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

General Information of Drug (ID: DR0044)
Drug Name
MGI-114
Synonyms
Irofulven; Irofulven [USAN:INN]; MGI 114; MGI-114; (R)-6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one; (R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one; 158440-71-2; 6-(Hydroxymethyl)acylfulvene; 6-Hydroxymethylacylfulvene; 6B799IH05A; Acylfulvene, 6-(hydroxymethyl)-; HMAF; NSC 683863; NSC-683863; Spiro(cyclopropane-1,5'(5H)-inden)-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (R)-; UNII-6B799IH05A
Indication Lung cancer [ICD11: 2C25] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 246.3 Topological Polar Surface Area 57.5
Heavy Atom Count 18 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
148189
ChEBI ID
CHEBI:135002
CAS Number
158440-71-2
Formula
C15H18O3
Canonical SMILES
CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
InChI
1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
InChIKey
NICJCIQSJJKZAH-AWEZNQCLSA-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
Irofulven metabolite 3 (M3) DM016777
154731645
Oxidation - Hydroxylation 1 [3]
Irofulven metabolite 4 (M4) DM015722
10869073
Oxidation - Hydroxylation 1 [3]
Irofulven metabolite 6 (M6) DM016278
68216055
Unclear - Unclear 1 [3]
Irofulven-glucuronide conjugate (M') DM019904 N. A. Conjugation - Glucuronidation 1 [3]
Irofulven-glutathione conjugate (M1) DM019905 N. A. Conjugation - Glutathione conjugation 1 [3]
Opened-ring metabolite (M2) DM015988
21626046
Unclear - Unclear 1 [3]
Irofulven metabolite 5 (M5) DM016512
118440085
Oxidation - Hydroxylation 2 [3]
Irofulven metabolite 5 (M5) DM016512
118440085
Unclear - Unclear 2 [3]
M2-glucuronide conjugate (M'2) DM019901 N. A. Conjugation - Glucuronidation 2 [3]
M2-glutathione conjugate (M'1) DM019900 N. A. Conjugation - Glutathione conjugation 2 [3]
M2-glutathione conjugate (M0) DM019902 N. A. Conjugation - Glutathione conjugation 2 [3]
M4-glucuronide conjugate (M'4) DM019903 N. A. Conjugation - Glucuronidation 2 [3]
M5-glucuronide conjugate (M'5) DM019899 N. A. Conjugation - Glucuronidation 3 [3]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012677 MGI-114 Irofulven metabolite 4 (M4) Oxidation - Hydroxylation Unclear [3]
MR012680 MGI-114 Irofulven metabolite 6 (M6) Unclear - Unclear Unclear [3]
MR012682 MGI-114 Opened-ring metabolite (M2) Unclear - Unclear Unclear [3]
MR012687 MGI-114 Irofulven-glucuronide conjugate (M') Conjugation - Glucuronidation Unclear [3]
MR012688 MGI-114 Irofulven-glutathione conjugate (M1) Conjugation - Glutathione conjugation Unclear [3]
MR012689 MGI-114 Irofulven metabolite 3 (M3) Oxidation - Hydroxylation Unclear [3]
MR012678 Irofulven metabolite 4 (M4) Irofulven metabolite 5 (M5) Unclear - Unclear Unclear [3]
MR012686 Irofulven metabolite 4 (M4) M4-glucuronide conjugate (M'4) Conjugation - Glucuronidation Unclear [3]
MR012681 Irofulven metabolite 6 (M6) Irofulven metabolite 5 (M5) Oxidation - Hydroxylation Unclear [3]
MR012683 Opened-ring metabolite (M2) M2-glutathione conjugate (M'1) Conjugation - Glutathione conjugation Unclear [3]
MR012684 Opened-ring metabolite (M2) M2-glucuronide conjugate (M'2) Conjugation - Glucuronidation Unclear [3]
MR012685 Opened-ring metabolite (M2) M2-glutathione conjugate (M0) Conjugation - Glutathione conjugation Unclear [3]
MR012679 Irofulven metabolite 5 (M5) M5-glucuronide conjugate (M'5) Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 13 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Prostaglandin reductase 1 (PTGR1) DME0429 Homo sapiens
PTGR1_HUMAN
1.3.1.16
[2]
References
1 ClinicalTrials.gov (NCT00003666) Irofulven in Treating Patients With Relapsed or Refractory Non-small Cell Lung Cancer.
2 Up-regulation of human prostaglandin reductase 1 improves the efficacy of hydroxymethylacylfulvene, an antitumor chemotherapeutic agent. J Pharmacol Exp Ther. 2012 Nov;343(2):426-33.
3 Pharmacokinetics, metabolism, and routes of excretion of intravenous irofulven in patients with advanced solid tumors

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