Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H30O2 |
Molecular Weight | 314.4617 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=RJKFOVLPORLFTN-LEKSSAKUSA-N
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
Molecular Formula | C21H30O2 |
Molecular Weight | 314.4617 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-906_Progesterone_prntlbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8282004
http://www.rxlist.com/endometrin-drug/clinical-pharmacology.htm
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-906_Progesterone_prntlbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8282004
http://www.rxlist.com/endometrin-drug/clinical-pharmacology.htm
Progesterone is indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids of uterine cancer. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. Progesterone is a naturally occurring steroid that is secreted by the ovary, placenta, and adrenal gland. In the presence of adequate estrogen, progesterone transforms a proliferative endometrium into a secretory endometrium. Progesterone is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo is implanted, progesterone acts to maintain a pregnancy. Progesterone shares the pharmacological actions of the progestins. Progesterone binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is metabolized primarily by the liver largely to pregnanediols and pregnanolones. Pregnanediols and pregnanolones are conjugated in the liver to glucuronide and sulfate metabolites. Progesterone metabolites that are excreted in the bile may be deconjugated and may be further metabolized in the gut via reduction, dehydroxylation, and epimerization. Common progesterone side effects may include: drowsiness, dizziness; breast pain; mood changes; headache; constipation, diarrhea, heartburn; bloating, swelling in your hands or feet; joint pain; hot flashes; or vaginal discharge.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17015480 |
|||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17118173 |
|||
Target ID: CHEMBL1994 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8282004 |
0.01 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PROGESTERONE Approved UseIs indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids of uterine cancer. Launch Date2007 |
|||
Primary | PROGESTERONE Approved UseIs indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids of uterine cancer. Launch Date2007 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60.6 ng/mL |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PROGESTERONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
14.87 ng/mL |
90 mg single, vaginal dose: 90 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
PROGESTERONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
15.97 ng/mL |
90 mg 1 times / day steady-state, vaginal dose: 90 mg route of administration: Vaginal experiment type: STEADY-STATE co-administered: |
PROGESTERONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
175.7 ng × h/mL |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PROGESTERONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
296.78 ng × h/mL |
90 mg single, vaginal dose: 90 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
PROGESTERONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
391.98 ng × h/mL |
90 mg 1 times / day steady-state, vaginal dose: 90 mg route of administration: Vaginal experiment type: STEADY-STATE co-administered: |
PROGESTERONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
34.8 h |
90 mg single, vaginal dose: 90 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
PROGESTERONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
45 h |
90 mg 1 times / day steady-state, vaginal dose: 90 mg route of administration: Vaginal experiment type: STEADY-STATE co-administered: |
PROGESTERONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 10.5 uM] | ||||
yes [IC50 4.8 uM] | ||||
yes [IC50 42.1 uM] | ||||
yes [Inhibition 100 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/9328296/ Page: 3.0 |
yes [Ki 17 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9328296/ Page: 3.0 |
yes [Ki 9 uM] | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/19813763/ |
yes | |||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/9328296/ Page: 5.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9328296/ Page: 5.0 |
yes | |||
yes | ||||
yes | likely (co-administration study) Comment: Ketoconazole is a known inhibitor of cytochrome P450 3A4, hence these data suggest that ketoconazole or other known inhibitors of this enzyme may increase the bioavailability of progesterone Sources: https://pubmed.ncbi.nlm.nih.gov/8424894/ |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Thrombospondin-1 and -2 in node-negative breast cancer: correlation with angiogenic factors, p53, cathepsin D, hormone receptors and prognosis. | 2001 |
|
The rate-determining step in P450 C21-catalyzing reactions in a membrane-reconstituted system. | 2001 Apr 6 |
|
Dexamethasone up-regulates type II IL-1 receptor in mouse primary activated astrocytes. | 2001 Feb |
|
Human types 1 and 3 3 alpha-hydroxysteroid dehydrogenases: differential lability and tissue distribution. | 2001 Feb |
|
Endothelins enhance prostaglandin (PGE(2) and PGF(2alpha)) biosynthesis and release by human luteal cells: evidence of a new paracrine/autocrine regulation of luteal function. | 2001 Feb |
|
Action of chicken II GnRH on the human placenta. | 2001 Feb |
|
Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C. | 2001 Feb |
|
