Estradiol mustard

Estradiol mustard, also known as chlorphenacyl estradiol diester, as well as estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate, is a synthetic, steroidal estrogen and cytostatic antineoplastic agent and a chlorphenacyl nitrogen mustard-coupled estrogen ester that was never marketed.[1] It is selectively distributed into estrogen receptor (ER)-positive tissues such as ER-expressing tumors like those seen in breast and prostate cancers.[2] For this reason, estradiol mustard and other cytostatic-linked estrogens like estramustine phosphate have reduced toxicity relative to non-linked nitrogen mustard cytostatic antineoplastic agents.[2] However, they may stimulate breast tumor growth due to their inherent estrogenic activity and are said to be devoid of major therapeutic efficacy in breast cancer,[3] although estramustine phosphate has been approved for and is used (almost exclusively) in the treatment of prostate cancer.[4]

Estradiol mustard
Clinical data
Other namesNSC-112259; Chlorphenacyl estradiol diester; Estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate
Drug classChemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
  • [(8R,9S,13S,14S,17S)-3-[2-[4-[Bis(2-chloroethyl)amino]phenyl]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC42H50Cl4N2O4
Molar mass788.67 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CC4=CC=C(C=C4)N(CCCl)CCCl)CCC5=C3C=CC(=C5)OC(=O)CC6=CC=C(C=C6)N(CCCl)CCCl
  • InChI=1S/C42H50Cl4N2O4/c1-42-17-16-36-35-13-11-34(51-40(49)26-29-2-7-32(8-3-29)47(22-18-43)23-19-44)28-31(35)6-12-37(36)38(42)14-15-39(42)52-41(50)27-30-4-9-33(10-5-30)48(24-20-45)25-21-46/h2-5,7-11,13,28,36-39H,6,12,14-27H2,1H3/t36-,37-,38+,39+,42+/m1/s1
  • Key:LRSFXIJGHRPOQQ-VZRQQIPSSA-N

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 898–. ISBN 978-1-4757-2085-3.
  2. Asai M, Takeuchi H, Okada H (1978). "In vivo interaction between steroidal alkylating agents and oestrogen receptors in rabbit uteri". Acta Endocrinol. 87 (1): 173–80. doi:10.1530/acta.0.0870173. PMID 579532.
  3. V. H. T. James; J. R. Pasqualini (22 October 2013). Hormonal Steroids: Proceedings of the Sixth International Congress on Hormonal Steroids. Elsevier Science. pp. 75–. ISBN 978-1-4831-9067-9.
  4. Richard J. Ablin; Malcolm D. Mason (5 September 2007). Metastasis of Prostate Cancer. Springer Science & Business Media. pp. 311–. ISBN 978-1-4020-5847-9.


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