Estrone sulfate
Names | |
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IUPAC name
17-Oxoestra-1,3,5(10)-trien-3-yl hydrogen sulfate
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Systematic IUPAC name
(3aS,3bR,9bS,11aS)-11a-Methyl-1-oxo-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate | |
Other names
E1S; Oestrone sulfate; Estrone 3-sulfate; Estra-1,3,5(10)-trien-17-one 3-sulfate
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Identifiers | |
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3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.006.888 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C18H22O5S | |
Molar mass | 350.429 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a
In addition to its role as a natural hormone, estrone sulfate is used as a
Biological function
E1S itself is biologically inactive, with less than 1% of the
Unlike unconjugated estradiol and estrone, which are
E1S, serving as a precursor and intermediate for estrone and estradiol, may be involved in the
Estrogen | Other names | RBA (%)a
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REP (%)b | |||
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ER | ERα
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ERβ
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Estradiol | E2 | 100 | 100 | 100 | ||
Estradiol 3-sulfate
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E2S; E2-3S | ? | 0.02 | 0.04 | ||
Estradiol 3-glucuronide | E2-3G | ? | 0.02 | 0.09 | ||
Estradiol 17β-glucuronide
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E2-17G | ? | 0.002 | 0.0002 | ||
Estradiol benzoate | EB; Estradiol 3-benzoate | 10 | 1.1 | 0.52 | ||
Estradiol 17β-acetate | E2-17A | 31–45 | 24 | ? | ||
Estradiol diacetate | EDA; Estradiol 3,17β-diacetate | ? | 0.79 | ? | ||
Estradiol propionate
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EP; Estradiol 17β-propionate | 19–26 | 2.6 | ? | ||
Estradiol valerate | EV; Estradiol 17β-valerate | 2–11 | 0.04–21 | ? | ||
Estradiol cypionate | EC; Estradiol 17β-cypionate | ?c | 4.0 | ? | ||
Estradiol palmitate | Estradiol 17β-palmitate | 0 | ? | ? | ||
Estradiol stearate | Estradiol 17β-stearate | 0 | ? | ? | ||
Estrone | E1; 17-Ketoestradiol | 11 | 5.3–38 | 14 | ||
Estrone sulfate | E1S; Estrone 3-sulfate | 2 | 0.004 | 0.002 | ||
Estrone glucuronide | E1G; Estrone 3-glucuronide | ? | <0.001 | 0.0006 | ||
Ethinylestradiol | EE; 17α-Ethynylestradiol | 100 | 17–150 | 129 | ||
Mestranol | EE 3-methyl ether | 1 | 1.3–8.2 | 0.16 | ||
Quinestrol | EE 3-cyclopentyl ether | ? | 0.37 | ? | ||
Footnotes: a = ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure ). Sources: See template page.
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Chemistry
E1S, also known as estrone 3-sulfate or as estra-1,3,5(10)-trien-17-one 3-sulfate, is a
Biochemistry
Biosynthesis
E1S is produced via
Sex | Sex hormone | Reproductive phase |
Blood production rate |
Gonadal secretion rate |
Metabolic clearance rate |
Reference range (serum levels) | |
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SI units | Non-SI units | ||||||
Men | Androstenedione | –
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2.8 mg/day | 1.6 mg/day | 2200 L/day | 2.8–7.3 nmol/L | 80–210 ng/dL |
Testosterone | –
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6.5 mg/day | 6.2 mg/day | 950 L/day | 6.9–34.7 nmol/L | 200–1000 ng/dL | |
Estrone | –
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150 μg/day | 110 μg/day | 2050 L/day | 37–250 pmol/L | 10–70 pg/mL | |
Estradiol | –
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60 μg/day | 50 μg/day | 1600 L/day | <37–210 pmol/L | 10–57 pg/mL | |
Estrone sulfate | –
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80 μg/day | Insignificant | 167 L/day | 600–2500 pmol/L | 200–900 pg/mL | |
Women | Androstenedione | –
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3.2 mg/day | 2.8 mg/day | 2000 L/day | 3.1–12.2 nmol/L | 89–350 ng/dL |
Testosterone | –
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190 μg/day | 60 μg/day | 500 L/day | 0.7–2.8 nmol/L | 20–81 ng/dL | |
Estrone | Follicular phase | 110 μg/day | 80 μg/day | 2200 L/day | 110–400 pmol/L | 30–110 pg/mL | |
