Identification

Name
Progesterone
Accession Number
DB00396  (APRD00700)
Type
Small Molecule
Groups
Approved, Vet approved
Description

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].

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Progesterone InjectionSolution50 mgIntramuscularActavis Pharma Company2016-04-13Not applicableCanada
CrinoneGel45 mg/1.125gVaginalActavis Pharma, Inc.1997-05-132020-02-29Us
CrinoneGel90 mg/1.125gVaginalColumbia Laboratories1997-05-13Not applicableUs
CrinoneGel90 mg/1.125gVaginalAllergan, Inc.1997-05-13Not applicableUs
CrinoneGel8 %VaginalEmd Serono, A Division Of Emd Inc., Canada2000-05-20Not applicableCanada
CrinoneGel90 mg/1.125gVaginalActavis Pharma, Inc.1997-05-132015-03-31Us
CrinoneGel90 mg/1.125gVaginalColumbia Laboratories1997-05-13Not applicableUs
CrinoneGel45 mg/1.125gVaginalAllergan, Inc.1997-05-13Not applicableUs
CrinoneGel45 mg/1.125gVaginalActavis Pharma, Inc.1997-05-132015-02-28Us
CrinoneGel45 mg/1.125gVaginalColumbia Laboratories1997-05-13Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PMS-progesterone Inj 50mg/ml USPLiquid50 mgIntramuscularPharmascience Inc1989-12-312004-01-21Canada
ProgesteroneCapsule200 mg/1OralGolden State Medical Supply, Inc.2017-04-05Not applicableUs
ProgesteroneCapsule100 mg/1OralGolden State Medical Supply2014-04-232017-01-02Us
ProgesteroneCapsule200 mg/1OralBionpharma Inc.2018-11-28Not applicableUs
ProgesteroneCapsule, liquid filled200 mg/1Oralbryant ranch prepack2012-03-01Not applicableUs
ProgesteroneCapsule100 mg/1OralBanner Life Sciences Llc.2015-10-01Not applicableUs
ProgesteroneCapsule200 mg/1OralBionpharma Inc.2016-09-20Not applicableUs
ProgesteroneCapsule, liquid filled200 mg/1OralTeva Pharmaceuticals USA, Inc.2012-03-01Not applicableUs00093 5354 01 nlmimage10 e73673e3
ProgesteroneCapsule100 mg/1OralBanner Pharmacaps2014-01-01Not applicableUs10888 7135 02 nlmimage10 834941ca
ProgesteroneCapsule100 mg/1OralAmneal Pharmaceuticals LLC2017-09-11Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BijuvaProgesterone (100 mg/1) + Estradiol (1 mg/1)CapsuleOralTherapeuticsMD, Inc.2019-01-15Not applicableUs
Estrogel PropakProgesterone (100 mg) + Estradiol (0.06 %)Capsule; Gel, meteredOral; TransdermalMerck Ltd.2013-04-082016-06-08Canada
International/Other Brands
Agolutin (Biotika) / Crinone / Cyclogest (Actavis) / Gesterol / Gestone (Nordic Pharma) / Progestasert / Progestogel (Besins) / Qi Ning (Aisheng Pharmaceutical) / Relantan (Aversi) / Susten (Sun Pharma) / Utrogestan (Besins) / Utrogestran (Faran Laboratories) / Utrovin (Bestochem) / Vasclor (Verisfield)
Categories
UNII
4G7DS2Q64Y
CAS number
57-83-0
Weight
Average: 314.4617
Monoisotopic: 314.224580204
Chemical Formula
C21H30O2
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

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].

Associated Conditions
Associated Therapies
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].

TargetActionsOrganism
AProgesterone receptor
agonist
Humans
UEstrogen receptor alpha
agonist
inhibitor
downregulator
Humans
AMineralocorticoid receptor
antagonist
agonist
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].

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].

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].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDisease
11-beta-Hydroxylase Deficiency (CYP11B1)Disease
Apparent Mineralocorticoid Excess SyndromeDisease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase DeficiencyDisease
Corticosterone Methyl Oxidase I Deficiency (CMO I)Disease
3-beta-Hydroxysteroid Dehydrogenase DeficiencyDisease
SteroidogenesisMetabolic
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase DeficiencyDisease
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
DrugInteraction
(R)-warfarinProgesterone may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinProgesterone may decrease the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Progesterone.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Progesterone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Progesterone.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Progesterone.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Progesterone.
6-Deoxyerythronolide BThe metabolism of Progesterone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Progesterone.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be increased when combined with Progesterone.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take at the same time everyday.
  • Take with food.

