Estradiol
Names | |
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Pronunciation | /ˌɛstrəˈdaɪoʊl/ ES-trə-DY-ohl[1][2] |
IUPAC name
Estra-1,3,5(10)-triene-3,17β-diol
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Systematic IUPAC name
(1S,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,7-diol | |
Other names
Oestradiol; E2; 17β-Estradiol; 17β-Oestradiol
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.000.022 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C18H24O2 | |
Molar mass | 272.38 g/mol |
-186.6·10−6 cm3/mol | |
Pharmacology | |
G03CA03 (WHO) | |
License data | |
ester), subdermal implant
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Pharmacokinetics: | |
Oral: <5%[3] | |
~98%:[3][4] • Albumin: 60% • SHBG: 38% • Free: 2% | |
Liver (via hydroxylation, sulfation, glucuronidation) | |
Oral: 13–20 hours[3] Sublingual: 8–18 hours[5] Topical (gel): 36.5 hours[6] | |
Urine: 54%[3] Feces: 6%[3] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Estradiol (E2), also spelled oestradiol, is an
Though estradiol levels in males are much lower than in females, estradiol has important roles in males as well. Apart from humans and other mammals, estradiol is also found in most vertebrates and crustaceans, insects, fish, and other animal species.[8][9]
Estradiol is produced especially within the
In addition to its role as a natural hormone, estradiol is used as a
Biological function
Sexual development
The development of
Reproduction
Female reproductive system
In the female, estradiol acts as a growth hormone for tissue of the reproductive organs, supporting the lining of the
Male reproductive system
The effect of estradiol (and estrogens in general) upon male reproduction is complex. Estradiol is produced by action of aromatase mainly in the Leydig cells of the mammalian testis, but also by some germ cells and the Sertoli cells of immature mammals.[14] It functions (in vitro) to prevent apoptosis of male sperm cells.[15] While some studies in the early 1990s claimed a connection between globally declining
Males with certain
Skeletal system
Estradiol has a profound effect on bone. Individuals without it (or other estrogens) will become tall and
Skin health
The
Hormone replacement therapy consisting of systemic treatment with estrogen alone or in combination with a progestogen, has well-documented and considerable beneficial effects on the skin of postmenopausal women.[25][26] These benefits include increased skin collagen content, skin thickness and elasticity, and skin hydration and surface lipids.[25][26] Topical estrogen has been found to have similar beneficial effects on the skin.[25] In addition, a study has found that topical 2% progesterone cream significantly increases skin elasticity and firmness and observably decreases wrinkles in peri- and postmenopausal women.[26] Skin hydration and surface lipids, on the other hand, did not significantly change with topical progesterone.[26] These findings suggest that progesterone, like estrogen, also has beneficial effects on the skin, and may be independently protective against skin aging.[26]
Nervous system
Estrogens can be produced in the
The positive and negative
Estrogen is considered to play a significant role in women's mental health, with links suggested between the hormone level, mood and well-being. Sudden drops or fluctuations in, or long periods of sustained low levels of estrogen may be correlated with significant mood-lowering. Clinical recovery from depression postpartum, perimenopause, and postmenopause was shown to be effective after levels of estrogen were stabilized and/or restored.[29][30]
The volumes of
