Progesterone

Progesterone

Names
IUPAC name Pregn-4-ene-3,20-dione[2][3]
Systematic IUPAC name (1S,3aS,3bS,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names P4;[1] Pregnenedione
Identifiers
CAS Number	57-83-0 Y
3D model ( JSmol )	Interactive image
ChEBI	CHEBI:17026 Y
ChEMBL	ChEMBL103 Y
ChemSpider	5773 Y
DrugBank	DB00396 Y
ECHA InfoCard	100.000.318
KEGG	C00410 N
PubChem CID	5994
UNII	4G7DS2Q64Y Y
CompTox Dashboard (EPA)	DTXSID3022370
InChI InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 N Key: RJKFOVLPORLFTN-LEKSSAKUSA-N Y
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
Properties
Chemical formula	C21H30O2
Molar mass	314.469 g/mol
Melting point	126
log P	4.04[4]
Pharmacology
ATC code	G03DA04 (WHO)
Routes of administration	subcutaneous injection, subcutaneous implant
Pharmacokinetics:
Bioavailability	OMP: <10%[5][6]
Protein binding	• CBG: 18% • SHBG: <1% • Free: 1–2%[7][8]
Metabolism	20α-HSDTooltip 20α-hydroxysteroid dehydrogenase)[9][10]
Biological half-life	OMP: 16–18 hours[5][6][11] IM: 22–26 hours[6][12] SC: 13–18 hours[12]
Excretion	Renal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Progesterone (P4) is an

Progesterone is the most important progestogen in the body. As a potent

Hormonal interactions

Progesterone has a number of physiological effects that are amplified in the presence of

Elevated levels of progesterone potently reduce the sodium-retaining activity of aldosterone, resulting in natriuresis and a reduction in extracellular fluid volume. Progesterone withdrawal, on the other hand, is associated with a temporary increase in sodium retention (reduced natriuresis, with an increase in extracellular fluid volume) due to the compensatory increase in aldosterone production, which combats the blockade of the mineralocorticoid receptor by the previously elevated level of progesterone.[43]

Early sexual differentiation

Progesterone plays a role in early human sexual differentiation.

Progesterone has key effects via non-genomic signalling on human sperm as they migrate through the female tract before

Progesterone is sometimes called the "hormone of pregnancy",^[54] and it has many roles relating to the development of the fetus:

• Progesterone converts the
  anovulatory dysfunctional uterine bleeding.
• During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy.^[56]
• Progesterone decreases contractility of the uterine
  preterm labor.^[56] Studies have shown that in women who are pregnant with a single fetus, asymptomatic in the prenatal stage, and at a high risk of giving pre-term birth spontaneously, vaginal progesterone medication has been found to be effective in preventing spontaneous pre-term birth. Women who are at a high risk of giving pre-term birth spontaneously are those who have a short cervix of less than 25 mm or have previously given pre-term birth spontaneously. Although pre-term births are generally considered to be less than 37 weeks, these studies found that vaginal progesterone is associated with fewer pre-term births of less than 34 weeks.^[57]
• A drop in progesterone levels is possibly one step that facilitates the onset of
  labor
  .
• In addition, progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production.

The

Lobuloalveolar development

Progesterone plays an important role in

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.[70]^[71] These benefits include increased skin collagen content, skin thickness and elasticity, and skin hydration and surface lipids.^[70][71] Topical estrogen has been found to have similar beneficial effects on the skin.^[70] 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.^[71] Skin hydration and surface lipids, on the other hand, did not significantly change with topical progesterone.^[71]

These findings suggest that progesterone, like estrogen, also has beneficial effects on the skin, and may be independently protective against skin aging.^[71]

Sexuality

Libido

Progesterone and its neurosteroid active metabolite allopregnanolone appear to be importantly involved in libido in females.^[72]

Homosexuality

Dr. Diana Fleischman, of the University of Portsmouth, and colleagues looked for a relationship between progesterone and sexual attitudes in 92 women. Their research, published in the Archives of Sexual Behavior found that women who had higher levels of progesterone scored higher on a questionnaire measuring homoerotic motivation. They also found that men who had high levels of progesterone were more likely to have higher homoerotic motivation scores after affiliative priming compared to men with low levels of progesterone.^{[73][74][75][76]}

