Estrone
From DrugPedia: A Wikipedia for Drug discovery
| Estrone
| |
| Systematic (IUPAC) name | |
| (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C18H22O2 |
| Mol. mass | 270.366 g/mol |
| Physical data | |
| Melt. point | 260.2 °C |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Protein binding | >95% |
| Metabolism | ? |
| Half life | 19 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
An aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone, a major mammalian estrogen. It is converted from ANDROSTENEDIONE directly, or from TESTOSTERONE via ESTRADIOL. In humans, it is produced primarily by the cyclic ovaries, PLACENTA, and the ADIPOSE TISSUE of men and postmenopausal women.
Pharmacology: Estrone, a synthetically prepared or naturally occurring steroidal estrogen obtained from pregnant equine urine, is the primary circulating estrogen after menopause. Estrone is naturally derived from the peripheral conversion of androstenedione by an aromatase enzyme found in adipose tissues and is converted to estradiol in peripheral tissues. Estropipate is piperazine-stabilized estrone sulfate. Estrone, and estropipate are used to treat abnormalities related to gonadotropin hormone dysfunction, vasomotor symptoms, atrophic vaginitis, and vulvar atrophy associated with menopause, and for the prevention of osteoporosis due to estrogen deficiency.
Mechanism of Action: Estrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, estrogen receptors, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Indication: For management of Menopausal and postmenopausal disorders
Contents |
[edit] PhysioChemical Properties
[edit] Melting Point
260.2 deg C EXP
[edit] Boiling Point
154 deg C EXP
[edit] log P
3.13 EXP
[edit] Water Solubility
30 mg/L at 25 EXP
[edit] Vapor Pressure
1.42E-07 mm Hg 25 EST
[edit] Henry's Law Constant
3.80E-10 atm-m3/mole 25 EST
[edit] Atmospheric OH Rate Constant
1.26E-10 cm3/molecule-sec 25 EST
[edit] 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.
