Page last updated: 2024-12-10

fosfestrol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

fosfestrol: Rx of prostatic carcinoma; RN given refers to parent cpd with unspecified isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3032325
CHEMBL ID1200598
CHEBI ID4532
SCHEMBL ID9370
MeSH IDM0046203

Synonyms (77)

Synonym
fosfestrolum
a0e0nma80f ,
fosfestrol [inn]
diethylstilbestrol diphosphate [usp]
phenol, 4,4'-((1e)-1,2-diethyl-1,2-ethenediyl)bis-, bis(dihydrogen phosphate)
unii-a0e0nma80f
stilphostrol
nsc10481
NCGC00181335-01
diethylstilbestrol bisphosphate
C08145
diethylstilbestrol diphosphate
fosfestrol
522-40-7
diethylstilbestrol diphosphate (usp)
stilphostrol (tn)
D00946
fosfestrol (jan/inn)
difostilben
stilbestrol diphosphate
st-52
honvan
fosfesterol
c18h22o8p2
diethyldioxystilbene diphosphate
diethylstilbestryl diphosphate
honvol
desdp
phenol, 4,4'-(1,2-diethyl-1,2-ethenediyl)bis-, bis(dihydrogen phosphate), (e)-
ccris 2778
einecs 208-328-8
diethylstilbesterol diphosphate
fosfestrolum [inn-latin]
alpha,alpha'-diethyl-(e)-4,4'-stilbenediol bis(dihydrogen phosphate)
phosphoestrolum
phosphestrol
st52-asta
4,4'-stilbenediol, alpha,alpha'-diethyl-, bis(dihydrogen phosphate), (e)-
chebi:4532 ,
CHEMBL1200598
[4-[(e)-4-(4-phosphonooxyphenyl)hex-3-en-3-yl]phenyl] dihydrogen phosphate
AKOS005267157
3-hexene-3,4-diylbis(4,1-phenylene) bis[dihydrogen (phosphate)]
dtxcid1026906
tox21_112794
dtxsid3046906 ,
cas-522-40-7
phenol, 4,4'-[(1e)-1,2-diethyl-1,2-ethenediyl]bis-, bis(dihydrogen phosphate)
.alpha.,.alpha.'-diethyl-(e)-4,4'-stilbenediol bis(dihydrogen phosphate)
fosfestrol [who-dd]
diethylstilbestrol diphosphate [orange book]
fosfestrol [mart.]
phenol, 4,4'-(1,2-diethyl-1,2-ethenediyl)bis-, bis(dihydrogen phosphate), (e)
fosfestrol [jan]
fosfestrol [mi]
diethylstilbestrol diphosphate [vandf]
SCHEMBL9370
(e)-hex-3-ene-3,4-diylbis(4,1-phenylene) bis(dihydrogen phosphate)
[4-[(e)-1-ethyl-2-(4-phosphonooxyphenyl)but-1-enyl]phenyl] dihydrogen phosphate
alpha,alpha'-diethyl-4,4'-stilbenediol diphosphoric acid ester
SR-01000945066-1
sr-01000945066
4-{1-ethyl-2-[4-(phosphonooxy)phenyl]-1-butenyl}phenyl dihydrogen phosphate
(e)-4,4'-(hex-3-ene-3,4-diyl)bis(4,1-phenylene) bis(dihydrogen phosphate)
Q1003185
BB 0266147
fosfestrolum (inn-latin)
diethylstilbestrol 4,4'-diphosphoric ester
(e)-4,4'-(1,2-ethenediyl)-bisphenol bis(dihydrogen phosphate)
st 52-asta
4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol bis(dihydrogen phosphate) (e)-
(e)-4,4'-(hex-3-ene-3,4-diyl)-bis(phenyl dihydrogen phosphate)
l02aa04
stilboestrol diphosphate
desp
fosfestrolo
fosfestrol (mart.)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"A clinical study of the adverse effects induced by the endocrine therapy with a high dose of estrogen in 45 patients with stage C or D prostatic carcinoma is conducted."( Adverse effects during endocrine therapy for prostatic carcinoma with a high dose of estrogen.
Ishisawa, N; Ohfuji, T; Osada, Y; Shinkawa, T, 1985
)
0.27
" However, in Japan the adverse effects of estrogen have been reported to be milder than in western countries, and estrogen still has an important role in the treatment of prostatic cancer in Japan."( [Side effects of estrogen administration to prostatic cancer patients: clinical and statistical survey of 109 prostatic cancer cases of Kyoto University Hospital].
Arai, Y; Oishi, K; Takeuchi, H; Yoshida, O, 1993
)
0.29

