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
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
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00947Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/ppa/fulvestrant.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16251200
Curator's Comment:: Fulvestrant does not cross the blood–brain barrier
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26407012 |
0.0631 nM [IC50] | ||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26407012 |
0.1 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FASLODEX Approved UseFASLODEX 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 Date1.01753278E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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: |
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
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: |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes | ||||
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/fulvestrant.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24793639
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
Edited
Fri Jun 25 21:04:39 UTC 2021
by
admin
on
Fri Jun 25 21:04:39 UTC 2021
|
Record UNII |
22X328QOC4
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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] | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | ||
|
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
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
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 |
|
|
|||