Estradiol mustard
Identifiers | |
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Systematic (IUPAC) name: [(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
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Synonyms | NSC-112259; Chlorphenacyl estradiol diester |
CAS Number | 22966-79-6 |
PubChem (CID) | 31586 |
ChemSpider | 29294 |
UNII | GEO3F3A4K1 |
ChEBI | CHEBI:82520 |
ChEMBL | CHEMBL1697793 |
Chemical and physical data | |
Formula | C42H50Cl4N2O4 |
Molar mass | 788.6694 g/mol |
3D model (Jmol) | Interactive image |
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Estradiol mustard (developmental code name NSC-112259), 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 alkylating antineoplastic agent and a 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 have reduced toxicity relative to non-linked nitrogen mustard alkylating 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 has been approved for and is used (almost exclusively) in the treatment of prostate cancer.[4]
See also[edit]
References[edit]
- ^ 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.
- ^ a b 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. PMID 579532.
- ^ 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.
- ^ 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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