Structure via PubChem · Public domain (PubChem)
fosfestrol
Sign in to saveAlso known as diethylstilbestryl diphosphate, Diethylstilbestrol bisphosphate, diethylstilbestrol diphosphate, Difostilben
Fosfestrol, sold under the brand name Honvan and also known as diethylstilbestrol diphosphate (DESDP), is an estrogen medication which is used in the treatment of prostate cancer in men. It is given by slow intravenous infusion once per day to once per week or by mouth once per day.
Chemical data
- Formula
- C18H22O8P2
- Molecular weight
- 428.3 g/mol
- IUPAC name
- [4-[(E)-4-(4-phosphonooxyphenyl)hex-3-en-3-yl]phenyl] dihydrogen phosphate
- SMILES
- CC/C(=C(/CC)\C1=CC=C(C=C1)OP(=O)(O)O)/C2=CC=C(C=C2)OP(=O)(O)O
- InChIKey
- NLORYLAYLIXTID-ISLYRVAYSA-N
- XLogP
- 2.5
- Polar surface area
- 134 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- oral, parenteral
- Indications
- neoplasm
via ChEMBL · EBI
Research
209 papers- Outcomes and toxicity of oral Fosfestrol in metastatic castration-resistant prostate cancer-a real-world experience.Ecancermedicalscience · 2023
- High-dose continuous-infusion fosfestrol in hormone-resistant prostate cancer.Cancer · 1993
- Oral self-nanoemulsifying drug delivery systems for enhancing bioavailability and anticancer potential of fosfestrol: In vitro and in vivo characterization.European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V · 2023
- The pharmacokinetics of fosfestrol and diethylstilbestrol in chronic hemodialysis patients with prostate cancer.International journal of urology : official journal of the Japanese Urological Association · 2001
- Fosfestrol-induced porphyria cutanea tarda.British journal of urology · 1989
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 428.079
Show 3 more facts
- chemical formula
- C₁₈H₂₂O₈P₂
- canonical SMILES
- CCC(=C(CC)C1=CC=C(C=C1)OP(=O)(O)O)C2=CC=C(C=C2)OP(=O)(O)O
- isomeric SMILES
- CC/C(=C(/CC)\C1=CC=C(C=C1)OP(=O)(O)O)/C2=CC=C(C=C2)OP(=O)(O)O
via Wikidata · CC0
~6 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Available forms
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- See also
- References
- Further reading
Fosfestrol, sold under the brand name Honvan and also known as diethylstilbestrol diphosphate (DESDP), is an estrogen medication which is used in the treatment of prostate cancer in men. It is given by slow intravenous infusion once per day to once per week or by mouth once per day.
Side effects of fosfestrol include nausea and vomiting, cardiovascular complications, blood clots, edema, and genital skin reactions, among others. Fosfestrol is an estrogen, and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol. It acts as a prodrug of diethylstilbestrol.
Excerpted from Wikipedia’s “fosfestrol” article, available under the CC BY-SA 4.0 licence.