Formoterol

Identification

Summary

Formoterol is an inhaled long-acting beta2-adrenergic receptor agonist used as a bronchodilator in the management of asthma and COPD.

Brand Names
Bevespi, Breyna, Breztri, Duaklir, Duaklir Genuair, Dulera, Foradil, Oxeze, Perforomist, Symbicort, Zenhale
Generic Name
Formoterol
DrugBank Accession Number
DB00983
Background

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 product 10,16 and in several formulations in combination with both inhaled corticosteroids 13,15 and long-acting muscarinic antagonists.12,11

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 344.4049
Monoisotopic: 344.173607266
Chemical Formula
C19H24N2O4
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

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAsthmaCombination Product in combination with: Budesonide (DB01222)•••••••••••••••••••
Used in combination to manageAsthmaCombination Product in combination with: Mometasone furoate (DB14512)•••••••••••••••••••
Management ofAsthma••••••••••••••••••
Used in combination to manageBronchial asthmaCombination Product in combination with: Budesonide (DB01222)••••••••••••••••••••••
Management ofBronchoconstriction••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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
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

Hover over products below to view reaction partners

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

Adverse Effects
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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

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
AbataceptThe metabolism of Formoterol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Formoterol can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Formoterol.
AcebutololThe therapeutic efficacy of Formoterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Formoterol is combined with Aceclofenac.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Formoterol fumarateW34SHF8J2K183814-30-4RATSWNOMCHFQGJ-AYJOUMQSSA-N
International/Other Brands
Foradil / Oxis Turbuhaler
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ForadilCapsule12 ug/1Respiratory (inhalation)Merck Sharp & Dohme B.V.2001-02-162017-01-31US flag
ForadilCapsule12 ug/1Respiratory (inhalation)Physicians Total Care, Inc.2004-05-28Not applicableUS flag
ForadilCapsule12 ug/1Respiratory (inhalation)Merck Sharp & Dohme B.V.2001-02-162017-01-31US flag
Foradil Dry Powder Capsules for InhalationCapsule12 mcgRespiratory (inhalation)Novartis1997-07-082023-01-20Canada flag
Oxeze TurbuhalerPowder6 mcg / actRespiratory (inhalation)Astrazeneca Ab1998-03-12Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Formoterol fumarateSolution20 ug/2mLRespiratory (inhalation)Northstar RxLLC2024-07-01Not applicableUS flag
Formoterol FumarateSolution20 ug/2mLRespiratory (inhalation)Alembic Pharmaceuticals Limited2021-11-22Not applicableUS flag
Formoterol FumarateSolution0.02 mg/2mLRespiratory (inhalation)Aucta Pharmaceuticals, Inc.2022-12-15Not applicableUS flag
Formoterol FumarateSolution20 ug/2mLRespiratory (inhalation)Mylan Pharmaceuticals Inc.2021-06-22Not applicableUS flag
Formoterol FumarateSolution20 ug/2mLRespiratory (inhalation)Rhodes Pharmaceuticals L.P.2023-11-15Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ABRIFFFormoterol fumarate (5 mcg) + Fluticasone propionate (125 mcg)Aerosol; SuspensionRespiratory (inhalation)Mundipharma Pharmaceuticals S.R.L.2014-07-08Not applicableItaly flag
ABRIFFFormoterol fumarate (10 mcg) + Fluticasone propionate (250 mcg)Aerosol; SuspensionRespiratory (inhalation)Mundipharma Pharmaceuticals S.R.L.2014-07-08Not applicableItaly flag
ABRIFFFormoterol fumarate (5 mcg) + Fluticasone propionate (50 mcg)Aerosol; SuspensionRespiratory (inhalation)Mundipharma Pharmaceuticals S.R.L.2014-07-08Not applicableItaly flag
ABRIFFFormoterol fumarate (5 mcg) + Fluticasone propionate (125 mcg)Aerosol; SuspensionRespiratory (inhalation)Mundipharma Pharmaceuticals S.R.L.2018-09-182021-02-01Italy flag
ABRIFFFormoterol fumarate (5 mcg) + Fluticasone propionate (125 mcg)Aerosol; SuspensionRespiratory (inhalation)Mundipharma Pharmaceuticals S.R.L.2018-09-182021-02-01Italy flag

