Progesterone

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Identification

Summary

Progesterone is a hormone used for a variety of functions, including contraception, control of abnormal uterine bleeding, maintenance of pregnancy, and prevention of endometrial hyperplasia.

Brand Names

Bijuva, Crinone, Endometrin, Prochieve, Prometrium

Generic Name

Progesterone

DrugBank Accession Number

DB00396

Background

Progesterone is a hormone that occurs naturally in females, and is essential for endometrial receptivity, embryo implantation, and the successful establishment of pregnancy. A low progesterone concentration or an insufficient response to progesterone can cause infertility and pregnancy loss ⁷. Progesterone is used in various contraceptive preparations to prevent ovulation and fertilization ¹⁵, ⁸ as well as in other formulations to promote and support pregnancy. Please see Medroxyprogesterone acetate, Megestrol acetate, Dydrogesterone and Hydroxyprogesterone entries for information on various other forms of progesterone.

Pharmaceutical progesterone is made from a plant source as a starting material and is chemically identical to progesterone of human ovarian origin ^Label. Progesterone is available in gelatinized capsule form, vaginal gel form, tablet form, vaginal insert form, and injection form, all used for various purposes ^{Label,20,22,21,23}.

Type

Small Molecule

Groups

Approved, Vet approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Progesterone (DB00396)

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Weight

Average: 314.4617
Monoisotopic: 314.224580204

Chemical Formula

C₂₁H₃₀O₂

Synonyms

• (S)-4-Pregnene-3,20-dione
• (S)-Pregn-4-en-3,20-dione
• (S)-Progesterone
• 17alpha-Progesterone
• 17α-progesterone
• 4-Pregnene-3,20-dione
• Agolutin
• Akrolutin
• Corpus Luteum Hormone
• delta(4)-Pregnene-3,20-dione
• Gelbkörperhormon
• Luteohormone
• Lutogynon
• Pregn-4-ene-3,20-dione
• Progesteron
• Progesterona
• Progestérone
• Progesterone
• Progesteronum

External IDs

• BP 14
• NSC-64377
• NSC-9704
• U 3672

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Pharmacology

Indication

Gelatinized capsules

The gelatinized capsules are indicated for use in the prevention of endometrial hyperplasia in non-hysterectomized postmenopausal women who are receiving conjugated estrogens tablets. They are also indicated for use in secondary amenorrhea ^Label.

Vaginal gel

Progesterone gel (8%) is indicated as progesterone supplementation or replacement as part of an Assisted Reproductive Technology (“ART”) treatment for infertile women with progesterone deficiency. The lower concentration progesterone gel (4%) is used in the treatment of secondary amenorrhea, with the use of the 8% concentration if there is no therapeutic response to the 4% gel ²⁰.

Vaginal insert

This form is indicated to support embryo implantation and early pregnancy by supplementation of corpus luteal function as part of an Assisted Reproductive Technology (ART) treatment program for infertile women ²¹.

Injection (intramuscular)

This drug is indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer ²³.

Tablets, contraceptive

The tablet form of progesterone in contraceptive formulations is indicated for the prevention of pregnancy ²².

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Abnormal uterine bleeding		••••••••••••			•••••••••
Treatment of	Amenorrhea		••••••••••••			•••• •••••••••
Prevention of	Endometrial hyperplasia caused by conjugated estrogen		••••••••••••		••••••••••••••
Used in combination to treat	Moderate to severe vasomotor symptoms	Combination Product in combination with: Estradiol (DB00783)	••••••••••••	••••••••••		•••••••
Prevention of	Pregnancy		••••••••••••

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Associated Therapies

• Assisted Reproductive Technology therapy

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Pharmacodynamics

Progesterone, depending on concentration and dosage form, and timing of exposure may have several pharmacodynamic effects. These actions, according, to various preparations, are listed below:

General effects

Progesterone is the main hormone of the corpus luteum and the placenta. It acts on the uterus by changing the proliferative phase to the secretory phase of the endometrium (inner mucous lining of the uterus). This hormone, stimulated by a hormone called luteinizing hormone (LH) is the main hormone during the secretory phase to prepare the corpus luteum and the endometrium for implantation of a fertilized ovum. As the luteal phase concludes, the progesterone hormone sends negative feedback to the anterior pituitary gland in the brain to decrease FSH (follicle stimulating hormone) and LH (luteinizing hormone) levels. This prevents ovulation and maturation of oocytes (immature egg cells). The endometrium then prepares for pregnancy by increasing its vascularity (blood vessels) and stimulating mucous secretion. This process occurs by progesterone stimulating the endometrium to decrease endometrial proliferation, leading to a decreased uterine lining thickness, developing more complex uterine glands, collecting energy in the form of glycogen, and providing more uterine blood vessel surface area suitable for supporting a growing embryo. As opposed to cervical mucous changes observed during the proliferative phase and ovulation, progesterone decreases and thickens the cervical mucus, rendering it less elastic. This change occurs because the fertilization time period has passed, and a specific consistency of mucous amenable to sperm entry is no longer required ¹⁶.

Gelatinized capsules

Progesterone capsules are an oral dosage form of micronized progesterone which, chemically identical to progesterone of ovarian origin. Progesterone capsules have all the properties of endogenous progesterone with induction of a secretory phase endometrium with gestagenic, antiestrogenic, slightly antiandrogenic and anti-aldosterone effects ²⁴. Progesterone opposes the effects of estrogen on the uterus, and is beneficial in women with unopposed estrogen exposure, which carries an increased risk of malignancy ²⁴.

Vaginal gel and vaginal insert

The gel preparation mimics the effects of naturally occurring progesterone. In the presence of adequate levels of estrogen, progesterone converts a proliferative endometrium into secretory endometrium. This means that the endometrium changes from a growing and thickening stage into a subsequent preparation stage for pregnancy, which involves further preparatory changes. Progesterone is necessary for the development of decidual tissue (specialized tissue amenable to supporting a possible pregnancy). Progesterone is required to increase endometrial receptivity for the implantation of a fertilized embryo. Once an embryo is implanted, progesterone helps to maintain the pregnancy ²⁰.

Injection (intramuscular)

Intramuscularly injected progesterone increases serum progesterone and aids in the prevention of endometrial tissue overgrowth due to unopposed estrogen (which leads to abnormal uterine bleeding and sometimes uterine cancer) ¹⁸, ²⁵. In the absence or deficiency of progesterone, the endometrium continually proliferates, eventually outgrowing its limited blood supply, shedding incompletely, and leading to abnormal and/or profuse bleeding as well as malignancy ¹⁸.

Tablets, contraceptive

Progesterone-only contraceptive tablets prevent conception by suppressing ovulation in about half of users, causing a thickening of cervical mucus to inhibit sperm movement, lowering the midcycle LH and FSH hormone peaks, slowing the movement of the ovum through the fallopian tubes, and causing secretory changes in the endometrium as described above ²².

Mechanism of action

Progesterone binds and activates its nuclear receptor, PR, which plays an important part in the signaling of stimuli that maintain the endometrium during its preparation for pregnancy.

