FULVESTRANT

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 Search

SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)[C@H](CCCCCCCCC[S+]([O-])CCCC(F)(F)C(F)(F)F)CC4=CC(O)=CC=C34

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	606.771
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00947
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26407012	Antagonist 2849		0.0631 nM [IC50]
MCF7 22 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26407012	Inhibitor 8504		0.1 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hormone receptor positive metastatic breast cancer 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021344s015lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
25.1 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021344Orig1s039lbl.pdf	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
11.4 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/15094758/	250 mg single, intramuscular dose: 250 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		FULVESTRANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
11400 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021344Orig1s039lbl.pdf	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
176 ng × day/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/15094758/	250 mg single, intramuscular dose: 250 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		FULVESTRANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
40 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021344Orig1s039lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021344Orig1s039lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/29901634	unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/29901634	Sources: https://pubmed.ncbi.nlm.nih.gov/29901634
500 mg 1 times / month multiple, intramuscular Dose: 500 mg, 1 times / month Route: intramuscular Route: multiple Dose: 500 mg, 1 times / month Sources: https://pubmed.ncbi.nlm.nih.gov/33261799	unhealthy, 56 years Health Status: unhealthy Age Group: 56 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/33261799	Disc. AE: Epidermal necrolysis... AEs leading to discontinuation/dose reduction: Epidermal necrolysis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/33261799

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/33261799	unhealthy, 56 years Health Status: unhealthy Age Group: 56 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/33261799

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	inhibitor 2438 inducer 440	inhibitor 2507 inducer 109

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057	UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A8 323	CYP1A2 832 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP2D6 2546	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no	weak (co-administration study) Comment: fulvestrant increased midazolam AUC by 11% but decreased Cmax by 25% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22	no	weak (co-administration study) Comment: fulvestrant increased midazolam AUC by 11% but decreased Cmax by 25% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21,22

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16339389/	yes
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16339389/	yes
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16339389/	yes
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16339389/	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21.0	yes	no (co-administration study) Comment: label: administration with rifampin (inducer) showed not effect on PK of fulvestrant Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-344_Fulvestrant_biopharmr.pdf#page=21 Page: 21.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31638	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31638
ChemicalBook	CB0698542	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0698542
eMolecules	6719147	https://www.emolecules.com/cgi-bin/more?vid=6719147
Selleck Chemicals	Fulvestrant	http://www.selleckchem.com/products/Fulvestrant.html

