Fosfestrol

Fosfestrol
Clinical data
Trade namesHonvan, others
Other namesDiethylstilbestrol diphosphate; Stilbestrol diphosphate; DESDP; DESP; DES-DP; DES-P
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intravenous, by mouth
Drug classNonsteroidal estrogen; Estrogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • [4-[4-(4-phosphonooxyphenyl)hex-3-en-3-yl]phenoxy]phosphonic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.573
Chemical and physical data
FormulaC18H22O8P2
Molar mass428.314 g·mol−1
3D model (JSmol)
SMILES
  • O=P(Oc1ccc(cc1)\C(=C(\c2ccc(OP(=O)(O)O)cc2)CC)CC)(O)O
InChI
  • InChI=1S/C18H22O8P2/c1-3-17(13-5-9-15(10-6-13)25-27(19,20)21)18(4-2)14-7-11-16(12-8-14)26-28(22,23)24/h5-12H,3-4H2,1-2H3,(H2,19,20,21)(H2,22,23,24)/b18-17+ Y
  • Key:NLORYLAYLIXTID-ISLYRVAYSA-N Y
  (verify)

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.[1][2][3] It is given by slow intravenous infusion once per day to once per week or by mouth once per day.[3][2]

Side effects of fosfestrol include nausea and vomiting, cardiovascular complications, blood clots, edema, and genital skin reactions, among others.[2] Fosfestrol is an estrogen, and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[2][1][4] It acts as a prodrug of diethylstilbestrol.[2][1][5]

Fosfestrol was patented in 1941 and was introduced for medical use in 1955.[6] It was previously marketed widely throughout the world, but now remains available in only a few countries.[7][8][6][3]

  1. ^ a b c Droz JP, Kattan J, Bonnay M, Chraibi Y, Bekradda M, Culine S (February 1993). "High-dose continuous-infusion fosfestrol in hormone-resistant prostate cancer". Cancer. 71 (3 Suppl): 1123–1130. doi:10.1002/1097-0142(19930201)71:3+<1123::AID-CNCR2820711434>3.0.CO;2-T. PMID 8428334. S2CID 23078614.
  2. ^ a b c d e von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U (2 July 2013). Hagers Handbuch der Pharmazeutischen Praxis: Band 8: Stoffe E-O. Springer-Verlag. pp. 301–. ISBN 978-3-642-57994-3.
  3. ^ a b c Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. pp. 2104–2105. ISBN 978-0-85369-840-1.
  4. ^ Cite error: The named reference Oettel1999 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Urotext2001 was invoked but never defined (see the help page).
  6. ^ a b Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
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