Progesterone receptor (PR) is a member of the nuclear/steroid hormone receptor (SHR) family of ligand-dependent transcription factors that is expressed primarily in female reproductive tissue as well as the central nervous system. As a result of its binding its associated steroid hormone, progesterone, the progesterone receptor (PR) modulates the expression of genes that regulate the development, differentiation, and proliferation of target tissues ¹⁴. In humans, PR is found to be highly expressed in the stromal (connective tissue) cells during the secretory phase and during pregnancy ¹⁰.

Progesterone may prevent pregnancy by changing the consistency of cervical mucus to be unfavorable for sperm penetration, and by inhibiting follicle-stimulating hormone (FSH), which normally causes ovulation. With perfect use, the first-year failure rate for progestin-only oral contraceptives is approximately 0.5%. The typical failure rate, however, is estimated to be approximately 5%, due to late or missed pills ²².

Target	Actions	Organism
AProgesterone receptor	agonist	Humans
AMineralocorticoid receptor	antagonist agonist	Humans
UEstrogen receptor	agonist inhibitor downregulator	Humans
USteroid 17-alpha-hydroxylase/17,20 lyase	substrate inhibitor	Humans
UKappa-type opioid receptor	activator potentiator	Humans
UAlpha-1-acid glycoprotein 1	binder	Humans
UGlucocorticoid receptor	partial agonist	Humans
UAndrogen receptor	agonist potentiator	Humans
USex hormone-binding globulin	binder potentiator	Humans
UEstrogen receptor beta	agonist downregulator	Humans

Absorption

Oral micronized capsules

Following oral administration of progesterone in the micronized soft-gelatin capsule formulation, peak serum concentration was achieved in the first 3 hours. The absolute bioavailability of micronized progesterone is unknown at this time. In postmenopausal women, serum progesterone concentration increased in a dose-proportional and linear fashion after multiple doses of progesterone capsules, ranging from 100 mg/day to 300 mg/day ^Label.

IM administration

After intramuscular (IM) administration of 10 mg of progesterone in oil, the maximum plasma concentrations were achieved in about 8 hours post-injection and plasma concentrations stayed above baseline for approximately 24 hours post-injection. Injections of 10, 25, and 50 mg lead to geometric mean values for maximum plasma concentration (CMAX) of 7, 28, and 50 ng/mL, respectively ²⁵. Progesterone administered by the intramuscular (IM) route avoids significant first-pass hepatic metabolism. As a result, endometrial tissue concentrations of progesterone achieved with IM administration are higher when compared with oral administration. Despite this, the highest concentrations of progesterone in endometrial tissue are reached with vaginal administration ¹¹.

Note on oral contraceptive tablet absorption

Serum progestin levels peak about 2 hours after oral administration of progesterone-only contraceptive tablets, followed by rapid distribution and elimination. By 24 hours after drug administration, serum levels remain near the baseline, making efficacy dependent upon strict adherence to the dosing schedule. Large variations in serum progesterone levels occur among individuals. Progestin-only administration leads to lower steady-state serum progestin levels and a shorter elimination half-life than concurrent administration with estrogens ²².

Volume of distribution

When administered vaginally, progesterone is well absorbed by uterine endometrial tissue, and a small percentage is distributed into the systemic circulation. The amount of progesterone in the systemic circulation appears to be of minimal importance, especially when implantation, pregnancy, and live birth outcomes appear similar for intramuscular and vaginal administration of progesterone ¹¹.

Protein binding

96%-99% bound to serum proteins, primarily to serum albumin (50%-54%) and transcortin (43%-48%) ^Label.

Metabolism

Progesterone is mainly metabolized by the liver. After oral administration, the major plasma metabolites found are 20 a hydroxy-Δ4 a-prenolone and 5 a-dihydroprogesterone. Some progesterone metabolites are found excreted in the bile and these metabolites may be deconjugated and subsequently metabolized in the gut by reduction, dehydroxylation, and epimerization ^Label. The major plasma and urinary metabolites are comparable to those found during the physiological progesterone secretion of the corpus luteum ²⁴.

Hover over products below to view reaction partners

• Progesterone
  • 6β-Hydroxyprogesterone
  • deoxycorticosterone
  • 11-deoxycorticosterone
  • 21-OH-progesterone
  • 17-OH progesterone
  • 5 a-dihydroprogesterone
  • 20 a hydroxy- Δ 4 a- prenolone
  • Pregnanolone + pregnanediol + pregnanetriol

Route of elimination

Progesterone metabolites are excreted mainly by the kidneys. Urinary elimination is observed for 95% of patients in the form of glycuroconjugated metabolites, primarily 3 a, 5 ß–pregnanediol (pregnandiol) ²⁴. The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites, excreted in the bile, may undergo enterohepatic recycling or may be found excreted in the feces.

Half-life

Absorption half-life is approximately 25-50 hours and an elimination half-life of 5-20 minutes (progesterone gel) ²⁰.

Progesterone, administered orally, has a short serum half-life (approximately 5 minutes). It is rapidly metabolized to 17-hydroxyprogesterone during its first pass through the liver ¹¹.

Clearance

Apparent clearance

1367 ± 348 (50mg of progesterone administered by vaginal insert once daily) ¹¹.

106 ± 15 L/h (50mg/mL IM injection once daily) ¹¹.

Adverse Effects

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Toxicity

Intraperitoneal LD50 (rat): 327 mg/kg ^MSDS.

Use in pregnancy

Only forms of progesterone that are indicated on product labeling for pregnancy should be used. Some forms of progesterone should not be used in pregnancy ^Label, ²². Refer to individual product monographs for information regarding use in pregnancy. Many studies have found no effects on fetal development associated with long-term use of contraceptive doses of oral progestins. Studies of infant growth and development that have been conducted have not demonstrated significant adverse effects, however, these studies are few in number. It is therefore advisable to rule out suspected pregnancy before starting any hormonal contraceptive ²².

Effects on fertility

Progesterone at high doses is an antifertility drug and high doses would be expected to impair fertility until cessation ²⁵. The progesterone contraceptive should not be used during pregnancy.

Carcinogenicity

Progesterone has been shown to induce or promote the formation of ovarian, uterine, mammary, and genital tract tumors in animals. The clinical relevance of these findings is unknown ²⁴. Certain epidemiological studies of patients using oral contraceptives have reported an increased relative risk of developing breast cancer, especially at a younger age and associated with a longer duration of use. These studies have mainly involved combined oral contraceptives, and therefore, it is unknown whether this risk is attributable to progestins, estrogens, or a combination of both. At this time, there is insufficient data to determine whether the use of progestin-only contraceptives increases the risk in a similar way to combined contraceptives. A meta-analysis of 54 studies showed a small increase in the frequency of breast cancer diagnosis for women who were currently using combined oral contraceptives, or had used them within the past 10 years. There was no increase in the frequency of having breast cancer diagnosed ten or more years after cessation of hormone use. Women with breast cancer should not use oral contraceptives, as there is no sufficient data to fully establish or negate the risk of cancer with hormonal contraceptive use ²².

Use in breastfeeding

Progesterone has been detected in the milk of nursing mothers ²¹, ²². No adverse effects, in general, have been found on breastfeeding ability or on the health, growth, or development of the growing infant. Despite this, isolated post-marketing cases of decreased milk production have been reported ²².