PubMed

Title	Date	PubMed
Dioxin induces an estrogen-like, estrogen receptor-dependent gene expression response in the murine uterus.	2006-05	16467188
Effect of methoxychlor and estradiol on cytochrome p450 enzymes in the mouse ovarian surface epithelium.	2006-02	16280380
Characterization of estrogen receptor betab in sea bream (Sparus auratus): phylogeny, ligand-binding, and comparative analysis of expression.	2006-01-15	16213504
Effects of endocrine disrupters on the expression of growth hormone and prolactin mRNA in the rainbow trout pituitary.	2006-01-15	16188257
ERE-independent ERalpha target genes differentially expressed in human breast tumors.	2005-12-21	16298037
Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR).	2005-12-01	15885729
CHIP (carboxyl terminus of Hsc70-interacting protein) promotes basal and geldanamycin-induced degradation of estrogen receptor-alpha.	2005-12	16037132
Progestin activation of nongenomic pathways via cross talk of progesterone receptor with estrogen receptor beta induces proliferation of endometrial stromal cells.	2005-12	16020483
Estrogenic effects of two derivatives of icariin on human breast cancer MCF-7 cells.	2005-11	16323292
Estrogen receptor alpha increases basal and cigarette smoke extract-induced expression of CYP1A1 and CYP1B1, but not GSTP1, in normal human bronchial epithelial cells.	2005-11	16010691
The phytoestrogen biochaninA weakens acute cardiac allograft rejection without affecting the reproductive system.	2005-10	16223672
Analysis of estrogen agonism and antagonism of tamoxifen, raloxifene, and ICI182780 in endometrial cancer cells: a putative role for the epidermal growth factor receptor ligand amphiregulin.	2005-10	16202921
Estrogen increases mitochondrial efficiency and reduces oxidative stress in cerebral blood vessels.	2005-10	15994367
Differential effect of estrogen receptor alpha and beta agonists on the receptor for advanced glycation end product expression in human microvascular endothelial cells.	2005-09-30	15878629
Glycogen synthase kinase-3 interacts with and phosphorylates estrogen receptor alpha and is involved in the regulation of receptor activity.	2005-09-23	16076840
Estrogen receptor-alpha regulates SOCS-3 expression in human breast cancer cells.	2005-09-16	16055089
Alternative splicing of Slo channel gene programmed by estrogen, progesterone and pregnancy.	2005-08-29	16102753
Selective oestrogen receptor modulators, aromatase inhibitors and the female breast.	2005-08	15976552
Effect of follicle-stimulating hormone and estrogen on the expression of betaglycan messenger ribonucleic acid levels in cultured rat granulosa cells.	2005-08	15878966
Differential effects of estrogen receptor antagonists on pituitary lactotroph proliferation and prolactin release.	2005-07-15	15950373
Opposite effects of estrogen receptors alpha and beta on MCF-7 sensitivity to the cytotoxic action of TNF and p53 activity.	2005-07-14	15870704
Estrogen-induced loss of progesterone receptor expression in normal and malignant ovarian surface epithelial cells.	2005-06-23	15806153
[Regulation of orphan receptor ERR alpha by estrogen and progesterone in endometrial carcinoma cell line].	2005-06-18	15968320
Receptor isoform and ligand-specific modulation of dihydrotestosterone-induced prostate specific antigen gene expression and prostate tumor cell growth by estrogens.	2005-06-16	15955889
Gene expression changes in rat prostate after activation or blocking of the androgen and estrogen receptor.	2005-06-15	15925091
Regulation of vitamin D receptor expression via estrogen-induced activation of the ERK 1/2 signaling pathway in colon and breast cancer cells.	2005-06	15930183
CSN5/Jab1 is involved in ligand-dependent degradation of estrogen receptor {alpha} by the proteasome.	2005-06	15899841
The estrogenic activity of synthetic progestins used in oral contraceptives enhances fatty acid synthase-dependent breast cancer cell proliferation and survival.	2005-06	15870863
Promoting insulin secretion in pancreatic islets by means of bisphenol A and nonylphenol via intracellular estrogen receptors.	2005-05	15778011
Transcriptional activation of the oxytocin promoter by oestrogens uses a novel non-classical mechanism of oestrogen receptor action.	2005-04	15842231
Resveratrol and estradiol rapidly activate MAPK signaling through estrogen receptors alpha and beta in endothelial cells.	2005-03-04	15615701
Differential effects of estrogens and progestins on the anticoagulant tissue factor pathway inhibitor in the rat.	2005-03	15857755
The putative tumor suppressor deleted in malignant brain tumors 1 is an estrogen-regulated gene in rodent and primate endometrial epithelium.	2005-03	15564322
Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells.	2005-02	15539556
Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays.	2005-02	15537743
Co-culture of primary human mammary fibroblasts and MCF-7 cells as an in vitro breast cancer model.	2005-02	15525692
Novel progestogenic activity of environmental endocrine disruptors in the upregulation of calbindin-D9k in an immature mouse model.	2005-01	15509668
Differential responses to doxorubicin-induced phosphorylation and activation of Akt in human breast cancer cells.	2005	16168102
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?	2005	15987442
Recruitment of uterine NK cells: induction of CXC chemokine ligands 10 and 11 in human endometrium by estradiol and progesterone.	2004-12-01	15557169
Induction of the paraoxonase-1 gene expression by resveratrol.	2004-12	15458977
The cooked food derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine is a potent oestrogen: a mechanistic basis for its tissue-specific carcinogenicity.	2004-12	15319301
Effect of anti-estrogens on the androgen receptor activity and cell proliferation in prostate cancer cells.	2004-12	15316697
Proliferation-stimulating effects of icaritin and desmethylicaritin in MCF-7 cells.	2004-11-19	15541416
Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways.	2004-11	15531431
Estrogen modulates microglial inflammatory mediator production via interactions with estrogen receptor beta.	2004-11	15256495
Leptin interferes with the effects of the antiestrogen ICI 182,780 in MCF-7 breast cancer cells.	2004-10-01	15475434
Development and characterization of a cell line that stably expresses an estrogen-responsive luciferase reporter for the detection of estrogen receptor agonist and antagonists.	2004-09	15166400
Estrogen receptor alpha, but not beta, plays a major role in 17beta-estradiol-induced murine cholesterol gallstones.	2004-07	15236189
Oestrogen receptor beta is required for androgen-stimulated proliferation of LNCaP prostate cancer cells.	2004-06	15171712

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 `Mon Mar 31 18:11:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:14 GMT 2025`
Record UNII	22X328QOC4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FULVESTRANT

Official Name

English

FASLODEX

Preferred 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

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