Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0131)
Drug Name
Arformoterol
Synonyms
Arformoterol; Arformoterol (INN); Arformoterol [INN]; Arformoterol tartrate; Atimos; Brovana; Formoterol [USAN:INN:BAN]; eformoterol; (-)-Formoterol; (R,R)-Formoterol; 67346-49-0; CHEBI:408174; CHEMBL1363; F91H02EBWT; HSDB 7287; N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide; N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide; UNII-F91H02EBWT
Indication Chronic obstructive pulmonary disease [ICD11: CA22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 344.4 Topological Polar Surface Area 90.8
Heavy Atom Count 25 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3083544
PubChem SID
7979300 ; 9471432 ; 14827391 ; 14900508 ; 36413919 ; 46506392 ; 48416036 ; 50940892 ; 51091794 ; 57355509 ; 85599207 ; 103450411 ; 104039882 ; 111687869 ; 126685257 ; 135230453 ; 136046712 ; 137001399 ; 142226212 ; 152109087 ; 160964600 ; 162201740 ; 163414832 ; 163686492 ; 175266951 ; 175269513 ; 179150479 ; 185998767 ; 187051782 ; 210281489 ; 223553207 ; 223678424 ; 224468537 ; 226396278 ; 241132564 ; 252425627
ChEBI ID
CHEBI:408174
CAS Number
67346-49-0
TTD Drug ID
D0D1DI
Formula
C19H24N2O4
Canonical SMILES
CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O
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)/t13-,19+/m1/s1
InChIKey
BPZSYCZIITTYBL-YJYMSZOUSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Formoterol beta-D-glucuronide DM005380
71316866
Conjugation - Glucuronidation 1 [3] , [4]
O-Desmethylarformoterol DM005381 N. A. Oxidation - O-dealkylation 1 [3] , [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013472 Arformoterol Formoterol beta-D-glucuronide Conjugation - Glucuronidation Unclear [3], [4]
MR013473 Arformoterol O-Desmethylarformoterol Oxidation - O-dealkylation CYP2C19 ... [3], [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Arformoterol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 A simplified procedure for the analysis of formoterol in human urine by liquid chromatography-electrospray tandem mass spectrometry: application to the characterization of the metabolic profile and stability of formoterol in urine
4 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.
5 Current pharmacogenomic recommendations in chronic respiratory diseases: Is there a biomarker ready for clinical implementation?

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