Pathways

Pathway	Category
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH	Disease
11-beta-Hydroxylase Deficiency (CYP11B1)	Disease
Apparent Mineralocorticoid Excess Syndrome	Disease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency	Disease
Corticosterone Methyl Oxidase I Deficiency (CMO I)	Disease
3-beta-Hydroxysteroid Dehydrogenase Deficiency	Disease
Steroidogenesis	Metabolic
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency	Disease
17-alpha-Hydroxylase Deficiency (CYP17)	Disease
21-Hydroxylase Deficiency (CYP21)	Disease
Corticosterone Methyl Oxidase II Deficiency (CMO II)	Disease

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Progesterone can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Progesterone can be increased when combined with Abatacept.
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Progesterone.
Abemaciclib	Progesterone may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
Abiraterone	The metabolism of Progesterone can be decreased when combined with Abiraterone.

Food Interactions

• Administer vitamin supplements.
• Avoid alcohol.
• Limit caffeine intake.
• Take at the same time every day.
• Take with food.

Products

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Product Images

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International/Other Brands

Agolutin (Biotika) / Cyclogest (Actavis) / Gesterol / Gestone (Nordic Pharma) / Progestasert / Progestogel (Besins) / Qi Ning (Aisheng Pharmaceutical) / Relantan (Aversi) / Susten (Sun Pharma) / Utrogestran (Faran Laboratories) / Utrovin (Bestochem) / Vasclor (Verisfield)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Act Progesterone Injection	Solution	50 mg / mL	Intramuscular	Teva Italia S.R.L.	2016-04-13	Not applicable
Crinone	Gel	90 mg/1.125g	Vaginal	Actavis Pharma, Inc.	1997-05-13	2020-10-31
Crinone	Gel	45 mg/1.125g	Vaginal	Actavis Pharma, Inc.	1997-05-13	2015-02-28
Crinone	Gel	8 %	Vaginal	Emd Serono, A Division Of Emd Inc., Canada	2000-05-20	Not applicable
Crinone	Gel	90 mg/1.125g	Vaginal	Columbia Laboratories	1997-05-13	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ach-progesterone	Capsule	100 mg	Oral	Accord Healthcare, S.L.U.	Not applicable	Not applicable
Auro-progesterone	Capsule	100 mg	Oral	Auro Pharma Inc	2020-03-16	Not applicable
PMS-progesterone	Capsule	200 mg	Oral	Pharmascience Inc	2019-02-07	Not applicable
PMS-progesterone	Capsule	100 mg	Oral	Pharmascience Inc	2018-08-08	Not applicable
PMS-progesterone Inj 50mg/ml USP	Liquid	50 mg / mL	Intramuscular	Pharmascience Inc	1989-12-31	2004-01-21

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Advanced Formula Progesto-Life	Cream	16.9 mg/1mL	Topical	Smoky Mountain Naturals, LLC - DBA SMNutrition	2022-04-01	Not applicable
P25 Progesterone Cream	Cream	25 mg/85g	Transdermal	SHYNE BRANDS	2021-06-10	Not applicable
P50 Progesterone Cream	Cream	1 mg/1mg	Transdermal	SHYNE BRANDS	2021-06-14	Not applicable
P75 Lav Progesterone Cream	Cream	1 mg/1mg	Transdermal	SHYNE BRANDS	2021-06-10	Not applicable
P75 Maxx with Retinol All Natural Progesterone 75 Cream	Cream	1 mg/1mg	Transdermal	SHYNE BRANDS	2021-06-10	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Bijuva	Progesterone (100 mg/1) + Estradiol (0.5 mg/1)	Capsule	Oral	Mayne Pharma Inc.	2023-03-31	Not applicable
Bijuva	Progesterone (100 mg) + Estradiol hemihydrate (0.5 mg)	Capsule	Oral	Knight Therapeutics Inc.	Not applicable	Not applicable
Bijuva	Progesterone (100 mg/1) + Estradiol (1 mg/1)	Capsule	Oral	Mayne Pharma Inc.	2023-12-18	Not applicable
Bijuva	Progesterone (100 mg/1) + Estradiol (1 mg/1)	Capsule	Oral	Mayne Pharma Inc.	2019-04-03	Not applicable
Bijuva	Progesterone (100 mg/1) + Estradiol (0.5 mg/1)	Capsule	Oral	Mayne Pharma Inc.	2023-12-01	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Advanced Formula Progesto-Life	Progesterone (16.9 mg/1mL)	Cream	Topical	Smoky Mountain Naturals, LLC - DBA SMNutrition	2022-04-01	Not applicable
Fluocinolone Acetonide 0.01% / Minoxidil 7% / Progesterone 0.1%	Progesterone (0.1 g/100g) + Fluocinolone acetonide (0.01 g/100g) + Minoxidil (7 g/100g)	Solution	Topical	Sincerus Florida, LLC	2019-05-09	Not applicable
Minoxidil 5% / Progesterone 0.1% / Tretinoin 0.025%	Progesterone (0.1 g/100g) + Minoxidil (5 g/100g) + Tretinoin (0.025 g/100g)	Solution	Topical	Sincerus Florida, LLC	2019-05-07	Not applicable
Minoxidil 7% / Progesterone 0.1%	Progesterone (0.1 g/100g) + Minoxidil (7 g/100g)	Solution	Topical	Sincerus Florida, LLC	2019-05-01	Not applicable
Minoxidil 7% / Progesterone 0.1% / Tretinoin 0.025%	Progesterone (0.1 g/100g) + Minoxidil (7 g/100g) + Tretinoin (0.025 g/100g)	Solution	Topical	Sincerus Florida, LLC	2019-05-07	Not applicable

Categories

ATC Codes

G03FA04 — Progesterone and estrogen

• G03FA — Progestogens and estrogens, fixed combinations
• G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G03DA04 — Progesterone

• G03DA — Pregnen (4) derivatives
• G03D — PROGESTOGENS
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

Drug Categories

• Adrenal Cortex Hormones
• BCRP/ABCG2 Inducers
• BCRP/ABCG2 Inhibitors
• BSEP/ABCB11 Inhibitors
• Corpus Luteum Hormones
• Cytochrome P-450 CYP2A6 Inducers
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C9 Inhibitors
• Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Inducers
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inducers
• Cytochrome P-450 CYP3A4 Inducers (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 CYP3A7 Inhibitors
• Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A7 Substrates
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Fused-Ring Compounds
• Genito Urinary System and Sex Hormones
• Gonadal Hormones
• Gonadal Steroid Hormones
• Hormonal Contraceptives for Systemic Use
• Hormones
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Hyperglycemia-Associated Agents
• OATP1B1/SLCO1B1 Inhibitors
• OATP1B3 inducers
• OCT1 inhibitors
• OCT2 Inhibitors
• P-glycoprotein inducers
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Pregnanes
• Pregnenediones
• Pregnenes
• Progesterone and Derivatives
• Progesterone, antagonists & inhibitors
• Progestin-containing Intrauterine Device
• Progestins
• Sex Hormones and Modulators of the Genital System
• Steroids

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

20-oxosteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives

Substituents

20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Cyclohexenone / Delta-4-steroid / Hydrocarbon derivative / Ketone

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid, 20-oxo steroid, C21-steroid hormone (CHEBI:17026) / Pregnane and derivatives [Fig], Progestagens (C00410) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030159)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

4G7DS2Q64Y

CAS number

57-83-0

InChI Key

RJKFOVLPORLFTN-LEKSSAKUSA-N

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

IUPAC Name

(1S,3aS,3bS,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

References

Synthesis Reference

Nejib M. Nasraoui, Alain Piasco, "Derivatives of 19-nor progesterone; process for producing them and the pharmaceutical compositions incorporating them." U.S. Patent US5223492, issued May, 1971.

