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Mestilbol

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Mestilbol
Clinical data

Trade names	Monomestro, Monomestrol
Other names	Monomethylstilbestrol; Diethylstilbestrol monomethyl ether
Drug class	Nonsteroidal estrogen; Estrogen ether
Identifiers
IUPAC name 4-[(E)-4-(4-methoxyphenyl)hex-3-en-3-yl]phenol
CAS Number	18839-90-2
PubChem CID	3032340
ChemSpider	2297337
UNII	N44U12UW5N
ChEBI	CHEBI:34702
CompTox Dashboard (EPA)	DTXSID90860231 DTXSID7022469, DTXSID90860231
Chemical and physical data
Formula	C₁₉H₂₂O₂
Molar mass	282.383 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(=C(CC)C1=CC=C(C=C1)OC)C2=CC=C(C=C2)O
InChI InChI=1S/C19H22O2/c1-4-18(14-6-10-16(20)11-7-14)19(5-2)15-8-12-17(21-3)13-9-15/h6-13,20H,4-5H2,1-3H3/b19-18+ Key:CKMDPZMWUZDKAI-VHEBQXMUSA-N

Mestilbol (brand name MonomestroorMonomestrol), also known as diethylstilbestrol monomethyl ether, is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol.^[1]^[2]^[3] It was developed by Wallace & Tiernan Company,^[3] patented in 1940,^[4] and introduced for medical use in the 1940s,^[5] but is now no longer marketed. Mestilbol was available both as oral tablets and in oil for intramuscular injection.^[3]^[6] The drug is gradually demethylated in the body into diethylstilbestrol and hence is a prodrug of diethylstilbestrol.^[7] Mestilbol is a highly active estrogen,^[6] although somewhat less so than diethylstilbestrol,^[8] but is longer-lasting in comparison.^[9]

References[edit]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 396. ISBN 978-1-4757-2085-3.

^ Negwer M (1987). Organic-chemical drugs and their synonyms: (an international survey). VCH Publishers. p. 923. ISBN 978-0-89573-552-2.

^ ^a ^b ^c Council on Drugs (American Medical Association) (1955). New and Nonofficial Drugs. Lippincott. pp. 419–420.

^ US 2385468, Emmet RE, "Monoalkyl ethers of diethylstilboestrol", issued 25 September 1945, assigned to US Filter Wallace and Tiernan Inc

^ Sevringhaus EL (1944). "Therapy of the Patient in the Menopause: Endocrine Methods". The Journal of Clinical Endocrinology & Metabolism. 4 (12): 597–604. doi:10.1210/jcem-4-12-597. ISSN 0021-972X.

^ ^a ^b Postgraduate Medicine. McGraw-Hill. 1949. p. 347.

^ Annales de Bourgogne. Centre d'études bourguignonnes. 1940.

^ Russell La Fayette C, Loeb RL (1951). A Textbook of Medicine. Saunders.

^ Salter WT (1952). A Textbook of Pharmacology: Principles and Application of Pharmacology to the Practice of Medicine. Saunders.

Estrogens and antiestrogens

Estrogens

ER agonists

Steroidal: Alfatradiol
Certain androgens/anabolic steroids (e.g., testosterone, testosterone esters, methyltestosterone, metandienone, nandrolone esters) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone)
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol^†
Estradiol
Estradiol esters (e.g., estradiol acetate, estradiol benzoate, estradiol cypionate, estradiol enanthate, estradiol undecylate, estradiol valerate, polyestradiol phosphate, estradiol ester mixtures (Climacteron))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate, polyestriol phosphate)
Estrogenic substances
Estrone
Estrone esters
- Estrone sulfate
- Estropipate (piperazine estrone sulfate)
Ethinylestradiol^#
- Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
- Prasterone enanthate
- Prasterone sulfate
Promestriene
Quinestradol
Quinestrol

Progonadotropins

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

Antiestrogens

ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene^† Anordrin Bazedoxifene Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
Aromatase inhibitors	First-generation: Aminoglutethimide Testolactone Second-generation: Fadrozole Formestane Third-generation: Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix, elagolix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)
Others	Mixed mechanism of action: Danazol Gestrinone Androstenedione immunogens: Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)