Compound-Compound Interactions

ExcerptReferenceRelevance
"We evaluated the usefulness of hormonal therapy combined with UFT as initial treatment in comparison with hormonal therapy alone in 92 patients with Stage D2 prostatic cancer treated at the Department of Urology, Dokkyo University School of Medicine between 1974 and 1993."( [Clinical evaluation of chemohormonal therapy as an initial treatment for stage D2 prostatic cancer--effect of UFT administration combined with hormonal therapy].
Chen, JA; Honda, M; Hosoya, Y; Imai, T; Maeda, S; Suzuki, T; Takasaki, E, 1995
)
0.29
" We evaluated the efficacy of cytotoxic chemotherapy in combination with hormone therapy in patients with newly diagnosed metastatic prostatic cancer."( [Comparison of hormone therapy alone and in combination with chemotherapy of cisplatin and methotrexate in newly diagnosed patients with stage D2 prostatic cancer].
Komatus, H; Maesawa, H; Tago, K; Tanabe, N; Ueno, A, 1996
)
0.29
"This prospective and randomized clinical study was initiated to compare the efficacy and safety of combined androgen blockade with combination with UFT in patients with untreated prostate cancer."( Prospective and randomized comparison of combined androgen blockade versus combination with oral UFT as an initial treatment for prostate cancer.
Kuriyama, M; Ohshima, S; Ono, Y; Sahashi, M; Shimizu, H; Takahashi, Y; Tanaka, T, 2001
)
0.31
" This technique has been used most commonly to treat prostate cancers in combination with hormonal therapy."( Rotational 3D-conformal radiation therapy (conformation therapy) combined with hormone therapy for the treatment of stage B2/C prostate cancer in Japanese men.
Igaki, H; Kaizu, T; Karasawa, K; Matsuda, T; Niibe, Y; Shinohara, M; Tanaka, Y, 2003
)
0.32
"Rotational 3D-conformal radiation therapy combined with hormone therapy might be promising for the treatment of prostate cancer."( Rotational 3D-conformal radiation therapy (conformation therapy) combined with hormone therapy for the treatment of stage B2/C prostate cancer in Japanese men.
Igaki, H; Kaizu, T; Karasawa, K; Matsuda, T; Niibe, Y; Shinohara, M; Tanaka, Y, 2003
)
0.32

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
"The objective of the current research work was to fabricate a fosfestrol (FST)-loaded self-nanoemulsifying drug delivery system (SNEDDS) to escalate the oral solubility and bioavailability and thereby the effectiveness of FST against prostate cancer."( Oral self-nanoemulsifying drug delivery systems for enhancing bioavailability and anticancer potential of fosfestrol: In vitro and in vivo characterization.
Alsalhi, A; Bhagwat, DA; Galatage, ST; Manjappa, AS; Sabei, FY; Salawi, A; Trivedi, R, 2023
)
1.36
"5-fold rise in bioavailability was observed after oral administration of FSTNE than plain FST."( Oral self-nanoemulsifying drug delivery systems for enhancing bioavailability and anticancer potential of fosfestrol: In vitro and in vivo characterization.
Alsalhi, A; Bhagwat, DA; Galatage, ST; Manjappa, AS; Sabei, FY; Salawi, A; Trivedi, R, 2023
)
1.12
"FSTNE remarkably enhanced the in vitro anticancer activity and Caco-2 cell permeability, and in vivo bioavailability of FST."( Oral self-nanoemulsifying drug delivery systems for enhancing bioavailability and anticancer potential of fosfestrol: In vitro and in vivo characterization.
Alsalhi, A; Bhagwat, DA; Galatage, ST; Manjappa, AS; Sabei, FY; Salawi, A; Trivedi, R, 2023
)
1.12

Dosage Studied

ExcerptRelevanceReference
" As a result the use of Cytonal at least in the dosage hitherto used is no longer worth being advocated."( [Cellular immunity in prostatic cancer modified by Cytonal, Estrazyt and Turisteron].
Fiedler, R; Klebingat, KJ; Lorenz, G; Panzig, E; Steinhauser, I, 1987
)
0.27
" In rats, stilphostrol does not selectively liberate DES in the prostate compared to dosing with DES itself."( Bioavailability, distribution and pharmacokinetics of diethystilbestrol produced from stilphostrol.
Abramson, FP; Miller, HC, 1982
)
0.26
" As a rule of dosing schedule for chemo-hormonal therapy, 30-60mg/sq m of etoposide was continuously administered for 5 days before operation in addition to 250-500 mg of diethylbestrol diphosphate given for 30 days after operation."( [Surgical neoadjuvant chemo-hormonal therapy for advanced prostatic carcinoma].
Maruoka, M; Miyauchi, T; Nagayama, T; Nishikawa, Y, 1994
)
0.29
"517 mumol/l, which corresponded to an only three-fold dosage variation."( A 125I-radioimmunoassay for diethylstilbestrol in serum of patients with prostatic cancer treated with stilphostrol.
Economou, EV; Evangelatos, GP; Ithakissios, DS; Livaniou, E, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aryl phosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.06500.000229.305416,493.5996AID743075; AID743077; AID743079
Bloom syndrome protein isoform 1Homo sapiens (human)Potency39.81070.540617.639296.1227AID2528
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (191)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990109 (57.07)18.7374
1990's53 (27.75)18.2507
2000's25 (13.09)29.6817
2010's2 (1.05)24.3611
2020's2 (1.05)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.04

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.04 (24.57)
Research Supply Index5.43 (2.92)
Research Growth Index4.16 (4.65)
Search Engine Demand Index55.95 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials27 (13.50%)5.53%
Reviews12 (6.00%)6.00%
Case Studies31 (15.50%)4.05%
Observational0 (0.00%)0.25%
Other130 (65.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
A Randomized Phase III Trial of Dexamethasone and Aspirin (DA) Versus Dexamethasone, Diethylstilbestrol and Aspirin (DAS) in Locally Advanced or Metastatic Cancer of the Prostate - Immediate Versus Deferred Diethylstilbestrol [NCT00316927]Phase 3260 participants (Anticipated)Interventional2002-12-31Completed
Docetaxel and Diethylstilbestrol in the Treatment of Androgen Independent Prostate Cancer: A Phase II Study [NCT00136526]Phase 230 participants (Actual)Interventional2002-12-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]