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. [PubMed:17747122]
  2. Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. [PubMed:4922128]
  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. [PubMed:15135772]
  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. [PubMed:3184927]
  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. [PubMed:10584066]
  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. [PubMed:9328296]
  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. [PubMed:20104424]
  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. [PubMed:27567593]
  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. [PubMed:23071418]
  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. [PubMed:30013421]
  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. [PubMed:24606090]
  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. [PubMed:29550390]
  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. [PubMed:19753133]
  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. [PubMed:27380738]
  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
ChEBI
17026
ChEMBL
CHEMBL103
Therapeutic Targets Database
DAP000549
PharmGKB
PA451123
HET
STR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Progesterone
ATC Codes
G03FA04 — Progesterone and estrogenG03DA04 — Progesterone
AHFS Codes
  • 68:32.00 — Progestins
PDB Entries
1a28 / 1dbb / 1h60 / 1mrq / 1w0f / 1ya3 / 2aa5 / 2aa6 / 2aba / 2hzq
show 18 more
FDA label
Download (266 KB)
MSDS
Download (24 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingDiagnosticEndometrial Receptivity;RNA; Progesterone1
0Not Yet RecruitingTreatmentFunctional Ovarian Cyst / Progesterone1
0RecruitingBasic ScienceHyperandrogenism / Puberty1
0RecruitingTreatmentCannabis Use Disorders / Cannabis Withdrawal1
1Active Not RecruitingBasic ScienceFemale Puberty1
1CompletedNot AvailableDependence, Cocaine1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentInfertilities1
1CompletedTreatmentMenopause1
1CompletedTreatmentTobacco Use Disorders1
1RecruitingBasic ScienceHyperandrogenism / Normal Puberty / Polycystic Ovaries Syndrome1
1RecruitingOtherNormal / Polycystic Ovarian Syndrome1
1RecruitingTreatmentPremature Obstetric Labor1
1TerminatedBasic ScienceFemale Reproductive Physiology1
1TerminatedTreatmentPregnancy1
1, 2CompletedOtherAging / One to five years postmenopausal1
1, 2CompletedTreatmentInfertilities1
1, 2CompletedTreatmentPostmenopausal Endometrium1
1, 2CompletedTreatmentTraumatic Brain Injury (TBI)1
1, 2RecruitingPreventionPerimenopausal Disorder / Stress, Emotional1
1, 2RecruitingTreatmentUnwanted Pregnancies1
2CompletedBasic ScienceOrthostatic Intolerance1
2CompletedPreventionPreterm Delivery1
2CompletedPreventionProlonged QT Interval in EKG and Sudden Death1
2CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentAtherosclerosis / Healthy Volunteers / Vascular Diseases1
2CompletedTreatmentBipolar Disorder (BD) / Mania / Schizoaffective Disorders1
2CompletedTreatmentCervical Intraepithelial Neoplasia (CIN)1
2CompletedTreatmentControlled Ovarian Stimulation / Ovarian Stimulation1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentHeavy Uterine Bleeding / Uterine Leiomyomas1
2CompletedTreatmentInfertilities1
2CompletedTreatmentMenopause1
2CompletedTreatmentTobacco Use Disorders1
2Not Yet RecruitingTreatmentIVF1
2Not Yet RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
2RecruitingPreventionAbortions spontaneous / Premature Births1
2RecruitingPreventionPregnancy termination therapy1
2RecruitingTreatmentBrain Development / Congenital Heart Disease (CHD) / Fetal Neuroprotection / Neurodevelopmental Disability / Periventricular Leucomalacia / Surgery, Cardiac1
2RecruitingTreatmentCardiovascular Disease (CVD) / Estrogen Deficiency / Hypothalamic Amenorrhea1
2RecruitingTreatmentInfertilities1
2TerminatedTreatmentMenopause1
2TerminatedTreatmentVulvar Lichen Sclerosus1
2Unknown StatusDiagnosticPremenstrual Syndrome1
2Unknown StatusPreventionPremature Labour1
2Unknown StatusTreatmentEndometrial Cancers / Endometrial Hyperplasia1
2Unknown StatusTreatmentMenopause1
2Unknown StatusTreatmentPremenstrual Syndrome1
2, 3CompletedPreventionPreterm Delivery1
2, 3CompletedTreatmentAlzheimer's Disease (AD)1
2, 3CompletedTreatmentDependence, Cocaine1
2, 3CompletedTreatmentMenopause1
2, 3Not Yet RecruitingTreatmentPremature Births / Short Cervix1
2, 3RecruitingPreventionPremature Births / Twin Pregnancy With Antenatal Problem1
2, 3RecruitingTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
2, 3RecruitingTreatmentAtypical Endometrial Hyperplasia / Endometrial Cancers1
2, 3TerminatedTreatmentComplications, Pregnancy1
2, 3Unknown StatusScreeningPreeclampsia1
2, 3WithdrawnPreventionCervical incompetence / Cervical Shortening / Premature Births / Preterm Labor With Preterm Delivery, Unspecified Trimester, Fetus 21
3Active Not RecruitingTreatmentMenopausal Hot Flushes / Night Sweats1