Categories

ATC Codes
R03AL09 — Formoterol, glycopyrronium bromide and beclometasoneR03AL05 — Formoterol and aclidinium bromideR03AK09 — Formoterol and mometasoneR03AL10 — Formoterol and tiotropium bromideR03CC15 — FormoterolR03AL11 — Formoterol, glycopyrronium bromide and budesonideR03AL07 — Formoterol and glycopyrronium bromideR03AK08 — Formoterol and beclometasoneR03AC13 — FormoterolR03AK07 — Formoterol and budesonideR03AK11 — Formoterol and fluticasone
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Amphetamine or derivatives / Anisole / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines, secondary alcohol, phenols, formamides, secondary amino compound (CHEBI:63082)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5ZZ84GCW8B
CAS number
73573-87-2
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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]
Human Metabolome Database
HMDB0015118
KEGG Drug
D07990
KEGG Compound
C07805
PubChem Compound
3410
PubChem Substance
46507099
ChemSpider
3292
BindingDB
86453
RxNav
25255
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
FDA label
Download (1.48 MB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)2somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAsthma7somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableChronic Obstructive (MeSH) / Lung Disorder / Retrospective Studies1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)5somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableHealthy Volunteers (HV)1somestatusstop reasonjust information to hide

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; suspensionRespiratory (inhalation)
PowderRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)12 MCG
Aerosol, meteredRespiratory (inhalation)6 MCG
SolutionRespiratory (inhalation)12 mcg
GasRespiratory (inhalation)9.83 µg
GasRespiratory (inhalation)12 MIKROGRAMM
GasRespiratory (inhalation)12 UG
Aerosol, meteredRespiratory (inhalation)0.012 mg/inhalation
Aerosol, meteredRespiratory (inhalation)
PowderRespiratory (inhalation)
SolutionRespiratory (inhalation)
PowderBuccal0.012 mg
CapsuleRespiratory (inhalation)12 UG
Powder, meteredRespiratory (inhalation)343 mcg
Powder, meteredRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
Aerosol; suspensionRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)12 mcg
CapsuleRespiratory (inhalation)
Capsule; powderRespiratory (inhalation)
SuspensionBuccal
GasRespiratory (inhalation)
SuspensionRespiratory (inhalation)
Spray, suspensionRespiratory (inhalation)
Aerosol, sprayRespiratory (inhalation)
SuspensionOral; Respiratory (inhalation)
Aerosol; suspensionRespiratory (inhalation)12 MCG
CapsuleRespiratory (inhalation)12 ug/1
Capsule, coatedRespiratory (inhalation)0.0012 mg
PowderRespiratory (inhalation)12 mcg
Powder, meteredRespiratory (inhalation)12 mcg/capsule
CapsuleRespiratory (inhalation)12 mcg
CapsuleRespiratory (inhalation)12 µg
GasRespiratory (inhalation)12 µg
Capsule, coatedRespiratory (inhalation)0.012 mg
SolutionRespiratory (inhalation)12 Mikrogramm
Aerosol, powderRespiratory (inhalation)12 UG
Aerosol, powderRespiratory (inhalation)6 UG
SolutionRespiratory (inhalation)0.02 mg/2mL