US5223492

General References

1. Allen WM: THE ISOLATION OF CRYSTALLINE PROGESTIN. Science. 1935 Aug 2;82(2118):89-93. [Article]
2. Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. [Article]
3. Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF: Local synthesis and dual actions of progesterone in the nervous system: neuroprotection and myelination. Growth Horm IGF Res. 2004 Jun;14 Suppl A:S18-33. [Article]
4. Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA: Progesterone receptors regulate gallbladder motility. J Surg Res. 1988 Dec;45(6):505-12. [Article]
5. Payne VA, Chang YT, Loew GH: Homology modeling and substrate binding study of human CYP2C18 and CYP2C19 enzymes. Proteins. 1999 Nov 1;37(2):204-17. [Article]
6. Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [Article]
7. Young SL, Lessey BA: Progesterone function in human endometrium: clinical perspectives. Semin Reprod Med. 2010 Jan;28(1):5-16. doi: 10.1055/s-0029-1242988. Epub 2010 Jan 26. [Article]
8. Lopez LM, Ramesh S, Chen M, Edelman A, Otterness C, Trussell J, Helmerhorst FM: Progestin-only contraceptives: effects on weight. Cochrane Database Syst Rev. 2016 Aug 28;(8):CD008815. doi: 10.1002/14651858.CD008815.pub4. [Article]
9. Khandelwal M: Vaginal progesterone in risk reduction of preterm birth in women with short cervix in the midtrimester of pregnancy. Int J Womens Health. 2012;4:481-90. doi: 10.2147/IJWH.S28944. Epub 2012 Sep 14. [Article]
10. Okada H, Tsuzuki T, Murata H: Decidualization of the human endometrium. Reprod Med Biol. 2018 Feb 1;17(3):220-227. doi: 10.1002/rmb2.12088. eCollection 2018 Jul. [Article]
11. Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. [Article]
12. Child T, Leonard SA, Evans JS, Lass A: Systematic review of the clinical efficacy of vaginal progesterone for luteal phase support in assisted reproductive technology cycles. Reprod Biomed Online. 2018 Jun;36(6):630-645. doi: 10.1016/j.rbmo.2018.02.001. Epub 2018 Feb 22. [Article]
13. Check JH: Luteal Phase Support in assisted reproductive technology treatment: focus on Endometrin(R) (progesterone) vaginal insert. Ther Clin Risk Manag. 2009 Aug;5(4):403-7. Epub 2009 Jun 4. [Article]
14. Grimm SL, Hartig SM, Edwards DP: Progesterone Receptor Signaling Mechanisms. J Mol Biol. 2016 Sep 25;428(19):3831-49. doi: 10.1016/j.jmb.2016.06.020. Epub 2016 Jul 2. [Article]
15. Danielle B. Cooper; Rotimi Adigun (2018). Oral contraceptives. StatPearls Publishing.
16. Dhanalakshmi K. Thiyagarajan; Rebecca Jeanmonod (2019). Physiology, Menstrual Cycle. StatPearls publishing.
17. Drug approval package FDA [Link]
18. Merck Manuals: Abnormal Uterine Bleeding Due to Ovulatory Dysfunction (AUB-O) [Link]
19. AAFP: Abnormal uterine bleeding [Link]
20. Progesterone gel: Crinone® 4% and Crinone® 8% [File]
21. Endometrin FDA label, vaginal insert [File]
22. Norethindrone FDA label [File]
23. Progesterone injection, FDA label [File]
24. Utrogestan capsules, medsafe NZ label [File]
25. PROGESTERONE INJECTION USP IN SESAME OIL FOR INTRAMUSCULAR USE ONLY [File]

External Links

Human Metabolome Database

HMDB0001830

KEGG Drug

D00066

KEGG Compound

C00410

PubChem Compound

5994

PubChem Substance

46508968

ChemSpider

5773

BindingDB

8903

RxNav

8727

ChEBI

17026

ChEMBL

CHEMBL103

ZINC

ZINC000004428529

Therapeutic Targets Database

DAP000549

PharmGKB

PA451123

PDBe Ligand

STR

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Progesterone

PDB Entries

1a28 / 1dbb / 1h60 / 1mrq / 1w0f / 1ya3 / 2aa5 / 2aa6 / 2aba / 2hzq …

show 24 more

FDA label

Download (266 KB)

MSDS

Download (24 KB)

Clinical Trials

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package

Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not Available	Active Not Recruiting	Basic Science	Hyperandrogenemia / Polycystic Ovarian Syndrome (PCOS)	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Autoimmune Disorder / Infertility	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Dementia	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Female Infertility / Frozen-thawed Embryo Transfers / Infertility	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Frozen Embryo Pregnancy Rate	1	somestatus	stop reason	just information to hide

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Explore data packages curated & structured to speed up your pharmaceutical research

View Sample Data

Pharmacoeconomics

Manufacturers

• Bristol myers squibb
• Amarin pharmaceuticals inc
• Solvay pharmaceuticals
• Esi pharmacal
• Unimed pharmaceuticals llc
• Watson laboratories inc
• App pharmaceuticals llc
• Eli lilly and co
• Pharmaforce inc
• Alza corp
• Ferring pharmaceuticals inc

Packagers

• Abraxis BioScience Inc.
• APP Pharmaceuticals
• Ascend Therapeutics
• Carlisle Laboratories Inc.
• Catalent Pharma Solutions
• Columbia Labs
• Consolidated Midland Corp.
• Cutis Pharma Inc.
• Darby Dental Supply Co. Inc.
• Fleet Laboratories Ltd.
• Lyne Laboratories Inc.
• Marlex Pharmaceuticals
• Martica Enterprises Inc.
• Martin Surgical Supply
• Merit Pharmaceuticals
• My Healthcare Packaging Ltd. Contract Packaging
• Paddock Labs
• Pharmaceutics International Inc.
• Pharmaforce Inc.
• Physicians Total Care Inc.
• Primedics Laboratories
• Redpharm Drug
• Solvay Pharmaceuticals
• Spectrum Chemicals and Laboratory Products
• V Sab Medical Labs Inc.
• Watson Pharmaceuticals