3Active Not RecruitingTreatmentMenstrual Cramps / Perimenopause1
3CompletedBasic ScienceMenopause1
3CompletedPreventionAlzheimer's Disease (AD) / Memory Disorders1
3CompletedPreventionBone Diseases / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Ischemia / One to five years postmenopausal / Osteoporosis / Thrombotic events1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Arteriosclerosis / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia / One to five years postmenopausal1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / One to five years postmenopausal / Unstable Angina Pectoris1
3CompletedPreventionNeonatal Complications / Premature Births / Preterm Delivery1
3CompletedPreventionPregnancy1
3CompletedPreventionPregnancy Trimester, Second / Premature Births1
3CompletedPreventionPremature Births1
3CompletedPreventionPreterm Delivery1
3CompletedPreventionPreterm Delivery / Short Cervix / Short Uterine Cervical Length1
3CompletedTreatmentAssisted Reproductive Technology therapy4
3CompletedTreatmentBrain Injury1
3CompletedTreatmentFertility1
3CompletedTreatmentInfertilities4
3CompletedTreatmentMenopause1
3CompletedTreatmentPremature Births1
3Not Yet RecruitingPreventionPremature Births / Twin Pregnancy1
3RecruitingPreventionObstetric Labor, Premature [C13.703.420.491] / Twins, Dizygotic [M01.438.873.920]1
3RecruitingTreatmentEndometrial Polyps1
3RecruitingTreatmentEndometriosis1
3RecruitingTreatmentExercise-related Amenorrhea1
3RecruitingTreatmentInfertilities1
3RecruitingTreatmentPrimary Ovarian Insufficiency1
3RecruitingTreatmentShort Cervical Length1
3TerminatedPreventionMorbidity / Perinatal Mortality / Preterm Delivery1
3TerminatedTreatmentMenopause related conditions1
3TerminatedTreatmentSecondary Amenorrhea1
3TerminatedTreatmentThreatened Abortion in First Trimester1
3TerminatedTreatmentTraumatic Brain Injury (TBI)1
3Unknown StatusPreventionPremature Births1
3WithdrawnTreatmentAmenorrhea / Bone Loss1
3WithdrawnTreatmentInfertilities1
3WithdrawnTreatmentLuteal Phase Defect1
4Active Not RecruitingPreventionPreterm Delivery1
4CompletedBasic ScienceContraception / Fertility1
4CompletedBasic SciencePerimenopausal Depression1
4CompletedBasic ScienceSuicidal Thoughts1
4CompletedPreventionContraception / Pregnancy1
4CompletedPreventionDrug-induced QT Interval Prolongation / Long qt Syndrome / Prolonged QT Interval in EKG and Sudden Death1
4CompletedPreventionPremature Labour1
4CompletedPreventionPreterm Delivery1
4CompletedTreatmentAbortions spontaneous / Subchorionic Hematoma in the First Trimester Pregnancy1
4CompletedTreatmentConcussions1
4CompletedTreatmentFertility / Optimal Stimulation Protocol / Reproductive Endocrinology1
4CompletedTreatmentHealthy Volunteers / One to five years postmenopausal1
4CompletedTreatmentInfertilities7
4CompletedTreatmentInfertilities / Polycystic Ovarian Syndrome1
4CompletedTreatmentInfertilities / Progesterone Levels1
4CompletedTreatmentPremature Labour1
4CompletedTreatmentPremature Ovarian Failure (POF)1
4CompletedTreatmentRecurrent Abortion1
4CompletedTreatmentReproductive Techniques, Assisted1
4CompletedTreatmentSecondary Amenorrhea1
4CompletedTreatmentThreatened Premature Labor1
4Not Yet RecruitingPreventionAbnormalities, Drug-Induced / Long qt Syndrome1
4Not Yet RecruitingTreatmentDydrogesterone / Genital Diseases, Female / Genital Diseases, Male / Hormones / Hormones, Hormone Substitutes, and Hormone Antagonists / Infertilities / Infertility, Female / Physiological Effects of Drugs / Progesterone / Progestins1
4Not Yet RecruitingTreatmentInfertilities1
4RecruitingBasic ScienceSuicidal Thoughts1
4RecruitingPreventionPremature Births1
4RecruitingPreventionPremature Labour1
4RecruitingSupportive CareAssisted Reproductive Technology therapy / Infertilities1
4RecruitingTreatmentCessation, Smoking1
4RecruitingTreatmentFrozen Embryo Transfer / Pregnancy Loss1
4RecruitingTreatmentInfertilities3
4RecruitingTreatmentNicotine Dependence / Nicotine Withdrawal1
4RecruitingTreatmentPremature Labour1
4SuspendedTreatmentInfertilities1
4TerminatedTreatmentObstetric Labour, Premature1
4Unknown StatusNot AvailablePharmacogenomics / Systems Biology1
4Unknown StatusPreventionArteriosclerosis / Menopause1
4Unknown StatusPreventionPregnancy1
4Unknown StatusTreatmentCryopreservation / Implantation, Embryo / Progesteron1
4Unknown StatusTreatmentIVF - Luteal Phase Support After Embryo Transfer1
4Unknown StatusTreatmentPregnancy / Pregnancy Loss1
4Unknown StatusTreatmentProgesterone Supplementation1
Not AvailableActive Not RecruitingBasic ScienceHyperandrogenemia / Polycystic Ovaries Syndrome1
Not AvailableActive Not RecruitingBasic ScienceHyperandrogenism / Polycystic Ovaries Syndrome1
Not AvailableCompletedNot AvailableAssisted Reproductive Technology therapy2
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableInfertility, Subfertility1
Not AvailableCompletedNot AvailableNeonates / Pregnancy3
Not AvailableCompletedNot AvailablePolycystic Ovarian Syndrome1
