Estrone

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'''Estrone(oestrone)'''
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[http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1063&show=SHOW-3D Show 3-D Structure]
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{{drugbox
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'''Pubchem(5870)'''
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| 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
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| CAS_number = 53-16-7
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| ATC_suffix = CA07
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| ATC_supplemental = {{ATC|G03|CC04}}
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| PubChem = 5870
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| DrugBank = APRD00588
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| chemical_formula=C<sub>18</sub>H<sub>22</sub>O<sub>2</sub>
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| molecular_weight = 270.366 g/mol
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| bioavailability =
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| protein_bound = >95%
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| metabolism =
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| elimination_half-life = 19 hours
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| excretion =
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| pregnancy_category =
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| legal_status =
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| routes_of_administration =
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| melting_point = 260.2
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|
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}}
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.
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.
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'''KEGG Pathway'''(C00468,D00067)
 
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*Androgen and estrogen metabolism
 
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Activity Estrogen
 
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NEXTBIO
 
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'''Drug Type:'''  Small Molecule; Approved
 
'''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.
'''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.
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'''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.
'''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
Indication: For management of Menopausal and postmenopausal disorders
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==PhysioChemical Properties==
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===Melting Point===
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260.2 deg C EXP
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===Boiling Point===
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154 deg C EXP
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==log P==
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3.13 EXP
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===Water Solubility===
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30 mg/L at 25<sup></sup> EXP
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===Vapor Pressure===
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1.42E-07 mm Hg 25 EST
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===Henry's Law Constant===
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3.80E-10 atm-m3/mole 25 EST
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===Atmospheric OH Rate Constant===
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1.26E-10 cm3/molecule-sec 25 EST
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'''Half Life:''' 19 hours
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==Synthesis==
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Estrone is synthesized via [[aromatase]] from [[androstenedione]], a derivative of [[progesterone]]. The conversion consists of the de-[[methylation]] of C-19 and the [[aromatic]]ity of the 'A' ring. This reaction is similar to the conversion of [[testosterone]] to [[estradiol]].
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Lipinski’s “Rule of Five” Prediction for a Compound’s ABSORPTION OR PERMEABILITY PROPERTIES
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[[Category:Estrogens]]
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4 GOOD
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[[Category:Hormones]]
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3 INDETERMINATE
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2 INDETERMINATE
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1 INDETERMINATE
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0 POOR
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Table I:'''
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|-
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! style="background:brown; color:white" |Physical Property
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units
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! style="background:brown; color:white" |Temp (deg C)
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! style="background:brown; color:white" |Source
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|-
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|Melting Point
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|260.2
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|deg C
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|EXP
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|-
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|Boiling Point
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|154
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|deg C
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|EXP
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|-
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|log P (octanol-water)
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|3.13
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|(none)
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|  
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|EXP
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|-
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|Water Solubility
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|30
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|mg/L
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|25
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|EXP
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|-
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|Vapor Pressure
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|1.42E-07
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|mm Hg
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|25
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|EST
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|-
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|Henry's Law Constant
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|3.80E-10
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|atm-m3/mole
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|25
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|EST
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|-
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|Atmospheric OH Rate Constant
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|1.26E-10
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|cm3/molecule-sec
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|25
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|EST
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|-
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|}
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Current revision

Show 3-D Structure

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 53-16-7
ATC code  ?
PubChem 5870
DrugBank APRD00588
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.