Mestilbol

Mestilbol (brand name Monomestro or Monomestrol), 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]

Mestilbol
Clinical data
Trade namesMonomestro, Monomestrol
Other namesMonomethylstilbestrol; Diethylstilbestrol monomethyl ether
Drug classNonsteroidal estrogen; Estrogen ether
Identifiers
IUPAC name
  • 4-[(E)-4-(4-methoxyphenyl)hex-3-en-3-yl]phenol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H22O2
Molar mass282.383 g·mol−1
3D model (JSmol)
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

See also

References
  1. 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.
  2. Negwer M (1987). Organic-chemical drugs and their synonyms: (an international survey). VCH Publishers. p. 923. ISBN 978-0-89573-552-2.
  3. Council on Drugs (American Medical Association) (1955). New and Nonofficial Drugs. Lippincott. pp. 419–420.
  4. US 2385468, Emmet RE, "Monoalkyl ethers of diethylstilboestrol", issued 25 September 1945, assigned to US Filter Wallace and Tiernan Inc
  5. 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.
  6. Postgraduate Medicine. McGraw-Hill. 1949. p. 347.
  7. Annales de Bourgogne. Centre d'études bourguignonnes. 1940.
  8. Russell La Fayette C, Loeb RL (1951). A Textbook of Medicine. Saunders.
  9. Salter WT (1952). A Textbook of Pharmacology: Principles and Application of Pharmacology to the Practice of Medicine. Saunders.



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