There is also evidence the programming of adult male sexual behavior in many vertebrates is largely dependent on estradiol produced during prenatal life and early infancy.[32] It is not yet known whether this process plays a significant role in human sexual behavior, although evidence from other mammals tends to indicate a connection.[33]
Estrogen has been found to increase the secretion of oxytocin and to increase the expression of its receptor, the oxytocin receptor, in the brain.[34] In women, a single dose of estradiol has been found to be sufficient to increase circulating oxytocin concentrations.[35]
Gynecological cancers
Estradiol has been tied to the development and progression of cancers such as breast cancer, ovarian cancer and endometrial cancer. Estradiol affects target tissues mainly by interacting with two
Cardiovascular system
Estrogen affects certain
During
Absolute incidence of first VTE per 10,000 person–years during pregnancy and the postpartum period | ||||||||
---|---|---|---|---|---|---|---|---|
Swedish data A | Swedish data B | English data | Danish data | |||||
Time period | N | Rate (95% CI) | N | Rate (95% CI) | N | Rate (95% CI) | N | Rate (95% CI) |
Outside pregnancy | 1105 | 4.2 (4.0–4.4) | 1015 | 3.8 (?) | 1480 | 3.2 (3.0–3.3) | 2895 | 3.6 (3.4–3.7) |
Antepartum | 995 | 20.5 (19.2–21.8) | 690 | 14.2 (13.2–15.3) | 156 | 9.9 (8.5–11.6) | 491 | 10.7 (9.7–11.6) |
Trimester 1 | 207 | 13.6 (11.8–15.5) | 172 | 11.3 (9.7–13.1) | 23 | 4.6 (3.1–7.0) | 61 | 4.1 (3.2–5.2) |
Trimester 2 | 275 | 17.4 (15.4–19.6) | 178 | 11.2 (9.7–13.0) | 30 | 5.8 (4.1–8.3) | 75 | 5.7 (4.6–7.2) |
Trimester 3 | 513 | 29.2 (26.8–31.9) | 340 | 19.4 (17.4–21.6) | 103 | 18.2 (15.0–22.1) | 355 | 19.7 (17.7–21.9) |
Around delivery | 115 | 154.6 (128.8–185.6) | 79 | 106.1 (85.1–132.3) | 34 | 142.8 (102.0–199.8) | –
| |
Postpartum | 649 | 42.3 (39.2–45.7) | 509 | 33.1 (30.4–36.1) | 135 | 27.4 (23.1–32.4) | 218 | 17.5 (15.3–20.0) |
Early postpartum | 584 | 75.4 (69.6–81.8) | 460 | 59.3 (54.1–65.0) | 177 | 46.8 (39.1–56.1) | 199 | 30.4 (26.4–35.0) |
Late postpartum | 65 | 8.5 (7.0–10.9) | 49 | 6.4 (4.9–8.5) | 18 | 7.3 (4.6–11.6) | 319 | 3.2 (1.9–5.0) |
Incidence rate ratios (IRRs) of first VTE during pregnancy and the postpartum period | ||||||||
Swedish data A | Swedish data B | English data | Danish data | |||||
Time period | IRR* (95% CI) | IRR* (95% CI) | IRR (95% CI)† | IRR (95% CI)† | ||||
Outside pregnancy | Reference (i.e., 1.00)
| |||||||
Antepartum | 5.08 (4.66–5.54) | 3.80 (3.44–4.19) | 3.10 (2.63–3.66) | 2.95 (2.68–3.25) | ||||
Trimester 1 | 3.42 (2.95–3.98) | 3.04 (2.58–3.56) | 1.46 (0.96–2.20) | 1.12 (0.86–1.45) | ||||
Trimester 2 | 4.31 (3.78–4.93) | 3.01 (2.56–3.53) | 1.82 (1.27–2.62) | 1.58 (1.24–1.99) | ||||
Trimester 3 | 7.14 (6.43–7.94) | 5.12 (4.53–5.80) | 5.69 (4.66–6.95) | 5.48 (4.89–6.12) | ||||
Around delivery | 37.5 (30.9–44.45) | 27.97 (22.24–35.17) | 44.5 (31.68–62.54) | –
| ||||
Postpartum | 10.21 (9.27–11.25) | 8.72 (7.83–9.70) | 8.54 (7.16–10.19) | 4.85 (4.21–5.57) | ||||
Early postpartum | 19.27 (16.53–20.21) | 15.62 (14.00–17.45) | 14.61 (12.10–17.67) | 8.44 (7.27–9.75) | ||||
Late postpartum | 2.06 (1.60–2.64) | 1.69 (1.26–2.25) | 2.29 (1.44–3.65) | 0.89 (0.53–1.39) | ||||
Notes: Swedish data A = Using any code for VTE regardless of confirmation. Swedish data B = Using only algorithm-confirmed VTE. Early postpartum = First 6 weeks after delivery. Late postpartum = More than 6 weeks after delivery. * = Adjusted for age and calendar year. † = Unadjusted ratio calculated based on the data provided. Source: [41] |
Other functions
Estradiol has complex effects on the
Certain gynecological conditions are dependent on estrogen, such as
Biological activity
Estradiol acts primarily as an