Dosage Forms

Form	Route	Strength
Solution	Intramuscular	50 mg / mL
Cream	Topical	16.9 mg/1mL
Gel	Vaginal	8.000 g
Capsule	Oral
Gel	Cutaneous	1.000 g
Cream; gel	Vaginal
Gel	Vaginal	4 %
Gel	Vaginal	45 mg/1.125g
Gel	Vaginal	8 %
Gel	Vaginal	80 MG/G
Gel	Vaginal	90 MG
Gel	Vaginal	90 mg/1.125g
Gel	Vaginal	90.000 mg
Gel	Vaginal	8 g
Gel	Vaginal	8 % w/w
Solution	Intramuscular	50.000 mg
Suppository	Vaginal	200 mg
Tablet	Vaginal	400 mg
Suppository	Vaginal	400 mg
Suppository	Rectal; Vaginal	400 mg
Gel	Topical	1.00 g
Injection	Intramuscular
Insert	Vaginal	100 mg/1
Insert	Vaginal	100 mg
Tablet	Vaginal	100.000 mg
Tablet, effervescent	Vaginal	100 mg
Cream	Vaginal	2.5 G
Insert	Vaginal	200 MG
Capsule; spray, metered	Oral; Transdermal
Ring	Vaginal	11 mg/1d
Intrauterine device	Intrauterine; Vaginal	1 g
Capsule	Vaginal
Capsule	Oral; Vaginal	400.000 mg
Solution	Intramuscular	100 mg
Capsule	Oral; Vaginal	100.000 mg
Capsule, liquid filled	Oral; Vaginal	200 mg
Capsule, liquid filled	Oral; Vaginal	100 mg
Liquid	Intramuscular	50 mg / mL
Solution	Subcutaneous	25 mg / 1.112 mL
Suspension	Intramuscular
Capsule	Oral; Vaginal	200.000 mg
Solution	Topical
Solution	Intramuscular	25 mg
Capsule		200.000 mg
Cream	Transdermal	25 mg/85g
Cream	Transdermal	1 mg/1mg
Injection, powder, for solution
Injection, solution
Injection, solution		25 mg
Capsule	Oral	200 mg
Gel	Cutaneous	1.00 g
Gel		1.000 g
Injection, solution	Parenteral	25 mg
Capsule, liquid filled	Oral	400 mg
Drug delivery system	Vaginal	2.074 g
Injection	Intramuscular
Injection	Intramuscular	25 mg/ml
Injection	Intramuscular	50 mg/ml
Injection, solution	Intramuscular; Subcutaneous
Capsule	Not applicable	200 mg/1
Capsule, liquid filled	Oral	100 mg
Solution	Parenteral	100 mg
Capsule, liquid filled	Oral	200 mg
Capsule, liquid filled	Vaginal	200 mg
Capsule	Not applicable	100 mg/1
Capsule, gelatin coated	Not applicable	200 mg/1
Capsule, liquid filled	Oral	100 mg/1
Capsule, liquid filled	Oral	200 mg/1
Injection	Intramuscular	50 mg/1
Injection, solution	Intramuscular	50 mg/1mL
Injection, solution	Intramuscular
Gel	Topical	1 g
Gel
Solution	Intramuscular	25 mg/ml
Solution	Intramuscular	50 mg/ml
Capsule	Oral	100 mg
Capsule	Oral	100 mg/1
Capsule	Oral	200 mg/1
Capsule	Oral; Vaginal	200 MG
Injection, solution	Intramuscular	10 MG
Injection, solution	Intramuscular	25 MG
Injection, solution	Intramuscular	5 MG
Injection, solution	Intramuscular	50 mg/ml
Injection, solution	Parenteral	100 MG/ML
Injection, solution	Parenteral	50 MG/ML
Suspension	Parenteral	200 mg
Capsule
Capsule	Vaginal
Capsule	Vaginal	200 mg
Gel		90 mg
Solution	Intramuscular
Capsule		100 mg
Capsule		200 mg
Tablet	Vaginal	100 mg
Gel		1 %w/w

Prices

Unit description	Cost	Unit
Prochieve 4% Gel (18 Applicators Per Box)	160.18USD	tube
Crinone 8% Gel (1 Box = 6 Applications)	84.26USD	box
Prochieve 8% Gel 1.45 gm Tube	14.83USD	tube
Crinone 8% gel	13.61USD	g
Prochieve 8% gel	12.0USD	g
Prochieve 4% gel	8.56USD	g
Progesterone 50 mg/ml	6.6USD	ml
Progesterone oil 50 mg/ml vial	3.88USD	ml
Prometrium 200 mg capsule	3.84USD	capsule
First-progesterone vgs 400 susuppositoryp	3.33USD	each
First-progesterone vgs 200 suppository	3.15USD	each
First-progesterone vgs 100 suppository	3.0USD	each
First-progesterone vgs 50 suppository	2.93USD	each
First-progesterone vgs 25 suppository	2.88USD	each
Prometrium 100 mg capsule	1.69USD	capsule
Progesterone powder micronized	0.74USD	g
Progesterone powder milled	0.73USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5543150	No	1996-08-06	2013-09-15
US7300664	No	2007-11-27	2019-11-17
US7320800	No	2008-01-22	2019-11-17
US7393543	No	2008-07-01	2019-11-17
US9006222	No	2015-04-14	2032-11-21
US9114145	No	2015-08-25	2032-11-21
US8846649	No	2014-09-30	2032-11-21
US9301920	No	2016-04-05	2032-11-21
US8846648	No	2014-09-30	2032-11-21
US9114146	No	2015-08-25	2032-11-21
US8633178	No	2014-01-21	2032-11-21
US10052386	No	2018-08-21	2032-11-21
US8993548	No	2015-03-31	2032-11-21
US8987237	No	2015-03-24	2032-11-21
US8993549	No	2015-03-31	2032-11-21
US10206932	No	2019-02-19	2032-11-21
US10639375	No	2020-05-05	2032-11-21
US10548904	No	2020-02-04	2029-02-03
US8580293	No	2013-11-12	2030-01-21
US10537584	No	2020-01-21	2029-02-03
US10675288	No	2020-06-09	2032-11-21
US10806740	No	2020-10-20	2032-11-21
US11033626	No	2021-06-15	2032-11-21
US11103513	No	2021-08-31	2032-11-21
US11110099	No	2021-09-07	2032-11-21
US11103516	No	2021-08-31	2032-11-21
US8933059	No	2015-01-13	2032-11-21
US11166963	No	2021-11-09	2032-11-21
US11529360	No	2012-11-21	2032-11-21
US11793819	No	2012-11-21	2032-11-21
US11865179	No	2012-11-21	2032-11-21

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	128-132	https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx
boiling point (°C)	394.13°C (rough estimate)	https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx
water solubility	<0.1 g/100 mL at 19 ºC	https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx
logP	3.87	http://www.hmdb.ca/metabolites/HMDB0001830
logS	-4.43	http://www.hmdb.ca/metabolites/HMDB0001830
pKa	Strongest acidic: , Strongest basic: 18.92, -4.8	http://www.hmdb.ca/metabolites/HMDB0001830

Predicted Properties

Property	Value	Source
Water Solubility	0.00546 mg/mL	ALOGPS
logP	3.58	ALOGPS
logP	4.15	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	18.47	Chemaxon
pKa (Strongest Basic)	-4.8	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	34.14 Å2	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	92.71 m3·mol-1	Chemaxon
Polarizability	37.26 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.982
Caco-2 permeable	+	0.7724
P-glycoprotein substrate	Substrate	0.5449
P-glycoprotein inhibitor I	Inhibitor	0.8841
P-glycoprotein inhibitor II	Inhibitor	0.6043
Renal organic cation transporter	Non-inhibitor	0.6931
CYP450 2C9 substrate	Non-substrate	0.847
CYP450 2D6 substrate	Non-substrate	0.8795
CYP450 3A4 substrate	Substrate	0.7408
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9533
CYP450 2C19 inhibitor	Non-inhibitor	0.6514
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8203
Ames test	Non AMES toxic	0.9626
Carcinogenicity	Non-carcinogens	0.9151
Biodegradation	Not ready biodegradable	0.9575
Rat acute toxicity	1.8041 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7451
hERG inhibition (predictor II)	Non-inhibitor	0.7454

