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

General Information of Drug (ID: DR0109)
Drug Name
Amsacrine
Synonyms
Acridinyl Anisidide; Acridinylanisidide; Amekrin; Amsacrina; Amsacrina [INN-Spanish]; Amsacrinum; Amsacrinum [INN-Latin]; Amsidine; Amsidyl; Amsine; Lamasine; SN 21429; SN-11841; amsacrine; m-AMSA; meta-Amsacrine; 4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide; 4'-(9-Acridinylamino)methanesulfon-m-anisidide; 4'-(9-Acridinylamino)methanesulphon-m-anisidide; 51264-14-3; AMSA; C21H19N3O3S; CI-880; N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide; NSC 156303; NSC 249992; NSC-249992; NSC249992; UNII-00DPD30SOY; mAMSA
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 393.5 Topological Polar Surface Area 88.7
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
2179
PubChem SID
4711 ; 137181 ; 597748 ; 5128698 ; 7849380 ; 7978704 ; 8137254 ; 8151483 ; 11110803 ; 11406388 ; 11447254 ; 11533500 ; 12013305 ; 14927834 ; 29221358 ; 46507539 ; 47440375 ; 48110554 ; 48415564 ; 48422855 ; 49815687 ; 49855467 ; 50110958 ; 53789073 ; 57321186 ; 78687979 ; 90341308 ; 99453443 ; 103166066 ; 103919715 ; 103925608 ; 104299838 ; 118043462 ; 121379628 ; 124633410 ; 124879323 ; 124879324 ; 125824264 ; 126659536 ; 126687025 ; 127318462 ; 127318463 ; 127318464 ; 127318465 ; 127318466 ; 127318467 ; 127318468 ; 127318469 ; 127318470 ; 127318471
ChEBI ID
ChEBI:2687
CAS Number
51264-14-3
TTD Drug ID
D0G9YH
Formula
C21H19N3O3S
Canonical SMILES
COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42
InChI
1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)
InChIKey
XCPGHVQEEXUHNC-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
Quinone diimine DM001570 N. A. Oxidation - Oxidation 1 [3]
Amsacrine-Glutathione conjugate DM001571 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000233 Amsacrine Quinone diimine Oxidation - Oxidation Unclear [3]
MR000232 Quinone diimine Amsacrine-Glutathione conjugate Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT00180102) AML2003 - Standard-Therapy vs Intensified Therapy for Adult Acute Myeloid Leukemia Patients <= 60 Years.
2 Phase I pharmacokinetic study of the novel antitumor agent SR233377. Clin Cancer Res. 2000 Aug;6(8):3088-94.
3 The effect of buthionine sulphoximine, cimetidine and phenobarbitone on the disposition of amsacrine in the rabbit Cancer Chemother Pharmacol. 1986;18(3):208-12. doi: 10.1007/BF00273387.

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