{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-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 | image = Estradiol mustard.svg | image_class = skin-invert-image | width = 250px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Chemotherapeutic agent; Estrogen; Estrogen ester
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = | CAS_number = 22966-79-6 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 31586 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 29294 | UNII = GEO3F3A4K1 | KEGG = | ChEBI = 82520 | ChEMBL = 1697793 | synonyms = NSC-112259; Estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate
<!--Chemical data--> | C=42 | H=50 | Cl=4 | N=2 | O=4 | SMILES = 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 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = LRSFXIJGHRPOQQ-VZRQQIPSSA-N }}
'''Estradiol mustard''', also known as '''estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate''', is a semisynthetic, steroidal estrogen and cytostatic antineoplastic agent and a phenylacetic acid nitrogen mustard-coupled estrogen ester that was never marketed.<ref name="Elks2014">{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA898|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=898–}}</ref> It is selectively distributed into estrogen receptor (ER)-positive tissues such as ER-expressing tumors like those seen in breast and prostate cancers.<ref name="pmid579532">{{cite journal | vauthors = Asai M, Takeuchi H, Okada H | title = In vivo interaction between steroidal alkylating agents and oestrogen receptors in rabbit uteri | journal = Acta Endocrinologica | volume = 87 | issue = 1 | pages = 173–180 | date = January 1978 | pmid = 579532 | doi = 10.1530/acta.0.0870173 }}</ref> 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.<ref name="pmid579532" /> 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,<ref name="JamesPasqualini2013">{{cite journal | vauthors = Leclercq G, Devleeschouwer N, Heuson JC | title = Guide-lines in the design of new antiestrogens and cytotoxic-linked estrogens for the treatment of breast cancer | journal = Journal of Steroid Biochemistry | volume = 19 | issue = 1A | pages = 75–85 | date = July 1983 | pmid = 6887875 | doi = 10.1016/S0022-4731(83)80009-0| url = https://books.google.com/books?id=1VMJAwAAQBAJ&pg=PA75 |publisher=Elsevier Science|isbn=978-1-4831-9067-9 | veditors = James VH, Pasqualini JR | url-access = subscription }}</ref> although estramustine phosphate has been approved for and is used (almost exclusively) in the treatment of prostate cancer.<ref name="AblinMason2007">{{cite book | vauthors = Scullin P, O'Sullivan JM, Parker CC | chapter = Strategies for the Implementation of Chemotherapy| veditors = Ablin RJ, Mason MD |title=Metastasis of Prostate Cancer| chapter-url= https://books.google.com/books?id=AAo2qVvcVJcC&pg=PA311 |date=5 September 2007|publisher=Springer Science & Business Media|isbn=978-1-4020-5847-9|pages=311–}}</ref>
== See also == * List of hormonal cytostatic antineoplastic agents * List of estrogen esters § Estradiol esters
== References == {{Reflist}}
{{Estradiol}} {{Estrogen receptor modulators}}
Category:Abandoned drugs Category:Antineoplastic drugs Category:Chloroethyl compounds Category:Estradiol esters Category:Nitrogen mustards Category:Synthetic estrogens
{{Estrane-stub}} {{Genito-urinary-drug-stub}} {{Antineoplastic-drug-stub}}