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

General Information of Drug (ID: DR1208)
Drug Name
Ospemifene
Synonyms
Ophena; Ospemifene; Ospemifene [USAN:INN:BAN]; Osphena; Osphena (TN); senshio; 128607-22-7; 2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol; Deamino-hydroxytoremifene; Deaminotoremifene; 2-(p-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol; 2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethanol; B0P231ILBK; CCRIS 9205; CHEBI:73275; Ethanol, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-; Ethanol, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-; FC-1271a; Fc-1271; UNII-B0P231ILBK
Indication Dyspareunia [ICD11: GA12] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 378.9 Topological Polar Surface Area 29.5
Heavy Atom Count 27 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3036505
PubChem SID
10048556 ; 12015426 ; 14804521 ; 36104653 ; 53788245 ; 57353466 ; 77768422 ; 96025641 ; 111641440 ; 135106463 ; 137013915 ; 142415636 ; 160708695 ; 162169319 ; 175267362 ; 175426911 ; 178103921 ; 179149775 ; 198991711 ; 201248858 ; 224253139 ; 227208701 ; 249583801 ; 251916528 ; 251917875 ; 252215972 ; 252430798 ; 252472856
ChEBI ID
CHEBI:73275
CAS Number
128607-22-7
TTD Drug ID
D02CTS
Formula
C24H23ClO2
Canonical SMILES
C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC=C(C=C3)OCCO)CCCl
InChI
1S/C24H23ClO2/c25-16-15-23(19-7-3-1-4-8-19)24(20-9-5-2-6-10-20)21-11-13-22(14-12-21)27-18-17-26/h1-14,26H,15-18H2/b24-23-
InChIKey
LUMKNAVTFCDUIE-VHXPQNKSSA-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
3-hydroxylation Ospemifene DM002322
22504558
Unclear 1 [2]
4'-hydroxylation Ospermifene DM002323
3036504
Unclear 1 [2]
4-hydroxylation Ospemifene DM002319
22504506
Unclear 1 [2]
Ospemifene carboxylic acid DM002321
101121046
Unclear 1 [2]
4-hydroxycarboxylic acid DM002320
156596440
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001857 Ospemifene 4-hydroxylation Ospemifene Unclear CYP3A4 ... [2]
MR001858 Ospemifene Ospemifene carboxylic acid Unclear Unclear [2]
MR001859 Ospemifene 3-hydroxylation Ospemifene Unclear Unclear [2]
MR001860 Ospemifene 4'-hydroxylation Ospermifene Unclear CYP3A [2]
MR001855 4-hydroxylation Ospemifene 4-hydroxycarboxylic acid Unclear Unclear [2]
MR001856 Ospemifene carboxylic acid 4-hydroxycarboxylic acid Unclear Unclear [2]
⏷ 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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Ospemifene was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Ospemifene metabolism in humans in vitro and in vivo: metabolite identification, quantitation, and CYP assignment of major hydroxylations. Drug Metabol Drug Interact. 2013;28(3):153-61.

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