Not AvailableCompletedNot AvailableThreatened Miscarriage1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Infertilities1
Not AvailableCompletedBasic ScienceCoronary Heart Disease (CHD)1
Not AvailableCompletedBasic ScienceHyperandrogenemia / Polycystic Ovary Syndrome (PCOS)1
Not AvailableCompletedBasic SciencePostpartum Depression1
Not AvailableCompletedOtherBMI >30 kg/m2 / Obstructive Sleep Apnea (OSA) / Polycystic Ovaries Syndrome / Polycystic Ovary Syndrome (PCOS)1
Not AvailableCompletedPreventionPremature Births1
Not AvailableCompletedPreventionThe Association Between Progesterone Levels and Smoking Related Symptomatology and Nicotine Cravings / The Association Between Progesterone Levels and Smoking-related Symptomatology and Nicotine Cravings1
Not AvailableCompletedPreventionTobacco Cessation1
Not AvailableCompletedPreventionTobacco Use Cessation / Tobacco Use Disorders1
Not AvailableCompletedScreeningOther Diseases or Conditions1
Not AvailableCompletedTreatmentCocaine Abuse / Cocaine-Related Disorders1
Not AvailableCompletedTreatmentCocaine Abuse / Dependence, Cocaine / Postpartum Period1
Not AvailableCompletedTreatmentFertilization in Vitro / Infertilities / Recurrent Implantation Failure (RIF)1
Not AvailableCompletedTreatmentInfants, Premature / Premature Births1
Not AvailableCompletedTreatmentInfertilities2
Not AvailableCompletedTreatmentInfertilities / OHSS1
Not AvailableCompletedTreatmentLuteal Phase Defect1
Not AvailableCompletedTreatmentMarijuana Dependence1
Not AvailableCompletedTreatmentMenopausal and Postmenopausal Disorders1
Not AvailableCompletedTreatmentOvarian Failure, Premature1
Not AvailableCompletedTreatmentPregnancy1
Not AvailableCompletedTreatmentPremature Births1
Not AvailableCompletedTreatmentPremature Labour1
Not AvailableCompletedTreatmentOne to five years postmenopausal1
Not AvailableNot Yet RecruitingPreventionPremature Births / Short Cervix / Twin Pregnancy1
Not AvailableNot Yet RecruitingTreatmentART1
Not AvailableNot Yet RecruitingTreatmentAssisted Reproductive Technology therapy / Luteal Phase Support / Progesterone1
Not AvailableNot Yet RecruitingTreatmentHigh Risk Pregnancies1
Not AvailableNot Yet RecruitingTreatmentInfertilities / Infertility Due to Nonimplantation1
Not AvailableRecruitingNot AvailableInfertilities1
Not AvailableRecruitingOtherPremature Births / Short Cervix1
Not AvailableRecruitingPreventionPlacenta Previa1
Not AvailableRecruitingPreventionPremature Births1
Not AvailableRecruitingPreventionTwin; Pregnancy, Affecting Fetus or Newborn1
Not AvailableRecruitingTreatmentThreatened Miscarriage1
Not AvailableSuspendedNot AvailableNicotine Dependence2
Not AvailableTerminatedBasic ScienceHyperandrogenism / Polycystic Ovaries Syndrome1
Not AvailableTerminatedPreventionAntepartum Hemorrhage / Premature Births1
Not AvailableTerminatedPreventionPreeclampsia1
Not AvailableTerminatedTreatmentDependence, Cocaine / Nicotine Dependence1
Not AvailableTerminatedTreatmentOne to five years postmenopausal / Postmenopausal Syndrome1
Not AvailableTerminatedTreatmentPregnancy1
Not AvailableTerminatedTreatmentSubfertility1
Not AvailableUnknown StatusTreatmentInfertilities3
Not AvailableWithdrawnNot AvailablePregnancy / Premature Births1
Not AvailableWithdrawnPreventionIntrauterine Growth Retardation / Premature Births / Premature separation of placenta / Prophylaxis of preeclampsia / Threatened Abortion1
Not AvailableWithdrawnTreatmentPremature Labour1

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
FormRouteStrength
SolutionIntramuscular50 mg
CapsuleOral
GelVaginal45 mg/1.125g
GelVaginal8 %
GelVaginal90 mg/1.125g
InsertVaginal100 mg
InsertVaginal100 mg/1
Capsule; gel, meteredOral; Transdermal
LiquidIntramuscular50 mg
Capsule, liquid filledOral100 mg/1
Capsule, liquid filledOral200 mg/1
InjectionIntramuscular50 mg/1
Injection, solutionIntramuscular50 mg/1mL
CapsuleOral100 mg/1
CapsuleOral100 mg
CapsuleOral200 mg/1
CapsuleVaginal200 mg
Prices
Unit descriptionCostUnit
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 Tube14.83USD tube
Crinone 8% gel13.61USD g
Prochieve 8% gel12.0USD g
Prochieve 4% gel8.56USD g
Progesterone 50 mg/ml6.6USD ml
Progesterone oil 50 mg/ml vial3.88USD ml
Prometrium 200 mg capsule3.84USD capsule
First-progesterone vgs 400 susuppositoryp3.33USD each
First-progesterone vgs 200 suppository3.15USD each
First-progesterone vgs 100 suppository3.0USD each
First-progesterone vgs 50 suppository2.93USD each
First-progesterone vgs 25 suppository2.88USD each
Prometrium 100 mg capsule1.69USD capsule
Progesterone powder micronized0.74USD g
Progesterone powder milled0.73USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5543150No1996-08-062013-09-15Us
US7300664No2007-11-272019-11-17Us
US7320800No2008-01-222019-11-17Us
US7393543No2008-07-012019-11-17Us
US9006222No2012-11-212032-11-21Us
US9114145No2012-11-212032-11-21Us
US8846649No2012-11-212032-11-21Us
US9301920No2012-11-212032-11-21Us
US8846648No2012-11-212032-11-21Us
