Methallenestril

Methallenestril (INN) (brand names Cur-men, Ercostrol, Geklimon, Novestrine, Vallestril), also known as methallenoestril (BAN) and as methallenestrol, as well as Horeau's acid,[1][2] is a synthetic nonsteroidal estrogen and a derivative of allenolic acid and allenestrol (specifically, a methyl ether of it) that was formerly used to treat menstrual issues but is now no longer marketed.[3][4][5][6] It is a seco-analogue of bisdehydrodoisynolic acid, and although methallenestril is potently estrogenic in rats, in humans it is only weakly so in comparison.[7] Vallestril was a brand of methallenestril issued by G. D. Searle & Company in the 1950s.[8] Methallenestril is taken by mouth.[9] By the oral route, a dose of 25 mg methallenestril is approximately equivalent to 1 mg diethylstilbestrol, 4 mg dienestrol, 20 mg hexestrol, 25 mg estrone, 2.5 mg conjugated estrogens, and 0.05 mg ethinylestradiol.[9]

Methallenestril

Clinical data
Trade names	Cur-men, Ercostrol, Geklimon, Novestrine, Vallestril (also spelled Vallestrol or Vallestryl)
Other names	Methallenoestril; Methallenestrol; Methallenoestrol; Horeau's acid; Allenestrol 6-methyl ether; α,α-Dimethyl-β-ethylallenolic acid 6-methyl ether; β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropionic acid
Routes of administration	By mouth
Drug class	Nonsteroidal estrogen
ATC code	G03CB03 (WHO) G03CC03 (WHO)
Identifiers
IUPAC name 3-(6-Methoxynaphthalen-2-yl)-2,2-dimethylpentanoic acid
CAS Number	517-18-0
PubChem CID	10599
ChemSpider	10154
UNII	XL025389JS
CompTox Dashboard (EPA)	DTXSID7023275
ECHA InfoCard	100.007.485
Chemical and physical data
Formula	C18H22O3
Molar mass	286.371 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(C)(C)C(=O)O
InChI InChI=1S/C18H22O3/c1-5-16(18(2,3)17(19)20)14-7-6-13-11-15(21-4)9-8-12(13)10-14/h6-11,16H,5H2,1-4H3,(H,19,20) Key:KHLJKRBMZVNZOC-UHFFFAOYSA-N
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See also

• Carbestrol
• Fenestrel
• Doisynoestrol
• Doisynolic acid

References

1. Erich Heftmann (1970). Steroid Biochemistry. Academic Press. p. 144.
2. Dodds, E. C. (1949). "Synthetic aestrogens". Journal of Pharmacy and Pharmacology. 1 (1): 137–147. doi:10.1111/j.2042-7158.1949.tb12391.x. ISSN 0022-3573. PMID 18114509.
3. C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1295–. ISBN 978-0-412-46630-4.
4. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.
5. John A. Thomas; Edward J. Keenan (1986). Principles of Endocrine Pharmacology. Springer Science & Business Media. pp. 171–. ISBN 978-1-4684-5036-1.
6. Herbai G, Ljunghall S (1983). "Normalization of hypercalcaemia of primary hyperparathyroidism by treatment with methallenestril, a synthetic oestrogen with low oestrogenicity". Urol. Int. 38 (6): 371–3. doi:10.1159/000280925. PMID 6659184.
7. Raymond Eller Kirk; Donald Frederick Othmer (1980). Encyclopedia of chemical technology. Wiley. p. 670. ISBN 978-0-471-02065-3.
8. Library of Congress. Copyright Office (1965). Catalog of Copyright Entries. Third Series: 1963: July-December. Copyright Office, Library of Congress. pp. 1984–.
9. Swyer GI (April 1959). "The oestrogens". Br Med J. 1 (5128): 1029–31. doi:10.1136/bmj.1.5128.1029. PMC 1993181. PMID 13638626.