muscle and opening up the airways. It possesses both a rapid onset of action (approximately 2-3 minutes)8 and a long duration of action (up to 12 hours).16 The use of long-acting beta-agonists (LABAs), such as formoterol, without concomitant inhaled corticosteroids in asthmatic patients should be avoided, as LABA monotherapy has been associated with an increased risk of asthma-related death.16

Mechanism of action

Formoterol is a relatively selective long-acting agonist of beta2-adrenergic receptors,10,16 although it does carry some degree of activity at beta1 and beta3 receptors.9 Beta2 receptors are found predominantly in bronchial smooth muscle (with a relatively minor amount found in cardiac tissue) whereas beta1 receptors are the predominant adrenergic receptors found in the heart - for this reason, selectivity for beta2 receptors is desirable in the treatment of pulmonary diseases such as COPD and asthma.10 Formoterol has demonstrated an approximately 200-fold greater activity at beta2 receptors over beta1 receptors.10

On a molecular level, activation of beta receptors by agonists like formoterol stimulates intracellular adenylyl cyclase, an enzyme responsible for the conversion of ATP to cyclic AMP (cAMP). The increased levels of cAMP in bronchial smooth muscle tissue result in relaxation of these muscles and subsequent dilation of the airways, as well as inhibition of the release of hypersensitivity mediators (e.g. histamine, leukotrienes) from culprit cells, especially mast cells.10

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
UBeta-1 adrenergic receptor
agonist
Humans
UBeta-3 adrenergic receptor
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The pulmonary bioavailability of formoterol has been estimated to be about 43% of the delivered dose, while the total systemic bioavailability is approximately 60% of the delivered dose (as systemic bioavailability accounts for absorption in the gut).16

Formoterol is rapidly absorbed into plasma following inhalation. In healthy adults, formoterol Tmax ranged from 0.167 to 0.5 hours.13 Following a single dose of 10 mcg, Cmax and AUC were 22 pmol/L and 81 pmol.h/L, respectively. In asthmatic adult patients, Tmax ranged from 0.58 to 1.97 hours.13 Following single-dose administration of 10mcg, Cmax and AUC0-12h were 22 pmol/L and 125 pmol.h/L, respectively; following multiple-dose administration of 10 mcg, Cmax and AUC0-12h were 41 pmol/L and 226 pmol.h/L, respectively. Absorption appears to be proportional to dose across standard dosing ranges.13,10

Volume of distribution
Not Available
Protein binding

Plasma protein binding to serum albumin in vitro is approximately 31%-38% over a plasma concentration range of 5-500 ng/mL - it should be noted, however, that these concentrations are higher than that seen following inhalation.10

Metabolism

Formoterol is metabolized primarily via direct glucuronidation of the parent drug and via O-demethylation of the parent drug followed by glucuronidation.10,7 Minor pathways include sulfate conjugation of the parent drug and deformylation of the parent drug followed by sulfate conjugation, though these minor pathways have not been fully characterized. The major pathway of formoterol metabolism is a direct glucuronidation of the parent drug at its phenolic hydroxyl group, while the second most prominent pathway involves O-demethylation following by glucuronidation at the phenolic hydroxyl group.10,7

In vitro studies of formoterol disposition indicate that O-demethylation of formoterol involves a number of cytochrome P450 isoenzymes (CYP2D6, CYP2C19, CYP2C9, and CYP2A6) and glucuronidation involves a number of UDP-glucuronosyltransferase isoenzymes (UGT1A1, UGT1A8, UGT1A9, UGT2B7, and UGT2B15), though specific roles for individual enzymes have not been elucidated.10

Route of elimination

Elimination differs depending on the route and formulation administered. Following oral administration in 2 healthy subjects, approximately 59-62% and 32-34% of an administered dose was eliminated in the urine and feces, respectively.14 Another study which attempted to mimic inhalation via combined intravenous/oral administration noted approximately 62% of the administered dose in the urine and 24% in the feces.7 Following inhalation in patients with asthma, approximately 10% and 15-18% of the administered dose was excreted in urine as unchanged parent drug and direct formoterol glucuronides, respectively, and corresponding values in patients with COPD were 7% and 6-9%, respectively.14

Half life

The average terminal elimination half-life of formoterol following inhalation is 7-10 hours, depending on the formulation given.10,16,4 The plasma half-life of formoterol has been estimated to be 3.4 hours following oral administration and 1.7-2.3 hours following inhalation.1

Clearance

Renal clearance of formoterol following inhalation is approximately 157 mL/min.10

