Mestilbol
Clinical data
Trade namesMonomestro, Monomestrol
Other namesMonomethylstilbestrol; Diethylstilbestrol monomethyl ether
Drug classNonsteroidal estrogen; Estrogen ether
Identifiers
  • 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)
  • CCC(=C(CC)C1=CC=C(C=C1)OC)C2=CC=C(C=C2)O
  • 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 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]

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. ^ a b c 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. ^ a b 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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