Kit; solutionRespiratory (inhalation)20 ug/2mL
TabletOral10 cg
CapsuleOral12 mcg
Powder, meteredRespiratory (inhalation)6 MCG
Powder, meteredRespiratory (inhalation)12 MICROGRAMMI
Aerosol, powderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)100 mcg
Aerosol, meteredRespiratory (inhalation)0.100 mg
SolutionRespiratory (inhalation)
Capsule, coatedOral
AerosolBuccal
Aerosol, metered; solutionRespiratory (inhalation)
PowderRespiratory (inhalation)12 Mikrogramm
PowderRespiratory (inhalation)12 mcg / act
PowderRespiratory (inhalation)6 mcg / act
Powder, meteredRespiratory (inhalation)4.5 MICROGRAMMI
Powder, meteredRespiratory (inhalation)9 MICROGRAMMI
PowderRespiratory (inhalation)4.5 mcg
Aerosol, powderRespiratory (inhalation)12 µg
Aerosol, powderRespiratory (inhalation)6 µg
SolutionRespiratory (inhalation)20 ug/2mL
AerosolRespiratory (inhalation)
Aerosol, metered; suspensionRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)160 mcg
Aerosol, meteredRespiratory (inhalation)40 mcg
Aerosol, meteredRespiratory (inhalation)80 mcg
SuspensionBuccal; Respiratory (inhalation)
PowderBuccal
Powder, meteredRespiratory (inhalation)160 mcg
Powder, meteredRespiratory (inhalation)80 mcg
CapsuleRespiratory (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)Region
US6182655No2001-02-062016-12-05US flag
US6887459No2005-05-032020-11-28US flag
US6488027No2002-12-032019-03-08US flag
US6814953No2004-11-092021-06-22US flag
US7348362No2008-03-252021-06-22US flag
US7462645No2008-12-092021-06-22US flag
US6667344No2003-12-232021-06-22US flag
US7759328Yes2010-07-202023-07-29US flag
US7897646Yes2011-03-012019-03-09US flag
US8143239Yes2012-03-272023-07-29US flag
US8461211Yes2013-06-112019-03-09US flag
US8575137Yes2013-11-052023-07-29US flag
US6123924No2000-09-262017-09-26US flag
US7967011Yes2011-06-282022-02-11US flag
US8616196Yes2013-12-312029-10-07US flag
US8387615Yes2013-03-052025-05-10US flag
US7587988Yes2009-09-152026-10-10US flag
US7367333Yes2008-05-062019-05-11US flag
US8528545Yes2013-09-102029-04-16US flag
US8875699Yes2014-11-042025-05-10US flag
US8623922No2014-01-072021-06-22US flag
US6068832No2000-05-302017-08-27US flag
US7067502Yes2006-06-272020-11-21US flag
US7566705Yes2009-07-282020-11-21US flag
US7078412No2006-07-182020-07-16US flag
US9056100No2015-06-162020-07-07US flag
US6681768No2004-01-272022-08-07US flag
US8051851No2011-11-082027-04-22US flag
USRE46417No2017-05-302020-09-05US flag
US9333195No2016-05-102020-07-07US flag
US9463161No2016-10-112030-05-28US flag
US9415009No2016-08-162030-05-28US flag
US8808713No2014-08-192030-05-28US flag
US8324266No2012-12-042030-05-28US flag
US8703806No2014-04-222030-05-28US flag
US8815258No2014-08-262031-03-17US flag
US9730890No2017-08-152021-06-22US flag
US10085974No2018-10-022029-03-13US flag
US10034867No2018-07-312020-07-07US flag
US10166247Yes2019-01-012023-07-29US flag
US7750023No2010-07-062020-07-07US flag
US8129405No2012-03-062020-07-07US flag
US10588895No2020-03-172022-01-14US flag
US10716753No2020-07-212030-05-28US flag
US11000517No2021-05-112029-03-13US flag
US11311558Yes2003-07-292023-07-29US flag
US11331442No2018-05-102038-05-10US flag
US11833292No2018-10-052038-10-05US flag