US9114146No2012-11-212032-11-21Us
US8633178No2012-11-212032-11-21Us
US10052386No2012-11-212032-11-21Us
US8993548No2012-11-212032-11-21Us
US8987237No2012-11-212032-11-21Us
US8993549No2012-11-212032-11-21Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)128-132https://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 ºChttps://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx
logP3.87http://www.hmdb.ca/metabolites/HMDB0001830
logS-4.43http://www.hmdb.ca/metabolites/HMDB0001830
pKaStrongest acidic: , Strongest basic: 18.92, -4.8http://www.hmdb.ca/metabolites/HMDB0001830
Predicted Properties
PropertyValueSource
Water Solubility0.00546 mg/mLALOGPS
logP3.58ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)18.47ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.71 m3·mol-1ChemAxon
Polarizability37.26 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.982
Caco-2 permeable+0.7724
P-glycoprotein substrateSubstrate0.5449
P-glycoprotein inhibitor IInhibitor0.8841
P-glycoprotein inhibitor IIInhibitor0.6043
Renal organic cation transporterNon-inhibitor0.6931
CYP450 2C9 substrateNon-substrate0.847
CYP450 2D6 substrateNon-substrate0.8795
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9533
CYP450 2C19 inhibitorNon-inhibitor0.6514
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8203
Ames testNon AMES toxic0.9626
CarcinogenicityNon-carcinogens0.9151
BiodegradationNot ready biodegradable0.9575
Rat acute toxicity1.8041 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7451
hERG inhibition (predictor II)Non-inhibitor0.7454
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-0fbc-5910000000-422e38df6de7e8b0a4b7
GC-MS Spectrum - GC-MSGC-MSsplash10-0fbc-5910000000-385f45345742235da8e0
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-024l-6923000000-639c7405f69825de7f90
GC-MS Spectrum - EI-BGC-MSsplash10-0229-2941000000-1e075d8489b79cf4e34a
GC-MS Spectrum - EI-BGC-MSsplash10-0229-3963000000-f35e3d9faf6b2ee87465
GC-MS Spectrum - GC-MSGC-MSsplash10-0fbc-5910000000-422e38df6de7e8b0a4b7
GC-MS Spectrum - GC-MSGC-MSsplash10-0fbc-5910000000-385f45345742235da8e0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6x-2910000000-1baafb91a3e0b988caa7
Mass Spectrum (Electron Ionization)MSsplash10-006x-7931000000-f6ad83adccd7e016fa29
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-014i-1009000000-0f8b7c3e6c2265c3889f
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-052b-8900000000-0b0167121b798e7e7534
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-052b-9400000000-881510cbcecd9cb61f4f
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , PositiveLC-MS/MSsplash10-024l-6923000000-639c7405f69825de7f90
MS/MS Spectrum - EI-B (HITACHI M-52) , PositiveLC-MS/MSsplash10-0229-2941000000-1e075d8489b79cf4e34a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kb-7955000000-a22f06eac940cd4f753d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0139000000-6b47f75a44df3e20fa3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aba-0950000000-b26d04d179294aa67cc7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aba-0920000000-d0a3365efe1f8a589564
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05aj-0910000000-61d7a07e6be85600e1f1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0009000000-67c6f0147801f0ece957
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05mk-8956000000-aa5fe992c41261b62fbf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052b-6910000000-5e26497eb2d0150a30ac
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052b-9700000000-523fe1ad11bfcbb46f85
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-054k-9400000000-e3d581bd8685e1d3f35d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-5900000000-8a409fe2508f58822f8a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-8900000000-fc9280df2a7dee451abb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0290000000-0f9dd31ff254325dd522
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0290000000-b59a04537c8d112aa2ab
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0190000000-b5fed26f17626a75c34c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0190000000-58920a9d93488054d8d5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-002k-0190000000-5f1ba0db62e0ade93f30
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0229000000-c83c60bdf0d3b91077c9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4j-5921000000-fccf432e6f84ed354acd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-4921100000-41abb61d58cd1d7a0f7c
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Progestogin-skeleton / 20-oxosteroid / Oxosteroid / 3-oxosteroid / 3-oxo-delta-4-steroid / Delta-4-steroid / Cyclohexenone / Cyclic ketone / Ketone / Organic oxygen compound
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)

Targets

Details
1. Progesterone receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific 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. Progesterone receptor ...
