U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula C32H47F5O3S
Molecular Weight 606.771
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FULVESTRANT

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(C[C@@H](CCCCCCCCC[S+]([O-])CCCC(F)(F)C(F)(F)F)[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=VWUXBMIQPBEWFH-WCCTWKNTSA-N
InChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-,27+,28+,29-,30+,41?/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/ppa/fulvestrant.html

Fulvestrant is a drug treatment of hormone receptor-positive metastatic breast cancer in post-menopausal women with disease progression following anti-estrogen therapy. It is an estrogen receptor antagonist with no agonist effects, which works both by down-regulating and by degrading the estrogen receptor. Fulvestrant competitively and reversibly binds to estrogen receptors present in cancer cells and achieves its anti-estrogen effects through two separate mechanisms. First, fulvestrant binds to the receptors and downregulates them so that estrogen is no longer able to bind to these receptors. Second, fulvestrant degrades the estrogen receptors to which it is bound. Both of these mechanisms inhibit the growth of tamoxifen-resistant as well as estrogen-sensitive human breast cancer cell lines. Fulvestrant is used for the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy. Fulvestrant is marketed under the trade name Faslodex, by AstraZeneca.

CNS Activity

Curator's Comment: Fulvestrant does not cross the blood–brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.0631 nM [IC50]
0.1 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FASLODEX

Approved Use

FASLODEX is an estrogen receptor antagonist indicated for the: Treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following antiestrogen therapy.

Launch Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
25.1 ng/mL
500 mg single, intramuscular
dose: 500 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
FULVESTRANT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11400 ng × h/mL
500 mg single, intramuscular
dose: 500 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
FULVESTRANT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40 day
250 mg single, intramuscular
dose: 250 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
FULVESTRANT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
500 mg 1 times / month multiple, intramuscular
Highest studied dose
Dose: 500 mg, 1 times / month
Route: intramuscular
Route: multiple
Dose: 500 mg, 1 times / month
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: breast cancer
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
500 mg 1 times / month multiple, intramuscular
Dose: 500 mg, 1 times / month
Route: intramuscular
Route: multiple
Dose: 500 mg, 1 times / month
Sources:
unhealthy, 56 years
n = 1
Health Status: unhealthy
Condition: ductal carcinoma of the breast
Age Group: 56 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Epidermal necrolysis...
AEs leading to
discontinuation/dose reduction:
Epidermal necrolysis (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Epidermal necrolysis 1 patient
Disc. AE
500 mg 1 times / month multiple, intramuscular
Dose: 500 mg, 1 times / month
Route: intramuscular
Route: multiple
Dose: 500 mg, 1 times / month
Sources:
unhealthy, 56 years
n = 1
Health Status: unhealthy
Condition: ductal carcinoma of the breast
Age Group: 56 years
Sex: F
Population Size: 1
Sources:
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
weak (co-administration study)
Comment: fulvestrant increased midazolam AUC by 11% but decreased Cmax by 25%
Page: 21,22
no
weak (co-administration study)
Comment: fulvestrant increased midazolam AUC by 11% but decreased Cmax by 25%
Page: 21,22
Drug as victim
PubMed