ERα/ERβ are in inactive state trapped in multimolecular chaperone complexes organized around the heat shock protein 90 (HSP90), containing p23 protein, and immunophilin, and located in majority in cytoplasm and partially in nucleus. In the E2 classical pathway or estrogen classical pathway, estradiol enters the
Given by
Estrogen | RBA (%) |
Uterine weight (%) | Uterotrophy |
LH levels (%) | RBA (%)
|
---|---|---|---|---|---|
Control | – | 100 | – | 100 | – |
Estradiol (E2) | 100 | 506 ± 20 | +++ | 12–19 | 100 |
Estrone (E1) | 11 ± 8 | 490 ± 22 | +++ | ? | 20 |
Estriol (E3) | 10 ± 4 | 468 ± 30 | +++ | 8–18 | 3 |
Estetrol (E4) | 0.5 ± 0.2 | ? | Inactive | ? | 1 |
17α-Estradiol | 4.2 ± 0.8 | ? | ? | ? | ? |
2-Hydroxyestradiol | 24 ± 7 | 285 ± 8 | +b | 31–61 | 28 |
2-Methoxyestradiol | 0.05 ± 0.04 | 101 | Inactive | ? | 130 |
4-Hydroxyestradiol | 45 ± 12 | ? | ? | ? | ? |
4-Methoxyestradiol | 1.3 ± 0.2 | 260 | ++ | ? | 9 |
4-Fluoroestradiola | 180 ± 43 | ? | +++ | ? | ? |
2-Hydroxyestrone | 1.9 ± 0.8 | 130 ± 9 | Inactive | 110–142 | 8 |
2-Methoxyestrone | 0.01 ± 0.00 | 103 ± 7 | Inactive | 95–100 | 120 |
4-Hydroxyestrone | 11 ± 4 | 351 | ++ | 21–50 | 35 |
4-Methoxyestrone | 0.13 ± 0.04 | 338 | ++ | 65–92 | 12 |
16α-Hydroxyestrone | 2.8 ± 1.0 | 552 ± 42 | +++ | 7–24 | <0.5 |
2-Hydroxyestriol | 0.9 ± 0.3 | 302 | +b | ? | ? |
2-Methoxyestriol | 0.01 ± 0.00 | ? | Inactive | ? | 4 |
Notes: Values are mean ± SD or range. ER RBA = endogenous ). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.
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Biochemistry
Biosynthesis
Estradiol, like other
During the reproductive years, most estradiol in women is produced by the granulosa cells of the ovaries by the aromatization of androstenedione (produced in the theca folliculi cells) to estrone, followed by conversion of estrone to estradiol by 17β-HSD. Smaller amounts of estradiol are also produced by the adrenal cortex, and, in men, by the testes.[medical citation needed]
Estradiol is not produced in the gonads only; in particular, fat cells produce active precursors to estradiol, and will continue to do so even after menopause.[51] Estradiol is also produced in the brain and in arterial walls.
In men, approximately 15 to 25% of circulating estradiol is produced in the testicles.[52][53] The rest is synthesized via peripheral aromatization of testosterone into estradiol and of androstenedione into estrone (which is then transformed into estradiol via peripheral 17β-HSD).[52][53] This peripheral aromatization occurs predominantly in adipose tissue, but also occurs in other tissues such as bone, liver, and the brain.[52] Approximately 40 to 50 µg of estradiol is produced per day in men.[52]
Distribution
In plasma, estradiol is largely bound to SHBG and albumin. Only about 2.21% (± 0.04%) of estradiol is free and biologically active. The percentage remains constant throughout the menstrual cycle.[54]
Metabolism
Metabolic pathways of estradiol in humans
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Inactivation of estradiol includes conversion to less-active estrogens, such as estrone and estriol. Estriol is the major urinary
Estradiol is also metabolized via
Estradiol is additionally
Excretion
Estradiol is
Levels
Levels of estradiol in premenopausal women are highly variable throughout the menstrual cycle and reference ranges widely vary from source to source.[62] Estradiol levels are minimal and according to most laboratories range from 20 to 80 pg/mL during the early to mid follicular phase (or the first week of the menstrual cycle, also known as menses).[63][64] Levels of estradiol gradually increase during this time and through the mid to late follicular phase (or the second week of the menstrual cycle) until the pre-ovulatory phase.[62][63] At the time of pre-ovulation (a period of about 24 to 48 hours), estradiol levels briefly surge and reach their highest concentrations of any other time during the menstrual cycle.