Arformoterol (CHEM022274)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:26:29 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022274
Identification
Common NameArformoterol
ClassSmall Molecule
DescriptionArformoterol is a bronchodilator. It works by relaxing muscles in the airways to improve breathing. Arformoterol inhalation is used to prevent bronchoconstriction in people with chronic obstructive pulmonary disease, including chronic bronchitis and emphysema. The use of arformoterol is pending revision due to safety concerns in regards to an increased risk of severe exacerbation of asthma symptoms, leading to hospitalization as well as death in some patients using long acting beta agonists for the treatment of asthma.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-FormoterolChEBI
(R,R)-FormoterolChEBI
3-Formylamino-4-hydroxy-alpha-(N-1-methyl-2-p-methoxyphenethylaminomethyl)benzyl alcohol.hemifumarateHMDB
OxisHMDB
Formoterol fumarateHMDB
BD 40aHMDB
ForadilHMDB
Formoterol, ((r*,r*)-(+-))-isomerHMDB
EformoterolHMDB
FormoterolHMDB
Formoterol fumarate, ((r*,r*)-(+-))-isomerHMDB
Chemical FormulaC19H24N2O4
Average Molecular Mass344.405 g/mol
Monoisotopic Mass344.174 g/mol
CAS Registry Number67346-49-0
IUPAC NameN-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide
Traditional Namearformoterol
SMILESCOC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1
InChI IdentifierInChI=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)/t13-,19+/m1/s1
InChI KeyBPZSYCZIITTYBL-YJYMSZOUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Anilide
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • N-arylamide
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxamide group
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Organic oxide
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
  • N-[2-hydroxy-5-(1-hydroxy-2-\{[1-(4-methoxyphenyl)propan-2-yl]amino\}ethyl)phenyl]formamide (CHEBI:408174 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.87 m³·mol⁻¹ChemAxon
Polarizability36.56 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-2902000000-10d83ebb89a446028d15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-1290400000-a5f812e6f46ebe2c4573Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0119000000-960431f56a40133b8573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0937000000-93717c858174f9fabf66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-d7f4b9eb1c7882357173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-4209000000-f9910c5b8f497127e7caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fu-3619000000-7dd84dcd46e229246839Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9400000000-58f5ee81bd6c210528d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0059000000-c0053d7ff48e5b7bf21eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bb-0797000000-ccdaa7ef72717418b1b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022c-1911000000-a90ad156589941d202e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0039000000-690e9c11e66c66a1a005Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-3795000000-80c4a6628c8460481d11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0017-5391000000-9e5db81cdfc6dd49e8eaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01274
HMDB IDHMDB0015399
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkArformoterol
Chemspider ID2340731
ChEBI ID408174
PubChem Compound ID3083544
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83.
2. Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78.
3. Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7.
4. Donohue JF, Hanania NA, Sciarappa KA, Goodwin E, Grogan DR, Baumgartner RA, Hanrahan JP: Arformoterol and salmeterol in the treatment of chronic obstructive pulmonary disease: a one year evaluation of safety and tolerance. Ther Adv Respir Dis. 2008 Apr;2(2):37-48. doi: 10.1177/1753465808089455.
5. Panettieri RA Jr, MacIntyre N, Sims M, Kerwin E, Fogarty C, Noonan M, Claus R, Andrews WT: Comparison of the efficacy and safety of arformoterol 15 microg twice daily and arformoterol 30 microg once daily in COPD: a single-dose, multicenter, randomized, modified-blind, two-way crossover study. Clin Ther. 2009 Aug;31(8):1716-23. doi: 10.1016/j.clinthera.2009.08.012.
6. Hanania NA, Donohue JF, Nelson H, Sciarappa K, Goodwin E, Baumgartner RA, Hanrahan JP: The safety and efficacy of arformoterol and formoterol in COPD. COPD. 2010 Feb;7(1):17-31. doi: 10.3109/15412550903499498.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15324892
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18990965
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20214460
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20406080