trans-Clomiphene Citrate Chemical Properties

Melting point:

143-145°C

storage temp. 

Amber Vial, -20°C Freezer

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicated)

form 

Solid

color 

White to Off-White

Stability:

Light Sensitive

InChI

InChI=1S/C26H28ClNO.C6H8O7/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,3-4,19-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25+;

InChIKey

PYTMYKVIJXPNBD-BTKVJIOYSA-N

SMILES

Cl/C(/C1C([H])=C([H])C([H])=C([H])C=1[H])=C(\C1C([H])=C([H])C([H])=C([H])C=1[H])/C1C([H])=C([H])C(=C([H])C=1[H])OC([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])[H].O([H])C(C(=O)O[H])(C([H])([H])C(=O)O[H])C([H])([H])C(=O)O[H]

trans-Clomiphene Citrate Usage And Synthesis

Uses

trans-Clomiphene Citrate, stereoisomer of Clomiphene Citrate (C587025), a synthetic estrogen agonist-antagonist. Gonad-stimulating principle.

Toxicology

The effects of the cis and trans isomers of clomiphene citrate on the uterine hexokinase activity of immature ovariectomized rats were studied in long- and short-term experiments. At a dose level of 600 μg/kg, both trans-Clomiphene Citrate and cis-Clomiphene Citrate caused a similar increase in total uterine hexokinase activity observable in 18 hr. When enzyme activity was expressed per g of the uterus (specific activity), significant increases were noted 18 hr after a single injection of trans clomiphene or after 4 daily injections of either isomer. Treatment of these animals with 170-estradiol (5 μg/kg) caused an elevation of both the specific and total hexokinase activities within 18 hr[1].

References

[1] D L DiPietro, D A Goss, F J Sanders. “Effect of cis and trans isomers of clomiphene citrate on uterine hexokinase activity.” Endocrinology 84 6 (1969): 1404–8.

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