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (11.5 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS	GC-MS	splash10-0fbc-5910000000-422e38df6de7e8b0a4b7
GC-MS Spectrum - GC-MS	GC-MS	splash10-0fbc-5910000000-385f45345742235da8e0
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-000g-1590000000-3ebb52b90c541e38c0b4
GC-MS Spectrum - EI-B	GC-MS	splash10-024l-6923000000-639c7405f69825de7f90
GC-MS Spectrum - EI-B	GC-MS	splash10-0229-2941000000-1e075d8489b79cf4e34a
GC-MS Spectrum - EI-B	GC-MS	splash10-0229-3963000000-f35e3d9faf6b2ee87465
GC-MS Spectrum - GC-MS	GC-MS	splash10-0fbc-5910000000-422e38df6de7e8b0a4b7
GC-MS Spectrum - GC-MS	GC-MS	splash10-0fbc-5910000000-385f45345742235da8e0
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-0f6x-2910000000-1baafb91a3e0b988caa7
Mass Spectrum (Electron Ionization)	MS	splash10-006x-7931000000-f6ad83adccd7e016fa29
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-014i-1009000000-0f8b7c3e6c2265c3889f
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-052b-8900000000-0b0167121b798e7e7534
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-052b-9400000000-881510cbcecd9cb61f4f
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	LC-MS/MS	splash10-024l-6923000000-639c7405f69825de7f90
MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	LC-MS/MS	splash10-0229-2941000000-1e075d8489b79cf4e34a
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-004i-0950000000-ca28d8dfdf780c201716
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-000i-1900000000-857f6720dd17fb2547d1
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-004i-3930000000-fda87095285a83b85ad5
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00kb-7955000000-a22f06eac940cd4f753d
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0139000000-6b47f75a44df3e20fa3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0aba-0950000000-b26d04d179294aa67cc7
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0aba-0920000000-d0a3365efe1f8a589564
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-05aj-0910000000-61d7a07e6be85600e1f1
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0009000000-67c6f0147801f0ece957
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-05mk-8956000000-aa5fe992c41261b62fbf
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-052b-6910000000-5e26497eb2d0150a30ac
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-052b-9700000000-523fe1ad11bfcbb46f85
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-054k-9400000000-e3d581bd8685e1d3f35d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4j-5900000000-8a409fe2508f58822f8a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4j-8900000000-fc9280df2a7dee451abb
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0290000000-0f9dd31ff254325dd522
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0290000000-b59a04537c8d112aa2ab
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0002-0190000000-b5fed26f17626a75c34c
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0002-0190000000-58920a9d93488054d8d5
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-002k-0190000000-5f1ba0db62e0ade93f30
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0229000000-c83c60bdf0d3b91077c9
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4j-5921000000-fccf432e6f84ed354acd
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4i-4921100000-41abb61d58cd1d7a0f7c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kb-0496000000-9d32ec645400bae238ae
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0009000000-0af9fe9dbb70096e067e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03dj-0079000000-b26a1063e643392710a8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0101-0951000000-d2bf38ea3f5bc713f0db
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01p9-0093000000-ca47d1a54aac439e3143
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0adl-1920000000-ff0f04d9a59ab28bfab4
1H NMR Spectrum	1D NMR	Not Applicable
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	187.3581755	predicted	DarkChem Lite v0.1.0
[M-H]-	187.8123755	predicted	DarkChem Lite v0.1.0
[M-H]-	187.8051755	predicted	DarkChem Lite v0.1.0
[M-H]-	186.7997755	predicted	DarkChem Lite v0.1.0
[M-H]-	187.0225755	predicted	DarkChem Lite v0.1.0
[M-H]-	180.22621	predicted	DeepCCS 1.0 (2019)
[M+H]+	188.3041755	predicted	DarkChem Lite v0.1.0
[M+H]+	175.99825	predicted	DarkChem Standard v0.1.0
[M+H]+	189.1595755	predicted	DarkChem Lite v0.1.0
[M+H]+	187.3317755	predicted	DarkChem Lite v0.1.0
[M+H]+	187.5244755	predicted	DarkChem Lite v0.1.0
[M+H]+	182.30602	predicted	DeepCCS 1.0 (2019)
[M+Na]+	188.2207755	predicted	DarkChem Lite v0.1.0
[M+Na]+	187.9469755	predicted	DarkChem Lite v0.1.0
[M+Na]+	188.6825755	predicted	DarkChem Lite v0.1.0
[M+Na]+	187.4057755	predicted	DarkChem Lite v0.1.0
[M+Na]+	187.1997755	predicted	DarkChem Lite v0.1.0
[M+Na]+	188.95586	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	2.9	N/A	N/A	A28036 / A28045 / A28037 / A28038 / A28039 / A28047 / A28040 / A28041
EC 50 (nM)	1.5	N/A	N/A	A28046
EC 50 (nM)	>10000	N/A	N/A	A28038
EC 50 (nM)	1.8	N/A	N/A	A28039 / A28047 / A28041
EC 50 (nM)	0.92	N/A	N/A	A28048 / A28049
EC 50 (nM)	0.9	N/A	N/A	A28049 / A28051
EC 50 (nM)	0.5	N/A	N/A	A28050
EC 50 (nM)	2.2	N/A	N/A	A28050
EC 50 (nM)	0.1	N/A	N/A	A28052
EC 50 (nM)	15.2	N/A	N/A	A28042
IC 50 (nM)	5	N/A	N/A	A28043
IC 50 (nM)	17	N/A	N/A	A28044
IC 50 (nM)	3.5	N/A	N/A	A28048
IC 50 (nM)	>10000	N/A	N/A	A28042
Ki (nM)	3.5	N/A	N/A	A28035 / A28036 / A28045 / A28037 / A28038 / A28039 / A28047 / A28040 / A28041
Ki (nM)	3.8	N/A	N/A	A28046
Ki (nM)	3.4	N/A	N/A	A28050
Ki (nM)	5.1	N/A	N/A	A28042

Details

Binding Properties1. Progesterone receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Depending on the isoform, progesterone receptor functions as a transcriptional activator or repressor