Nervous system

Progesterone, like pregnenolone and dehydroepiandrosterone (DHEA), belongs to an important group of endogenous steroids called neurosteroids. It can be metabolized within all parts of the central nervous system.^[77]

Neurosteroids are

Previous studies have shown that progesterone supports the normal development of neurons in the brain, and that the hormone has a protective effect on damaged brain tissue. It has been observed in animal models that females have reduced susceptibility to traumatic brain injury and this protective effect has been hypothesized to be caused by increased circulating levels of estrogen and progesterone in females.^[80]

Proposed mechanism

The mechanism of progesterone protective effects may be the reduction of inflammation that follows brain trauma and hemorrhage.^[81][82]

Damage incurred by traumatic brain injury is believed to be caused in part by mass

Progesterone has also been shown to prevent apoptosis in neurons, a common consequence of brain injury.^[85] It does so by inhibiting enzymes involved in the apoptosis pathway specifically concerning the mitochondria, such as activated caspase 3 and cytochrome c.

Not only does progesterone help prevent further damage, it has also been shown to aid in

Addiction

Progesterone enhances the function of

• Sex differences in hormone levels may induce women to respond differently than men to nicotine. When women undergo cyclic changes or different hormonal transition phases (menopause, pregnancy, adolescence), there are changes in their progesterone levels.[90] Therefore, females have an increased biological vulnerability to nicotine's reinforcing effects compared to males and progesterone may be used to counter this enhanced vulnerability. This information supports the idea that progesterone can affect behavior.^[89]
• Similar to nicotine, cocaine also increases the release of dopamine in the brain. The neurotransmitter is involved in the reward center and is one of the main neurotransmitters involved with substance abuse and reliance. In a study of cocaine users, it was reported that progesterone reduced craving and the feeling of being stimulated by cocaine. Thus, progesterone was suggested as an agent that decreases cocaine craving by reducing the dopaminergic properties of the drug.^[91]

Societal

In a 2012 University of Amsterdam study of 120 women, women's luteal phase (higher levels of progesterone, and increasing levels of estrogen) was correlated with a lower level of competitive behavior in gambling and math contest scenarios, while their premenstrual phase (sharply-decreasing levels of progesterone, and decreasing levels of estrogen) was correlated with a higher level of competitive behavior.^[92]

Other effects

• Progesterone also has a role in skin elasticity and bone strength, in
  female sexuality, and the presence of progesterone receptors in certain muscle and fat tissue may hint at a role in sexually dimorphic proportions of those.^{[93][infringing link?}
  ]
• During pregnancy, progesterone is said to decrease uterine irritability.[94]
• During pregnancy, progesterone helps to suppress immune responses of the mother to fetal antigens, which prevents rejection of the fetus.^[94]
• Progesterone raises
  epidermal growth factor-1 (EGF-1) levels, a factor often used to induce proliferation, and used to sustain cultures, of stem cells.^[95]
• Progesterone increases core temperature (thermogenic function) during ovulation.[96]^[97]
• Progesterone reduces
  Bronchi are widened and mucus regulated. (PRs are widely present in submucosal tissue
  .)
• Progesterone acts as an antiinflammatory agent and regulates the immune response.
• Progesterone reduces
  gall-bladder activity.^[98]
• Progesterone normalizes blood clotting and vascular tone, zinc and copper levels, cell oxygen levels, and use of fat stores for energy.
• Progesterone may affect gum health, increasing risk of gingivitis (gum inflammation).^[99]
• Progesterone appears to prevent endometrial cancer (involving the uterine lining) by regulating the effects of estrogen.
• Progesterone plays an important role in the signaling of insulin release and pancreatic function, and may affect the susceptibility to diabetes or gestational diabetes.^[100][101]
• Progesterone levels in the blood were found to be lower in women who had higher weight and higher BMI among those who became pregnant through in vitro fertilization.^[102]
• Current data shows that micronized progesterone, which is chemically identical to the progesterone produced in women's bodies, in combination with estrogen in menopausal hormone therapy does not seem to have significant effects on venous thromboembolism (blood clots in veins) and ischemic stroke (lack of blood flow to the brain due to blockage of a blood vessel that supplies the brain). However, more studies need to be conducted to see whether or not micronized progesterone alone or in combined menopausal hormone therapy changes the risk of myocardial infarctions (heart attacks).^[103]
• There have not been any studies done yet on the effects of micronized progesterone on hair loss due to menopause.^[104]
• Despite suggestions for using hormone therapy to prevent loss of muscle mass in post-menopausal women (50 and older), menopausal hormone therapy involving either estrogen alone or estrogen and progesterone has not been found to preserve muscle mass.^[105] Menopausal hormone therapy also does not result in body weight reduction, BMI reduction, or change in glucose metabolism.^[106]

