{"ATC Code":"G03DA04","Abbreviation":"P4","Aliases":["Agolutin","Prometrium","Luteol","Gestormone","Glanducorpin","Pregnenedione","Progesterol","Progesteronum","Progestone","Progestron"],"Biological Half-Life":"Absorption half-life is approximately 25-50 hours and an elimination half-life of 5-20 minutes (progesterone gel).    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.","Boiling Point":"394.13°C (rough estimate)","CAS":"57-83-0","ChEBI":"CHEBI:17026","ChEMBL":"CHEMBL103","ChemicalClasses":["steroid"],"Chirality":"absolute","Color/Form":"Prisms","Decomposition":"When heated to decomposition, it emits acrid smoke and irritating fumes.","Density":"1.171 at 68 °F (NTP, 1992) - Denser than water; will sink g/cm\u003csup\u003e3\u003c/sup\u003e","Dosing Info":[],"Drug Classes":"Breast Feeding; Lactation; Milk, Human; Hormones; Progesterone Congeners","Drug 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.   **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.  **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.  **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.   **Tablets, contraceptive**  The tablet form of progesterone in contraceptive formulations is indicated for the prevention of pregnancy.","Drug Warnings":"/BOXED WARNING/ WARNING: CARDIOVASCULAR DISORDERS, BREAST CANCER and PROBABLE DEMENTIA FOR ESTROGEN PLUS PROGESTIN THERAPY. Cardiovascular Disorders and Probable Dementia:  Estrogens plus progestin therapy should not be used for the prevention of cardiovascular disease or dementia. The Women's Health Initiative (WHI) estrogen plus progestin substudy reported increased risks of deep vein thrombosis, pulmonary embolism, stroke and myocardial infarction in postmenopausal women (50 to 79 years of age) during 5.6 years of treatment with daily oral conjugated estrogens (CE) (0.625 mg) combined with medroxyprogesterone acetate (MPA) (2.5 mg), relative to placebo. The WHI Memory Study (WHIMS) estrogen plus progestin ancillary study of the WHI reported an increased risk of developing probable dementia in postmenopausal women 65 years of age or older during 4 years of treatment with daily CE (0.625 mg) combined with MPA (2.5 mg), relative to placebo. It is unknown whether this finding applies to younger postmenopausal women. Breast Cancer: The WHI estrogen plus progestin substudy also demonstrated an increased risk of invasive breast cancer. In the absence of comparable data, these risks should be assumed to be similar for other doses of CE and MPA, and other combinations and dosage forms of estrogens and progestins.  Progestins with estrogens should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.","DrugClasses":["hormone"],"EINECS":"200-350-6","Esters":["propionate"],"European Community (EC) Number":"200-350-6","FDA Pharmacological Classification":"4G7DS2Q64Y","HMDB ID":"HMDB0001830","HeavyAtomCount":23,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Hormones; Progesterone Congeners","IUPACName":"(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one","Impurities":["3-oxopregnen-4-ene-20-carboxaldehyde","6-dehydroprogesterone","20-methylidene-3-oxopregn-4-en-21-al","20.beta.-hydroxyprogesterone","3-oxopregn-4-en-20-yl acetate, (20s)-","pregna-4,14-diene-3,20-dione","21-(cyclohexylidene)pregn-4-ene-3,20-dione","isoprogesterone","1-dehydroprogesterone","20.alpha.-hydroxyprogesterone","3-oxopregn-4-en-20-yl acetate, (20r)-","9-dehydro-progesterone"],"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","InChIKey":"RJKFOVLPORLFTN-LEKSSAKUSA-N","MeSH Pharmacological Classification":"Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY. (See all compounds classified as Progestins.)","Melting Point":"250 to 252 °F (NTP, 1992)","MolecularFormula":"C\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"314.5 g/mol","Odor":"Odorless","Opticalactivity":"UNSPECIFIED","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.  **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. 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.   **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.    **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),. 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.  **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.","Physical Description":"Progesterone is a white powder. Melting point 121 °C. Stable in air. Insoluble in water. A female sex hormone. Low toxicity.","PrevSalts":[],"PubChemId":5994,"Record Description":["Progesterone can cause cancer according to an independent committee of scientific and health experts.","Progesterone is a white powder. Melting point 121 °C. Stable in air. Insoluble in water. A female sex hormone. Low toxicity.","Progesterone is a C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species. It has a role as a contraceptive drug, a progestin, a progesterone receptor agonist, a human metabolite and a mouse metabolite. It is a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.","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. Progesterone is used in various contraceptive preparations to prevent ovulation and fertilization, 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. Progesterone is available in gelatinized capsule form, vaginal gel form, tablet form, vaginal insert form, and injection form, all used for various purposes.","Progesterone is a Progesterone.","Progesterone has been reported in Abedus herberti, Cota palaestina, and other organisms with data available.","Therapeutic Progesterone is the therapeutic form of the naturally occurring hormone progesterone.  Progesterone binds to the progesterone receptor, resulting in dissociation of heat shock proteins, receptor phosphorylation, and transcription activation through direct or indirect interaction with transcription factors.  This agent exerts inhibitory effects on estrogens by decreasing the number of estrogen receptors and increasing its metabolism to inactive metabolites.  Progesterone induces secretory changes in the endometrium, decreases uterine contractility during pregnancy, and maintains pregnancy.","Progesterone is produced in the corpus luteum and by the placenta, as an antagonist of estrogens. Promotes proliferation of uterine mucosa and the implantation of the blastocyst, prevents further follicular development.","Progestin is any synthetic steroid hormone that resembles the naturally occurring hormone and has progesterone-like properties.","PROGESTERONE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1976 and has 3 approved and 41 investigational indications. This drug has a black box warning from the FDA.","The major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production.","The major progestational steroid that is secreted primarily by the CORPUS LUTEUM and the PLACENTA. Progesterone acts on the UTERUS, the MAMMARY GLANDS and the BRAIN. It is required in EMBRYO IMPLANTATION; PREGNANCY maintenance, and the development of mammary tissue for MILK production. Progesterone, converted from PREGNENOLONE, also serves as an intermediate in the biosynthesis of GONADAL STEROID HORMONES and adrenal CORTICOSTEROIDS.","See also: Estradiol; progesterone (component of); Estradiol Benzoate; Progesterone (component of); Estrone; progesterone (component of) ... View More ...","Progesterone can cause cancer according to an independent committee of scientific and health experts.","Progesterone is a C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species. It has a role as a contraceptive drug, a progestin, a progesterone receptor agonist, a human metabolite and a mouse metabolite. It is a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.","LiverTox|Endocrine|Birth control|Progestin"],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Progesterone","Name":"Progesterone","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q26963","Name":"Progesterone","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00396","Name":"Progesterone","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5994","Name":"Progesterone","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL103","Name":"Progesterone","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17026","Name":"Progesterone","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=57-83-0","Name":"Progesterone","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0001830","Name":"Progesterone","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C00410","Name":"Progesterone","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/4G7DS2Q64Y","Name":"Progesterone","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID3022370","Name":"Progesterone","Sub":false}]}],"SMILES":"CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C","Solubility":"less than 1 mg/mL at 66 °F (NTP, 1992)","Stability/Shelf Life":"Progesterone is stable when exposed to air. 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","Therapeutic Uses":"Progestins","Title":"Progesterone","UNII":"4G7DS2Q64Y","Wikidata":"Q26963","Wikipedia":"Progesterone","XLogP":3.9}