[62] Circulating levels are typically between 130 and 200 pg/mL at this time, but in some women may be as high as 300 to 400 pg/mL, and the upper limit of the reference range of some laboratories are even greater (for instance, 750 pg/mL).[62][63][65][66][67] Following ovulation (or mid-cycle) and during the latter half of the menstrual cycle or the luteal phase, estradiol levels plateau and fluctuate between around 100 and 150 pg/mL during the early and mid luteal phase, and at the time of the late luteal phase, or a few days before menstruation, reach a low of around 40 pg/mL.[62][64] The mean integrated levels of estradiol during a full menstrual cycle have variously been reported by different sources as 80, 120, and 150 pg/mL.[64][68][69] Although contradictory reports exist, one study found mean integrated estradiol levels of 150 pg/mL in younger women whereas mean integrated levels ranged from 50 to 120 pg/mL in older women.[69]
During the reproductive years of human females, levels of estradiol are somewhat higher than that of estrone, except during the early follicular phase of the menstrual cycle; thus, estradiol may be considered the predominant estrogen during human female reproductive years in terms of absolute serum levels and estrogenic activity.[
Group | E2 (prod) | E2 (levels) | E1 (levels) | Ratio |
---|---|---|---|---|
Pubertal girlsa Tanner stage I (childhood) Tanner stage II (ages 8–12) Tanner stage III (ages 10–13) Tanner stage IV (ages 11–14) Tanner stage V (ages 12–15) Follicular (days 1–14) Luteal (days 15–28) |
? ? ? ? ? ? |
9 (<9–20) pg/mL 15 (<9–30) pg/mL 27 (<9–60) pg/mL 55 (16–85) pg/mL 50 (30–100) pg/mL 130 (70–300) pg/mL |
13 (<9–23) pg/mL 18 (10–37) pg/mL 26 (17–58) pg/mL 36 (23–69) pg/mL 44 (30–89) pg/mL 75 (39–160) pg/mL |
? ? ? ? ? ? |
Prepubertal boys |
? | 2–8 pg/mL | ? | ? |
Oral contraceptive (anovulatory ) |
30–100 µg/day 100–160 µg/day 320–640 µg/day 300 µg/day ? |
40–60 pg/mL 60–100 pg/mL 200–400 pg/mL 190 pg/mL 12–50 pg/mL |
40–60 pg/mL ? 170–200 pg/mL 100–150 pg/mL ? |
0.5–1 ? 1–2 1.5 ? |
Postmenopausal women | 18 µg/day | 5–20 pg/mL | 30–70 pg/mL | 0.3–0.8 |
Third trimester (weeks 27–40) |
? ? ? |
1,000–5,000 pg/mL 5,000–15,000 pg/mL 10,000–40,000 pg/mL |
? ? ? |
? ? ? |
Mena | 20–60 µg/day | 27 (20–55) pg/mL | 20–90 pg/mL | 0.4–0.6 |
Footnotes: a = Format is "mean value (range)" or just "range". Sources: [71][72][73][74][75][61][76] |
Measurement
In women, serum estradiol is measured in a
Ranges
Individual laboratory results should always be interpreted using the ranges provided by the laboratory that performed the test.
Patient type | Lower limit | Upper limit | Unit |
---|---|---|---|
Adult male | 50[78] | 200[78] | pmol/L |
14 | 55 | pg/mL | |
Adult female (follicular phase, day 5) |
70[78] 95% PI (standard) |
500[78] 95% PI |
pmol/L |
110[79] 90% PI (used in diagram) |
220[79] 90% PI | ||
19 (95% PI) | 140 (95% PI) | pg/mL | |
30 (90% PI) | 60 (90% PI) | ||
Adult female ( preovulatory peak) |
400[78] | 1500[78] | pmol/L |
110 | 410 | pg/mL | |
Adult female (luteal phase) |
70[78] | 600[78] | pmol/L |
19 | 160 | pg/mL | |
Adult female – free (not protein bound) |
0.5[80][original research?] | 9[80][original research?] | pg/mL |
1.7[80][original research?] | 33[80][original research?] | pmol/L | |
Post-menopausal female | N/A[78] | < 130[78] | pmol/L |
N/A | < 35 | pg/mL |
In the normal menstrual cycle, estradiol levels measure typically <50 pg/mL at menstruation, rise with follicular development (peak: 200 pg/mL), drop briefly at ovulation, and rise again during the luteal phase for a second peak. At the end of the luteal phase, estradiol levels drop to their menstrual levels unless there is a pregnancy.