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. [PubMed:17013809]
  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. [PubMed:17015480]
  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. [PubMed:17138644]
  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. [PubMed:17169175]
  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. [PubMed:9506743]
  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. [PubMed:30013421]
Details
2. Estrogen receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Inhibitor
Downregulator
General Function
Zinc ion binding
Specific 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 tissu...
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. [PubMed:17118173]
  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. [PubMed:17341305]
  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. [PubMed:26153859]
  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. [PubMed:19094096]
  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. [PubMed:11014241]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Agonist
General Function
Zinc ion binding
Specific 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 targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 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. [PubMed:8282004]
  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. [PubMed:12039699]
  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. [PubMed:8928765]
  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. [PubMed:7588320]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid 17-alpha-monooxygenase activity
Specific Function
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
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. [PubMed:12596217]
  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. [PubMed:21092758]
  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. [PubMed:12464252]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
Potentiator
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
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. [PubMed:8867260]
  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. [PubMed:8918680]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as 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...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 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. [PubMed:16901474]
  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. [PubMed:12204624]
  3. Albani JR: Binding effect of progesterone on the dynamics of alpha1-acid glycoprotein. Biochim Biophys Acta. 1997 Aug 29;1336(2):349-59. [PubMed:9305808]
  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. [PubMed:12445481]
Details
7. Glucocorticoid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). 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 modula...
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. [PubMed:18060946]
  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. [PubMed:2214763]
  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. [PubMed:14617569]
Details
8. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Potentiator
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 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. [PubMed:1397870]
  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. [PubMed:10509795]
  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. [PubMed:19111796]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Potentiator
General Function
Androgen binding
Specific 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...
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. [PubMed:25349334]
  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. [PubMed:6538615]
  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. [PubMed:9408086]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Downregulator
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
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. [PubMed:20977477]
  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. [PubMed:19094096]
  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. [PubMed:11014241]
  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. [PubMed:17341305]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Quinney SK, Benjamin T, Zheng X, Patil AS: Characterization of Maternal and Fetal CYP3A-Mediated Progesterone Metabolism. Fetal Pediatr Pathol. 2017 Oct;36(5):400-411. doi: 10.1080/15513815.2017.1354411. Epub 2017 Sep 26. [PubMed:28949811]
  2. Bustos ML, Caritis SN, Jablonski KA, Reddy UM, Sorokin Y, Manuck T, Varner MW, Wapner RJ, Iams JD, Carpenter MW, Peaceman AM, Mercer BM, Sciscione A, Rouse DJ, Ramin SM: The association among cytochrome P450 3A, progesterone receptor polymorphisms, plasma 17-alpha hydroxyprogesterone caproate concentrations, and spontaneous preterm birth. Am J Obstet Gynecol. 2017 Sep;217(3):369.e1-369.e9. doi: 10.1016/j.ajog.2017.05.019. Epub 2017 May 15. [PubMed:28522317]
  3. CYP3A5 cytochrome P450 family 3 subfamily A member 5 [ Homo sapiens (human) ] [Link]
Details
2. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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. [PubMed:9328296]
  2. Du H, Wei Z, Yan Y, Xiong Y, Zhang X, Shen L, Ruan Y, Wu X, Xu Q, He L, Qin S: Functional Characterization of Human CYP2C9 Allelic Variants in COS-7 Cells. Front Pharmacol. 2016 Apr 25;7:98. doi: 10.3389/fphar.2016.00098. eCollection 2016. [PubMed:27199745]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Data are limited to the results of in vitro studies.