Specific Function

ATPase binding

Gene Name

PGR

Uniprot ID

P06401

Uniprot Name

Progesterone receptor

Molecular Weight

98979.96 Da

References

1. Madauss KP, Stewart EL, Williams SP: The evolution of progesterone receptor ligands. Med Res Rev. 2007 May;27(3):374-400. [Article]
2. Gizard F, Robillard R, Gross B, Barbier O, Revillion F, Peyrat JP, Torpier G, Hum DW, Staels B: TReP-132 is a novel progesterone receptor coactivator required for the inhibition of breast cancer cell growth and enhancement of differentiation by progesterone. Mol Cell Biol. 2006 Oct;26(20):7632-44. [Article]
3. Boonyaratanakornkit V, McGowan E, Sherman L, Mancini MA, Cheskis BJ, Edwards DP: The role of extranuclear signaling actions of progesterone receptor in mediating progesterone regulation of gene expression and the cell cycle. Mol Endocrinol. 2007 Feb;21(2):359-75. Epub 2006 Nov 30. [Article]
4. Tranguch S, Smith DF, Dey SK: Progesterone receptor requires a co-chaperone for signalling in uterine biology and implantation. Reprod Biomed Online. 2006 Nov;13(5):651-60. [Article]
5. Luconi M, Bonaccorsi L, Maggi M, Pecchioli P, Krausz C, Forti G, Baldi E: Identification and characterization of functional nongenomic progesterone receptors on human sperm membrane. J Clin Endocrinol Metab. 1998 Mar;83(3):877-85. [Article]
6. Okada H, Tsuzuki T, Murata H: Decidualization of the human endometrium. Reprod Med Biol. 2018 Feb 1;17(3):220-227. doi: 10.1002/rmb2.12088. eCollection 2018 Jul. [Article]
7. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>14	N/A	N/A	A28035
IC 50 (nM)	30	N/A	N/A	A28053
IC 50 (nM)	14	N/A	N/A	A28036 / A28037 / A28040 / A28041
Kd (nM)	0.39	N/A	N/A	A28053

Details

Binding Properties2. Mineralocorticoid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

Agonist

General Function

Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels

Specific Function

DNA-binding transcription factor activity

Gene Name

NR3C2

Uniprot ID

P08235

Uniprot Name

Mineralocorticoid receptor

Molecular Weight

107080.615 Da

References

1. Rupprecht R, Reul JM, van Steensel B, Spengler D, Soder M, Berning B, Holsboer F, Damm K: Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands. Eur J Pharmacol. 1993 Oct 15;247(2):145-54. [Article]
2. Quinkler M, Meyer B, Bumke-Vogt C, Grossmann C, Gruber U, Oelkers W, Diederich S, Bahr V: Agonistic and antagonistic properties of progesterone metabolites at the human mineralocorticoid receptor. Eur J Endocrinol. 2002 Jun;146(6):789-99. [Article]
3. Myles K, Funder JW: Progesterone binding to mineralocorticoid receptors: in vitro and in vivo studies. Am J Physiol. 1996 Apr;270(4 Pt 1):E601-7. doi: 10.1152/ajpendo.1996.270.4.E601. [Article]
4. Souque A, Fagart J, Couette B, Davioud E, Sobrio F, Marquet A, Rafestin-Oblin ME: The mineralocorticoid activity of progesterone derivatives depends on the nature of the C18 substituent. Endocrinology. 1995 Dec;136(12):5651-8. doi: 10.1210/endo.136.12.7588320. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>1000	N/A	N/A	A28034

Details

Binding Properties3. Estrogen receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

Inhibitor

Downregulator

General Function

Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)

Specific Function

14-3-3 protein binding

Gene Name

ESR1

Uniprot ID

P03372

Uniprot Name

Estrogen receptor

Molecular Weight

66215.45 Da

References

1. Lessey BA, Palomino WA, Apparao KB, Young SL, Lininger RA: Estrogen receptor-alpha (ER-alpha) and defects in uterine receptivity in women. Reprod Biol Endocrinol. 2006;4 Suppl 1:S9. [Article]
2. Montero Girard G, Vanzulli SI, Cerliani JP, Bottino MC, Bolado J, Vela J, Becu-Villalobos D, Benavides F, Gutkind S, Patel V, Molinolo A, Lanari C: Association of estrogen receptor-alpha and progesterone receptor A expression with hormonal mammary carcinogenesis: role of the host microenvironment. Breast Cancer Res. 2007;9(2):R22. [Article]
3. Mohammed H, Russell IA, Stark R, Rueda OM, Hickey TE, Tarulli GA, Serandour AA, Birrell SN, Bruna A, Saadi A, Menon S, Hadfield J, Pugh M, Raj GV, Brown GD, D'Santos C, Robinson JL, Silva G, Launchbury R, Perou CM, Stingl J, Caldas C, Tilley WD, Carroll JS: Progesterone receptor modulates ERalpha action in breast cancer. Nature. 2015 Jul 16;523(7560):313-7. doi: 10.1038/nature14583. Epub 2015 Jul 8. [Article]
4. Jayaraman A, Pike CJ: Progesterone attenuates oestrogen neuroprotection via downregulation of oestrogen receptor expression in cultured neurones. J Neuroendocrinol. 2009 Jan;21(1):77-81. doi: 10.1111/j.1365-2826.2008.01801.x. [Article]
5. Tessier C, Deb S, Prigent-Tessier A, Ferguson-Gottschall S, Gibori GB, Shiu RP, Gibori G: Estrogen receptors alpha and beta in rat decidua cells: cell-specific expression and differential regulation by steroid hormones and prolactin. Endocrinology. 2000 Oct;141(10):3842-51. doi: 10.1210/endo.141.10.7734. [Article]

Details4. Steroid 17-alpha-hydroxylase/17,20 lyase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Substrate

Inhibitor

General Function

A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:9452426). Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol (Probable) (PubMed:25301938, PubMed:9452426). Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:36640554, PubMed:9452426). Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA (PubMed:36640554). Also 16-alpha hydroxylates androgens, relevant for estriol synthesis (PubMed:25301938, PubMed:27339894). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:9452426)

Specific Function

heme binding

Gene Name

CYP17A1

Uniprot ID

P05093

Uniprot Name

Steroid 17-alpha-hydroxylase/17,20 lyase

Molecular Weight

57369.995 Da

References

1. Haidar S, Hartmann RW: C16 and C17 substituted derivatives of pregnenolone and progesterone as inhibitors of 17alpha-hydroxylase-C17, 20-lyase: synthesis and biological evaluation. Arch Pharm (Weinheim). 2002;335(11-12):526-34. [Article]
2. Vasaitis TS, Bruno RD, Njar VC: CYP17 inhibitors for prostate cancer therapy. J Steroid Biochem Mol Biol. 2011 May;125(1-2):23-31. doi: 10.1016/j.jsbmb.2010.11.005. Epub 2010 Nov 17. [Article]
3. Auchus RJ, Sampath Kumar A, Andrew Boswell C, Gupta MK, Bruce K, Rath NP, Covey DF: The enantiomer of progesterone (ent-progesterone) is a competitive inhibitor of human cytochromes P450c17 and P450c21. Arch Biochem Biophys. 2003 Jan 1;409(1):134-44. [Article]

Details5. Kappa-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Activator

Potentiator

General Function

G-protein coupled opioid receptor that functions as a receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as a receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain. Plays a role in mediating reduced physical activity upon treatment with synthetic opioids. Plays a role in the regulation of salivation in response to synthetic opioids. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Specific Function

dynorphin receptor activity

Gene Name

OPRK1

Uniprot ID

P41145

Uniprot Name

Kappa-type opioid receptor

Molecular Weight

42644.665 Da

References

1. Dawson-Basoa ME, Gintzler AR: Estrogen and progesterone activate spinal kappa-opiate receptor analgesic mechanisms. Pain. 1996 Jan;64(1):169-77. [Article]
2. Gordon FT, Soliman MR: The effects of estradiol and progesterone on pain sensitivity and brain opioid receptors in ovariectomized rats. Horm Behav. 1996 Sep;30(3):244-50. doi: 10.1006/hbeh.1996.0029. [Article]

