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

General Information of Drug (ID: DR1088)
Drug Name
Midodrine
Prodrug Info Midodrine is the prodrug of Desglymidodrine
Synonyms
Midodrin; Midodrina; Midodrina [INN-Spanish]; Midodrine [INN:BAN]; Midodrinum; Midodrinum [INN-Latin]; ProAmatine; ST-1085; St 1085; midodrine; (RS)-N'-(beta-Hydroxy-2,5-dimethoxy-phenethyl)glycinamid; 1-(2',5'-Dimethoxyphenyl)-2-glycinamidoethanol; 2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamid; 2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethylacetamide; 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide; 42794-76-3; CHEBI:6933; DL-N1-(beta-Hydroxy-2,5-dimethoxyphenethyl)glycinamid; EINECS 255-945-3
Indication Orthostatic hypotension [ICD11: BA21] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 254.28 Topological Polar Surface Area 93.8
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4195
PubChem SID
10092 ; 7433691 ; 8152622 ; 11336130 ; 11361369 ; 11364535 ; 11367097 ; 11369659 ; 11372749 ; 11373902 ; 11377821 ; 11462341 ; 11466219 ; 11467339 ; 11485126 ; 11485798 ; 11489361 ; 11491400 ; 11492007 ; 11495455 ; 14847816 ; 29223300 ; 46507373 ; 47365278 ; 47365279 ; 47662374 ; 47736573 ; 47810835 ; 48035214 ; 48259327 ; 48416280 ; 49698958 ; 50064787 ; 50122851 ; 50122852 ; 50949507 ; 56464179 ; 57322186 ; 85788446 ; 96024908 ; 104305704 ; 124963568 ; 125684389 ; 128965708 ; 134222029 ; 134337543 ; 135002277 ; 137240087 ; 137248546 ; 142173049
ChEBI ID
ChEBI:6933
CAS Number
133163-28-7
TTD Drug ID
D02XJY
Formula
C12H18N2O4
Canonical SMILES
COC1=CC(=C(C=C1)OC)C(CNC(=O)CN)O
InChI
1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)
InChIKey
PTKSEFOSCHHMPD-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
Desglymidodrine DM004422
43260
Unclear 1 [2]
Midodrine Metabolite M-2 DM004423
18627921
Oxidation - 5'-O-demethylation 2 [2]
Midodrine Metabolite M-5 DM004426
12216540
Unclear 2 [2]
Midodrine Metabolite M-4 DM004425
3044298
Unclear 3 [2]
Midodrine Metabolite M-6 DM004424
12216546
Unclear 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004748 Midodrine Desglymidodrine Unclear PES [2]
MR004749 Desglymidodrine Midodrine Metabolite M-2 Oxidation - 5'-O-demethylation CYP2D6 ... [2]
MR004752 Desglymidodrine Midodrine Metabolite M-5 Unclear Unclear [2]
MR004750 Midodrine Metabolite M-2 Midodrine Metabolite M-6 Unclear Unclear [2]
MR004751 Midodrine Metabolite M-2 Midodrine Metabolite M-4 Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Midodrine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The in vitro metabolism of desglymidodrine, an active metabolite of prodrug midodrine by human liver microsomes
3 Akathisia with combined use of midodrine and promethazine. JAMA. 2006 May 3;295(17):2000-1. Letter

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