Short-term administration of antivascular endothelial growth factor antibody in the late follicular phase delays follicular development in the rhesus monkey. | 2001 Feb |
|
Follow-up examination at the age of 15 months of extremely preterm infants after postnatal estradiol and progesterone replacement. | 2001 Feb |
|
Fertility and body composition after laparoscopic bilateral adrenalectomy in a 30-year-old female with congenital adrenal hyperplasia. | 2001 Feb |
|
Progesterone, but not medroxyprogesterone, inhibits vascular cell adhesion molecule-1 expression in human vascular endothelial cells. | 2001 Feb |
|
Enhanced verbal memory in nondemented elderly women receiving hormone-replacement therapy. | 2001 Feb |
|
Menstrual history and risk of hip fractures in postmenopausal women. The Iowa Women's Health Study. | 2001 Feb 1 |
|
Prognostic and predictive significance of ErbB-2 breast tumor levels measured by enzyme immunoassay. | 2001 Feb 1 |
|
Estrogen prevents oxidative stress-induced endothelial cell apoptosis in rats. | 2001 Feb 6 |
|
Re: Randomized trial of fenretinide to prevent second breast malignancy in women with early breast cancer. | 2001 Feb 7 |
|
Lp(a) lipoprotein--an independent risk factor for coronary heart disease after menopause. | 2001 Jan |
|
Reliability of ovulation tests in infertile women. | 2001 Jan |
|
Serum allopregnanolone in women with postpartum "blues". | 2001 Jan |
|
Sex steroids and bone. | 2001 Jan |
|
Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition. | 2001 Jan |
|
Concordance in judgments among c-erbB-2 (HER2/neu) overexpression detected by two immunohistochemical tests and gene amplification detected by Southern blot hybridization in breast carcinoma. | 2001 Jan |
|
The APC is dispensable for first meiotic anaphase in Xenopus oocytes. | 2001 Jan |
|
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors. | 2001 Jan |
|
Targeted disruption of luteinizing hormone/human chorionic gonadotropin receptor gene. | 2001 Jan |
|
Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function. | 2001 Jan |
|
Separable features of the ligand-binding domain determine the differential subcellular localization and ligand-binding specificity of glucocorticoid receptor and progesterone receptor. | 2001 Jan |
|
Estrogen receptor beta regulates sexually dimorphic neural responses to estradiol. | 2001 Jan |
|
Establishment and characterization of a steroidogenic human granulosa-like tumor cell line, KGN, that expresses functional follicle-stimulating hormone receptor. | 2001 Jan |
|
Glucocorticoids regulate plasma membrane potential during rat thymocyte apoptosis in vivo and in vitro. | 2001 Jan |
|
Assessment of mechanisms of thyroid hormone action in mouse Leydig cells: regulation of the steroidogenic acute regulatory protein, steroidogenesis, and luteinizing hormone receptor function. | 2001 Jan |
|
Biphasic action of prolactin in the regulation of murine Leydig tumor cell functions. | 2001 Jan |
|
Differential regulation of two forms of gonadotropin-releasing hormone messenger ribonucleic acid in human granulosa-luteal cells. | 2001 Jan |
|
Molecular cytogenetic comparison of apocrine hyperplasia and apocrine carcinoma of the breast. | 2001 Jan |
|
Prostaglandin receptors and role of G protein-activated pathways on corpora lutea of pseudopregnant rabbit in vitro. | 2001 Jan |
|
In vitro regulation of local secretion and contraction of the bovine oviduct: stimulation by luteinizing hormone, endothelin-1 and prostaglandins, and inhibition by oxytocin. | 2001 Jan |
|
Granulosa-luteal cell function in vitro and ovarian stimulation protocols. | 2001 Jan |
|
Charcoal treatment and risk of escape ovulation in oral contraceptive users. | 2001 Jan |
|
Reproductive hormones and blood pressure during pregnancy. | 2001 Jan |
|
Hormones and the brain: more studies. | 2001 Jan |
|
Low peripheral blood levels of the immunosuppressive cytokine interleukin 10 (IL-10) at the start of gonadotrophin stimulation indicates increased risk for development of ovarian hyperstimulation syndrome (OHSS). | 2001 Jan |
|
Effect of endogenous estrogen on blood flow through carotid arteries. | 2001 Jan |
|
The influence of menstrual cycle phase on skeletal muscle contractile characteristics in humans. | 2001 Jan 1 |
|
17beta-oestradiol acutely regulates Cl- secretion in rat distal colonic epithelium. | 2001 Jan 1 |
|
Effect of medroxyprogesterone acetate plus estradiol on endothelium-dependent vasodilation in postmenopausal women. | 2001 Jan 15 |
|
Functional involvement of Xenopus LIM kinases in progression of oocyte maturation. | 2001 Jan 15 |
|
Evidence that epithelial and mesenchymal estrogen receptor-alpha mediates effects of estrogen on prostatic epithelium. | 2001 Jan 15 |
|
Evaluation of in vitro methods for detecting the effects of various chemicals on the human progesterone receptor, with a focus on pyrethroid insecticides. | 2001 Jan 3 |
|
Estrogen, selective estrogen receptor modulation, and coronary heart disease: something or nothing. | 2001 Jan 3 |
|
Effects of low-frequency magnetic fields on implantation in rats. | 2001 Jan-Feb |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20540763
Curator's Comment: As a resule 34% reduction in cell proliferation was observed in the MB468 cells with treatment of P4, as compared with the cells with treatment of vehicle alone. As expected, P4 had no effects on cell proliferation of the parental MB231. However, the treatment of the mPRα stably-expressing MB231 cells with P4 induced a significant reduction of cell proliferation (28.1%). These data suggest that mPRα is also involved in regulating cell proliferation of BPBC cells.
