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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
Structure of Progesterone

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

HIDE SMILES / InChI

Molecular Formula C21H30O2
Molecular Weight 314.4617
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.01 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROGESTERONE
Primary
PROGESTERONE

Cmax

ValueDoseCo-administeredAnalytePopulation
60.6 ng/mL
300 mg 1 times / day multiple, oral
PROGESTERONE plasma
Homo sapiens
14.87 ng/mL
90 mg single, vaginal
PROGESTERONE plasma
Homo sapiens
15.97 ng/mL
90 mg 1 times / day steady-state, vaginal
PROGESTERONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
175.7 ng × h/mL
300 mg 1 times / day multiple, oral
PROGESTERONE plasma
Homo sapiens
296.78 ng × h/mL
90 mg single, vaginal
PROGESTERONE plasma
Homo sapiens
391.98 ng × h/mL
90 mg 1 times / day steady-state, vaginal
PROGESTERONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
34.8 h
90 mg single, vaginal
PROGESTERONE plasma
Homo sapiens
45 h
90 mg 1 times / day steady-state, vaginal
PROGESTERONE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
5 to 10 mg during 8 consecutive days
Route of Administration: Intramuscular
In Vitro Use Guide
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
Record UNII
4G7DS2Q64Y
Record Status Validated (UNII)
Record Version