PubMed

TitleDatePubMed
Methoxychlor stimulates estrogen-responsive messenger ribonucleic acids in mouse uterus through a non-estrogen receptor (non-ER) alpha and non-ER beta mechanism.
1999 Aug
Estrogen directly respresses gonadotropin-releasing hormone (GnRH) gene expression in estrogen receptor-alpha (ERalpha)- and ERbeta-expressing GT1-7 GnRH neurons.
1999 Nov
WISP-2 as a novel estrogen-responsive gene in human breast cancer cells.
2000 Aug 18
Molecular analysis of the inhibition of monocyte chemoattractant protein-1 gene expression by estrogens and xenoestrogens in MCF-7 cells.
2000 Jan
Activation of estrogen receptor beta is a prerequisite for estrogen-dependent upregulation of nitric oxide synthases in neonatal rat cardiac myocytes.
2001 Aug 3
Estradiol enhances and estriol inhibits the expression of CYP1A1 induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in a mouse ovarian cancer cell line.
2002 Jul 15
Synthetic estrogen-mediated activation of ERK 2 intracellular signaling molecule.
2003 Oct
Regulation of uterine hsp90alpha, hsp72 and HSF-1 transcription in B6C3F1 mice by beta-estradiol and bisphenol A: involvement of the estrogen receptor and protein kinase C.
2003 Sep 30
BMP7/ActRIIB regulates estrogen-dependent apoptosis: new biomarkers for environmental estrogens.
2004
Effects of the pesticides prochloraz and methiocarb on human estrogen receptor alpha and beta mRNA levels analyzed by on-line RT-PCR.
2004 Aug
Recruitment of uterine NK cells: induction of CXC chemokine ligands 10 and 11 in human endometrium by estradiol and progesterone.
2004 Dec 1
Augmented endothelial nitric oxide synthase (eNOS) protein expression in human pregnant myometrium: possible involvement of eNOS promoter activation by estrogen via both estrogen receptor (ER)alpha and ERbeta.
2004 Feb
17beta-estradiol antagonizes cardiomyocyte hypertrophy by autocrine/paracrine stimulation of a guanylyl cyclase A receptor-cyclic guanosine monophosphate-dependent protein kinase pathway.
2004 Jan 20
The unusual binding properties of the third distinct teleost estrogen receptor subtype ERbetaa are accompanied by highly conserved amino acid changes in the ligand binding domain.
2004 Jun
Fulvestrant is an effective and well-tolerated endocrine therapy for postmenopausal women with advanced breast cancer: results from clinical trials.
2004 Mar
Resveratrol modulates the phosphoinositide 3-kinase pathway through an estrogen receptor alpha-dependent mechanism: relevance in cell proliferation.
2004 Mar 20
Small nuclear RING finger protein expression during gonad development: regulation by gonadotropins and estrogen in the postnatal ovary.
2004 May
Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways.
2004 Nov
Proliferation-stimulating effects of icaritin and desmethylicaritin in MCF-7 cells.
2004 Nov 19
Leptin interferes with the effects of the antiestrogen ICI 182,780 in MCF-7 breast cancer cells.
2004 Oct 1
Development and characterization of a cell line that stably expresses an estrogen-responsive luciferase reporter for the detection of estrogen receptor agonist and antagonists.
2004 Sep
Effect of follicle-stimulating hormone and estrogen on the expression of betaglycan messenger ribonucleic acid levels in cultured rat granulosa cells.
2005 Aug
Alternative splicing of Slo channel gene programmed by estrogen, progesterone and pregnancy.
2005 Aug 29
Progestin activation of nongenomic pathways via cross talk of progesterone receptor with estrogen receptor beta induces proliferation of endometrial stromal cells.
2005 Dec
Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells.
2005 Feb
Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays.
2005 Feb
Co-culture of primary human mammary fibroblasts and MCF-7 cells as an in vitro breast cancer model.
2005 Feb
Novel progestogenic activity of environmental endocrine disruptors in the upregulation of calbindin-D9k in an immature mouse model.
2005 Jan
Differential effects of estrogen receptor antagonists on pituitary lactotroph proliferation and prolactin release.
2005 Jul 15
Receptor isoform and ligand-specific modulation of dihydrotestosterone-induced prostate specific antigen gene expression and prostate tumor cell growth by estrogens.
2005 Jul-Aug
Regulation of vitamin D receptor expression via estrogen-induced activation of the ERK 1/2 signaling pathway in colon and breast cancer cells.
2005 Jun
CSN5/Jab1 is involved in ligand-dependent degradation of estrogen receptor {alpha} by the proteasome.
2005 Jun
The putative tumor suppressor deleted in malignant brain tumors 1 is an estrogen-regulated gene in rodent and primate endometrial epithelium.
2005 Mar
Resveratrol and estradiol rapidly activate MAPK signaling through estrogen receptors alpha and beta in endothelial cells.
2005 Mar 4
Promoting insulin secretion in pancreatic islets by means of bisphenol A and nonylphenol via intracellular estrogen receptors.
2005 May
Estrogenic effects of two derivatives of icariin on human breast cancer MCF-7 cells.
2005 Nov
Estrogen increases mitochondrial efficiency and reduces oxidative stress in cerebral blood vessels.
2005 Oct
Differential effect of estrogen receptor alpha and beta agonists on the receptor for advanced glycation end product expression in human microvascular endothelial cells.
2005 Sep 30
Effect of methoxychlor and estradiol on cytochrome p450 enzymes in the mouse ovarian surface epithelium.
2006 Feb
Effects of endocrine disrupters on the expression of growth hormone and prolactin mRNA in the rainbow trout pituitary.
2006 Jan 15
Patents

