Fosfestrol

Fosfestrol
Clinical data
Trade names	Honvan, others
Other names	Diethylstilbestrol diphosphate; Stilbestrol diphosphate; DESDP; DESP; DES-DP; DES-P
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intravenous, by mouth
Drug class	Nonsteroidal estrogen; Estrogen ester
ATC code	L02AA04 (WHO) ;
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	522-40-7 ; 4719-75-9 (tetrasodium);
PubChem CID	3032325;
ChemSpider	2297327 ;
UNII	A0E0NMA80F;
KEGG	D00946 ;
ChEMBL	ChEMBL1200598 ;
CompTox Dashboard (EPA)	DTXSID3046906 ;
ECHA InfoCard	100.007.573
Chemical and physical data
Formula	C18H22O8P2
Molar mass	428.314 g·mol−1
3D model (JSmol)	Interactive image;
	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+ ; Key:NLORYLAYLIXTID-ISLYRVAYSA-N ;
	(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]

^ ^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.
^ ^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.
^ ^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.
^ Cite error: The named reference Oettel1999 was invoked but never defined (see the help page).
^ Cite error: The named reference Urotext2001 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[pmid8428334-1] 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.

[BruchhausenDannhardt2013-2] 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.

[Martindale-3] 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.

[Oettel1999-4] Cite error: The named reference Oettel1999 was invoked but never defined (see the help page).

[Urotext2001-5] Cite error: The named reference Urotext2001 was invoked but never defined (see the help page).

[Publishing2013-6] Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).

[IndexNominum2000-7] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[Drugs.com-8] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

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