During pregnancy, estrogen levels, including estradiol, rise steadily toward term. The source of these estrogens is the placenta, which aromatizes prohormones produced in the fetal adrenal gland.
Sex | Sex hormone | Reproductive phase |
Blood production rate |
Gonadal secretion rate |
Metabolic clearance rate |
Reference range (serum levels) | |
---|---|---|---|---|---|---|---|
SI units | Non-SI units | ||||||
Men | Androstenedione | –
|
2.8 mg/day | 1.6 mg/day | 2200 L/day | 2.8–7.3 nmol/L | 80–210 ng/dL |
Testosterone | –
|
6.5 mg/day | 6.2 mg/day | 950 L/day | 6.9–34.7 nmol/L | 200–1000 ng/dL | |
Estrone | –
|
150 μg/day | 110 μg/day | 2050 L/day | 37–250 pmol/L | 10–70 pg/mL | |
Estradiol | –
|
60 μg/day | 50 μg/day | 1600 L/day | <37–210 pmol/L | 10–57 pg/mL | |
Estrone sulfate | –
|
80 μg/day | Insignificant | 167 L/day | 600–2500 pmol/L | 200–900 pg/mL | |
Women | Androstenedione | –
|
3.2 mg/day | 2.8 mg/day | 2000 L/day | 3.1–12.2 nmol/L | 89–350 ng/dL |
Testosterone | –
|
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. |
Medical use
Estradiol is used as a
Chemistry
Structures of major endogenous estrogens
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Estradiol is an
Neuropsychopharmacology
In a randomized, double-blind, placebo-controlled study, estradiol was shown to have gender-specific effects on fairness sensitivity. Overall, when the division of a given amount of money was framed as either fair or unfair in a modified version of the ultimatum game, estradiol increased the acceptance rate of fair-framed proposals among men and decreased it among women. However, among the placebo-group "the mere belief of receiving estradiol treatment significantly increased the acceptance of unfair-framed offers in both sexes", indicating that so-called "environmental" factors played a role in organising the responses towards these presentations of the ultimatum game.[83]
History
The discovery of estrogen is usually credited to the
Estradiol, the most potent of the three major estrogens, was the last of the three to be identified.
Society and culture
Etymology
The name estradiol derives from estra-,
References
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Estradiol levels are minimal during the earliest days of the follicular phase, but increasing concentrations are released into the general circulation as the follicle matures. The highest levels are reached about 24 to 48 hours before the LH peak. In fact, the pre-ovulatory peak in estradiol represents its highest concentration during the entire menstrual cycle. Serum concentrations at this time are typically about 130–200 pg/mL, but concentrations as high as 300–400 pg/mL can be achieved in some women. Following a transient fall in association with ovulation, estradiol secretion is restored by production from the corpus luteum during the luteal phase. Plateau levels of around 100–150 pg/mL (Abraham, 1978; Thorneycroft et al., 1971) are most often seen during the period from −10 to −5 days before the onset of menses. With the regression of the corpus luteum, estradiol levels fall, gradually in some women and precipitously in others, during the last few days of the luteal phase. This ushers in the onset of menses, the sloughing of the endometrium. Serum estradiol during menses is approximately 30–50 pg/mL. (Source.)
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In most laboratories, serum estradiol levels range from 20 to 80 pg/mL during the early to midfollicular phase of the menstrual cycle and peak at 200 to 500 pg/mL during the preovulatory surge. During the midluteal phase, serum estradiol levels range from 60 to 200 pg/mL.
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Plasma levels of estradiol range from 40 to 80 pg/ml during the 1st week of the ovarian cycle (early follicular phase) and from 80 to 300 pg/ml during the 2nd week (mid- and late follicular phase including periovulatory peak). Then during the 3rd and 4th weeks, estradiol fluctuates between 100 and 150 pg/ml (early and mid-luteal phase) to 40 pg/ml a few days before menstruation (late luteal phase). The mean integrated estradiol level during a full 28-day normal cycle is around 80 pg/ml.
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Midcycle: 150-750 pg/mL
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Mid-cycle: 110-330 pg/mL
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Ovulatory: 200-400 pg/mL
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[...] following the menopause, circulating estradiol levels decrease from a premenopausal mean of 120 pg/ml to only 13 pg/ml.
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[...] [premenopausal] mean [estradiol] concentration of 150 pg/ml [...]
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