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meso-Butestrol

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Meso-Butestrol
Clinical data

Other names	meso-Butoestrol; SC-3402; mbE₃; meso-2,3-bis(4-Hydroxyphenyl)-n-butane
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name 4-[(2S,3R)-3-(4-hydroxyphenyl)butan-2-yl]phenol
CAS Number	2962-14-3^Y
PubChem CID	200945
ChemSpider	173970
UNII	PQ4GVS4T9S
ChEMBL	ChEMBL326340
CompTox Dashboard (EPA)	DTXSID00183802
Chemical and physical data
Formula	C₁₆H₁₈O₂
Molar mass	242.318 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H](C1=CC=C(C=C1)O)[C@@H](C)C2=CC=C(C=C2)O
InChI InChI=1S/C16H18O2/c1-11(13-3-7-15(17)8-4-13)12(2)14-5-9-16(18)10-6-14/h3-12,17-18H,1-2H3/t11-,12+ Key:GDUYFVYTXYOMSJ-TXEJJXNPSA-N

meso-Butestrol (developmental code name SC-3402), also known as 2,3-bis(4-hydroxyphenyl)butane, 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]

References[edit]

^ ^a ^b 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.

^ ^a ^b 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.

^ ^a ^b ^c 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.

^ ^a ^b 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.

^ ^a ^b 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.

^ ^a ^b 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. S2CID 9628572.

^ ^a ^b Martin L, Claringbold PJ (May 1960). "The mitogenic action of oestrogens in the vaginal epithelium of the ovariectomized mouse". J. Endocrinol. 20 (3): 173–86. doi:10.1677/joe.0.0200173. PMID 14421704.

^ Emmens CW, Cox RI, Martin L (1964). "The oestrogenic and anti-oestrogenic activity of compounds related to diethylstilboestrol". Acta Endocrinol. 45 (4_Suppl): SUPPL90:61–9. doi:10.1530/acta.0.045s061. PMID 14117596.