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Details

Stereochemistry EPIMERIC
Molecular Formula C32H47F5O3S
Molecular Weight 606.7731
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FULVESTRANT

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4C[C@@]([H])(CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F)[C@@]3([H])[C@]2([H])CC[C@]1([H])O)O

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

Molecular Formula C32H47F5O3S
Molecular Weight 606.7731
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1.01753278E12
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
Estrogenicity of bisphenol A in a human endometrial carcinoma cell line.
1999 Apr 25
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
Effects of environmental estrogens on tumor necrosis factor alpha-mediated apoptosis in MCF-7 cells.
1999 Nov
Transcriptional activation of c-fos protooncogene by 17beta-estradiol: mechanism of aryl hydrocarbon receptor-mediated inhibition.
1999 Sep
WISP-2 as a novel estrogen-responsive gene in human breast cancer cells.
2000 Aug 18
Proteinase inhibitor 9, an inhibitor of granzyme B-mediated apoptosis, is a primary estrogen-inducible gene in human liver cells.
2000 Feb 25
Molecular analysis of the inhibition of monocyte chemoattractant protein-1 gene expression by estrogens and xenoestrogens in MCF-7 cells.
2000 Jan
Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells.
2000 Oct
Activation of estrogen receptor beta is a prerequisite for estrogen-dependent upregulation of nitric oxide synthases in neonatal rat cardiac myocytes.
2001 Aug 3
Modulation of aromatase expression in human breast tissue.
2001 Dec
Inhibition of E2-induced expression of BRCA1 by persistent organochlorines.
2002
Modulation of estrogen receptor-dependent reporter construct activation and G0/G1-S-phase transition by polycyclic aromatic hydrocarbons in human breast carcinoma MCF-7 cells.
2002 Dec
Cadmium mimics the in vivo effects of estrogen in the uterus and mammary gland.
2003 Aug
Expression and mitogenic effect of fibroblast growth factor-9 in human endometriotic implant is regulated by aberrant production of estrogen.
2003 Nov
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
Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1.
2004 Feb
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
Estrogen modulates microglial inflammatory mediator production via interactions with estrogen receptor beta.
2004 Nov
Proliferation-stimulating effects of icaritin and desmethylicaritin in MCF-7 cells.
2004 Nov 19
Differential responses to doxorubicin-induced phosphorylation and activation of Akt in human breast cancer cells.
2005
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
Differential effects of estrogens and progestins on the anticoagulant tissue factor pathway inhibitor in the rat.
2005 Mar
Estrogenic effects of two derivatives of icariin on human breast cancer MCF-7 cells.
2005 Nov
Estrogen receptor alpha increases basal and cigarette smoke extract-induced expression of CYP1A1 and CYP1B1, but not GSTP1, in normal human bronchial epithelial cells.
2005 Nov
Estrogen receptor-alpha regulates SOCS-3 expression in human breast cancer cells.
2005 Sep 16
Glycogen synthase kinase-3 interacts with and phosphorylates estrogen receptor alpha and is involved in the regulation of receptor activity.
2005 Sep 23
Dioxin induces an estrogen-like, estrogen receptor-dependent gene expression response in the murine uterus.
2006 May
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:04:39 UTC 2021
Edited
by admin
on Fri Jun 25 21:04:39 UTC 2021
Record UNII
22X328QOC4
Record Status Validated (UNII)
Record Version
  • Download
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
FASLODEX
Brand Name English
ICI-182780
Code English
FULVESTRANT [JAN]
Common Name English
FULVESTRANT [ORANGE BOOK]
Common Name English
FULVESTRANT [WHO-DD]
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 [USP]
Common 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 Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
LIVERTOX 444
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
NDF-RT N0000175582
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
NCI_THESAURUS C2116
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
NDF-RT N0000000168
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
WHO-ATC L02BA03
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
NDF-RT N0000175826
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
EMA ASSESSMENT REPORTS FASLODEX (AUTHORIZED: BREAST NEOPLASMS)
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
Code System Code Type Description
HSDB
7658
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
NDF-RT
N0000000145
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY Estrogen Receptor Antagonists [MoA]
DRUG CENTRAL
1255
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
DRUG BANK
DB00947
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
FDA UNII
22X328QOC4
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
RXCUI
282357
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C1379
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
INN
7712
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
CAS
129453-61-8
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
EVMPD
SUB13933MIG
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
WIKIPEDIA
FULVESTRANT
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
PUBCHEM
104741
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
IUPHAR
1015
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
MERCK INDEX
M5583
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1358
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
EPA CompTox
129453-61-8
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
USP_CATALOG
1286650
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY USP-RS
MESH
C070081
Created by admin on Fri Jun 25 21:04:39 UTC 2021 , Edited by admin on Fri Jun 25 21:04:39 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TARGET -> INHIBITOR
Selective estrogen receptor degrader (SERD)
BINDING
IC50
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
DERIVATIVE -> PARENT
TARGET -> INHIBITOR
Selective estrogen receptor degrader (SERD)
BINDING
IC50
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METABOLITE -> PARENT
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CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC