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

General Information of Drug (ID: DR5942)
Drug Name
Lasofoxifene
Synonyms
Oporia; 180916-16-9; rac-Lasofoxifene; CP 336156; Fablyn; UNII-337G83N988; (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol; CHEMBL328190; 337G83N988; (-)-cis-5,6,7,8-Tetrahydro-6-phenyl-5-(p-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphthol; 180915-78-0; CP-336,156; LASOFOXIFENE HCL; Lasofoxifene [INN:BAN]; AC1L50OI; SCHEMBL26815; GTPL7542; CTK8F1062; BDBM20606; DTXSID50171037; GXESHMAMLJKROZ-IAPPQJPRSA-N; ZINC3918428; BCP03626; AKOS030241621; AN-3516; BCP9000842; DB06202; Oporia; Lasofoxifene [INN]; Cis-1R-(4'-pyrrolidinoethoxyphenyl)-2S-phenyl-6-hydroxy-1,2,3,4-tetrahydronaphthalene, tartrate salt; AZD9639
Indication Osteoporosis [ICD11: FB83] Approved [1]
Virus infection [ICD11: ICD11: 1A24-1D9Z] Discontinued in Phase 1 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 413.5 Topological Polar Surface Area 32.7
Heavy Atom Count 31 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
216416
ChEBI ID
CHEBI:135938
CAS Number
180916-16-9
TTD Drug ID
D09NMD
Formula
C28H31NO2
Canonical SMILES
C1CCN(C1)CCOC2=CC=C(C=C2)[C@H]3[C@H](CCC4=C3C=CC(=C4)O)C5=CC=CC=C5
InChI
InChI=1S/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1
InChIKey
GXESHMAMLJKROZ-IAPPQJPRSA-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
5-hydroxy-lasofoxifene (5-OHLAS) DM015621
10137509
Oxidation - 5-hydroxylation 1 [3]
7-hydroxy-lasofoxifene (7-OHLAS) DM015576
9954368
Oxidation - 7-hydroxylation 1 [3]
Lasofoxifene metabolite M11 DM016328
71749754
Conjugation - Sulfate conjugation 1 [5]
Lasofoxifene metabolite M13 DM016227
59911466
Unclear - Unclear 1 [5]
Lasofoxifene metabolite M15 DM017529 N. A. Unclear - Unclear 1 [5]
Lasofoxifene metabolite M7 DM017530 N. A. Unclear - Unclear 1 [5]
Lasofoxifene metabolite M13 DM016227
59911466
Unclear - Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008872 Lasofoxifene Lasofoxifene metabolite M15 Unclear - Unclear Unclear [5]
MR008874 Lasofoxifene 7-hydroxy-lasofoxifene (7-OHLAS) Oxidation - 7-hydroxylation CYP3A5 ... [3]
MR008875 Lasofoxifene 5-hydroxy-lasofoxifene (5-OHLAS) Oxidation - 5-hydroxylation CYP3A4 ... [3]
MR008876 Lasofoxifene Lasofoxifene metabolite M7 Unclear - Unclear Unclear [5]
MR008877 Lasofoxifene Lasofoxifene metabolite M11 Conjugation - Sulfate conjugation Unclear [5]
MR008878 Lasofoxifene Lasofoxifene metabolite M13 Unclear - Unclear Unclear [5]
MR008873 Lasofoxifene metabolite M15 Lasofoxifene metabolite M13 Unclear - Unclear Unclear [5]
⏷ Show the Full List of 7 MR(s)
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
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 12  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7542).
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800026623)
3 Disposition of lasofoxifene, a next-generation selective estrogen receptor modulator, in healthy male subjects
4 DrugBank(Pharmacology-Metabolism):Lasofoxifene
5 Metabolism, distribution, and excretion of a next generation selective estrogen receptor modulator, lasofoxifene, in rats and monkeys

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