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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:135938
CAS Number: 180916-16-9
DrugBank ID: DB06202
TTD ID: D09NMD

Repurposed Drugs (RPD)

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.