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

General Information of Drug (ID: DR0744)
Drug Name
Formoterol
Synonyms
Foradile; Formoterol (INN); Oxeze Turbuhaler; Oxeze Turbuhaler Foradil; Oxeze/Oxis; Oxis (TN); 2'-hydroxy-5'-{1-hydroxy-2-[(p-methoxy-alpha-methylphenethyl)amino]ethyl}formanilide; CHEBI:63082; N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl)propan-2-ylamino]ethyl]phenyl]formamide; FORMOTEROL FUMARATE; n-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide
Indication Asthma [ICD11: CA23] 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
3410
PubChem SID
10007 ; 5643479 ; 8152174 ; 14875897 ; 29222544 ; 46507099 ; 50125837 ; 50940891 ; 53790377 ; 57321784 ; 85209082 ; 92712339 ; 96024684 ; 103837996 ; 104303431 ; 117625425 ; 125564207 ; 126625648 ; 126656778 ; 126670908 ; 127551521 ; 134337561 ; 135610485 ; 136352502 ; 137070085 ; 142452394 ; 144224272 ; 152100598 ; 160964320 ; 162178864 ; 163329494 ; 176251370 ; 178100459 ; 179148573 ; 196111556 ; 198992021 ; 206246320 ; 221672992 ; 223400949 ; 223680169 ; 223781951 ; 226683973 ; 240785438
ChEBI ID
CHEBI:63082
CAS Number
73573-87-2
TTD Drug ID
D04KJO
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)
InChIKey
BPZSYCZIITTYBL-UHFFFAOYSA-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 deformylated metabolite DM002058
22642289
Unclear 1 [3]
Formoterol glucuronide metabolite 1 DM002060
135390707
Conjugation - O-Glucuronidation 1 [3] , [2]
Formoterol glucuronide metabolite 2 DM002061 N. A. Conjugation - O-Glucuronidation 1 [3] , [2]
Formoterol sulfate conjugate metabolite DM002062
92002910
Conjugation - Sulfation 1 [3]
O-demethylated formoterol DM002055
13073989
Oxidation - O-demethylation 1 [3] , [2]
Deformylated formoterol metabolite sulfate conjugate metabolite DM002059 N. A. Conjugation - Sulfation 2 [3]
O-demethylated formoterol glucuronide metabolite 1 DM002057 N. A. Unclear 2 [4] , [2]
O-demethylated formoterol glucuronide metabolite 2 DM002056 N. A. Unclear 2 [4] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002944 Formoterol O-demethylated formoterol Oxidation - O-demethylation CYP2D6 ... [3], [2]
MR002945 Formoterol Formoterol deformylated metabolite Unclear Unclear [3]
MR002946 Formoterol Formoterol glucuronide metabolite 1 Conjugation - O-Glucuronidation UGT1A1 ... [3], [2]
MR002947 Formoterol Formoterol glucuronide metabolite 2 Conjugation - O-Glucuronidation UGT1A1 ... [3], [2]
MR002948 Formoterol Formoterol sulfate conjugate metabolite Conjugation - Sulfation Unclear [3]
MR002943 Formoterol deformylated metabolite Deformylated formoterol metabolite sulfate conjugate metabolite Conjugation - Sulfation Unclear [3]
MR002941 O-demethylated formoterol O-demethylated formoterol glucuronide metabolite 2 Unclear UGT1A1 ... [4], [2]
MR002942 O-demethylated formoterol O-demethylated formoterol glucuronide metabolite 1 Unclear UGT1A1 ... [4], [2]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_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]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 8  DME(s)
References
1 Formoterol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA Approved Drug Products: Perforomist? inhalation solution
3 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.
4 DrugBank : Formoterol

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