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

General Information of Drug (ID: DR1746)
Drug Name
Dicumarol
Synonyms
Dicumarol; Dicoumarol; Bishydroxycoumarin; Dicoumarin; melitoxin; Bis-hydroxycoumarin; Antitrombosin; Baracoumin; Dicoumal; Dicumarine; Acadyl; Acavyl; Dicuman; Trombosan; Dicumol; Dufalone; Kumoran; Temparin; Cumid; Cuma; Dicumaol R; 3,3'-Methylenebis(4-hydroxycoumarin); Bis(4-hydroxycoumarin-3-yl)methane; Anathrombase; Dicoumarolum; Apekumarol; Dicoumerol; Dicumarinum; Dicumarolum; Bis-3,3'-(4-hydroxycoumarinyl)methane; Di-(4-hydroxy-3-coumarinyl)methane; Dicumarolo [DCIT]; Dwukumarol [Polish]; Di-4-hydroxy-3,3'-methylenedicoumarin; Dicumarol [INN-Spanish]; Dicoumarolum [INN-Latin]; 3,3'-Methylen-bis(4-hydroxy-cumarin); 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one); Dicumarol [USAN]; 66-76-2
Indication Menorrhagia [ICD11: GA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 336.3 Topological Polar Surface Area 93.1
Heavy Atom Count 25 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
54676038
PubChem SID
2636 ; 4054 ; 81051 ; 96557 ; 606498 ; 828851 ; 841964 ; 3138564 ; 3288931 ; 5394319 ; 7979068 ; 8149297 ; 10321191 ; 10532227 ; 11112184 ; 11131943 ; 11220586 ; 11336071 ; 11361310 ; 11363059 ; 11365621 ; 11368183 ; 11371493 ; 11374194 ; 11376345 ; 11462282 ; 11466813 ; 11467933 ; 11483984 ; 11486565 ; 11487960 ; 11490203 ; 11492323 ; 11493979 ; 11532436 ; 14851261 ; 17397886 ; 24439015 ; 24896643 ; 26611698 ; 26680286 ; 26747987 ; 26747988 ; 26758600 ; 36502598 ; 46505536 ; 47216838 ; 47291197 ; 47440330 ; 47515376
ChEBI ID
CHEBI:4513
CAS Number
66-76-2
TTD Drug ID
D02TJS
Formula
C19H12O6
Canonical SMILES
C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
InChI
1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
InChIKey
DOBMPNYZJYQDGZ-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
7-hydroxydicumarol DM000065 N. A. Oxidation - Hydroxylation 1 [2] , [4]
B055 DM000064 N. A. Unclear 1 [2]
Unclear DM009999 N. A. Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000826 Dicumarol B055 Unclear Unclear [2]
MR000827 Dicumarol 7-hydroxydicumarol Oxidation - Hydroxylation GUSB [2], [4]
MR000828 Dicumarol . Unclear CYP2C9 [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-glucuronidase (GUSB) DME0106 Homo sapiens
BGLR_HUMAN
3.2.1.31
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
References
1 Dicumarol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of dicumarol-14 C by rat-liver microsomes Pharmacol Res Commun. 1976 Oct;8(5):469-75. doi: 10.1016/0031-6989(76)90056-4.
3 Pharmacogenetics aspects of oral anticoagulants therapy. J Med Life. 2015 Apr-Jun;8(2):171-5.
4 Determination of dicumarol metabolites in bile of rats J Pharm Sci. 1975 Jul;64(7):1158-62. doi: 10.1002/jps.2600640705.

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