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

General Information of Drug (ID: DR0888)
Drug Name
Isosorbide dinitrate
Synonyms
Isoket; Isorbid; Isordil; Isordil Tembids; Isotrate; Korodil; Lomilan; Maycor; Myorexon; Nitrosorbid; Nitrosorbide; Nitrosorbon; Resoidan; Rifloc Retard; Rigedal; Sorbangil; Sorbide nitrate; Sorbide, dinitrate; Sorbidilat; Sorbidnitrate; Sorbislo; Sorbitrate; Sorbonit; Sorquad; Tinidil; Vascardin; Vasodilat; Vasorbate; 87-33-2; ISDN; Nosim; Xanyl; Cardio 10; Cardis; Carvanil; Carvasin; Cedocard; Claodical; Cornilat; Coronex; Corosorbide; Difutrat; Dilatrate; Dilatrate-SR; Dinitrosorbide; Emoper; Flindix; Harrical; ISOSORBIDE DINITRATE; Iso-Bid
Indication Anal fissure [ICD11: DB50] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 236.14 Topological Polar Surface Area 129
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
6883
PubChem SID
9659 ; 119630 ; 221635 ; 7847582 ; 7979661 ; 8149394 ; 8154490 ; 10321182 ; 11335611 ; 11360850 ; 11363057 ; 11365619 ; 11368181 ; 11371680 ; 11373568 ; 11376343 ; 11461822 ; 11466742 ; 11467862 ; 11484794 ; 11486584 ; 11488885 ; 11490416 ; 11491840 ; 11493977 ; 14749455 ; 14847315 ; 24881741 ; 26611790 ; 26679697 ; 29225819 ; 46506412 ; 47365129 ; 47365130 ; 48110402 ; 48259172 ; 48259173 ; 48259174 ; 48334428 ; 49699148 ; 49972418 ; 50123513 ; 50123514 ; 53790326 ; 53801192 ; 57260297 ; 57260298 ; 57323779 ; 57651697 ; 60723111
ChEBI ID
ChEBI:6061
CAS Number
87-33-2
TTD Drug ID
D0I1SK
Formula
C6H8N2O8
Canonical SMILES
C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O[N+](=O)[O-]
InChI
1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
InChIKey
MOYKHGMNXAOIAT-JGWLITMVSA-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
Fludarabine DM020055
657237
Unclear 1 [4]
Isosorbide 2-nitrate DM001013
62989
Other reaction - Denitration 1 [5] , [6]
Isosorbide mononitrate Nitric Oxide DM001010
27661
Other reaction - Denitration 1 [5] , [6]
Isosorbide DM001012
12597
Other reaction - Denitration 2 [5] , [6]
Isosorbide-5-mononitrate-2-glucuronide DM001011
62991
Conjugation - Glucuronidation 2 [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001245 Isosorbide dinitrate Isosorbide 5-mononitrate Other reaction - Denitration Unclear [5], [6]
MR001246 Isosorbide dinitrate Isosorbide 2-nitrate Other reaction - Denitration Unclear [5], [6]
MR001247 Isosorbide dinitrate Isosorbide dinitrate Nitric Oxide Unclear GSTM1 ... [4]
MR001244 Isosorbide 2-nitrate Isosorbide Other reaction - Denitration Unclear [5], [6]
MR001242 Isosorbide 5-mononitrate Isosorbide-5-mononitrate-2-glucuronide Conjugation - Glucuronidation Unclear [5], [6]
MR001243 Isosorbide 5-mononitrate Isosorbide Other reaction - Denitration Unclear [5], [6]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
Glutathione S-transferase mu-1 (GSTM1) DME0308 Homo sapiens
GSTM1_HUMAN
2.5.1.18
[4]
References
1 Isosorbide Dinitrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Isoforms of cytochrome P450 on organic nitrate-derived nitric oxide release in human heart vessels. FEBS Lett. 1999 Jun 11;452(3):165-9.
3 Nitroglycerin and isosorbide dinitrate stimulation of glutathione disulfide efflux from perfused rat liver. Biochem Pharmacol. 1989 Nov 1;38(21):3807-10.
4 Pharmacokinetics of isosorbide mononitrate Am J Cardiol. 1992 Nov 27;70(17):61G-66G. doi: 10.1016/0002-9149(92)90028-w.
5 Isosorbide dinitrate bioavailability, kinetics, and metabolism Clin Pharmacol Ther. 1985 Aug;38(2):140-9. doi: 10.1038/clpt.1985.150.
6 Pharmacokinetics and metabolism of isosorbide-dinitrate after intravenous and oral administration Eur J Clin Pharmacol. 1985;27(6):637-44. doi: 10.1007/BF00547041.

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