Toxicity

The oral LD50 in rats is 3130 mg/kg.17

Symptoms of overdose are likely consistent with formoterol's adverse effect profile (i.e. consistent with excessive beta-adrenergic stimulation) and may include angina, hyper or hypotension, tachycardia, arrhythmia, nervousness, headache, tremor, seizures, dry mouth, etc. Patients may experience laboratory abnormalities including hypokalemia, hyperglycemia, and metabolic acidosis.10 Treatment of overdosage should consist of symptomatic and supportive therapy, with a particular focus on cardiac monitoring. Consider the use of a cardioselective beta-adrenergic blocker to oppose excessive adrenergic stimulation if clinically appropriate.10

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.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Formoterol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Formoterol.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Formoterol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Formoterol is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Formoterol is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when Formoterol is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Formoterol is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
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-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when Formoterol is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamine4-Bromo-2,5-dimethoxyphenethylamine may increase the sympathomimetic activities of Formoterol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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. Zhang M, Fawcett JP, Shaw JP: Stereoselective urinary excretion of formoterol and its glucuronide conjugate in human. Br J Clin Pharmacol. 2002 Sep;54(3):246-50. doi: 10.1046/j.1365-2125.2002.01641.x. [PubMed:12236843]
  3. 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]
  4. Tronde A, Gillen M, Borgstrom L, Lotvall J, Ankerst J: Pharmacokinetics of budesonide and formoterol administered via 1 pressurized metered-dose inhaler in patients with asthma and COPD. J Clin Pharmacol. 2008 Nov;48(11):1300-8. doi: 10.1177/0091270008322122. [PubMed:18974284]
  5. 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]
  6. Horvath G, Schmid N, Fragoso MA, Schmid A, Conner GE, Salathe M, Wanner A: Epithelial organic cation transporters ensure pH-dependent drug absorption in the airway. Am J Respir Cell Mol Biol. 2007 Jan;36(1):53-60. doi: 10.1165/rcmb.2006-0230OC. Epub 2006 Aug 17. [PubMed:16917073]
  7. Rosenborg J, Larsson P, Tegner K, Hallstrom G: Mass balance and metabolism of [(3)H]Formoterol in healthy men after combined i.v. and oral administration-mimicking inhalation. Drug Metab Dispos. 1999 Oct;27(10):1104-16. [PubMed:10497135]
  8. Anderson GP: Formoterol: pharmacology, molecular basis of agonism, and mechanism of long duration of a highly potent and selective beta 2-adrenoceptor agonist bronchodilator. Life Sci. 1993;52(26):2145-60. doi: 10.1016/0024-3205(93)90729-m. [PubMed:8099696]
  9. 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]
  10. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
  11. FDA Approved Drug Products: Bevespi Aerosphere inhalation aerosol [Link]
  12. FDA Approved Drug Products: Duaklir® Pressair® inhalation powder [Link]
  13. FDA Approved Drug Products: Dulera® inhalation aerosol [Link]
  14. FDA Approved Drug Products: Foradil® Aerolizer inhalation powder [Link]
  15. FDA Approved Drug Products: Symbicort (budesonide/formoterol fumarate) inhalation aerosol [Link]
  16. Health Canada Product Monograph: Oxeze (formoterol) dry powder inhaler [Link]
  17. CaymanChem: Formoterol MSDS [Link]
  18. Global Initiative for Asthma: 2019 Guidelines Pocket Guide [Link]
External Links
Human Metabolome Database
HMDB0015118
KEGG Drug
D07990
KEGG Compound
C07805
PubChem Compound
3410
PubChem Substance
46507099
ChemSpider
3292
BindingDB
86453
ChEBI
63082
ChEMBL
CHEMBL1256786
Therapeutic Targets Database
DAP000247
PharmGKB
PA134687907
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Formoterol
ATC Codes
R03AL09 — Formoterol, glycopyrronium bromide and beclometasoneR03AL07 — Formoterol and glycopyrronium bromideR03AK08 — Formoterol and beclometasoneR03AC13 — FormoterolR03AK07 — Formoterol and budesonideR03AK11 — Formoterol and fluticasoneR03AL05 — Formoterol and aclidinium bromideR03AK09 — Formoterol and mometasone
AHFS Codes
  • 12:12.08.12 — Selective Beta 2-adrenergic Agonists
FDA label
Download (1.48 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceChronic Obstructive Pulmonary Disease Method Evaluation / COPD Method Evaluation1
1CompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceStudy is Being Conducted in Healthy Volunteers1
1CompletedTreatmentAsthma10
1CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)2
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)7
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentLung Cancers / Precancerous Conditions1
1RecruitingTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
1, 2CompletedTreatmentAsthma1
1, 2CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
1, 2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
1, 2Not Yet RecruitingTreatmentCough Variant Asthma1
2CompletedNot AvailableMild to Moderate Asthma1
2CompletedOtherAsthma1
2CompletedPreventionAcute Respiratory Distress Syndrome (ARDS)1
2CompletedTreatmentAirway Inflammation / Asthma1
