Estradiol mustard - Misplaced Pages

Chemical compound Pharmaceutical compound

Estradiol mustard
Clinical data

Other names	NSC-112259; Estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate
Drug class	Chemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
IUPAC name phenyl]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopentaphenanthren-17-yl] 2-phenyl]acetate
CAS Number	22966-79-6
PubChem CID	31586
ChemSpider	29294
UNII	GEO3F3A4K1
ChEBI	CHEBI:82520
ChEMBL	ChEMBL1697793
CompTox Dashboard (EPA)	DTXSID5020574
Chemical and physical data
Formula	C₄₂H₅₀Cl₄N₂O₄
Molar mass	788.67 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(1CC2OC(=O)CC4=CC=C(C=C4)N(CCCl)CCCl)CCC5=C3C=CC(=C5)OC(=O)CC6=CC=C(C=C6)N(CCCl)CCCl
InChI 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

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. It is selectively distributed into estrogen receptor (ER)-positive tissues such as ER-expressing tumors like those seen in breast and prostate cancers. 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. 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, although estramustine phosphate has been approved for and is used (almost exclusively) in the treatment of prostate cancer.

References

Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 898–. ISBN 978-1-4757-2085-3.
^ Asai M, Takeuchi H, Okada H (January 1978). "In vivo interaction between steroidal alkylating agents and oestrogen receptors in rabbit uteri". Acta Endocrinologica. 87 (1): 173–180. doi:10.1530/acta.0.0870173. PMID 579532.
Leclercq G, Devleeschouwer N, Heuson JC (July 1983). James VH, Pasqualini JR (eds.). "Guide-lines in the design of new antiestrogens and cytotoxic-linked estrogens for the treatment of breast cancer". Journal of Steroid Biochemistry. 19 (1A). Elsevier Science: 75–85. doi:10.1016/S0022-4731(83)80009-0. ISBN 978-1-4831-9067-9. PMID 6887875.
Scullin P, O'Sullivan JM, Parker CC (5 September 2007). "Strategies for the Implementation of Chemotherapy". In Ablin RJ, Mason MD (eds.). Metastasis of Prostate Cancer. Springer Science & Business Media. pp. 311–. ISBN 978-1-4020-5847-9.

v t e Estradiol
Topics	Estradiol (as a hormone) Estradiol (as a medication) Pharmacodynamics of estradiol Pharmacokinetics of estradiol Estrogen (as a hormone) Estrogen (as a medication) Menopausal hormone therapy Feminizing hormone therapy Estradiol-containing birth control pill Combined injectable birth control High-dose estrogen Hydroxylation of estradiol
Esters	Estradiol acetate Estradiol acetylsalicylate Estradiol anthranilate Estradiol benzoate butyrate Estradiol benzoate cyclooctenyl ether Estradiol benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol diacetate Estradiol dibutyrate Estradiol dienantate Estradiol dipropionate Estradiol distearate Estradiol disulfate Estradiol diundecylate Estradiol diundecylenate Estradiol enantate Estradiol furoate Estradiol glucuronide Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol phenylpropionate Estradiol phosphate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol salicylate Estradiol stearate Estradiol sulfamate Estradiol sulfate Estradiol undecylate Estradiol undecylenate Estradiol valerate Estramustine phosphate (estradiol normustine phosphate) Estrogen ester Polyestradiol phosphate
Related	Estrone Estriol Estetrol Ethinylestradiol Conjugated estrogens Esterified estrogens Estrone sulfate Estropipate (piperazine estrone sulfate)

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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See also

References