Biochemistry

Biosynthesis

In mammals, progesterone, like all other steroid hormones, is synthesized from pregnenolone, which itself is derived from cholesterol.

Cholesterol undergoes double oxidation to produce

The conversion of pregnenolone to progesterone takes place in two steps. First, the 3β-

Progesterone in turn is the precursor of the mineralocorticoid

Pregnenolone and progesterone can also be synthesized by yeast.^[109]

Approximately 25 mg of progesterone is secreted from the ovaries per day in women, while the adrenal glands produce about 2 mg of progesterone per day.^[110]

Distribution

Progesterone binds extensively to

v t e Metabolism of progesterone in humans[129] Progesterone 17α-Hydroxyprogesterone 11-Deoxycorticosterone Pregnanetriols (8 isomers) 5α-Dihydroprogesterone 5β-Dihydroprogesterone Allopregnanolone Isopregnanolone Pregnanolone Epipregnanolone Pregnanediols (8 isomers) 17α-Hydroxylase 21-Hydroxylase Multiple 5α-Reductase 5β-Reductase 3α-HSD 3β-HSD 3α-HSD 3β-HSD 20α-HSD 20β-HSD This diagram illustrates the hydroxyl (–OH) groups .

Levels

In women, progesterone levels are relatively low during the preovulatory phase of the menstrual cycle, rise after ovulation, and are elevated during the luteal phase, as shown in the diagram above. Progesterone levels tend to be less than 2 ng/mL prior to ovulation and greater than 5 ng/mL after ovulation. If pregnancy occurs, human chorionic gonadotropin is released, maintaining the corpus luteum and allowing it to maintain levels of progesterone. Between 7 and 9 weeks, the placenta begins to produce progesterone in place of the corpus luteum in a process called the luteal-placental shift.^[131]

After the luteal-placental shift, progesterone levels start to rise further and may reach 100 to 200 ng/mL at term. Whether a decrease in progesterone levels is critical for the initiation of

Progesterone levels are low in children and postmenopausal women.^[132] Adult males have levels similar to those in women during the follicular phase of the menstrual cycle.

Ranges

Blood test results should always be interpreted using the reference ranges provided by the laboratory that performed the results. Example reference ranges are listed below.

Reference ranges for the blood content of progesterone during the menstrual cycle

Sources

Animal

Progesterone is produced in high amounts in the

During human pregnancy, progesterone is produced in increasingly high amounts by the ovaries and placenta. At first, the source is the corpus luteum that has been "rescued" by the presence of human chorionic gonadotropin (hCG) from the conceptus. However, after the 8th week, production of progesterone shifts to the placenta. The placenta utilizes maternal cholesterol as the initial substrate, and most of the produced progesterone enters the maternal circulation, but some is picked up by the fetal circulation and used as substrate for fetal corticosteroids. At term the placenta produces about 250 mg progesterone per day.

An additional animal source of progesterone is milk products. After consumption of milk products the level of bioavailable progesterone goes up.^[144]

Plants

In at least one plant, Juglans regia, progesterone has been detected.^[145] In addition, progesterone-like steroids are found in Dioscorea mexicana. Dioscorea mexicana is a plant that is part of the yam family native to Mexico.^[146] It contains a steroid called diosgenin that is taken from the plant and is converted into progesterone.^[147] Diosgenin and progesterone are also found in other Dioscorea species, as well as in other plants that are not closely related, such as fenugreek.

