Diethylstilbestrol dilaurate

Last updated
Diethylstilbestrol dilaurate
Diethylstilbestrol dilaurate.svg
Clinical data
Trade names Acnestrol-Lotion
Identifiers
  • 4-[(3E)-4-[4-(Dodecanoyloxy)phenyl]hex-3-en-3-yl]phenyl dodecanoate
Chemical and physical data
Formula C42H64O4
Molar mass 632.970 g·mol−1
3D model (JSmol)
  • CCCCCCCCCCCC(=O)OC1=CC=C(C=C1)C(\CC)=C(/CC)C1=CC=C(OC(=O)CCCCCCCCCCC)C=C1
  • InChI=1S/C42H64O4/c1-5-9-11-13-15-17-19-21-23-25-41(43)45-37-31-27-35(28-32-37)39(7-3)40(8-4)36-29-33-38(34-30-36)46-42(44)26-24-22-20-18-16-14-12-10-6-2/h27-34H,5-26H2,1-4H3/b40-39+
  • Key:GEWSRLGHTICJOA-XQQUEIPISA-N

Diethylstilbestrol dilaurate (brand name Acnestrol-Lotion) is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol (DES) that was previously marketed but is now no longer available. [1] [2] It was formulated and used as a micronized topical medication to treat acne in adolescent boys and young men. [2] [3] The drug was marketed as early as 1951. [4]

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<span class="mw-page-title-main">Diethylstilbestrol</span> Chemical compound

Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with a history of recurrent miscarriage, hormone therapy for menopausal symptoms and estrogen deficiency, treatment of prostate cancer and breast cancer, and other uses. By 2007, it was only used in the treatment of prostate cancer and breast cancer. In 2011, Hoover and colleagues reported on adverse health outcomes linked to DES including infertility, miscarriage, ectopic pregnancy, preeclampsia, preterm birth, stillbirth, infant death, menopause prior to age 45, breast cancer, cervical cancer, and vaginal cancer. While most commonly taken by mouth, DES was available for use by other routes as well, for instance, vaginal, topical, and by injection.

<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

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<span class="mw-page-title-main">Fosfestrol</span> Chemical compound

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. It is given by slow intravenous infusion once per day to once per week or by mouth once per day.

<span class="mw-page-title-main">Chlorotrianisene</span> Chemical compound

Chlorotrianisene (CTA), also known as tri-p-anisylchloroethylene (TACE) and sold under the brand name Tace among others, is a nonsteroidal estrogen related to diethylstilbestrol (DES) which was previously used in the treatment of menopausal symptoms and estrogen deficiency in women and prostate cancer in men, among other indications, but has since been discontinued and is now no longer available. It is taken by mouth.

<span class="mw-page-title-main">Acefluranol</span> Chemical compound

Acefluranol, also known as 2,3-bis(3,4-diacetoxy-5-fluorophenyl)pentane, is a nonsteroidal antiestrogen of the stilbestrol group that was never marketed. It is a polyfluorinated biphenyl that is related to polybrominated and polychlorinated biphenyls and diethylstilbestrol.

<span class="mw-page-title-main">Paroxypropione</span> Chemical compound

Paroxypropione, also known as paraoxypropiophenone, is a synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed. It was first synthesized in 1902. The antigonadotropic properties of the drug were discovered in 1951 and it entered clinical use shortly thereafter.

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<span class="mw-page-title-main">Dimestrol</span> Chemical compound

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<span class="mw-page-title-main">Furostilbestrol</span> Chemical compound

Furostilbestrol (INN), also known as diethylstilbestrol di(2-furoate) or simply as diesthylstilbestrol difuroate, is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that was never marketed. It is an ester of diethylstilbestrol and was described in the literature in 1952.

Hexestrol dicaprylate, or dioctanoylhexestrol, is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that is no longer marketed. It is a long-acting ester of hexestrol.

<span class="mw-page-title-main">Mestilbol</span> Chemical compound

Mestilbol, also known as diethylstilbestrol monomethyl ether, is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol. It was developed by Wallace & Tiernan Company, patented in 1940, and introduced for medical use in the 1940s, but is now no longer marketed. Mestilbol was available both as oral tablets and in oil for intramuscular injection. The drug is gradually demethylated in the body into diethylstilbestrol and hence is a prodrug of diethylstilbestrol. Mestilbol is a highly active estrogen, although somewhat less so than diethylstilbestrol, but is longer-lasting in comparison.

<span class="mw-page-title-main">Terfluranol</span> Synthetic estrogen

Terfluranol is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that was developed for the treatment of breast cancer but was never marketed. It was described in the medical literature in 1974.

<span class="mw-page-title-main">Pentafluranol</span> Chemical compound

Pentafluranol is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that was developed for the treatment of benign prostatic hyperplasia never marketed. It was described in the medical literature in 1974.

<span class="mw-page-title-main">Diethylstilbestrol diacetate</span> Chemical compound

Diethylstilbestrol diacetate (DESDA) is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol (DES) that was introduced for clinical use in the 1940s and was formerly marketed but is now no longer available.

<span class="mw-page-title-main">Diethylstilbestrol monobenzyl ether</span> Chemical compound

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<span class="mw-page-title-main">Diethylstilbestrol disulfate</span> Chemical compound

Diethylstilbestrol disulfate is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol (DES) that was formerly marketed but is now no longer available. It is described as an antineoplastic agent.

<span class="mw-page-title-main">ICI-85966</span> Chemical compound

ICI-85966, also known as diethylstilbestrol (DES) bis(di carbamate), is a synthetic, nonsteroidal estrogen and cytostatic antineoplastic agent of the stilbestrol group and a nitrogen mustard ester of diethylstilbestrol (DES) which was developed for the treatment of breast cancer and prostate cancer but was never marketed.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

References

  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 397. ISBN   978-1-4757-2085-3.
  2. 1 2 Canadian Pharmaceutical Association (1963). Compendium of pharmaceutical specialties (Canada) 1963. Canadian Pharmaceutical Association. p. 14.
  3. Frank SB (1971). Acne Vulgaris. Thomas. p. 259. ISBN   9780398006020.
  4. New York State Journal of Medicine. Medical Society of the State of New York. April 1951. p. 1313.