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

General Information of Drug (ID: DR0889)
Drug Name
Isosorbide mononitrate
Synonyms
Isomonat; Isomonit; Isosorbide 5-mononitrate; Isosorbide 5-nitrate; Isosorbide-5-mononitrate; Iturol; Medocor; Monicor; Monisid; Monizid; Mono Corax; Monoclair; Monodur Durules; Monoket; Monolong; Mononit; Monopront; Monosorbitrate; Monosordil; Monotrate; Multitab; Nitramin; Olicard; Olicardin; Orasorbil; Percorina; Pertil; Promocard; Sigacora; Sorbimon; Titarane; Turimonit; Uniket; Vasdilat; vasotrate; 16051-77-7; ISMN; ISMO; Imdur; Ismox; Corangin; Duride; Edistol; Elantan; Epicordin; Etimonis; ISOSORBIDE MONONITRATE; Imazin; Imodur; Imtrate; Ismexin
Indication Angina pectoris [ICD11: BA40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 191.14 Topological Polar Surface Area 93.7
Heavy Atom Count 13 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
27661
PubChem SID
9916 ; 1996243 ; 3140015 ; 7847696 ; 7979662 ; 8169915 ; 14748507 ; 15171521 ; 34670166 ; 46506594 ; 48416135 ; 49972423 ; 50113025 ; 53801154 ; 57310486 ; 78898435 ; 87325445 ; 87571756 ; 92308037 ; 103408641 ; 104231660 ; 104300601 ; 109658188 ; 115354129 ; 117383795 ; 125311718 ; 126603354 ; 126608841 ; 126616754 ; 126665019 ; 129859949 ; 134338317 ; 134992567 ; 136903837 ; 137003475 ; 142599818 ; 143449442 ; 144075642 ; 144205134 ; 152165118 ; 152250184 ; 160808664 ; 160964356 ; 163087759 ; 163589576 ; 164811402 ; 175266479 ; 175610990 ; 176266501 ; 177748777
ChEBI ID
ChEBI:6062
CAS Number
16051-77-7
TTD Drug ID
D0YS7D
Formula
C6H9NO6
Canonical SMILES
C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O
InChI
1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
InChIKey
YWXYYJSYQOXTPL-SLPGGIOYSA-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
Isosorbide DM001012
12597
Other reaction - Denitrosylation 1 [2]
Isosorbide mononitrate Nitric Oxide DM001010
27661
Unclear 1 [2] , [3]
Isosorbide-5-mononitrate-2-glucuronide DM001011
62991
Conjugation - O-Glucuronidation 1 [2]
Sorbitol DM003091
5780
Other reaction - Denitrosylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001248 Isosorbide mononitrate Isosorbide-5-mononitrate-2-glucuronide Conjugation - O-Glucuronidation Unclear [2]
MR001249 Isosorbide mononitrate Isosorbide Other reaction - Denitrosylation Unclear [2]
MR001250 Isosorbide mononitrate Isosorbide mononitrate Nitric Oxide Unclear ADH5 ... [2], [3]
MR001251 Isosorbide mononitrate Sorbitol Other reaction - Denitrosylation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alcohol dehydrogenase class-III (ADH5) DME0132 Homo sapiens
ADHX_HUMAN
1.1.1.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Glutathione S-transferase mu-1 (GSTM1) DME0308 Homo sapiens
GSTM1_HUMAN
2.5.1.18
[2]
Putative xanthine dehydrogenase molybdenum-binding subunit XdhA (xdhA) DMEN026 Escherichia coli
XDHA_ECOLI
2.7.2.3
[2]
References
1 Isosorbide Mononitrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics of isosorbide mononitrate Am J Cardiol. 1992 Nov 27;70(17):61G-66G. doi: 10.1016/0002-9149(92)90028-w.
3 Isoforms of cytochrome P450 on organic nitrate-derived nitric oxide release in human heart vessels. FEBS Lett. 1999 Jun 11;452(3):165-9.

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