To test whether the female sex hormone controls cell proliferation of MB468 (basal phenotype breast cancers) cells, cell were incubated the with progesterone (P4) (30 ng/ml) for 24 hours.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:52:48 GMT 2025
by
admin
on
Mon Mar 31 17:52:48 GMT 2025
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Record UNII |
4G7DS2Q64Y
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
664818
Created by
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WHO-VATC |
QG03FA04
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NDF-RT |
N0000005934
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LIVERTOX |
803
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LOINC |
83109-9
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FDA ORPHAN DRUG |
82694
Created by
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CFR |
21 CFR 556.540
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LOINC |
83110-7
Created by
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DSLD |
4218 (Number of products:3)
Created by
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LOINC |
12820-7
Created by
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LOINC |
44729-2
Created by
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CFR |
21 CFR 522.1940
Created by
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LOINC |
24109-1
Created by
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CFR |
21 CFR 862.1430
Created by
admin on Mon Mar 31 17:52:48 GMT 2025 , Edited by admin on Mon Mar 31 17:52:48 GMT 2025
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WHO-ATC |
G03FA04
Created by
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LOINC |
14890-8
Created by
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EU-Orphan Drug |
EU/3/13/1101
Created by
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LOINC |
17483-9
Created by
admin on Mon Mar 31 17:52:48 GMT 2025 , Edited by admin on Mon Mar 31 17:52:48 GMT 2025
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WHO-VATC |
QG03DA04
Created by
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CFR |
21 CFR 310.530
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NDF-RT |
N0000005934
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LOINC |
44730-0
Created by
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LOINC |
35223-7
Created by
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CFR |
21 CFR 862.1620
Created by
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NCI_THESAURUS |
C2296
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NDF-RT |
N0000175601
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NDF-RT |
N0000005934
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LOINC |
2838-1
Created by
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LOINC |
2839-9
Created by
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WHO-ATC |
G03DA04
Created by
admin on Mon Mar 31 17:52:48 GMT 2025 , Edited by admin on Mon Mar 31 17:52:48 GMT 2025
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FDA ORPHAN DRUG |
284809
Created by
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Code System | Code | Type | Description | ||
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2377
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PRIMARY | |||
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17026
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PRIMARY | |||
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1568007
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PRIMARY | |||
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64377
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PRIMARY | |||
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PROGESTERONE
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PRIMARY | |||
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57-83-0
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PRIMARY | |||
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CHEMBL103
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PRIMARY | |||
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DTXSID3022370
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PRIMARY | |||
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4G7DS2Q64Y
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PRIMARY | |||
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5994
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PRIMARY | |||
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DB00396
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PRIMARY | |||
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D011374
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PRIMARY | |||
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100000090354
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PRIMARY | |||
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PROGESTERONE
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PRIMARY | Description: Colourless crystals or a white to slightly yellowish white, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 8 parts of ethanol (~750 g/l) TS. Category: Progestational steroid. Storage: Progesterone should be kept in a well-closed container, protected from light. Additional information: Progesterone may exist in 2 polymorphic forms, one of which melts at about 130?C, the other at about 121?C. Definition: Progesterone contains not less than 97.0% and not more than 102.0% of C21H30O2, calculated with reference to the dried substance. | ||
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m9159
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PRIMARY | Merck Index | ||
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SUB10076MIG
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PRIMARY | |||
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2279
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PRIMARY | |||
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200-350-6
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PRIMARY | |||
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Progesterone
Created by
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PRIMARY | |||
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C777
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PRIMARY | |||
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4G7DS2Q64Y
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PRIMARY | |||
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417
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PRIMARY | |||
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3389
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PRIMARY | |||
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9704
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PRIMARY | |||
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8727
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PRIMARY | |||
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C400424
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PRIMARY | |||
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259409
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ALTERNATIVE | |||
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Progesterone (medication)
Created by
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PRIMARY |
Related Record | Type | Details | ||
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DERIVATIVE -> PARENT |
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DERIVATIVE -> PARENT |
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TARGET -> AGONIST |
IC50
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TARGET -> AGONIST |
BINDING
IC50
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ANALOGUE->TARGET |
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TARGET -> AGONIST |
BINDING
IC50
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DERIVATIVE -> PARENT | |||
|
ENZYME->SUBSTRATE |
Vmax
|
||
|
AGONIST -> TARGET |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|