Details6. Alpha-1-acid glycoprotein 1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Binder

General Function

Functions as a transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction

Specific Function

Not Available

Gene Name

ORM1

Uniprot ID

P02763

Uniprot Name

Alpha-1-acid glycoprotein 1

Molecular Weight

23539.43 Da

References

1. Albani JR: Progesterone binding to the tryptophan residues of human alpha1-acid glycoprotein. Carbohydr Res. 2006 Nov 6;341(15):2557-64. Epub 2006 Aug 8. [Article]
2. De Ceukeleire M, Albani JR: Interaction between carbohydrate residues of alpha(1)-acid glycoprotein (orosomucoid) and progesterone. A fluorescence study. Carbohydr Res. 2002 Sep 3;337(15):1405-10. [Article]
3. Albani JR: Binding effect of progesterone on the dynamics of alpha1-acid glycoprotein. Biochim Biophys Acta. 1997 Aug 29;1336(2):349-59. [Article]
4. Nishi K, Sakai N, Komine Y, Maruyama T, Halsall HB, Otagiri M: Structural and drug-binding properties of alpha(1)-acid glycoprotein in reverse micelles. Biochim Biophys Acta. 2002 Dec 16;1601(2):185-91. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>1000	N/A	N/A	A28035 / A28036 / A28037 / A28049 / A28040 / A28041
Ki (nM)	31	N/A	N/A	A28035 / A28039
Ki (nM)	30.5	N/A	N/A	A28036 / A28037 / A28038 / A28041

Details

Binding Properties7. Glucocorticoid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Partial agonist

General Function

Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth (By similarity)

Specific Function

core promoter sequence-specific DNA binding

Gene Name

NR3C1

Uniprot ID

P04150

Uniprot Name

Glucocorticoid receptor

Molecular Weight

85658.57 Da

References

1. Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN: Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins. Am J Obstet Gynecol. 2007 Dec;197(6):599.e1-7. [Article]
2. Xu XF, Hoebeke J, Bjorntorp P: Progestin binds to the glucocorticoid receptor and mediates antiglucocorticoid effect in rat adipose precursor cells. J Steroid Biochem. 1990 Aug 14;36(5):465-71. [Article]
3. Leo JC, Guo C, Woon CT, Aw SE, Lin VC: Glucocorticoid and mineralocorticoid cross-talk with progesterone receptor to induce focal adhesion and growth inhibition in breast cancer cells. Endocrinology. 2004 Mar;145(3):1314-21. doi: 10.1210/en.2003-0732. Epub 2003 Nov 14. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	37	N/A	N/A	A28035 / A28036 / A28037 / A28040 / A28041
Ki (nM)	8.5	N/A	N/A	A28035 / A28036 / A28037 / A28038 / A28039 / A28041
Ki (nM)	35	N/A	N/A	A28042

Details

Binding Properties8. Androgen receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

Potentiator

General Function

Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues (PubMed:19022849). Transcription factor activity is modulated by bound coactivator and corepressor proteins like ZBTB7A that recruits NCOR1 and NCOR2 to the androgen response elements/ARE on target genes, negatively regulating androgen receptor signaling and androgen-induced cell proliferation (PubMed:20812024). Transcription activation is also down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3

Specific Function

androgen binding

Gene Name

AR

Uniprot ID

P10275

Uniprot Name

Androgen receptor

Molecular Weight

99187.115 Da

References

1. Miedema BW, Kelly KA, Camilleri M, Hanson RB, Zinsmeister AR, O'Connor MK, Brown ML: Human gastric and jejunal transit and motility after Roux gastrojejunostomy. Gastroenterology. 1992 Oct;103(4):1133-43. [Article]
2. Bentel JM, Birrell SN, Pickering MA, Holds DJ, Horsfall DJ, Tilley WD: Androgen receptor agonist activity of the synthetic progestin, medroxyprogesterone acetate, in human breast cancer cells. Mol Cell Endocrinol. 1999 Aug 20;154(1-2):11-20. [Article]
3. Yuan X, Balk SP: Mechanisms mediating androgen receptor reactivation after castration. Urol Oncol. 2009 Jan-Feb;27(1):36-41. doi: 10.1016/j.urolonc.2008.03.021. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	115	N/A	N/A	A27953

Details

Binding Properties9. Sex hormone-binding globulin

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Binder

Potentiator

General Function

Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration

Specific Function

androgen binding

Gene Name

SHBG

Uniprot ID

P04278

Uniprot Name

Sex hormone-binding globulin

Molecular Weight

43778.755 Da

References

1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
2. Dalton ME: The effect of progesterone administration on sex hormone binding globulin binding capacity in women with severe premenstrual syndrome. J Steroid Biochem. 1984 Jan;20(1):437-9. [Article]
3. Misao R, Nakanishi Y, Fujimoto J, Tamaya T: Effects of danazol and progesterone on sex hormone-binding globulin mRNA expression in human endometrial cancer cell line Ishikawa. J Steroid Biochem Mol Biol. 1997 Jul;62(4):321-5. [Article]

Details10. Estrogen receptor beta

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

Downregulator

General Function

Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1/ER-alpha, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560)

Specific Function

DNA binding

Gene Name

ESR2

Uniprot ID

Q92731

Uniprot Name

Estrogen receptor beta

Molecular Weight

59215.765 Da

References

1. Aguirre C, Jayaraman A, Pike C, Baudry M: Progesterone inhibits estrogen-mediated neuroprotection against excitotoxicity by down-regulating estrogen receptor-beta. J Neurochem. 2010 Dec;115(5):1277-87. doi: 10.1111/j.1471-4159.2010.07038.x. Epub 2010 Oct 26. [Article]
2. Jayaraman A, Pike CJ: Progesterone attenuates oestrogen neuroprotection via downregulation of oestrogen receptor expression in cultured neurones. J Neuroendocrinol. 2009 Jan;21(1):77-81. doi: 10.1111/j.1365-2826.2008.01801.x. [Article]
3. Tessier C, Deb S, Prigent-Tessier A, Ferguson-Gottschall S, Gibori GB, Shiu RP, Gibori G: Estrogen receptors alpha and beta in rat decidua cells: cell-specific expression and differential regulation by steroid hormones and prolactin. Endocrinology. 2000 Oct;141(10):3842-51. doi: 10.1210/endo.141.10.7734. [Article]
4. Montero Girard G, Vanzulli SI, Cerliani JP, Bottino MC, Bolado J, Vela J, Becu-Villalobos D, Benavides F, Gutkind S, Patel V, Molinolo A, Lanari C: Association of estrogen receptor-alpha and progesterone receptor A expression with hormonal mammary carcinogenesis: role of the host microenvironment. Breast Cancer Res. 2007;9(2):R22. [Article]

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Drug created at June 13, 2005 13:24 / Updated at October 11, 2024 18:19