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

General Information of Drug (ID: DR1279)
Drug Name
Phenprocoumon
Synonyms
Phenprocoumarol; Phenprocoumarole; Phenprocoumone; Phenprocoumone [INN-French]; Phenprocoumonum; Phenprocoumonum [INN-Latin]; Phenprocumone; Phenprocumonum; Ro 1-4849; 3-(1'-Phenyl-propyl)-4-oxycoumarin; 3-(1-Phenylpropyl)-4-hydroxycoumarin; Falithrom; Fencumar; Fenprocoumona [INN-Spanish]; Fenprocumone; Fenprocumone [DCIT]; Liquamar; Marcoumar; Marcumar; PHENPROCOUMON; 3-(alpha-Ethylbenzyl)-4-hydroxycoumarin; 4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one; 4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one; 435-97-2
Indication Thrombosis [ICD11: DB61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 280.3 Topological Polar Surface Area 46.5
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
54680692
PubChem SID
612021 ; 7845703 ; 7980293 ; 8030662 ; 10522853 ; 14848717 ; 29228465 ; 42684251 ; 46506423 ; 47207126 ; 47815891 ; 48416418 ; 49956264 ; 56394971 ; 57309600 ; 57325861 ; 76965160 ; 93302774 ; 103179879 ; 103950577 ; 104253508 ; 104321863 ; 106673762 ; 125823525 ; 126658557 ; 127770897 ; 134338056 ; 134974499 ; 135692445 ; 137126448 ; 137239431 ; 142971044 ; 160964285 ; 162011455 ; 162224643 ; 162652374 ; 163418248 ; 164042860 ; 174529392 ; 176262013 ; 178103445 ; 179326620 ; 184545898 ; 186014484 ; 198993025 ; 219400682 ; 223670210 ; 223705291 ; 226427577 ; 227840593
ChEBI ID
ChEBI:50438
CAS Number
435-97-2
TTD Drug ID
D0QV5T
Formula
C18H16O3
Canonical SMILES
CCC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O
InChI
1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
InChIKey
DQDAYGNAKTZFIW-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
4'-hydroxy-R-phenprocoumon DM001235
91987768
Oxidation - 4'-Hydroxylation 1 [4]
6-hydroxy-R-phenprocoumon DM001236
91987769
Oxidation - 6-Hydroxylation 1 [4]
7-hydroxy-R-phenprocoumon DM001238
101721000
Oxidation - 7-Hydroxylation 1 [4]
8-hydroxy-R-phenprocoumon DM001237
101721002
Oxidation - 8-Hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002025 Phenprocoumon 4'-hydroxy-R-phenprocoumon Oxidation - 4'-Hydroxylation CYP2C9 ... [4]
MR002026 Phenprocoumon 6-hydroxy-R-phenprocoumon Oxidation - 6-Hydroxylation CYP2C9 ... [4]
MR002027 Phenprocoumon 8-hydroxy-R-phenprocoumon Oxidation - 8-Hydroxylation CYP2C9 ... [4]
MR002028 Phenprocoumon 7-hydroxy-R-phenprocoumon Oxidation - 7-Hydroxylation CYP2C9 ... [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Phenprocoumon was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of cytochromes P450 2C9 and 3A4 as the major catalysts of phenprocoumon hydroxylation in vitro. Eur J Clin Pharmacol. 2004 May;60(3):173-82.
3 Genetic polymorphisms of cytochrome P450 2C9 causing reduced phenprocoumon (S)-7-hydroxylation in vitro and in vivo. Xenobiotica. 2004 Sep;34(9):847-59.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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