2CompletedTreatmentAirway Obstruction / Asthma1
2CompletedTreatmentAllogeneic Stem Cell Transplantation / Obliterative Bronchiolitis1
2CompletedTreatmentAsthma27
2CompletedTreatmentAsthma in Children2
2CompletedTreatmentAsthma / Bronchial Asthma / Chronic Asthma1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)26
2CompletedTreatmentExercised Induced Asthma1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentMild Persistent Asthma1
2CompletedTreatmentObstructive Airway Disease1
2CompletedTreatmentStable Asthma1
2Not Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2SuspendedTreatmentAlzheimer's Disease (AD) / Cognitive Dysfunctions1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2Unknown StatusTreatmentAsthma1
2Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2WithdrawnTreatmentAsthma1
2WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedTreatmentAllergies1
2, 3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Lung Diseases, Obstructive1
2, 3RecruitingDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
2, 3TerminatedTreatmentACOS (Fixed Airflow Obstruction and Elevated Eosinophils)1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)2
3CompletedNot AvailableAsthma2
3CompletedNot AvailableBronchial Asthma1
3CompletedTreatmentAsthma65
3CompletedTreatmentAsthma / Bioequivalence1
3CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentBronchial Asthma5
3CompletedTreatmentBronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
3CompletedTreatmentCOPD Patients1
3CompletedTreatmentChildhood Asthma1
3CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)46
3CompletedTreatmentChronic Obstructive Pulmonary Disorder2
3CompletedTreatmentMild to Moderate Asthma1
3CompletedTreatmentSmoking1
3Enrolling by InvitationTreatmentAsthma, Allergic1
3Enrolling by InvitationTreatmentChronic Obstructive Pulmonary Disease (COPD) / Chronic Respiratory Failure1
3Not Yet RecruitingPreventionAcute Respiratory Failure / Hypoxemia / Pneumonia1
3Not Yet RecruitingTreatmentAsthma3
3RecruitingTreatmentAsthma1
3RecruitingTreatmentBronchiectasis1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)3
3TerminatedTreatmentBronchial Asthma1
3TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentEmphysema / Poor Sleeping Quality1
3WithdrawnPreventionExercise-Induced Bronchospasm1
3WithdrawnTreatmentAsthma in Children1
3WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Active Not RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4Active Not RecruitingTreatmentAsthma / Status Asthmaticus1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2
4CompletedTreatmentAcute Bronchial Obstruction, Asthma1
4CompletedTreatmentAsthma16
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentBronchiectasis1
4CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Pulmonary Emphysema1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)27
4CompletedTreatmentPersistent Asthma1
4Enrolling by InvitationTreatmentBronchiectasis / Chronic Obstructive Pulmonary Disease (COPD)1
4Not Yet RecruitingTreatmentAsthma / Severe Eosinophilic Asthma1
4Not Yet RecruitingTreatmentCough Variant Asthma1
4RecruitingNot AvailableAsthma1
4RecruitingBasic ScienceAsthma1
4RecruitingOtherChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentAirway Inflammation / Asthma1
4RecruitingTreatmentAsthma-chronic obstructive pulmonary disease overlap syndrome / Chronic Obstructive Pulmonary Disease (COPD) / Quality of Life / Small Airway Disease1
4RecruitingTreatmentBronchial Asthma1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD) / Exercise / Lung Function Decreased / Quality of Life1
4RecruitingTreatmentPrimary Central Nervous System Lymphoma (PCNSL)1
4RecruitingTreatmentPulmonary Disease,Chronic Obstructive1
4TerminatedTreatmentAsthma1
4TerminatedTreatmentAsthma Acute1
4TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4TerminatedTreatmentExercised Induced Asthma1
4TerminatedTreatmentSafety of Long Acting Beta Agnoists1
4TerminatedTreatmentSevere IgE-mediated Asthma1
4Unknown StatusNot AvailableAsthma1
4Unknown StatusDiagnosticChronic Obstructive Pulmonary Disease (COPD) / Emphysema / Small Airway Disease1
4Unknown StatusTreatmentAsthma2
4Unknown StatusTreatmentBronchial Asthma1
4WithdrawnTreatmentAsthma1
4WithdrawnTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableActive Not RecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailableAsthma5
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailablePatients Satisfaction1
Not AvailableCompletedNot AvailablePerception of Physicians & Patients of AMD1
Not AvailableCompletedBasic ScienceAsthma1
Not AvailableCompletedDiagnosticAsthma1
Not AvailableCompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease1
Not AvailableCompletedTreatmentAsthma3
Not AvailableCompletedTreatmentBronchiectasis1
Not AvailableCompletedTreatmentType 1 Diabetes Mellitus1
Not AvailableNot Yet RecruitingBasic ScienceHypertrophy / Physical Activity / Physiologic Hypertrophy1
Not AvailableNot Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingNot AvailableAsthma1
Not AvailableRecruitingHealth Services ResearchHealth, Subjective / Hyperreactivity, Bronchial1
Not AvailableRecruitingPreventionAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Air Pollution1
Not AvailableTerminatedTreatmentAsthma1
Not AvailableUnknown StatusNot AvailableAllergic Rhinitis (AR) / Asthma1
Not AvailableUnknown StatusPreventionExacerbation of asthma1
Not AvailableUnknown StatusTreatmentAsthma1