Luteal phase | 260 μg/day | 150 μg/day | 2200 L/day | 310–660 pmol/L | 80–180 pg/mL | ||
Postmenopause | 40 μg/day | Insignificant | 1610 L/day | 22–230 pmol/L | 6–60 pg/mL | ||
Estradiol | Follicular phase | 90 μg/day | 80 μg/day | 1200 L/day | <37–360 pmol/L | 10–98 pg/mL | |
Luteal phase | 250 μg/day | 240 μg/day | 1200 L/day | 699–1250 pmol/L | 190–341 pg/mL | ||
Postmenopause | 6 μg/day | Insignificant | 910 L/day | <37–140 pmol/L | 10–38 pg/mL | ||
Estrone sulfate | Follicular phase | 100 μg/day | Insignificant | 146 L/day | 700–3600 pmol/L | 250–1300 pg/mL | |
Luteal phase | 180 μg/day | Insignificant | 146 L/day | 1100–7300 pmol/L | 400–2600 pg/mL | ||
Progesterone | Follicular phase | 2 mg/day | 1.7 mg/day | 2100 L/day | 0.3–3 nmol/L | 0.1–0.9 ng/mL | |
Luteal phase | 25 mg/day | 24 mg/day | 2100 L/day | 19–45 nmol/L | 6–14 ng/mL | ||
Notes and sources
Notes: "The concentration of a steroid in the circulation is determined by the rate at which it is secreted from glands, the rate of metabolism of precursor or prehormones into the steroid, and the rate at which it is extracted by tissues and metabolized. The secretion rate of a steroid refers to the total secretion of the compound from a gland per unit time. Secretion rates have been assessed by sampling the venous effluent from a gland over time and subtracting out the arterial and peripheral venous hormone concentration. The metabolic clearance rate of a steroid is defined as the volume of blood that has been completely cleared of the hormone per unit time. The production rate of a steroid hormone refers to entry into the blood of the compound from all possible sources, including secretion from glands and conversion of prohormones into the steroid of interest. At steady state, the amount of hormone entering the blood from all sources will be equal to the rate at which it is being cleared (metabolic clearance rate) multiplied by blood concentration (production rate = metabolic clearance rate × concentration). If there is little contribution of prohormone metabolism to the circulating pool of steroid, then the production rate will approximate the secretion rate." Sources: See template. |
Distribution
Whereas free steroids like estradiol are
Studies in animals and humans have had mixed findings on uptake of exogenously administered E1S in normal and
Metabolism
The
Ovarian tumors have been found to express steroid sulfatase and have been found to convert E1S into estradiol.[30][31] This may contribute to the often elevated levels of estradiol observed in women with ovarian cancer.[30][31]
Metabolic pathways of estradiol in humans
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Levels
E1S levels have been characterized in humans.
References
- ^ S2CID 1825531.
- ISBN 978-0-08-055309-2.
- ^ S2CID 24616324.
- PMID 9048584.
- ^ ISBN 978-1-4614-6837-0.
- ISBN 978-0-323-34157-8.
- ISBN 978-1-4987-0230-0.
- ^ S2CID 46663814.
- ^ PMID 30029731.
- ^ S2CID 14296237.
- ^ S2CID 4547808.
- ^ PMID 26213785.
- PMID 21854228.
- PMID 30186172.
- ^ PMID 23717534.
- ^ PMID 28326039.
- ^ ISBN 978-1-4757-2085-3.
- ^ S2CID 42846339.
The source of E1SO4 in humans is from the peripheral conversion of E1 and E2, 6,7 [...] In human females there is little evidence for the ovarian secretion of E1SO4. 7 Since most of our monkeys were ovariectomized, we cannot say that the rhesus ovaries do not secrete E1SO4, but it is probably unlikely.
- PMID 5014608.
- PMID 5008222.
- PMID 3910206.
- S2CID 90621016.
- ^ Brooks, S. C., Horn, L., Pack, B. A., Rozhin, J., Hansen, E., & Goldberg, R. (1980). Estrogen metabolism and function in vivo and in vitro. In Estrogens in the Environment (Vol. 5, pp. 147-167). Elsevier/North Holland New York.
- ^ PMID 15561802.
- ^ S2CID 23065230.
- ^ S2CID 260167615.
- S2CID 22100628.
- PMID 15351093.
- PMID 7358033.
- ^ S2CID 25306673.
- ^ S2CID 25115594.
- S2CID 26940935.
- ^ PMID 579025.
- PMID 3653846.
- ^ PMID 9474019.
- ISSN 0077-1015.
Further reading
- Rezvanpour A, Don-Wauchope AC (March 2017). "Clinical implications of estrone sulfate measurement in laboratory medicine". Critical Reviews in Clinical Laboratory Sciences. 54 (2): 73–86. S2CID 1825531.