Details of the Drug

General Information of Drug (ID: DMHA18P)

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
Disease Entry ICD 11 Status REF
Osteoporosis FB83.0 Approved [1]
Virus infection 1A24-1D9Z Discontinued in Phase 1 [2]
Affected Organisms
Humans and other mammals
ATC Code
G03XC03: Lasofoxifene
G03XC: Selective estrogen receptor modulators
G03X: OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 413.5
Logarithm of the Partition Coefficient (xlogp) 6.1
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 6.0-7.3 h [3]
Clearance
The apparent oral clearance of drug is 6.6 l L/h [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 6 days [5]
Metabolism
The drug is metabolized via the hepatic CYP3A4/CYP3A5 and CYP2D6 accounts for nearly half of total metabolism of lasofoxifene [4]
Vd
The volume of distribution (Vd) of drug is 1350 L [4]
Chemical Identifiers
Formula
C28H31NO2
IUPAC Name
(5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
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
Cross-matching ID
PubChem CID
216416
ChEBI ID
CHEMBL328190
CAS Number
180916-16-9
UNII
337G83N988
DrugBank ID
DB06202
TTD ID
D09NMD
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Modulator [6]
Respiratory syncytial virus protein F (RSV F) TT57ID8 FUS_HRSVA Modulator [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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 Lewiecki EM: Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis. Ther Clin Risk Manag. 2009;5:817-27. Epub 2009 Nov 2.
4 EMA Summary of product characteristics
5 Lasofoxifene: Evidence of its therapeutic value in osteoporosis. Core Evid. 2010 Jun 15;4:113-29.
6 Pfizer. Product Development Pipeline. March 31 2009.
7 Prospects for the development of fusion inhibitors to treat human respiratory syncytial virus infection. Curr Opin Drug Discov Devel. 2009 Jul;12(4):479-87.