Another plant that contains substances readily convertible to progesterone is

Medical use

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

Progesterone is used as a

symptoms and low sex hormone levels in women.^[116][152] It may also be used alone to treat menopausal symptoms. Studies have shown that transdermal progesterone (skin patch) and oral micronized progesterone are effective treatments for certain symptoms of menopause such as hot flashes and night sweats, which are otherwise referred to as vasomotor symptoms or VMS.^[153]

It is also used in women to support

gynecological disorders.^{[154][155][156][157]} Progesterone has been shown to prevent miscarriage in women with 1) vaginal bleeding early in their current pregnancy and 2) a previous history of miscarriage.^[158] Progesterone can be taken by mouth, through the vagina, and by injection into muscle or fat, among other routes.^[116]

Chemistry

See also: List of neurosteroids

Progesterone is a

dione), one at the C3 position and the other at the C20 position.^[159][160]

Synthesis

Progesterone is commercially produced by semisynthesis. Two main routes are used: one from yam diosgenin first pioneered by Marker in 1940, and one based on soy phytosterols scaled up in the 1970s. Additional (not necessarily economical) semisyntheses of progesterone have also been reported starting from a variety of steroids. For the example, cortisone can be simultaneously deoxygenated at the C-17 and C-21 position by treatment with iodotrimethylsilane in chloroform to produce 11-keto-progesterone (ketogestin), which in turn can be reduced at position-11 to yield progesterone.^[161]

Marker semisynthesis

Main article: Marker degradation

An economical semisynthesis of progesterone from the plant steroid diosgenin isolated from yams was developed by Russell Marker in 1940 for the Parke-Davis pharmaceutical company.^[162] This synthesis is known as the Marker degradation.

The

16-DPA intermediate is important to the synthesis of many other medically important steroids. A very similar approach can produce 16-DPA from solanine.^[163]

Soy semisynthesis

Progesterone can also be made from the

Percy Julian

.

Total synthesis

A

orthoester is hydrolyzed to produce the ketone 15. The cyclopentene A-ring is then opened by oxidizing with ozone to produce 16. Finally, the diketone 17 undergoes an intramolecular aldol condensation by treating with aqueous potassium hydroxide to produce progesterone.^[169]

History

Danzig, who extracted this new compound from several thousand liters of urine.^[173]

London, England, a compromise was made between the groups and the name progesterone (progestational steroidal ketone) was created.^[17][176]

Veterinary use

The use of progesterone tests in dog breeding to pinpoint ovulation is becoming more widely used. There are several tests available but the most reliable test is a blood test with blood drawn by a veterinarian and sent to a lab for processing. Results can usually be obtained with 24 to 72 hours. The rationale for using progesterone tests is that increased numbers begin in close proximity to preovulatory surge in gonadotrophins and continue through ovulation and estrus. When progesterone levels reach certain levels they can signal the stage of estrus the female is. Prediction of birth date of the pending litter can be very accurate if ovulation date is known. Puppies deliver with a day or two of 9 weeks gestation in most cases. It is not possible to determine pregnancy using progesterone tests once a breeding has taken place, however. This is due to the fact that, in dogs, progesterone levels remain elevated throughout the estrus period.[177]

Pricing

Pricing for progesterone can vary depending location, insurance coverage, discount coupons, quantity, shortages, manufacturers, brand or generic versions, different pharmacies, and so on. As of currently, 30 capsules of 100 mg of the generic version, Prometrium, from CVS Pharmacy is around $40 without any discounts or insurance applied. The brand version, Progesterone, is around $450 for 30 capsules without any discounts or insurance applied.^[178] In comparison, Walgreens offers 30 capsules of 100 mg in the generic version for $51 without insurance or coupons applied. The brand name costs around $431 for 30 capsules of 100 mg.^[179]

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External links

• Progesterone MS Spectrum
• Progesterone at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
• Kimball JW (27 May 2007). "Progesterone". Kimball's Biology Pages. Archived from the original on 18 June 2008. Retrieved 18 June 2008.