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Quinney SK, Benjamin T, Zheng X, Patil AS: Characterization of Maternal and Fetal CYP3A-Mediated Progesterone Metabolism. Fetal Pediatr Pathol. 2017 Oct;36(5):400-411. doi: 10.1080/15513815.2017.1354411. Epub 2017 Sep 26. [PubMed:28949811]
  2. Sharma S, Ellis EC, Dorko K, Zhang S, Mattison DR, Caritis SN, Venkataramanan R, Strom SC: Metabolism of 17alpha-hydroxyprogesterone caproate, an agent for preventing preterm birth, by fetal hepatocytes. Drug Metab Dispos. 2010 May;38(5):723-7. doi: 10.1124/dmd.109.029918. Epub 2010 Jan 22. [PubMed:20097724]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [PubMed:11259318]
  2. 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. [PubMed:9328296]
  3. Gomes LG, Huang N, Agrawal V, Mendonca BB, Bachega TA, Miller WL: Extraadrenal 21-hydroxylation by CYP2C19 and CYP3A4: effect on 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2009 Jan;94(1):89-95. doi: 10.1210/jc.2008-1174. Epub 2008 Oct 28. [PubMed:18957504]
  4. Mitsuda M, Iwasaki M, Asahi S: Cynomolgus monkey cytochrome P450 2C43: cDNA cloning, heterologous expression, purification and characterization. J Biochem. 2006 May;139(5):865-72. doi: 10.1093/jb/mvj093. [PubMed:16751594]
  5. Richardson TH, Jung F, Griffin KJ, Wester M, Raucy JL, Kemper B, Bornheim LM, Hassett C, Omiecinski CJ, Johnson EF: A universal approach to the expression of human and rabbit cytochrome P450s of the 2C subfamily in Escherichia coli. Arch Biochem Biophys. 1995 Oct 20;323(1):87-96. doi: 10.1006/abbi.1995.0013. [PubMed:7487078]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Jang GR, Wrighton SA, Benet LZ: Identification of CYP3A4 as the principal enzyme catalyzing mifepristone (RU 486) oxidation in human liver microsomes. Biochem Pharmacol. 1996 Sep 13;52(5):753-61. [PubMed:8765473]
  2. Sevrioukova IF, Poulos TL: Understanding the mechanism of cytochrome P450 3A4: recent advances and remaining problems. Dalton Trans. 2013 Mar 7;42(9):3116-26. doi: 10.1039/c2dt31833d. Epub 2012 Sep 27. [PubMed:23018626]
  3. Polic V, Auclair K: Allosteric Activation of Cytochrome P450 3A4 via Progesterone Bioconjugation. Bioconjug Chem. 2017 Apr 19;28(4):885-889. doi: 10.1021/acs.bioconjchem.6b00604. Epub 2017 Mar 29. [PubMed:28339191]
  4. Williams PA, Cosme J, Vinkovic DM, Ward A, Angove HC, Day PJ, Vonrhein C, Tickle IJ, Jhoti H: Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science. 2004 Jul 30;305(5684):683-6. Epub 2004 Jul 15. [PubMed:15256616]
  5. Tsunoda SM, Harris RZ, Mroczkowski PJ, Benet LZ: Preliminary evaluation of progestins as inducers of cytochrome P450 3A4 activity in postmenopausal women. J Clin Pharmacol. 1998 Dec;38(12):1137-43. [PubMed:11301566]
  6. Choi SY, Koh KH, Jeong H: Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. doi: 10.1124/dmd.112.046276. Epub 2012 Jul 26. [PubMed:22837389]
  7. Prometrium FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 17-alpha-monooxygenase activity
Specific Function
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
Gene Name
CYP17A1
Uniprot ID
P05093
Uniprot Name
Steroid 17-alpha-hydroxylase/17,20 lyase
Molecular Weight
57369.995 Da
References
  1. Kossor DC, Kominami S, Takemori S, Colby HD: Role of the steroid 17 alpha-hydroxylase in spironolactone-mediated destruction of adrenal cytochrome P-450. Mol Pharmacol. 1991 Aug;40(2):321-5. [PubMed:1875914]
  2. Kater CE, Biglieri EG: Disorders of steroid 17 alpha-hydroxylase deficiency. Endocrinol Metab Clin North Am. 1994 Jun;23(2):341-57. [PubMed:8070426]
  3. Petrunak EM, DeVore NM, Porubsky PR, Scott EE: Structures of human steroidogenic cytochrome P450 17A1 with substrates. J Biol Chem. 2014 Nov 21;289(47):32952-64. doi: 10.1074/jbc.M114.610998. Epub 2014 Oct 9. [PubMed:25301938]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Schwarz D, Kisselev P, Schunck WH, Chernogolov A, Boidol W, Cascorbi I, Roots I: Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30. [PubMed:10975606]
  2. Niwa T, Yabusaki Y, Honma K, Matsuo N, Tatsuta K, Ishibashi F, Katagiri M: Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. doi: 10.1080/004982598239290 . [PubMed:9667077]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, Gillam EM, Inoue K: Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. [PubMed:10426814]
  2. Li F, Zhu W, Gonzalez FJ: Potential role of CYP1B1 in the development and treatment of metabolic diseases. Pharmacol Ther. 2017 Oct;178:18-30. doi: 10.1016/j.pharmthera.2017.03.007. Epub 2017 Mar 16. [PubMed:28322972]
  3. Jansson I, Stoilov I, Sarfarazi M, Schenkman JB: Effect of two mutations of human CYP1B1, G61E and R469W, on stability and endogenous steroid substrate metabolism. Pharmacogenetics. 2001 Dec;11(9):793-801. [PubMed:11740343]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Choi SY, Koh KH, Jeong H: Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. doi: 10.1124/dmd.112.046276. Epub 2012 Jul 26. [PubMed:22837389]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Niwa T, Hiroi T, Tsuzuki D, Yamamoto S, Narimatsu S, Fukuda T, Azuma J, Funae Y: Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23. doi: 10.1016/j.molbrainres.2004.06.030. [PubMed:15469888]