Sample Use Guides

Usual Adult Dose for Breast Cancer Initial dose: 500 mg IM on days 1, 15, and 29, then once a month thereafter.
Route of Administration: Intramuscular
In human and rat mesangial cells, increased type IV collagen and fibronectin gene transcription induced by TGF-b1 was downregulated by Fulvestrant at concentrations ranging from 10(-10) M to 10(-7) M.
Name Type Language
FULVESTRANT
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FULVESTRANT [MART.]
Common Name English
ZD-9238
Code English
FULVESTRANT [MI]
Common Name English
FULVESTRANT [USP-RS]
Common Name English
FULVESTRANT [VANDF]
Common Name English
FULVESTRANT [USP IMPURITY]
Common Name English
Fulvestrant [WHO-DD]
Common Name English
FASLODEX
Brand Name English
ICI-182780
Code English
FULVESTRANT [JAN]
Common Name English
FULVESTRANT [ORANGE BOOK]
Common Name English
NSC-759879
Code English
FULVESTRANT [USP MONOGRAPH]
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL, 7-(9-((4,4,5,5,5-PENTAFLUOROPENTYL)SULFINYL)NONYL)-, (7.ALPHA.,17.BETA.)-
Systematic Name English
fulvestrant [INN]
Common Name English
ZD9238
Code English
ICI 182,780
Code English
FULVESTRANT [EP MONOGRAPH]
Common Name English
FULVESTRANT [EMA EPAR]
Common Name English
7.ALPHA.-(9-(4,4,5,5,5-PENTAFLUOROPENTYLSULPHINYL)NONYL)ESTRA-1,3,5(10)-TRIENE-3,17.BETA.-DIOL
Systematic Name English
FULVESTRANT [USAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QL02BA03
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
LIVERTOX NBK548072
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
NDF-RT N0000175582
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
NCI_THESAURUS C2116
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
NDF-RT N0000000168
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
WHO-ATC L02BA03
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
NDF-RT N0000175826
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
EMA ASSESSMENT REPORTS FASLODEX (AUTHORIZED: BREAST NEOPLASMS)
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
Code System Code Type Description
HSDB
7658
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
NDF-RT
N0000000145
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY Estrogen Receptor Antagonists [MoA]
DRUG CENTRAL
1255
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
DRUG BANK
DB00947
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
FDA UNII
22X328QOC4
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
RXCUI
282357
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY RxNorm
NSC
759879
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
NCI_THESAURUS
C1379
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
DAILYMED
22X328QOC4
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
SMS_ID
100000089504
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
INN
7712
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
USAN
KK-128
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
CHEBI
31638
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
CAS
129453-61-8
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
EVMPD
SUB13933MIG
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
WIKIPEDIA
FULVESTRANT
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
PUBCHEM
104741
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
RS_ITEM_NUM
1286650
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
IUPHAR
1015
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
MERCK INDEX
m5583
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1358
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022369
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY
MESH
C070081
Created by admin on Fri Dec 15 15:51:42 GMT 2023 , Edited by admin on Fri Dec 15 15:51:42 GMT 2023
PRIMARY