meso-Butestrol

meso-Butestrol (developmental code name SC-3402), also known as 2,3-bis(4-hydroxyphenyl)valeronitrile, is a synthetic nonsteroidal estrogen which was never marketed.[1][2][3][4][5][6][7] It is a so-called "short-acting" or "impeded" estrogen.[1][2][3][5][4][6][7] meso-Butestrol is structurally related to diethylstilbestrol and other stilbestrols.[8] The fully potent counterpart to meso-butestrol is meso-hexestrol, analogously to the relationship of dimethylstilbestrol to diethylstilbestrol.[3]

Meso-Butestrol

Clinical data
Other names	meso-Butoestrol; SC-3402; mbE3; 2,3-bis(4-Hydroxyphenyl)valeronitrile; meso-2,3-bis(4-Hydroxyphenyl)-n-butane
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name 2,3-bis(4-hydroxyphenyl)pentanenitrile
CAS Number	65-14-5
PubChem CID	101531
ChemSpider	91742
ChEMBL	ChEMBL463767
Chemical and physical data
Formula	C17H17NO2
Molar mass	267.328 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCC(C1=CC=C(C=C1)O)C(C#N)C2=CC=C(C=C2)O
InChI InChI=1S/C17H17NO2/c1-2-16(12-3-7-14(19)8-4-12)17(11-18)13-5-9-15(20)10-6-13/h3-10,16-17,19-20H,2H2,1H3 Key:MUSZSITXXJNLPD-UHFFFAOYSA-N

See also

• Butestrol

References

1. Miller BG, Emmens CW (September 1969). "The oestrogenic potency in the mouse of several substances closely related to diethylstilboestrol and meso-hexoestrol". J. Endocrinol. 45 (1): 9–15. doi:10.1677/joe.0.0450009. PMID 5347383.
2. Terenius L (May 1970). "Two modes of interaction between oestrogen and anti-oestrogen". Acta Endocrinol. 64 (1): 47–58. doi:10.1530/acta.0.0640047. PMID 5468795.
3. Terenius L (March 1971). "Structure-activity relationships of anti-oestrogens with regard to interaction with 17-beta-oestradiol in the mouse uterus and vagina". Acta Endocrinol. 66 (3): 431–47. doi:10.1530/acta.0.0660431. PMID 5107780.
4. Terenius L (June 1971). "The Allen-Doisy test for estrogens reinvestigated". Steroids. 17 (6): 653–61. doi:10.1016/0039-128x(71)90081-x. PMID 5104534.
5. Clark JH, Markaverich BM (1983). "The agonistic and antagonistic effects of short acting estrogens: a review". Pharmacol. Ther. 21 (3): 429–53. doi:10.1016/0163-7258(83)90063-3. PMID 6356176.
6. Lunan CB, Klopper A (September 1975). "Antioestrogens. A review". Clin. Endocrinol. (Oxf). 4 (5): 551–72. doi:10.1111/j.1365-2265.1975.tb01568.x. PMID 170029.
7. Martin L, Claringbold PJ (May 1960). "The mitogenic action of oestrogens in the vaginal epithelium of the ovariectomized mouse". J. Endocrinol. 20: 173–86. doi:10.1677/joe.0.0200173. PMID 14421704.
8. Emmens CW, Cox RI, Martin L (1964). "The oestrogenic and anti-oestrogenic activity of compounds related to diethylstilboestrol". Acta Endocrinol. 45: SUPPL90:61–9. doi:10.1530/acta.0.045s061. PMID 14117596.