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
Aerosol, meteredRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
CapsuleRespiratory (inhalation)12 ug/1
CapsuleRespiratory (inhalation)
PowderRespiratory (inhalation)
SolutionRespiratory (inhalation)20 ug/2mL
AerosolRespiratory (inhalation)
PowderRespiratory (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
US7067502Yes2006-06-272020-11-21Us
US7566705Yes2009-07-282020-11-21Us
US7078412No2006-07-182020-07-16Us
US9056100No2015-06-162020-07-07Us
US6681768No2004-01-272022-08-07Us
US8051851No2011-11-082027-04-22Us
USRE46417No2017-05-302020-09-05Us
US9333195No2016-05-102020-07-07Us
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
US10085974No2018-10-022029-03-13Us
US10034867No2018-07-312020-07-07Us
US10166247Yes2019-01-012023-07-29Us
US7750023No2010-07-062020-07-07Us
US8129405No2012-03-062020-07-07Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySlightly (as fumarate salt)Foradil FDA Label
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
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. 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. 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]
  3. 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]
  4. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
  5. FDA Approved Drug Products: Foradil® Aerolizer inhalation powder [Link]
Kind
Protein
Organism
Humans
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
Humans
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
Humans
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. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
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. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
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. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
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. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
5. UDP-glucuronosyltransferase 1A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A8
Uniprot ID
Q9HAW9
Uniprot Name
UDP-glucuronosyltransferase 1-8
Molecular Weight
59741.035 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Salomon JJ, Hagos Y, Petzke S, Kuhne A, Gausterer JC, Hosoya K, Ehrhardt C: Beta-2 Adrenergic Agonists Are Substrates and Inhibitors of Human Organic Cation Transporter 1. Mol Pharm. 2015 Aug 3;12(8):2633-41. doi: 10.1021/mp500854e. Epub 2015 Mar 18. [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
  1. Salomon JJ, Hagos Y, Petzke S, Kuhne A, Gausterer JC, Hosoya K, Ehrhardt C: Beta-2 Adrenergic Agonists Are Substrates and Inhibitors of Human Organic Cation Transporter 1. Mol Pharm. 2015 Aug 3;12(8):2633-41. doi: 10.1021/mp500854e. Epub 2015 Mar 18. [PubMed:25751092]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Horvath G, Schmid N, Fragoso MA, Schmid A, Conner GE, Salathe M, Wanner A: Epithelial organic cation transporters ensure pH-dependent drug absorption in the airway. Am J Respir Cell Mol Biol. 2007 Jan;36(1):53-60. doi: 10.1165/rcmb.2006-0230OC. Epub 2006 Aug 17. [PubMed:16917073]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Horvath G, Schmid N, Fragoso MA, Schmid A, Conner GE, Salathe M, Wanner A: Epithelial organic cation transporters ensure pH-dependent drug absorption in the airway. Am J Respir Cell Mol Biol. 2007 Jan;36(1):53-60. doi: 10.1165/rcmb.2006-0230OC. Epub 2006 Aug 17. [PubMed:16917073]

Drug created on June 13, 2005 07:24 / Updated on January 27, 2020 23:58