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Estrone
Systematic (IUPAC) name
3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one
Identifiers
CAS number 53-16-7
ATC code G03CA07 G03CC04
PubChem 5870
DrugBank APRD00588
Chemical data
Formula C 18H22O2  
Mol. mass 270.366 g/mol
Physical data
Melt. point 254.5 °C (490 °F)
Pharmacokinetic data
Bioavailability  ?
Protein binding >95%
Metabolism  ?
Half life 19 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

Estrone (also oestrone) is an estrogenic hormone secreted by the ovary as well as adipose tissue.[1]

Estrone is one of the three estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones, estradiol is present almost always in the reproductive female body, and estriol is abundant primarily during pregnancy.

Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.

Estrone is the only one of the three estrogens which is present in any quantity in post-menopausal women.

Synthesis

Estrone is synthesized via aromatase from androstenedione, a derivative of progesterone. The conversion consists of the de-methylation of C-19 and the aromaticity of the 'A' ring. This reaction is similar to the conversion of testosterone to estradiol.

Additional images

References

  1. ^ "Estrone -PubChem". National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5870&loc=ec_rcs. Retrieved 2009-09-06.  
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