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-MSsplash10-00or-2902000000-10d83ebb89a446028d15
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-0339000000-4770ea45defc3ce5dd7d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-0039000000-580612758f9fa39d013d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0axs-0595000000-98fa7f0601b82bf7bd69
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4m-2291000000-4d74be9d2942b9535015
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1943000000-6ce745c4ba53a4187edb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0293000000-9aa9d932000b1476cd8c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.1723367
predicted
DarkChem Lite v0.1.0
[M-H]-183.3181
predicted
DeepCCS 1.0 (2019)
[M+H]+187.1848367
predicted
DarkChem Lite v0.1.0
[M+H]+186.01819
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.5801367
predicted
DarkChem Lite v0.1.0
[M+Na]+194.83327
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General 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 30-fold greater affinity than it does norepinephrine
Specific Function
adenylate cyclase binding
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. [Article]
  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. [Article]
  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. [Article]
  4. Coleman RA, Johnson M, Nials AT, Vardey CJ: Exosites: their current status, and their relevance to the duration of action of long-acting beta 2-adrenoceptor agonists. Trends Pharmacol Sci. 1996 Sep;17(9):324-30. [Article]
  5. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
  6. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
  7. FDA Approved Drug Products: Foradil® Aerolizer inhalation powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General 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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling. Involved in the regulation of sleep/wake behaviors (PubMed:31473062)
Specific Function
alpha-2A adrenergic receptor binding
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51222.97 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General 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
Specific Function
beta-3 adrenergic receptor binding
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
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
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
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
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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56517.005 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:15472229, PubMed:16595710, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:18719240, PubMed:19545173, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15472229, PubMed:16595710, PubMed:23288867). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens and estrogens (PubMed:15472229, PubMed:16595710, PubMed:18719240, PubMed:23288867). Produces dihydrotestosterone (DHT) diglucuronide from the DHT after two subsequent glucoronidation steps (PubMed:16595710). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
Specific Function
enzyme binding
Gene Name
UGT1A8
Uniprot ID
Q9HAW9
Uniprot Name
UDP-glucuronosyltransferase 1A8
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
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
Specific Function
enzyme binding
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1A9
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
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
Specific Function
glucuronosyltransferase activity
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60720.15 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:7835232). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (testosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Displays glucuronidation activity toward several classes of xenobiotic substrates, including phenolic compounds (eugenol, 4-nitrophenol, 4-hydroxybiphenyl) and phenylpropanoids (naringenin, coumarins) (PubMed:7835232). Catalyzes the glucuronidation of monoterpenoid alcohols such as borneol, menthol and isomenthol, a class of natural compounds used in essential oils (By similarity)
Specific Function
glucuronosyltransferase activity
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15472229, PubMed:18004206, PubMed:18004212, PubMed:18719240, PubMed:19830808, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004206, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol, estrone and estriol (PubMed:15472229, PubMed:18719240, PubMed:23288867). Involved in the glucuronidation of bilirubin, a degradation product occurring in the normal catabolic pathway that breaks down heme in vertebrates (PubMed:17187418, PubMed:18004206, PubMed:19830808, PubMed:24525562). Also catalyzes the glucuronidation the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:18004212, PubMed:20610558)
Specific Function
enzyme binding
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1A1
Molecular Weight
59590.91 Da
References
  1. FDA Approved Drug Products: Perforomist® inhalation solution [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function
antioxidant activity
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
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
Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930)
Specific Function
(R)-carnitine transmembrane transporter activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:10196521, PubMed:10966924, PubMed:12538837, PubMed:17460754, PubMed:20858707). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:10966924). Functions as a Na(+)- and Cl(-)-independent, bidirectional uniporter (PubMed:12538837). Implicated in monoamine neurotransmitters uptake such as dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, histamine, serotonin and tyramine, thereby supporting a role in homeostatic regulation of aminergic neurotransmission in the brain (PubMed:10196521, PubMed:16581093, PubMed:20858707). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with low efficiency (PubMed:17460754). May be involved in the uptake and disposition of cationic compounds by renal clearance from the blood flow (PubMed:10966924). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (Probable). Mediates the transport of polyamine spermidine and putrescine (By similarity). Mediates the bidirectional transport of polyamine agmatine (PubMed:12538837). Also transports guanidine (PubMed:10966924). May also mediate intracellular transport of organic cations, thereby playing a role in amine metabolism and intracellular signaling (By similarity)
Specific Function
monoamine transmembrane transporter activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter that mediates the transport of endogenous and microbial zwitterions and organic cations (PubMed:10215651, PubMed:15107849, PubMed:15795384, PubMed:16729965, PubMed:20601551, PubMed:22206629, PubMed:22569296, PubMed:29530864). Functions as a Na(+)-dependent and pH-dependent high affinity microbial symporter of potent food-derived antioxidant ergothioeine (PubMed:15795384, PubMed:29530864, PubMed:33124720). Transports one sodium ion with one ergothioeine molecule (By similarity). Involved in the absorption of ergothioneine from the luminal/apical side of the small intestine and renal tubular cells, and into non-parenchymal liver cells, thereby contributing to maintain steady-state ergothioneine level in the body (PubMed:20601551). Also mediates the bidirectional transport of acetycholine, although the exact transport mechanism has not been fully identified yet (PubMed:22206629). Most likely exports anti-inflammatory acetylcholine in non-neuronal tissues, thereby contributing to the non-neuronal cholinergic system (PubMed:22206629, PubMed:22569296). Displays a general physiological role linked to better survival by controlling inflammation and oxidative stress, which may be related to ergothioneine and acetycholine transports (PubMed:15795384, PubMed:22206629). May also function as a low-affinity Na(+)-dependent transporter of L-carnitine through the mitochondrial membrane, thereby maintaining intracellular carnitine homeostasis (PubMed:10215651, PubMed:15107849, PubMed:16729965). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (PubMed:35307651)
Specific Function
acetylcholine transmembrane transporter activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General 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 (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function
(R)-carnitine transmembrane transporter activity
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Organic cation/carnitine transporter 2
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 30, 2024 22:47