Progestogen

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This article is about progestogens as hormones. For their use as medications, see Progestogen (medication).
Progestogen
mPRδ, others))
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Progestogens, also sometimes written progestagens or gestagens,[1] are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR).[2][3] Progesterone is the major and most important progestogen in the body. The progestogens are named for their function in maintaining pregnancy (i.e., progestational), although they are also present at other phases of the estrous and menstrual cycles.[2][3]

The progestogens are one of three types of sex hormones, the others being estrogens like estradiol and androgens/anabolic steroids like testosterone. In addition, they are one of the five major classes of steroid hormones, the others being the androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as the neurosteroids. All endogenous progestogens are characterized by their basic 21-carbon skeleton, called a pregnane skeleton (C21). In similar manner, the estrogens possess an estrane skeleton (C18), and androgens, an androstane skeleton (C19).

The terms progesterone, progestogen, and progestin are mistakenly used interchangeably both in the scientific literature and in clinical settings.

19-nortestosterone derivative norethisterone. The progestins are structural analogues of progesterone and have progestogenic activity similarly, but differ from progesterone in their pharmacological properties in various ways.[5]

In addition to their roles as natural hormones, progestogens are used as

transgender hormone therapy for transgender women; for information on progestogens as medications, see the progesterone (medication) and progestogen (medication)
articles.

Types and examples

The most important progestogen in the body is

5α-dihydrodeoxycorticosterone (5α-DHDOC).[18] They are all metabolites
of progesterone, lying downstream of progesterone in terms of biosynthesis.

Biological function

The major

sperm capacitation, and testosterone synthesis. Progestogens also have effects in other parts of the body. Unlike estrogens, progestogens have little or no role in feminization.[20]

Biochemistry

Biosynthesis

Main article: Progesterone § Biosynthesis
Steroidogenesis, with progestogens and their precursors inside the yellow box.[21]

Progesterone is produced from

17α-hydroxypregnenolone, are the precursors of all other endogenous steroids, including the androgens, estrogens, glucocorticoids, mineralocorticoids, and neurosteroids. Thus, many tissues producing steroids, including the adrenal glands, testes, and ovaries
, produce progestogens.

In some tissues, the

theca cells, which is then further converted into estrogen in the granulosa cells. Fetal adrenal glands also produce pregnenolone in some species, which is converted into progesterone and estrogens by the placenta (see below). In the human, the fetal adrenals produce dehydroepiandrosterone
(DHEA) via the pregnenolone pathway.

Production rates, secretion rates, clearance rates, and blood levels of major sex hormones
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.

Ovarian production

Progesterone is the major progestogen produced by the

Luteal cells
possess the necessary enzymes to convert cholesterol to pregnenolone, which is subsequently converted into progesterone. Progesterone is highest in the diestrus phase of the estrous cycle.

Placental production

The role of the placenta in progestogen production varies by species. In the sheep, horse, and human, the placenta takes over the majority of progestogen production, whereas in other species the corpus luteum remains the primary source of progestogens. In the sheep and human, progesterone is the major placental progestogen.

The equine placenta produces a variety of progestogens, primarily

5α-dihydroprogesterone and 5α,20α-tetrahydroprogesterone
, beginning on day 60. A complete luteo-placental shift occurs by day 120–150.

Chemistry

See also: List of progestogens

The endogenous progestogens are

hydroxyl groups
at the C3 and C20 positions.

Medical use

Main articles: Progestogen (medication), Progesterone (medication), Pharmacodynamics of progesterone, and Pharmacokinetics of progesterone

gynecological disorders, to suppress sex hormone
levels for various purposes, and for other indications.

References

  1. ^
    ISBN 978-1-4496-5800-7
    .
  2. ^
    ISBN 978-1-4511-1314-3
    .
  3. ^
    ISBN 978-81-8147-009-6
    .
  4. ISBN 978-1-4165-6201-6
    .
  5. ^
    ISBN 978-0749313630
    .
  6. ISBN 978-0-521-34095-3
    .
  7. ISBN 978-1-118-45057-4
    .
  8. S2CID 5503049
    .
  9. PMID 18060946
    .
  10. ISBN 978-0-08-092150-1
    .
  11. ^
    ISBN 978-1-259-64116-9
    . In addition to progesterone, 20α- and 20β-hydroxyprogesterone (20α- and 20β-hydroxy-4-pregnene-3-one) also are found. These compounds have about one-fifth the progestational activity of progesterone in humans and other species.
  12. S2CID 11205767
    .
  13. S2CID 40245594
    .
  14. PMID 405534
    .
  15. S2CID 28420255
    . In the Clauberg bioassay the 3β-hydroxy-4-pregnen-20-one shows about the same potency as progesterone (34). In regard to the biological activity of the 3α epimer no data are available.
  16. PMID 13480263
    .
  17. ISBN 978-3-642-88385-9
    .
  18. S2CID 26030656
    .
  19. S2CID 115377
    .
  20. ^ "Progesterone". www.hormone.org. Retrieved 2021-12-11.
  21. ISSN 2002-4436
    .

Further reading

External links


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