  2. Niwa T, Okada K, Hiroi T, Imaoka S, Narimatsu S, Funae Y: Effect of psychotropic drugs on the 21-hydroxylation of neurosteroids, progesterone and allopregnanolone, catalyzed by rat CYP2D4 and human CYP2D6 in the brain. Biol Pharm Bull. 2008 Mar;31(3):348-51. [PubMed:18310890]
  3. Miller RT, Miksys S, Hoffmann E, Tyndale RF: Ethanol self-administration and nicotine treatment increase brain levels of CYP2D in African green monkeys. Br J Pharmacol. 2014 Jun;171(12):3077-88. doi: 10.1111/bph.12652. [PubMed:24611668]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [PubMed:12387747]
  2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514]
  3. Leonessa F, Kim JH, Ghiorghis A, Kulawiec RJ, Hammer C, Talebian A, Clarke R: C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump. J Med Chem. 2002 Jan 17;45(2):390-8. [PubMed:11784143]
  4. Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T, Hori R: Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem. 1992 Dec 5;267(34):24248-52. [PubMed:1360010]
  5. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
  6. Yamazaki M, Neway WE, Ohe T, Chen I, Rowe JF, Hochman JH, Chiba M, Lin JH: In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther. 2001 Mar;296(3):723-35. [PubMed:11181899]
  7. Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684]
  8. Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [PubMed:8621716]
  9. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022]
  3. Lozano E, Herraez E, Briz O, Robledo VS, Hernandez-Iglesias J, Gonzalez-Hernandez A, Marin JJ: Role of the plasma membrane transporter of organic cations OCT1 and its genetic variants in modern liver pharmacology. Biomed Res Int. 2013;2013:692071. doi: 10.1155/2013/692071. Epub 2013 Jul 31. [PubMed:23984399]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022]
Details
5. Bile salt export pump
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759]
  2. Abu-Hayyeh S, Williamson C: Progesterone metabolites as farnesoid X receptor inhibitors. Dig Dis. 2015;33(3):300-6. doi: 10.1159/000371565. Epub 2015 May 27. [PubMed:26045261]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: Reversal of MRP-mediated multidrug resistance in human lung cancer cells by the antiprogestatin drug RU486. Biochem Biophys Res Commun. 1999 May 19;258(3):513-8. [PubMed:10329417]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191]
  2. Abu-Hayyeh S, Williamson C: Progesterone metabolites as farnesoid X receptor inhibitors. Dig Dis. 2015;33(3):300-6. doi: 10.1159/000371565. Epub 2015 May 27. [PubMed:26045261]
  3. Abu-Hayyeh S, Martinez-Becerra P, Sheikh Abdul Kadir SH, Selden C, Romero MR, Rees M, Marschall HU, Marin JJ, Williamson C: Inhibition of Na+-taurocholate Co-transporting polypeptide-mediated bile acid transport by cholestatic sulfated progesterone metabolites. J Biol Chem. 2010 May 28;285(22):16504-12. doi: 10.1074/jbc.M109.072140. Epub 2010 Feb 20. [PubMed:20177056]
  4. Kim RB, Leake B, Cvetkovic M, Roden MM, Nadeau J, Walubo A, Wilkinson GR: Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity. J Pharmacol Exp Ther. 1999 Dec;291(3):1204-9. [PubMed:10565843]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data regarding this transporter activity are limited to in vitro studies.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Gui C, Obaidat A, Chaguturu R, Hagenbuch B: Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3. Curr Chem Genomics. 2010 Mar 1;4:1-8. doi: 10.2174/1875397301004010001. [PubMed:20448812]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Mao Q, Unadkat JD: Role of the breast cancer resistance protein (BCRP/ABCG2) in drug transport--an update. AAPS J. 2015 Jan;17(1):65-82. doi: 10.1208/s12248-014-9668-6. Epub 2014 Sep 19. [PubMed:25236865]
  2. Mao Q: BCRP/ABCG2 in the placenta: expression, function and regulation. Pharm Res. 2008 Jun;25(6):1244-55. doi: 10.1007/s11095-008-9537-z. [PubMed:18202831]
  3. Wu X, Zhang X, Sun L, Zhang H, Li L, Wang X, Li W, Su P, Hu J, Gao P, Zhou G: Progesterone negatively regulates BCRP in progesterone receptor-positive human breast cancer cells. Cell Physiol Biochem. 2013;32(2):344-54. doi: 10.1159/000354442. Epub 2013 Aug 14. [PubMed:23988382]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Patik I, Szekely V, Nemet O, Szepesi A, Kucsma N, Varady G, Szakacs G, Bakos E, Ozvegy-Laczka C: Identification of novel cell-impermeant fluorescent substrates for testing the function and drug interaction of Organic Anion-Transporting Polypeptides, OATP1B1/1B3 and 2B1. Sci Rep. 2018 Feb 8;8(1):2630. doi: 10.1038/s41598-018-20815-1. [PubMed:29422623]
  2. Gui C, Obaidat A, Chaguturu R, Hagenbuch B: Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3. Curr Chem Genomics. 2010 Mar 1;4:1-8. doi: 10.2174/1875397301004010001. [PubMed:20448812]

Drug created on June 13, 2005 07:24 / Updated on March 21, 2019 04:44